[go: up one dir, main page]

WO2025019749A1 - Hexafluoro-2-butene compositions, storage and handling - Google Patents

Hexafluoro-2-butene compositions, storage and handling Download PDF

Info

Publication number
WO2025019749A1
WO2025019749A1 PCT/US2024/038689 US2024038689W WO2025019749A1 WO 2025019749 A1 WO2025019749 A1 WO 2025019749A1 US 2024038689 W US2024038689 W US 2024038689W WO 2025019749 A1 WO2025019749 A1 WO 2025019749A1
Authority
WO
WIPO (PCT)
Prior art keywords
less
hfo
weight
butene
hexafluoro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/038689
Other languages
French (fr)
Inventor
Sheng Peng
William H. Zimmerman
Michael A. Bradley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chemours Co FC LLC
Original Assignee
Chemours Co FC LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chemours Co FC LLC filed Critical Chemours Co FC LLC
Publication of WO2025019749A1 publication Critical patent/WO2025019749A1/en
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02Materials undergoing a change of physical state when used
    • C09K5/04Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10Components
    • C09K2205/12Hydrocarbons
    • C09K2205/126Unsaturated fluorinated hydrocarbons

Definitions

  • HFO-1336mzz hexafluoro-2-butene
  • ODP ozone depletion potential
  • GWP global warming potential
  • these low ODP and GWP materials are used as refrigerants, solvents, foam expansion agents, cleaning agents, aerosol propellants, dielectrics, fire extinguishants, and power cycle working fluids.
  • Many commercial refrigerants include halogenated olefinic compounds.
  • Hydrofluoroolefins (HFOs) and hydrochlorofluoro olefins (HCFOs) have found utility as modern refrigerants due to their low global warming potential (GWP).
  • Olefinic compounds are unsaturated hydrocarbons including one or more pairs of carbon atoms linked by double bond. The unsaturated double bond provides a reactive moiety which is subject to attack by various reactive species.
  • olefinic refrigerants may encounter adverse materials or extremely undesirable conditions that cause the double bond to react to form unwanted by- products, which reduce the refrigerant products’ performance and effectiveness.
  • Preparation of olefinic refrigerants including but not limited to 1,1,1,4,4,4 hexfluoro-2-butene (HFO-1336mzz) and mixtures of the Z- and E- isomers have been described in US Patent Publication No.20190248719, the disclosure of which is incorporated herein by reference in its entirety.
  • Z-1,1,1,4,4,4 hexfluoro-2-butene can be isomerized to E-1,1,1,4,4,4 hexfluoro-2-butene, as disclosed in for example U.S. Patent No.10,479,745, the disclosure of which is incorporated herein by reference in its entirety.
  • Z-HFO-1336mzz and E-HFO1336mzz compositions, systems and methods of preparing, transporting, transferring, storing and using these olefinic refrigerants with reduced levels of chlorinated reaction products, moisture and/or NCG components are desired.
  • HFO-1336mzz high purity HFO-1336mzz isomers, e.g., compositions with at least 99% Z- HFO-1336mzz or 99% E-HFO-1336mzz.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz with reduced levels of impurities which comprise, consist essentially or, or consist of one of chlorine containing compounds moisture (H 2 O) and NAG/NCG, wherein the presence of chlorine compounds and moisture can contribute to formation of HCl which in turn leads to metal corrosion and product quality issue such as high acidity.
  • impurities comprise, consist essentially or, or consist of one of chlorine containing compounds moisture (H 2 O) and NAG/NCG, wherein the presence of chlorine compounds and moisture can contribute to formation of HCl which in turn leads to metal corrosion and product quality issue such as high acidity.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 1000ppm, 500 ppm , 250 ppm by weight of chlorine species.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 100 ppm by weight moisture.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 10 vol% or less than 5 vol%, or less than 3 vol%, or less than 1.5 vol% of NAG.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing acidity of ⁇ 1 ppm by weight by weight.
  • the present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing chloride of ⁇ 3 ppm by weight by weight.
  • compositions include: (1) greater than 99.5 percent 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), (2) greater than 99% E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), or (3) greater than 99% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E).
  • compositions which comprise, consist essentially of, or consist of one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and at least one of, (c) optionally chlorinated compounds in an amount between 0 and less than 500 ppm by weight, between 1ppm by weight and 500 ppm by weight, 100 ppm by weight, or 50 ppm
  • compositions contain both HFO- 1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition.
  • HFO- 1336mzz isomers
  • E E-1,1,1,4,4,4 hexafluoro-2-butene
  • Z Z-1,1,1,4,4,4 hexafluoro-2-butene
  • compositions contain both HFO- 1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition .
  • HFO- 1336mzz isomers
  • E E-1,1,1,4,4,4 hexafluoro-2-butene
  • Z Z-1,1,1,4,4,4 hexafluoro-2-butene
  • optionally chlorinated compounds in an amount between 0 and less than 1000 ppm by weight, between 1ppm by weight and 750 ppm by weight, 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight; optionally moisture in an amount of between 0 and less than 500 ppm by weight, between 1 ppm by weight and 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight , and (f) optionally non-condensable gases (NAG) in an amount of less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol%.
  • NAG optionally non-condensable gases
  • compositions contain only one of HFO-1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E- isomer or Z-isomer is not present in a detectable amount based analysis of the composition.
  • HFO-1336mzz the E-1,1,1,4,4,4 hexafluoro-2-butene
  • Z Z-1,1,1,4,4,4 hexafluoro-2-butene
  • compositions comprise, consist essentially of, or consist of one or more of the HFO-1336mzz isomers and additional compounds in an amount of 0 and less than 0.5% (5000 ppm by weight (0.05) percent wherein one of the E-isomer or Z-isomer is present in an amount of 0.5 percent or less and the remainder of the composition is the other isomer.
  • compositions comprise, consist essentially of, or consist of HFO-1336mzz, one or more additional compounds selected from 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E), 1,1-dichloroethene (HCO-1130a), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz).
  • HCFC-346mdf 2-chloro-1,1,1,1,4,4,4-hexafluorobutane
  • Z Z-2-chloro- 1,1,1,4,4,4-hexa
  • compositions comprise, consist essentially of, or consist of HFO-1336mzz, one or more additional compounds selected from 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E), 1,1-dichloroethene (HCO-1130a), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less.
  • compositions comprise, consist essentially of, or consist of one of greater than 99 percent 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz) and one or more additional compounds selected from Group C, wherein Group C includes 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2- chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,
  • compositions include between greater than 99% and less than about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein (HFO-1336mzz) which comprises between greater than 99% and less than about 99.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or between greater than 99% about 99.5% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)).
  • HFO-1336mzz 1,1,1,4,4,4-hexafluoro-2-butene
  • compositions include between greater than 99% and about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein the HFO-1336mzz comprises, consists essentially of, or consists of either between greater than 99% E-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(E)) and up to about 0.5% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) or 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and up to about 0.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and at least one additional compound from Group A, Group B or Group C.
  • HFO-1336mzz 1,1,1,4,4,4-hexafluoro-2-
  • compositions include between greater than 99% and about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein the HFO-1336mzz comprises, consists essentially of, or consists of either between greater than 99% E-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(E)) and up to about 0.5% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) or 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and up to about 0.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and at least one additional compound from Group A, Group B or Group C, wherein the chlorinated species are present in an amount of 1000 ppm by
  • compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition.
  • HFO-1336mzz hexafluoro-2-butene
  • compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition, wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less.
  • HFO-1336mzz hexafluoro-2-butene
  • compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition, wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, and optionally containing less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG.
  • compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition.
  • HFO-1336mzz hexafluoro-2-butene
  • compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz), wherein the hexafluoro-2-butene (HFO-1336mzz) comprises at least 99% HFO-1336mzz(E) and at most 0.5% HFO-1336mzz(Z) or at least 99% HFO- 1336mzz(Z) and at most 0.5% HFO-1336mzz(E), and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds respectively selected from Group A or Group B based on 100% of the composition or the total amount of the amount of the compositions, wherein the respective amounts of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hex
  • compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz), wherein the hexafluoro-2-butene (HFO-1336mzz) comprises at least 99% HFO-1336mzz(E) and at most 0.5% HFO-1336mzz(Z) or at least 99% HFO- 1336mzz(Z) and at most 0.5% HFO-1336mzz(E), and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds respectively selected from Group A or Group B based on 100% of the composition or the total amount of the amount of the compositions, wherein the respective amounts of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), ,1,1,4,4,4-hexafluorobut
  • chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, and optionally containing less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG.
  • a method relates to the transportation, transfer, and storage and use of any of the HFO-1336mzz isomers compositions containing E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z- isomer is presence in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, minimizing/reducing/eliminating the presence of impurities such as chlorine containing species, moisture/water, and/or NAG/NCG compounds.
  • impurities such as chlorine containing species, moisture/water, and/or NAG/NCG compounds.
  • the HFO-1336mzz compositions are charged to an existing container or a new container, under pressure and closed to avoid leaking.
  • a vacuum is first pulled to remove any inert gases before charging. If the container was previously filled with 1336mzz(Z), and there is no pressure in the container, then fresh HFO- 1336mzz compositions are directly charged to the previously used container.
  • the container enables distribution, blending, transport, transfer, storage, recovery and usage of the HFO-1336mzz compositions disclosed herein.
  • a container has a volume of 500 L to 1000 L, or 750 L to 950 L, or 850 L to 950 L is used for transportation, transfer, and storage, such as that described in US Patent Publication No.20220136748 the disclosure of which is incorporated herein by reference in its entirety. Due to the vertical orientation, the container lends itself to ease of processing of said refrigerant. It should be noted that any vertical cylinder designed for flammable refrigerants, can also be conveniently used for non-flammable refrigerants. Depending on the refrigerant being used in the inventive process, the pressure, flammability and volume will follow the appropriate design codes.
  • the vertical ton tank will follow the ASME design construction and pressure rating, while in the EU the vertical ton tank will follow ADR and in Japan the vertical ton tank will follow HPGL
  • a vacuum is first pulled to remove any inert gases before charging. If the container was previously filled with 1336mzz(Z), and there is no pressure in the container, then fresh HFO- 1336mzz compositions are directly charged to the previously used container.
  • the container enables distribution, blending, transport, transfer, storage, recovery and usage of the HFO-1336mzz compositions disclosed herein.
  • One embodiment of the invention disclosed herein relates to a container, tank, transport vessel filed with at least the HFO-1336mzz E- and Z- isomer compositions alone, or combined with the additional compounds of one of Groups A or B described herein, and impurities, if present, comprising at most 1000 ppm by weight of chlorine containing species, preferably at most 500 ppm by weight of chlorine containing species, at most 100 ppm by weight or moisture/water, and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% of NAG/NCG compounds.
  • Certain embodiments disclosed herein relate to processes for packaging compositions in a container which include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds; (c) such that the packaging minimizes/eliminates the addition and/or presence of moisture and/or NAG compounds, such that the moisture content is less 100 ppm by weight and/or the NAG content is less than 10 vol%, or less than 9 vol% or less than 8 vol
  • Moisture can be removed by contacting the HFO-1336mzz compositions disclosed herein with a medium sufficient for removal of moisture when filling a container, tank or transport vessel.
  • the medium e.g., a desiccants may be composed of activated alumina, silica gel, or zeolite based molecular sieves.
  • Representative molecular sieves include MOLSIV XH-7, XH-6, XH-9 and XH-11 (UOP LLC, Des Plaines, Ill.) Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control.
  • Figure 1 depicts an exemplary heat transfer system including or connected to a container containing the composition in accordance with an embodiment of the invention.
  • Figure 2 depicts system for charging a refrigerant circuit connected to a container filled with a composition in accordance with an embodiment of the invention.
  • the present invention relates to HFO-1336mzz isomer compositions containing E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, transportation, transfer, and storage of the composition disclosed herein, and use thereof which involves minimizing/reducing/eliminating the presence of impurities such as chlorine containing species, moisture, and/or NAG/NCG compounds.
  • impurities such as chlorine containing species, moisture, and/or NAG/NCG compounds.
  • hydrohaloalkene is intended to mean a chemical compound selected from the classes of hydrofluoroolefms (HFOs) and hydrochlorofluoroolefins (HCFOs) which include a double bond between adjacent carbon atoms and can contain 1 to 8 carbon atoms.
  • the term “dehydrofluorination,” “dehydrofluorinating” or “dehydrofluorinated,” as used herein, means a process during which hydrogen and fluorine on adjacent carbons in a molecule are removed;
  • the term “dehydrochlorination,” “dehydrochlorinating,” or “dehydrochlorinated,” as used herein, means a process during which hydrogen and chlorine on adjacent carbons in a molecule are removed.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
  • “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B is true (or present).
  • the transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith.
  • the term “substantially free” means that less than about 0.0005 percent by weight is present (5 ppm by weight). As used herein the term “about” in certain embodiments can mean ⁇ 1%, ⁇ 2%, ⁇ 3% and up to and including ⁇ 10% of an identified value, including all whole numbers and fractions thereof. As used herein the term “substantially,” “main” or “major” should be construed to mean at least 51 percent.
  • compositions according to the present invention are free of or substantially free of certain Fluorinated Substances which includes any substance that (i) contains at least one fully fluorinated methyl (–CF3) or methylene (– CF2–) carbon atom (without any H/Cl/Br/I attached to it); and (ii) meets the criterion for persistence in soil/sediment and water established in Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023, the disclosure of which is hereby incorporated by reference (https://echa.europa.eu/documents/10162/f605d4b5-7c17-7414-8823-
  • Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation (https://reachonline.eu/reach/en/annex-xiii-1-1.1-1.1.1.html as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023, accessed on May 2, 2023), include, but are not limited to, TFA.
  • TFA analytical standard may be used in either gas chromatography or ion chromatography and is available from, for example, Sigma Aldrich.
  • degradation products of compositions according to the present invention are free of or substantially free of Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023, accessed on May 2, 2023).
  • Non-Condensable Gas is meant to gases such as oxygen and nitrogen (air), carbon dioxide, argon and carbon monoxide.
  • Non- absorbable gas (NAG), non-condensable gas (NCG), or simply non-condensables are all terms used to reference gases such as air, nitrogen, argon, carbon dioxide, and oxygen.
  • impurities comprise, but are not limited to moisture (water), non-absorbable gas (NAG), non-condensable gas (NCG), or simply non-condensables are all terms used to reference gases such as air, nitrogen, argon, carbon dioxide, and oxygen, and chlorine containing HCC, HCFC, HCFO and HCO compounds.
  • compositions comprise, consist essentially of, or consist of greater than 99% HFO-1336mzz(Z) based on the total amount of the composition and one or more additional compounds selected from Group A, wherein Group A includes 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC- 346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a, Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-heptafluoro-2-butene (HFO-1327mz), wherein the chlorinated species are present in an amount of greater than 0 to
  • compositions comprise, consist essentially of, or consist of greater than 99 percent HFO-1336mzz(E)and one or more additional compounds selected from Group B, wherein Group B includes at least one of: 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft), 2-Chloro
  • compositions include one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and c. additional compounds selected from at least one of: i.
  • 2-chloro-1,1,1,1,4,4,4-hexafluorobutane in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • ii. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene HCFO-1326mxz(Z) in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • iii. E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • 1,1-dichloroethene (HCO-1130a) in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • v. 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) in an amount between 0.0001% and 0.05% based on the total amount of the composition and vi.
  • 1,1,1,2,4,4,4-hexafluoro-2-butene in an amount between 0.0001% and 0.05% based on the total amount of the composition, with the proviso that the total amount of additional compounds does not exceed 0.05%, and optionally wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture, and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG are present and the total amount of the composition is 100 percent.
  • compositions include one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); c. and additional compounds selected from at least one of: i.
  • 1-chloro-3,3,3-trifluoropropene in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • v. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene HCFO-1326mxz(Z) in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • HFO-1336ft 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • viii 2-chloro-1,1,1-trifluoroethane (HCFC-133a) in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • x 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene
  • 1,1,1,2,4,4,4-heptafluorobutane in an amount between 0.0001% and 0.05% based on the total amount of the composition
  • HCFC-123a 1,2-dichloro-1,1,2-trifluoroethane
  • the composition comprises, consists essentially of, or consists of E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) as the main or major component, and one or more, two or more, three or more, four or more, or five or more of additional compounds/members selected from: a) 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), b) 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), c) 1,1,1,3,3-Pentafluoropropane (HFC-245fa), d) 1,1-dichloroethene (HCO-1130a), e) 2-chloro-3,3,3-trifluoropropene (HCFO-1233x
  • compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); (c) and optionally (1) chlorinated compound are present in an amount of 500 ppm by weight or less, preferably 100ppm by weight or less, and most preferably 50 ppm by weight or less, (2) moisture is present in an amount of less than 500 ppm by weight, ⁇ 100 ppm by weight, or ⁇ 20 ppm by weight and/or NAG is present in an
  • compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds; (c) and optionally (1) chlorinated compound are present in an amount of 100 ppm by weight or less, preferably less than 500 and most preferably 100 ppm by weight
  • Certain embodiments disclosed herein relate to processes for packaging compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds, to minimize/eliminate the addition and/or presence of moisture and/or NAG compounds, such that moisture content is less than 500 ppm by weight, 100 ppm by weight, or 20
  • compositions comprise, consist essentially of, or consist of greater than 99 percent HFO-1336mzz(E) and one or more additional compounds selected from Group B, wherein Group B includes *2- chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- 1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), 2-chloro-1,1,1- trifluoroethane (HCFC-133a), 1,1,4,4,4 -pentafluoro -2
  • the composition comprises, consists essentially of, or consists of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz) as the main or major component, and one or more, two or more, three or more, four or more , or five or more additional compounds/members wherein (1) the total amount of additional compounds/members is selected from between: greater than 0 and less than 0.5 percent, greater than 0 and less than 0.4 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than about 0.1 percent, or greater than 0 and less than about 0.01 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%, and/or (2) the amount of an additional compound/member is selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.00
  • the total amount of compounds other than 1,1,1,4,4,4 hexafluoro-2-butene is selected from between: greater than 0 and less than 0.05 percent, greater than 0 and less than 0.04 percent, greater than 0 and less than 0.03 percent, greater than 0 and less than 0.02 percent, greater than 0 and less than about 0.01 percent based on the total amount of the composition.
  • One embodiment of the invention disclosed herein relates to using a refrigerant or heat transfer fluid composition
  • a refrigerant or heat transfer fluid composition comprising the Z-HFO-1336mzz or E-HFO- 1336mzz isomer mixtures with reduced moisture, NCG or chlorinated compounds alone or as blends in refrigeration, air-conditioning, or heat pump apparatus, said method comprising introducing the composition disclosed herein containing reduced levels of impurities into said apparatus having (a) centrifugal compressor; (b) multi-stage centrifugal compressor, or (c) single slab/single pass heat exchanger; wherein said refrigerant or heat transfer composition is employed in said apparatus to result in heating or cooling.
  • Figure 1 illustrates a system 100 having at least a first loop 112 and an optional second loop 116.
  • First loop 112 is shown connected to second loop 116 through heat exchanger 114.
  • Loop system 112 generally includes at least one exchanger 110, a pressure regulator 104, at least one exchanger 106, a compressor 108, and charging valve 102 that may be arranged in seriatim as shown.
  • the motive force 126 (compressor, pump, etc.) circulates Z-HFO-1336mzz or E-HFO-1336mzz isomer mixtures respectively containing 99% Z-HFO-1336mzz or E- HFO-1336mzz with reduced moisture and NCG content and less than 500 ppm by weight of chlorinated compounds alone, or in blends thereof to various electrical components, such as batteries, electric motors, computer components in need of thermal management to regulate temperature.
  • Thermal energy from one or more of components 118, 120, 122 and 124 is used to exchange heat with the working fluid and can be used to heat other fluids, e.g., air, water or other fluid.
  • Valving (not shown) is included in all flow lines to assist with the thermal management, as are thermal energy exchangers upstream or downstream of components 118, 120, 122 and 124. Although four components in need of thermal management are illustrated, less components or more components can be included, e.g., 2, 3, 5, 6, 7 or more.
  • Another embodiment of the invention relates to using either Z-HFO-1336mzz or E-HFO-1336mzz alone or as blends in heat transfer systems, including but not limited to refrigeration systems, refrigerators, air conditioning systems, heat pumps, chillers, and mobile air conditioning systems, as for example illustrated in Figure 2.
  • FIG. 2 illustrates a system 200 where a source of refrigerant 210 (either Z-HFO-1336mzz or E- HFO-1336mzz alone, isomer blends or as refrigerant blends) having reduced moisture and NCG content, and less than 500 ppm by weight of chlorinated compounds can be connected to a refrigerant circuit 250 of a refrigerant system which includes, generally in seriatim, charging valve 212, expansion device 214, heat exchange 220, compressor 230, heat exchange 240 and flow lines 213, 215, 222, 231 and 241.
  • the refrigerant 210 is charged via line 211 which is in fluid communication with charging valve 212, which when opened and charges refrigerant circuit 250.
  • a container used for storing the foregoing compositions can be constructed of any suitable material and design that is capable of sealing the compositions therein while maintaining gaseous and liquids phases.
  • suitable containers comprise pressure resistant containers such as a tank, a filling cylinder, and a secondary filing cylinder.
  • the container can be constructed from any suitable material such as carbon steel, manganese steel, chromium-molybdenum steel, among other low-alloy steels, stainless steel and in some case an aluminum alloy.
  • the container can include a pierce top or valves suitable for dispensing flammable substances.
  • the inventive composition is employed for servicing an existing A/C or refrigerant system wherein the composition is stored in a container having a threaded seal.
  • a composition claim embodiment comprising E 1,1,1,4,4,4 hexafluoro-2- butene (HFO-1336mzz(E)) or Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and one or more additional compounds selected from one of hydrofluorocarbons (HFCs), hydrochlorocarbons (HCCs), hydrofluoroolefins (HFOs), and hydrochlorofluoroolefins (HCFOs), wherein based on the total amount of the composition at least 99 percent HFO-1336mzz(E) and HFO-1336mzz(Z) and at most 500ppm by weight of chlorine containing compounds are present.
  • HFCs hydrofluorocarbons
  • HCCs hydrochlorocarbons
  • HFOs hydrofluoroolefins
  • HCFOs hydrochlorofluoroolefins
  • composition of claim embodiment 1 comprising one of: (1) greater than 99% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), or (2) greater than 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E). 3.
  • composition of claim embodiment 1 comprising greater than 99% E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z). 4.
  • composition of claim embodiment 1 comprising greater than 99% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E) 5.
  • the composition of any of claim embodiments 1-4 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 6.
  • composition of any of claim embodiments 1-7 wherein the additional compounds are selected from at least one of 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), 2-chloro-3,3,3- trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2- chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), 1,1,1,2,4,4,4-hexaflu
  • composition any of claim embodiments 1-7 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3- pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), ), 1,2- dichloro-1,1,2-trifluoroethane (HCFC-123a),and 3,3,3-trifluoro-2-(trifluor)
  • composition of any of claim embodiments 1-7wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(E)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz).
  • HFO- 1336mzz(E) 2-chloro-1,1,1,1,4,4,4-hexa
  • composition of any of claim embodiments 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 12. The composition of any of claim embodiments 9 or 10 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 13. The composition of any of claim embodiments 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less and non- condensable gases in an amount of 5 vol % or less. 14. The composition of any of claim embodiments 1-10 wherein the amount of chlorine compounds present is selected from 100 ppm by weight or less, or 50 ppm by weight or less. 15.
  • composition of any of claim embodiments 1-15 wherein a total amount of the additional compounds is selected from one of less than 0.5 percent, less than 0.4 percent, less than 0.3 percent, less than 0.2 percent, or less than 0.1 percent.
  • amount of NCG compounds is selected from one of less than 5 vol%, less than 4 vol%, less than 3 vol%, or less than 1.5 vol%. 17.
  • composition of any of claims embodiment 1 or 3 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z. 18.
  • composition of any of claim embodiments 1 or 4 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), and E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)).
  • HCFC-346mdf 2-chloro-1,1,1,1,4,4,4- hexafluorobutane
  • HCO-1130a 1,1-dichloroethene
  • Z Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene
  • composition of claim embodiment 17 wherein the amount of chlorine compounds present is selected from one of 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less.
  • the composition of claim embodiment 17 wherein the amount of chlorine compounds present is selected from one of 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less.
  • a composition claim embodiment which comprise one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b.
  • HFO- 1336mzz(Z) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and at least one of, wherein “a” or “b” optionally include at least one of: i. chlorinated compounds in an amount between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight; ii. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and iii.
  • non-condensable gases in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%.. 22.
  • a composition claim embodiment comprises E-1,1,1,4,4,4 hexafluoro-2- butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, and at least one of, c.
  • chlorinated compounds in an amount between 0 and less than 1000 ppm by weight, 500 ppm by weight or 100 ppm by weight; d. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and e. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5, less than 4 ppm by weight, less than 3 ppm by weight, less than 2 ppm by weight and less than 1.5 ppm by weight.
  • NCG non-condensable gases
  • composition of any of claim embodiments 22, 23 or 24 containing less than 10 vol% of NAG 26.
  • a method for packaging a container of refrigerant embodiment comprising, f. providing a container suitable for holding a composition containing at least 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), g. optionally conditioning the container for receiving the composition, h. sealable connecting a container to a source of the HFO-1336mzz composition, i.
  • HFO-1336mzz composition which comprises, E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: i.
  • additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4- hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2- (trifluoromethyl)-1-propene (HFO-1336ft) or ii.
  • HFO-1336mzz(Z) 2-chloro
  • additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro- 1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz); and optionally at least one of: iii.
  • chlorinated compounds in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight, iv. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight, and v. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%.
  • NCG non-condensable gases
  • HCFC-346mdf 2-chloro-1,1,1,1,4,4,4-hexafluorobutane
  • HCFO-1233xf 2- chloro-3,3,3-trifluoropropene
  • HCFO-1233zd 1-chloro-3,3,3- trifluoropropene
  • a method claim embodiment comprising storing a composition comprising E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: l.
  • additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) or m.
  • HFO-1336mzz(Z) 2-chlor
  • additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC- 356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2- butene (HFO-1327mz); wherein chlorinated compounds is maintained in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm
  • a composition claim embodiment comprising an E-HFO1336mzz and Z- HFO-1336mzz mixture, at least two additional compounds are selected from HFC, HCC, HFO, and HCFO, of which at least one of is an HCC or HCFO compound present in an amount of less than 500 ppm by weight, and further including reduced moisture in an amount of less than 100 ppm by weight and reduced NCG in an amount of less than 5vol %, and wherein one of E-HFO1336mzz and Z-HFO-1336mzz is present in an amount of at least 99% based on the total amount of the composition. 33.
  • composition of claim embodiment 31 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3- pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft).
  • HFO- 1336mzz(Z) 2-
  • composition of claim embodiment 31 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(E)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz).
  • HFO- 1336mzz(E) 2-chloro-1,1,1,1,4,4,4-hexafluorobut
  • composition of claim embodiments 33 or 34 wherein the total amount of additional compounds is selected from between: greater than 0 and less than 0.5 percent, greater than 0 and less than 0.4 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than about 0.1 percent, or greater than 0 and less than about 0.01 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%, and/or (2) the amount of an additional compound/member is selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100% and/or (3) the respective amount of an additional compound/member is independently selected from one of greater than 0 and less than about 0.2 percent, greater than
  • composition of claim embodiment 31 wherein the additional compounds are selected from at least one of: n. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, o. 1,1,1,3,3-pentafluoropropane (HFC-245fa) in an amount greater than 0 and less than about 0.1 percent, p. 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in an amount greater than 0 and less than about 0.05 percent, q.
  • HCFC-346mdf 2-chloro-1,1,1,1,4,4,4-hexafluorobutane
  • HFC-245fa 1,1,1,3,3-pentafluoropropane
  • p. 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in an amount greater than 0 and less than about 0.05 percent
  • 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) in an amount greater than 0 and less than about 0.05 percent
  • r. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount greater than 0 and less than about 0.05 percent
  • s. 1,1,1,2,4,4,4-hexafluoro-2-butene HFO-1327mz
  • HFO-1336ft 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene
  • composition of claim embodiment 31 wherein the additional compounds are selected from at least one of: u. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, v. 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) in an amount greater than 0 and less than about 0.1 percent, w. 1,1-dichloroethene (HCO-1130a) in an amount greater than 0 and less than about 0.05 percent, x.
  • HCFC-346mdf 2-chloro-1,1,1,1,4,4,4-hexafluorobutane
  • HFC-356mff 1,1,1,4,4,4-hexafluorobutane
  • HCO-1130a 1,1-dichloroethene
  • NCG non-condensable gases
  • NCG non-condensable gases

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to production, purification, storage, handling and packaging of high purity HFO-1336mzz isomers compositions with at least 99% Z-HFO-1336mzz or 99% E-HFO-1336mzz.

Description

HEXAFLUORO-2-BUTENE COMPOSITIONS, STORAGE AND HANDLING FIELD The invention relates to hexafluoro-2-butene (HFO-1336mzz) compositions, storage and handling. BACKGROUND Hydrofluoroolefins (HFOs) having low ozone depletion potential (ODP) and low global warming potential(GWP) have been replacing saturated CFCs (chlorofluorocarbons) and HCFCs (hydrochlorofluorocarbons) in a variety of applications for several years, as well as hydrofluorocarbons which tend to have high GWP values. As a result, these low ODP and GWP materials are used as refrigerants, solvents, foam expansion agents, cleaning agents, aerosol propellants, dielectrics, fire extinguishants, and power cycle working fluids. Many commercial refrigerants include halogenated olefinic compounds. Hydrofluoroolefins (HFOs) and hydrochlorofluoro olefins (HCFOs) have found utility as modern refrigerants due to their low global warming potential (GWP). Olefinic compounds are unsaturated hydrocarbons including one or more pairs of carbon atoms linked by double bond. The unsaturated double bond provides a reactive moiety which is subject to attack by various reactive species. During the transfer, transportation, storage and use, olefinic refrigerants may encounter adverse materials or extremely undesirable conditions that cause the double bond to react to form unwanted by- products, which reduce the refrigerant products’ performance and effectiveness.. Preparation of olefinic refrigerants, including but not limited to 1,1,1,4,4,4 hexfluoro-2-butene (HFO-1336mzz) and mixtures of the Z- and E- isomers have been described in US Patent Publication No.20190248719, the disclosure of which is incorporated herein by reference in its entirety. Z-1,1,1,4,4,4 hexfluoro-2-butene can be isomerized to E-1,1,1,4,4,4 hexfluoro-2-butene, as disclosed in for example U.S. Patent No.10,479,745, the disclosure of which is incorporated herein by reference in its entirety. Z-HFO-1336mzz and E-HFO1336mzz compositions, systems and methods of preparing, transporting, transferring, storing and using these olefinic refrigerants with reduced levels of chlorinated reaction products, moisture and/or NCG components are desired. Thus the need remains for improved production, purification, storage and handling of high purity HFO-1336mzz isomers, e.g., compositions with at least 99% Z- HFO-1336mzz or 99% E-HFO-1336mzz. SUMMARY The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz with reduced levels of impurities which comprise, consist essentially or, or consist of one of chlorine containing compounds moisture (H2O) and NAG/NCG, wherein the presence of chlorine compounds and moisture can contribute to formation of HCl which in turn leads to metal corrosion and product quality issue such as high acidity. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 1000ppm, 500 ppm , 250 ppm by weight of chlorine species. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 100 ppm by weight moisture. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing less than 10 vol% or less than 5 vol%, or less than 3 vol%, or less than 1.5 vol% of NAG. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing acidity of < 1 ppm by weight by weight. The present invention relates to 1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz), its Z- and E- isomers, compositions thereof, and the storage and handling of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), E- HFO-1336mzz and Z- HFO- 1336mzz, optionally containing chloride of < 3 ppm by weight by weight. In certain embodiment disclosed herein compositions include: (1) greater than 99.5 percent 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), (2) greater than 99% E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), or (3) greater than 99% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E). It should be noted that “less than” a particular percent includes zero percent of that component present in the composition being described. In other embodiments disclosed herein includes composition which comprise, consist essentially of, or consist of one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and at least one of, (c) optionally chlorinated compounds in an amount between 0 and less than 500 ppm by weight, between 1ppm by weight and 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight; (d) optionally moisture in an amount of between 0 and less than 500 ppm by weight, between 1 ppm by weight and 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight , and (e) optionally non-condensable gases (NAG) in an amount of between 0 and less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol%. It should be noted that “up to” a particular weight (ppm or weight percent) does not require the presence of that particular component as “up to” includes zero. In certain embodiment disclosed herein compositions contain both HFO- 1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition. In certain embodiment disclosed herein compositions contain both HFO- 1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition . and at least one of, optionally chlorinated compounds in an amount between 0 and less than 1000 ppm by weight, between 1ppm by weight and 750 ppm by weight, 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight; optionally moisture in an amount of between 0 and less than 500 ppm by weight, between 1 ppm by weight and 500 ppm by weight, 100 ppm by weight, or 50 ppm by weight, preferably less than 100 and most preferably 50 ppm by weight , and (f) optionally non-condensable gases (NAG) in an amount of less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol%. In certain embodiment disclosed herein compositions contain only one of HFO-1336mzz isomers, i.e., the E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E- isomer or Z-isomer is not present in a detectable amount based analysis of the composition. In certain embodiment disclosed herein compositions comprise, consist essentially of, or consist of one or more of the HFO-1336mzz isomers and additional compounds in an amount of 0 and less than 0.5% (5000 ppm by weight (0.05) percent wherein one of the E-isomer or Z-isomer is present in an amount of 0.5 percent or less and the remainder of the composition is the other isomer. In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of HFO-1336mzz, one or more additional compounds selected from 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E), 1,1-dichloroethene (HCO-1130a), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz). In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of HFO-1336mzz, one or more additional compounds selected from 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E), 1,1-dichloroethene (HCO-1130a), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less. In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of one of greater than 99 percent 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz) and one or more additional compounds selected from Group C, wherein Group C includes 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2- chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 3,3,3-trifluoro-2-(trifluoromethyl)- 1-propene (HFO-1336ft) 2-chloro-1,1,1-trifluoroethane (HCFC-133a), 1,1,4,4,4 - pentafluoro -2-butene (HFO-1345mzz), 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a , wherein the chlorinated species are present in an amount of 1000 ppm by weight or less, preferably less than 500 and most preferably 100 ppm by weight or less.. In certain embodiment disclosed herein compositions include between greater than 99% and less than about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein (HFO-1336mzz) which comprises between greater than 99% and less than about 99.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or between greater than 99% about 99.5% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)). In certain embodiment disclosed herein compositions include between greater than 99% and about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein the HFO-1336mzz comprises, consists essentially of, or consists of either between greater than 99% E-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(E)) and up to about 0.5% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) or 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and up to about 0.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and at least one additional compound from Group A, Group B or Group C. In certain embodiment disclosed herein compositions include between greater than 99% and about 99.5% 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz) based on the total amount of the composition, wherein the HFO-1336mzz comprises, consists essentially of, or consists of either between greater than 99% E-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(E)) and up to about 0.5% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) or 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and up to about 0.5% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and at least one additional compound from Group A, Group B or Group C, wherein the chlorinated species are present in an amount of 1000 ppm by weight or less, preferably less than 500 and most preferably 100 ppm by weight or less. In certain embodiments disclosed herein compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition. In certain embodiments disclosed herein compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition, wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less. In certain embodiments disclosed herein compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition, wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, and optionally containing less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG. . In certain embodiments disclosed herein compositions include greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz) and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds selected from Group A, Group B or Group C based on 100% of the composition. In certain embodiments disclosed herein compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz), wherein the hexafluoro-2-butene (HFO-1336mzz) comprises at least 99% HFO-1336mzz(E) and at most 0.5% HFO-1336mzz(Z) or at least 99% HFO- 1336mzz(Z) and at most 0.5% HFO-1336mzz(E), and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds respectively selected from Group A or Group B based on 100% of the composition or the total amount of the amount of the compositions, wherein the respective amounts of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1- dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- 1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) or 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro- 3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4- hexafluoro-2-butene (HFO-1327mz), ), 2-chloro-1,1,1-trifluoroethane (HCFC-133a), 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz), 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) and 3,3,3-trifluoro-2- (trifluoromethyl)-1-propene (HFO-1336ft) is a value between greater than 0 and less than 0.05 %, 0.04%, 0.03%, 0.02% or 0.01 %; between greater than 0.0001% and less than 0.04%, 0.03%, 0.02% or 0.01 % or between greater than 0.001% and less than 0.04 %, 0.04%, 0.03%, 0.02% or 0.01 %; based on the total composition, and all values and ranges therebetween, with the proviso that the total amount of the additional compounds is a value between greater than 0 and less than 0.05 %, 0.04%, 0.03%, 0.02% or 0.01 %. In certain embodiments disclosed herein compositions comprise, consist essentially of, or consist of greater than 99%, greater than 99.5%, greater than 99.6 %, greater than 99.7%, greater than 99.8%, or greater than 99.9% hexafluoro-2-butene (HFO-1336mzz), wherein the hexafluoro-2-butene (HFO-1336mzz) comprises at least 99% HFO-1336mzz(E) and at most 0.5% HFO-1336mzz(Z) or at least 99% HFO- 1336mzz(Z) and at most 0.5% HFO-1336mzz(E), and at most 0.05%, 0.04%, 0.3%, 0.2%, 0.1% of one or more additional compounds respectively selected from Group A or Group B based on 100% of the composition or the total amount of the amount of the compositions, wherein the respective amounts of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), ,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1- dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- 1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) or 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro- 3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4- hexafluoro-2-butene (HFO-1327mz), 2-chloro-1,1,1-trifluoroethane (HCFC-133a), 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz), 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a), and 3,3,3-trifluoro-2- (trifluoromethyl)-1-propene (HFO-1336ft) is a value between greater than 0 and less than 0.05 %, 0.04%, 0.03%, 0.02% or 0.01 %; between greater than 0.0001% and less than 0.04%, 0.03%, 0.02% or 0.01 % or between greater than 0.001% and less than 0.04 %, 0.04%, 0.03%, 0.02% or 0.01 %; based on the total composition, and all values and ranges therebetween, with the proviso that the total amount of the additional compounds is a value between greater than 0 and less than 0.05 %, 0.04%, 0.03%, 0.02% or 0.01 %. wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, and optionally containing less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG. In certain embodiments disclosed herein a method relates to the transportation, transfer, and storage and use of any of the HFO-1336mzz isomers compositions containing E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z- isomer is presence in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, minimizing/reducing/eliminating the presence of impurities such as chlorine containing species, moisture/water, and/or NAG/NCG compounds. In certain embodiment disclosed herein, the HFO-1336mzz compositions are charged to an existing container or a new container, under pressure and closed to avoid leaking. For a new container, a vacuum is first pulled to remove any inert gases before charging. If the container was previously filled with 1336mzz(Z), and there is no pressure in the container, then fresh HFO- 1336mzz compositions are directly charged to the previously used container. The container enables distribution, blending, transport, transfer, storage, recovery and usage of the HFO-1336mzz compositions disclosed herein. In one particular embodiment a container has a volume of 500 L to 1000 L, or 750 L to 950 L, or 850 L to 950 L is used for transportation, transfer, and storage, such as that described in US Patent Publication No.20220136748 the disclosure of which is incorporated herein by reference in its entirety. Due to the vertical orientation, the container lends itself to ease of processing of said refrigerant. It should be noted that any vertical cylinder designed for flammable refrigerants, can also be conveniently used for non-flammable refrigerants. Depending on the refrigerant being used in the inventive process, the pressure, flammability and volume will follow the appropriate design codes. In the US for example, the vertical ton tank will follow the ASME design construction and pressure rating, while in the EU the vertical ton tank will follow ADR and in Japan the vertical ton tank will follow HPGL For a new container, a vacuum is first pulled to remove any inert gases before charging. If the container was previously filled with 1336mzz(Z), and there is no pressure in the container, then fresh HFO- 1336mzz compositions are directly charged to the previously used container. The container enables distribution, blending, transport, transfer, storage, recovery and usage of the HFO-1336mzz compositions disclosed herein. One embodiment of the invention disclosed herein relates to a container, tank, transport vessel filed with at least the HFO-1336mzz E- and Z- isomer compositions alone, or combined with the additional compounds of one of Groups A or B described herein, and impurities, if present, comprising at most 1000 ppm by weight of chlorine containing species, preferably at most 500 ppm by weight of chlorine containing species, at most 100 ppm by weight or moisture/water, and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% of NAG/NCG compounds. Certain embodiments disclosed herein relate to processes for packaging compositions in a container which include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds; (c) such that the packaging minimizes/eliminates the addition and/or presence of moisture and/or NAG compounds, such that the moisture content is less 100 ppm by weight and/or the NAG content is less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% to avoid/reduce/eliminate oxidation and/or hydrolysis initiated by moisture and/or NAG compounds. Moisture can be removed by contacting the HFO-1336mzz compositions disclosed herein with a medium sufficient for removal of moisture when filling a container, tank or transport vessel. The medium, e.g., a desiccants may be composed of activated alumina, silica gel, or zeolite based molecular sieves. Representative molecular sieves include MOLSIV XH-7, XH-6, XH-9 and XH-11 (UOP LLC, Des Plaines, Ill.) Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification, including definitions, will control. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting. BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 depicts an exemplary heat transfer system including or connected to a container containing the composition in accordance with an embodiment of the invention. Figure 2 depicts system for charging a refrigerant circuit connected to a container filled with a composition in accordance with an embodiment of the invention. DETAILED DECSRIPTION The present invention relates to HFO-1336mzz isomer compositions containing E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, transportation, transfer, and storage of the composition disclosed herein, and use thereof which involves minimizing/reducing/eliminating the presence of impurities such as chlorine containing species, moisture, and/or NAG/NCG compounds. Before addressing details of embodiments described herein, some terms are defined or clarified as follows. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range. It is not intended that the scope of the invention be limited to the specific values recited when defining a range. Moreover, all ranges set forth herein are intended to include not only the particular ranges specifically described, but also any combination of values therein, including the minimum and maximum values recited. The term “compound” as used herein is meant to include all stereoisomers, geometric isomers, tautomers, and isotopes of the structures or chemical described. Compounds herein identified by name or structure as one particular tautomeric form are intended to include other tautomeric forms unless otherwise specified. The term “hydrohaloalkane,” as used herein means a molecule containing hydrogen, carbon, fluorine and/or chlorine and/or bromine and/or iodine, with no carbon- carbon double bond (halo=fluoro, chloro, bromo, iodo). Examples are described throughout the instant specification. The term “hydrohaloalkene” is intended to mean a chemical compound selected from the classes of hydrofluoroolefms (HFOs) and hydrochlorofluoroolefins (HCFOs) which include a double bond between adjacent carbon atoms and can contain 1 to 8 carbon atoms. The term “dehydrohalogenation,” as used herein, means loss of HX from a hydrohaloalkane, where X=F, Cl, Br, I, where H and X are on adjacent carbons in the hydrohaloalkane. For example, the term “dehydrofluorination,” “dehydrofluorinating” or “dehydrofluorinated,” as used herein, means a process during which hydrogen and fluorine on adjacent carbons in a molecule are removed; the term “dehydrochlorination,” “dehydrochlorinating,” or “dehydrochlorinated,” as used herein, means a process during which hydrogen and chlorine on adjacent carbons in a molecule are removed. As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B is true (or present). The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consists of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole. The transitional phrase “consisting essentially of” is used to define a composition, method that includes materials, steps, features, components, or elements, in addition to those literally disclosed provided that these additional included materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention, especially the mode of action to achieve the desired result of any of the processes of the present invention. The term ‘consisting essentially of’ occupies a middle ground between “comprising” and ‘consisting of.’ Where applicants have defined an invention or a portion thereof with an open- ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also include such an invention using the terms “consisting essentially of” or “consisting of.” Also, use of “a” or “an” are employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise. As used herein, the term “substantially free” means that less than about 0.0005 percent by weight is present (5 ppm by weight). As used herein the term “about” in certain embodiments can mean ± 1%, ± 2%, ± 3% and up to and including ±10% of an identified value, including all whole numbers and fractions thereof. As used herein the term “substantially,” “main” or “major” should be construed to mean at least 51 percent. In a preferred embodiment, compositions according to the present invention are free of or substantially free of certain Fluorinated Substances which includes any substance that (i) contains at least one fully fluorinated methyl (–CF3) or methylene (– CF2–) carbon atom (without any H/Cl/Br/I attached to it); and (ii) meets the criterion for persistence in soil/sediment and water established in Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000016_0001
accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023, the disclosure of which is hereby incorporated by reference (https://echa.europa.eu/documents/10162/f605d4b5-7c17-7414-8823-
Figure imgf000016_0002
In another embodiment, as used herein, “Fluorinated Substances” as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000016_0003
2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000016_0004
accessed on May 2, 2023). includes any substance that has a Henry’s Law constant < 250 Pa*m3/mol and contains at least one fully fluorinated methyl (–CF3) or methylene (– CF2–) carbon atom (without any H/Cl/Br/I attached to it). In embodiments, Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation (https://reachonline.eu/reach/en/annex-xiii-1-1.1-1.1.1.html as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000016_0005
accessed on May 2, 2023), include, but are not limited to, TFA. The phrase "free of" as used herein with respect to the presence of Fluorinated Substances, as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000016_0006
as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000016_0007
b49b9fd43aea as on present means the amount of such substances in the compositions is sufficiently low so as to not be detectable, including but not limited to 0%, when measured by gas chromatography with a flame ionization detector, gas chromatography with a mass detector by analysis of a gas sample or liquid sample, and/or ion chromatography by analysis of a water sample after bubbling the thermal fluid through water. Such methodologies are well known to those skilled in the art. The phrase "substantially free of" as used herein with respect to the presence of Fluorinated Substance as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation (https://reachonline.eu/reach/en/annex-xiii-1-1.1- 1.1.1.html as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023, (https://echa.europa.eu/documents/10162/f605d4b5-
Figure imgf000017_0001
the present compositions means that the amount of such substances in the compositions is > 0 wt.% and < 5 wt.%, or > 0 wt.% and < 4 wt.%, or > 0 wt.% and < 3 wt.%, or > 0 wt.% and < 2 wt.%, or > 0 wt.% and < 1 wt.%, and all values and ranges therebetween, when measured by gas chromatographic (GC) techniques, for example gas chromatography (GC) with a flame ionization or electron-capture detector, or GC coupled with a mass detector (gas chromatography/mass spectral (GC/MS) method), by ion chromatograph(IC) or ion chromatography mass spectrometry (IC-MS) techniques, or by high-performance liquid chromatography (HPLC) or high-performance liquid chromatography mass spectrometry (HPLC-MS) techniques. The TFA analytical standard may be used in either gas chromatography or ion chromatography and is available from, for example, Sigma Aldrich. In a preferred embodiment, degradation products of compositions according to the present invention are free of or substantially free of Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000017_0002
as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000017_0003
accessed on May 2, 2023). The phrase "free of" as used herein with respect to the formation of the Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000017_0004
1.1.1.html as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000017_0005
7c17-7414-8823-b49b9fd43aea as accessed on May 2, 2023) as degradation products of the present compositions means that the theoretical molar yield of such substances in environmental compartments of air, soil/sediment and water produced during tropospheric degradation of the compositions is sufficiently low so as to not be detectable, including but not limited to 0%, when measured by GC techniques, for example GC with a flame ionization or electron-capture detector or GC/MS method, by IC or IC-MS techniques, or by HPLC or HPLC-MS techniques. The phrase "substantially free of" as used herein with respect to the formation of Fluorinated Substances as defined by Annex XIII (Section 1.1.1) of the European Union’s REACH Regulation
Figure imgf000018_0001
1.1.1.html as accessed on May 2, 2023) and referenced in the Annex XV Restriction Report dated March 22, 2023,
Figure imgf000018_0002
accessed on May 2, 2023)by the present compositions means that the theoretical molar yield of such substances in environmental compartments of air, soil/sediment and water produced during tropospheric degradation of the compositions is > 0% and < 5%, or > 0% and < 4%, or > 0% and < 3%, or > 0% and < 2%, or > 0% and < 1%, and all values and ranges therebetween, when measured by GC techniques, for example GC with a flame ionization or electron-capture detector or GC/MS method, by IC or IC-MS techniques, or by HPLC or HPLC-MS techniques. As used herein the terms Non-Condensable Gas (NCG) is meant to gases such as oxygen and nitrogen (air), carbon dioxide, argon and carbon monoxide. Non- absorbable gas (NAG), non-condensable gas (NCG), or simply non-condensables are all terms used to reference gases such as air, nitrogen, argon, carbon dioxide, and oxygen. As used herein impurities comprise, but are not limited to moisture (water), non-absorbable gas (NAG), non-condensable gas (NCG), or simply non-condensables are all terms used to reference gases such as air, nitrogen, argon, carbon dioxide, and oxygen, and chlorine containing HCC, HCFC, HCFO and HCO compounds. Compounds referred to in this disclosure may be referred to by code, based on fluorochemical naming convention, chemical structure and/or chemical name. For convenience and reference, selected compounds with codes, structures and chemical names are listed in Table 1. TABLE 1 Code Name-ASHRAE Designation Formula R-245fa 1,1,1,2,2-pentafluoropropane (HFC-245fa) CF3CF2CH3 R-346mdf 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) C3CH2ClC2CF3 R-356mff 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) CF3CH2CH2CF3 R-1130a 1,1-dichloroethene (HCO-1130a) CCl2-CH2 R-1233xf 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) CF3CCl=CH2 R-1233zd 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) CF3CCH=CHCl E-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- E-CF3CCl=CH2CF3 R-1326 1326mxz(E), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- Z-CF3CCl=CH2CF3 R-1326 1326mxz(Z), R-1327mz 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) CF3CF=CH2CF3 R-1336mzz(E) E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) E-CF3CH=CHCF3 R-1336mzz(Z) Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) Z-CF3CH=CHCF3 R-1336ft 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) CH2=C(CF3)2 R-133a 2-chloro-1,1,1-trifluoroethane (HCFC-133a), CF3CClH2 R-1345mzz 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz), CF3CH= CHCF2H F-347mef 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef CF3CHFCH2CF3 R-123a 1, 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a), CClF2CCl2F In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of greater than 99% HFO-1336mzz(Z) based on the total amount of the composition and one or more additional compounds selected from Group A, wherein Group A includes: 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) , 1,1-dichloroethene (HCO-1130a) , Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz). In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of greater than 99% HFO-1336mzz(Z) based on the total amount of the composition and one or more additional compounds selected from Group A, wherein Group A includes 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC- 346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a, Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-heptafluoro-2-butene (HFO-1327mz), wherein the chlorinated species are present in an amount of greater than 0 to 10,000ppm by weight, 5,000 ppm by weight,, <1000ppm by weight, < 750ppm by weight, <500ppm by weight, preferably less than 100 and most preferably 50 ppm by weight or less. In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of greater than 99 percent HFO-1336mzz(E)and one or more additional compounds selected from Group B, wherein Group B includes at least one of: 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft), 2-Chloro-1,1,1-trifluoroethane (HCFC-133a), 1,14,4,4 -pentafluoro -2-butene (HFO-1345mzz), 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), and 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a). In certain embodiment disclosed herein compositions include one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and c. additional compounds selected from at least one of: i. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount between 0.0001% and 0.05% based on the total amount of the composition, ii. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount between 0.0001% and 0.05% based on the total amount of the composition, iii. E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E) in an amount between 0.0001% and 0.05% based on the total amount of the composition, iv. 1,1-dichloroethene (HCO-1130a) in an amount between 0.0001% and 0.05% based on the total amount of the composition, v. 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) in an amount between 0.0001% and 0.05% based on the total amount of the composition, and vi. 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) in an amount between 0.0001% and 0.05% based on the total amount of the composition, with the proviso that the total amount of additional compounds does not exceed 0.05%, and optionally wherein the chlorinated species are present in an amount of 500 ppm by weight or less, preferably less than 100 and most preferably 50 ppm by weight or less, less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight of moisture, and/or less than 10 vol%, or less than 9 vol% or less than 8 vol% or less than 7 vol% or less than 6 vol%, or less than 5 vol%, or less than 4 vol% , or less than 3 vol%, or less than 1.5 vol% NAG are present and the total amount of the composition is 100 percent. In other embodiments disclosed herein compositions include one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); c. and additional compounds selected from at least one of: i. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount between 0.0001% and 0.05% based on the total amount of the composition, ii. 1,1,1,3,3-Pentafluoropropane (HFC-245fa) in an amount between 0.0001% and 0.05% based on the total amount of the composition, iii. 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in an amount between 0.0001% and 0.05% based on the total amount of the composition, iv. 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) in an amount between 0.0001% and 0.05% based on the total amount of the composition, v. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount between 0.0001% and 0.05% based on the total amount of the composition, vi. 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) in an amount between 0.0001% and 0.05% based on the total amount of the composition, and vii. 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) in an amount between 0.0001% and 0.05% based on the total amount of the composition, viii. 2-chloro-1,1,1-trifluoroethane (HCFC-133a) in an amount between 0.0001% and 0.05% based on the total amount of the composition, ix. 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz) in an amount between 0.0001% and 0.05% based on the total amount of the composition, x. 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef) in an amount between 0.0001% and 0.05% based on the total amount of the composition, and xi. 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) in an amount between 0.0001% and 0.05% based on the total amount of the composition, based on the total amount of the composition, with the proviso that the total amount of additional compounds does not exceed 0.05% and the total amount of the composition is 100 percent. In certain embodiments disclosed herein the composition comprises, consists essentially of, or consists of E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) as the main or major component, and one or more, two or more, three or more, four or more, or five or more of additional compounds/members selected from: a) 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), b) 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), c) 1,1,1,3,3-Pentafluoropropane (HFC-245fa), d) 1,1-dichloroethene (HCO-1130a), e) 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), f) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), g) Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), h) E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), i) 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), j) 2-chloro-1,1,1-trifluoroethane (HCFC-133a), k) 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz), l) 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), m) 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a), and n) 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft), wherein (1) the total amount of additional compounds/members (compounds other than HFO-1336mzz) is selected from between greater than 0 and less than about 0.05, 0.4, 0.3, or 0.02 percent, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 percent, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, and/or (2) the respective amount of an additional compound is independently selected from one of greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 percent, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%. In other embodiments disclosed herein compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); (c) and optionally (1) chlorinated compound are present in an amount of 500 ppm by weight or less, preferably 100ppm by weight or less, and most preferably 50 ppm by weight or less, (2) moisture is present in an amount of less than 500 ppm by weight, <100 ppm by weight, or <20 ppm by weight and/or NAG is present in an amount of less than 10 vol% or less than 5 vol%, or less than 3 vol%, or less than 1.5 vol% of NAG. (d) NAG are present and the total amount of the composition is 100 percent. (e) NAG are present and the total amount of the composition is 100 percent. In other embodiments disclosed herein compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds; (c) and optionally (1) chlorinated compound are present in an amount of 100 ppm by weight or less, preferably less than 500 and most preferably 100 ppm by weight or less, (2) moisture < 500 ppm by weight, <100 ppm by weight, or <20 ppm by weight, and/or NAG of. less than 10 vol% or less than 5 vol%, or less than 3 vol%, or less than 1.5 vol% of NAG. Certain embodiments disclosed herein relate to processes for packaging compositions include one of: (a) at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and one or more Group A compounds, or (b) at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and one or more Group B compounds, to minimize/eliminate the addition and/or presence of moisture and/or NAG compounds, such that moisture content is less than 500 ppm by weight, 100 ppm by weight, or 20 ppm by weight and/or NAG content is less than 10 vol% or less than 5 vol%, or less than 3 vol%, or less than 1.5 vol% of NAG can be present to avoid/reduce/eliminate oxidation and/or hydrolysis initiated by moisture and./or NAG compounds. In certain embodiments disclosed herein relate to compositions comprise, consist essentially of, or consist of greater than 99 percent HFO-1336mzz(E) and one or more additional compounds selected from Group B, wherein Group B includes *2- chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- 1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), 2-chloro-1,1,1- trifluoroethane (HCFC-133a), 1,1,4,4,4 -pentafluoro -2-butene (HFO-1345mzz), 1,1,1,2,4,4,4-heptafluorobutane (HFC-347mef), 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft), wherein the chlorinated species are present in an amount of 1000 ppm by weight or less, preferably less than 500 and most preferably 100 ppm by weight or less. In certain embodiments disclosed herein the composition comprises, consists essentially of, or consists of 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz) as the main or major component, and one or more, two or more, three or more, four or more , or five or more additional compounds/members wherein (1) the total amount of additional compounds/members is selected from between: greater than 0 and less than 0.5 percent, greater than 0 and less than 0.4 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than about 0.1 percent, or greater than 0 and less than about 0.01 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%, and/or (2) the amount of an additional compound/member is selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100% and/or (3) the respective amount of an additional compound/member is independently selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%. In certain embodiments disclosed herein the total amount of compounds other than 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz) is selected from between: greater than 0 and less than 0.05 percent, greater than 0 and less than 0.04 percent, greater than 0 and less than 0.03 percent, greater than 0 and less than 0.02 percent, greater than 0 and less than about 0.01 percent based on the total amount of the composition. One embodiment of the invention disclosed herein relates to using a refrigerant or heat transfer fluid composition comprising the Z-HFO-1336mzz or E-HFO- 1336mzz isomer mixtures with reduced moisture, NCG or chlorinated compounds alone or as blends in refrigeration, air-conditioning, or heat pump apparatus, said method comprising introducing the composition disclosed herein containing reduced levels of impurities into said apparatus having (a) centrifugal compressor; (b) multi-stage centrifugal compressor, or (c) single slab/single pass heat exchanger; wherein said refrigerant or heat transfer composition is employed in said apparatus to result in heating or cooling. In one of the invention relates to using either Z-HFO-1336mzz or E-HFO- 1336mzz alone or as blends in heat transfer systems. Figure 1 illustrates a system 100 having at least a first loop 112 and an optional second loop 116. First loop 112 is shown connected to second loop 116 through heat exchanger 114. A supply 101 of Z-HFO- 1336mzz or E-HFO-1336mzz isomer mixtures respectively containing 99% Z-HFO- 1336mzz or E-HFO-1336mzz with reduced moisture and NCG content and less than 500ppm by weight of chlorinated compounds and filled according to the tank filling procedures described herein, is available for charging loop system 112 or for recharging or replacing existing refrigerants in loop system 112. Loop system 112 generally includes at least one exchanger 110, a pressure regulator 104, at least one exchanger 106, a compressor 108, and charging valve 102 that may be arranged in seriatim as shown. The motive force 126 (compressor, pump, etc.) circulates Z-HFO-1336mzz or E-HFO-1336mzz isomer mixtures respectively containing 99% Z-HFO-1336mzz or E- HFO-1336mzz with reduced moisture and NCG content and less than 500 ppm by weight of chlorinated compounds alone, or in blends thereof to various electrical components, such as batteries, electric motors, computer components in need of thermal management to regulate temperature. Thermal energy from one or more of components 118, 120, 122 and 124 is used to exchange heat with the working fluid and can be used to heat other fluids, e.g., air, water or other fluid. Valving (not shown) is included in all flow lines to assist with the thermal management, as are thermal energy exchangers upstream or downstream of components 118, 120, 122 and 124. Although four components in need of thermal management are illustrated, less components or more components can be included, e.g., 2, 3, 5, 6, 7 or more. Another embodiment of the invention relates to using either Z-HFO-1336mzz or E-HFO-1336mzz alone or as blends in heat transfer systems, including but not limited to refrigeration systems, refrigerators, air conditioning systems, heat pumps, chillers, and mobile air conditioning systems, as for example illustrated in Figure 2. Figure 2 illustrates a system 200 where a source of refrigerant 210 (either Z-HFO-1336mzz or E- HFO-1336mzz alone, isomer blends or as refrigerant blends) having reduced moisture and NCG content, and less than 500 ppm by weight of chlorinated compounds can be connected to a refrigerant circuit 250 of a refrigerant system which includes, generally in seriatim, charging valve 212, expansion device 214, heat exchange 220, compressor 230, heat exchange 240 and flow lines 213, 215, 222, 231 and 241. The refrigerant 210 is charged via line 211 which is in fluid communication with charging valve 212, which when opened and charges refrigerant circuit 250. A container used for storing the foregoing compositions and can be constructed of any suitable material and design that is capable of sealing the compositions therein while maintaining gaseous and liquids phases. Examples of suitable containers comprise pressure resistant containers such as a tank, a filling cylinder, and a secondary filing cylinder. The container can be constructed from any suitable material such as carbon steel, manganese steel, chromium-molybdenum steel, among other low-alloy steels, stainless steel and in some case an aluminum alloy. The container can include a pierce top or valves suitable for dispensing flammable substances. In one embodiment, the inventive composition is employed for servicing an existing A/C or refrigerant system wherein the composition is stored in a container having a threaded seal. An example of a suitable container for the composition that can be used for servicing automobiles is described in U.S. Patent No 10131486 and U.S. Pub No 2015/0108176A1, the disclosures of which are hereby incorporated by reference in their entireties. Another embodiment of the invention relates to using either Z-HFO-1336mzz or E-HFO-1336mzz alone or as blends in direct-to-chip cooling. Claim Embodiments 1. A composition claim embodiment comprising E 1,1,1,4,4,4 hexafluoro-2- butene (HFO-1336mzz(E)) or Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), and one or more additional compounds selected from one of hydrofluorocarbons (HFCs), hydrochlorocarbons (HCCs), hydrofluoroolefins (HFOs), and hydrochlorofluoroolefins (HCFOs), wherein based on the total amount of the composition at least 99 percent HFO-1336mzz(E) and HFO-1336mzz(Z) and at most 500ppm by weight of chlorine containing compounds are present. 2. The composition of claim embodiment 1 comprising one of: (1) greater than 99% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), or (2) greater than 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E). 3. The composition of claim embodiment 1 comprising greater than 99% E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z). 4. The composition of claim embodiment 1 comprising greater than 99% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E) 5. The composition of any of claim embodiments 1-4 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 6. The composition of any of claim embodiments 1-4 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 7. The composition of claim embodiment 5 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 8. The composition of any of claim embodiments 1-7 wherein the additional compounds are selected from at least one of 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), 2-chloro-3,3,3- trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2- chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), ), 1,2- dichloro-1,1,2-trifluoroethane (HCFC-123a),and 3,3,3-trifluoro-2-(trifluoromethyl)-1- propene (HFO-1336ft). 9. The composition any of claim embodiments 1-7 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3- pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), ), 1,2- dichloro-1,1,2-trifluoroethane (HCFC-123a),and 3,3,3-trifluoro-2-(trifluoromethyl)-1- propene (HFO-1336ft). 10. The composition of any of claim embodiments 1-7wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(E)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz). 11. The composition of any of claim embodiments 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 12. The composition of any of claim embodiments 9 or 10 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 13. The composition of any of claim embodiments 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less and non- condensable gases in an amount of 5 vol % or less. 14. The composition of any of claim embodiments 1-10 wherein the amount of chlorine compounds present is selected from 100 ppm by weight or less, or 50 ppm by weight or less. 15. The composition of any of claim embodiments 1-15 wherein a total amount of the additional compounds is selected from one of less than 0.5 percent, less than 0.4 percent, less than 0.3 percent, less than 0.2 percent, or less than 0.1 percent. 16. The composition of any of claim embodiments 1-15 wherein the amount of NCG compounds is selected from one of less than 5 vol%, less than 4 vol%, less than 3 vol%, or less than 1.5 vol%. 17. The composition of any of claims embodiment 1 or 3 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z. 18. The composition of any of claim embodiments 1 or 4 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), and E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)). 19. The composition of claim embodiment 17 wherein the amount of chlorine compounds present is selected from one of 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less. 20. The composition of claim embodiment 17 wherein the amount of chlorine compounds present is selected from one of 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less. 21. A composition claim embodiment which comprise one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and at least one of, wherein “a” or “b” optionally include at least one of: i. chlorinated compounds in an amount between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight; ii. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and iii. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%.. 22. A composition claim embodiment comprises E-1,1,1,4,4,4 hexafluoro-2- butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, and at least one of, c. chlorinated compounds in an amount between 0 and less than 1000 ppm by weight, 500 ppm by weight or 100 ppm by weight; d. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and e. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5, less than 4 ppm by weight, less than 3 ppm by weight, less than 2 ppm by weight and less than 1.5 ppm by weight. 23. The composition of claim embodiment 22 containing less than 500 ppm by weight of chlorine compounds. 24. The composition of any of claim embodiments 22 or 23 containing less than 100 ppm by weight moisture. 25. The composition of any of claim embodiments 22, 23 or 24 containing less than 10 vol% of NAG 26. A pressurized container filled with the composition of any of claim embodiments 1-25. A method for packaging a container of refrigerant embodiment comprising, f. providing a container suitable for holding a composition containing at least 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), g. optionally conditioning the container for receiving the composition, h. sealable connecting a container to a source of the HFO-1336mzz composition, i. filling the container with the HFO-1336mzz composition which comprises, E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: i. additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4- hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2- (trifluoromethyl)-1-propene (HFO-1336ft) or ii. additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro- 1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz); and optionally at least one of: iii. chlorinated compounds in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight, iv. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight, and v. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%. 28. The method of claim embodiment 27 wherein the chlorinated compounds are selected from: j. at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 2- chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z)), or k. at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), and E-2-chloro-1,1,1,4,4,4-hexafluoro-2- butene (HCFO-1326mxz(E)). 29. The method of claim embodiment 28 wherein said conditioning comprises providing an unused container and applying a vacuum to remove any container content. 30. A pressurized container embodiment filled according to the method of any of claim embodiments 27-29. 31. A method claim embodiment comprising storing a composition comprising E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: l. additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) or m. additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC- 356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2- butene (HFO-1327mz); wherein chlorinated compounds is maintained in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight, moisture is maintained in an amount selected from one of between 0 and less than less than 100 or less than 50 ppm by weight, and non-condensable gases (NCG) is maintained in amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%. 32. A composition claim embodiment comprising an E-HFO1336mzz and Z- HFO-1336mzz mixture, at least two additional compounds are selected from HFC, HCC, HFO, and HCFO, of which at least one of is an HCC or HCFO compound present in an amount of less than 500 ppm by weight, and further including reduced moisture in an amount of less than 100 ppm by weight and reduced NCG in an amount of less than 5vol %, and wherein one of E-HFO1336mzz and Z-HFO-1336mzz is present in an amount of at least 99% based on the total amount of the composition. 33. The composition of claim embodiment 31 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3- pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1- chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft). 34. The composition of claim embodiment 31 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO- 1336mzz(E)), 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4- hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro- 1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro- 2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz). 35. The composition of claim embodiments 33 or 34 wherein the total amount of additional compounds is selected from between: greater than 0 and less than 0.5 percent, greater than 0 and less than 0.4 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than about 0.1 percent, or greater than 0 and less than about 0.01 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%, and/or (2) the amount of an additional compound/member is selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100% and/or (3) the respective amount of an additional compound/member is independently selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 percent, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%. 36. The composition of claim embodiment 31 wherein the additional compounds are selected from at least one of: n. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, o. 1,1,1,3,3-pentafluoropropane (HFC-245fa) in an amount greater than 0 and less than about 0.1 percent, p. 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in an amount greater than 0 and less than about 0.05 percent, q. 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) in an amount greater than 0 and less than about 0.05 percent, r. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount greater than 0 and less than about 0.05 percent, s. 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) in an amount greater than 0 and less than about 0.1 percent, and t. 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) in an amount greater than 0 and less than about 0.1 percent. 37. The composition of claim embodiment 31 wherein the additional compounds are selected from at least one of: u. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, v. 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) in an amount greater than 0 and less than about 0.1 percent, w. 1,1-dichloroethene (HCO-1130a) in an amount greater than 0 and less than about 0.05 percent, x. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount greater than 0 and less than about 0.05 percent, y. E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)) in an amount greater than 0 and less than about 0.05 percent, and z. 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) in an amount greater than 0 and less than about 0.1 percent. 38. The composition of claim embodiments 36 or 37 wherein the total amount of chlorinated compounds is less than 0.01 percent. 39. The composition of claim embodiments 36 or 37 wherein the total amount of chlorinated compounds is less than 0.005 percent. 40. The composition of claim embodiment 38 wherein moisture is present in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight. 41. The composition of claim embodiment 39 wherein moisture is present in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight. 42. The composition of claim embodiment 38 wherein non-condensable gases (NCG) are present in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%.. 43. The composition of claim embodiment 39 wherein non-condensable gases (NCG) are present in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%. 44. A pressurized container claim embodiment filed with the compositions of claim embodiment 40. 45. A pressurized container filed with the compositions of claim embodiment 41. 46. A pressurized container filed with the compositions of claim embodiment 42. 47. A pressurized container filed with the compositions of claim embodiment 43. 48. Any of the processes of claim embodiments 27-29 and 31 wherein the compositions contacts an absorbent to reduce moisture to less than one of 500ppm by weight, 100ppm by weight or 20 ppm by weight. 49. Compositions according to any of the preceding claim embodiments wherein the compositions have been pretreated with an absorbent to reduce moisture to less than one of 500ppm by weight, 100ppm by weight or 20 ppm by weight. 50. Compositions according to any of the preceding claim embodiments wherein the compositions have been pretreated to reduce NCGs to less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%. 51. Compositions according to any of the preceding claim embodiments wherein the compositions have been pretreated with an absorbent to reduce moisture to less than one of 500ppm by weight, 100ppm by weight or 20 ppm by weight. 52. Compositions according to any of the preceding claim embodiments wherein the compositions have been treated to reduce the presence of chlorinated HCC and HCFO compounds to levels below one of 500 ppm by weight, 100 ppm by weight or 50 ppm by weight. 53. Compositions according to any of the preceding claim embodiments 1-52 having one of an acidity of < 1 ppm by weight by weight and chloride of < 3 ppm by weight by weight. Although certain aspects, embodiments and principals have been described above, it is understood that this description is made only way of example and not as limitation of the scope of the invention or appended claims. The foregoing various aspects, embodiments and principals can be used alone and in combinations with each other.

Claims

CLAIMS What is claimed is: 1. A composition comprising E 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) or Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or mixtures thereof, and one or more additional compounds selected from one of hydrofluorocarbons (HFCs), hydrochlorocarbons (HCCs), hydrofluoroolefins (HFOs), and hydrochlorofluoroolefins (HCFOs), wherein based on the total amount of the composition at least 99 percent HFO-1336mzz(E) and HFO-1336mzz(Z), and at most 500ppm by weight of chlorine containing compounds are present. 2. The composition of claim 1 comprising one of: (1) greater than 99% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), or (2) greater than 99% Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E). 3. The composition of claim 1 comprising greater than 99% E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and less than about 0.5 percent Z- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z). 4. The composition of claim 1 comprising greater than 99% Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)) and less than about 0.5 percent E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E) 5. The composition of any of claims 3 or 4 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 6. The composition of any of claims 3 or 4 wherein the composition comprises non- condensable gases in an amount of 5 vol % or less. 7. The composition of claim 5 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 8. The composition of claim 1 wherein the additional compounds are selected from at least one of 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), 2-chloro-3,3,3-trifluoropropene (HCFO- 1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2- butene (HCFO-1326mxz(E)), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), and 3,3,3- trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft). 9. The composition of claim 3 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO-1336mzz(Z)), 2-chloro- 1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft). 10. The composition of claim 4 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO-1336mzz(E)), 2-chloro- 1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2- butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz). 11. The composition of any of claims 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less. 12. The composition of any of claims 9 or 10 wherein the composition comprises non-condensable gases in an amount of 5 vol % or less. 13. The composition of any of claims 9 or 10 wherein the composition comprises moisture in an amount of 100 ppm by weight or less and non-condensable gases in an amount of 5 vol % or less. 14. The composition of claim 3 or 4 wherein the amount of chlorine compounds present is selected from one of 1000 ppm by weight or less, 750 ppm by weight or less, 500 ppm by weight or less,100 ppm by weight or less, or 50 ppm by weight or less.
15. The composition of any of claims 3 or 4 wherein a total amount of the additional compounds is selected from one of less than 0.5 percent, less than 0.4 percent, less than 0.3 percent, less than 0.2 percent, or less than 0.1 percent. 16. The composition of any of claims 3 or 4 wherein the amount of NCG compounds is selected from one of less than 3 vol % or less than 1.5 vol %. 17. The composition of claim 3 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC- 346mdf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z). 18. The composition of claim 4 wherein the chlorine containing compounds are selected from at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC- 346mdf), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), and E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)). 19. The composition of claim 17 wherein the amount of chlorine compounds present is selected from one of 1000 ppm by weight or less, 750 ppm by weight or less, 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less. 20. The composition of claim 19 wherein the amount of chlorine compounds present is selected from one of 500 ppm by weight or less, 100 ppm by weight or less, or 50 ppm by weight or less. 21. A composition which comprises one of: a. at least 99 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)), up to 0.5 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), or b. at least 99 percent Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z)), up to 0.5 percent E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)); and at least one of, wherein “a” or “b” optionally include at least one of: i. chlorinated compounds in an amount between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight; ii. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and iii. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol%, less than 3 vol%, or less than 1.5 vol%. 22. A composition comprises E-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition, and at least one of, a. chlorinated compounds in an amount between 0 and less than 1000 ppm by weight, 500 ppm by weight or 100 ppm by weight; b. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and c. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5, less than 4 ppm by weight, less than 3 ppm by weight, less than 2 ppm by weight and less than 1.5 ppm by weight. 23. The composition of claim 22 containing less than 500 ppm by weight of chlorine species. 24. The composition of any of claims 22 or 23 containing less than 100 ppm by weight moisture. 25. The composition of any of claims 22, 23 or 24 containing less than 10 vol % of NAG. 26. A pressurized container filled with the composition of any of claims 1-25.
7. A method for packaging a container of refrigerant comprising, a. providing a container suitable for holding a composition containing at least 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz), b. optionally conditioning the container for receiving the composition, c. sealable connecting a container to a source of the HFO-1336mzz composition, d. filling the container with a HFO-1336mzz composition which comprises, E- 1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO-1336mzz(Z), wherein one of the E-isomer or Z- isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: vi. additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) or vii. additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC- 356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4- hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro- 2-butene (HFO-1327mz); and at least one of: viii. chlorinated compounds in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight ix. moisture in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight , and x. non-condensable gases (NCG) in an amount selected from one of between 0 and less than 5 vol%, less than 4 vol% , less than 3 vol%, or less than 1.5 vol%. 28. The method of claim 27 wherein the chlorinated compounds are selected from: a. at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 2- chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO- 1326mxz(Z)), or b. at least one of 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1- dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), and E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO- 1326mxz(E)). 29. The method of claim 28 wherein said conditioning comprises providing and unused container and applying a vacuum to remove any container content 30. A pressurized container filled according to the method of any of claim 27 or 28. 31. A method comprising storing a composition comprising E-1,1,1,4,4,4 hexafluoro- 2-butene (HFO-1336mzz(E)) and the Z-1,1,1,4,4,4 hexafluoro-2-butene (HFO- 1336mzz(Z), wherein one of the E-isomer or Z-isomer is present in an amount of at most about 0.5 percent and the other isomer is present in an amount of at least 99 percent, based on the total amount of the composition and one of: a. additional compounds selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(Z)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC- 245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2- butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft), or b. additional compounds are selected from at least one of 1,1,1,4,4,4- hexafluorobutene (HFO-1336mzz(E)), 2-chloro-1,1,1,1,4,4,4- hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC- 356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz); wherein chlorinated compounds is maintained in an amount selected from between 0 and less than 500 ppm by weight, 100 ppm by weight or 50 ppm by weight, moisture is maintained in an amount selected from one of between 0 and less than less than 100 or less than 50 ppm by weight, and non-condensable gases (NCG) is maintained in amount selected from one of between 0 and less than 5 vol%, less than 4 vol%, less than 3 vol%, or less than 1.5 vol%. 32. A composition comprising an E-HFO1336mzz and Z-HFO-1336mzz mixture, at least two additional compounds are selected from HFC, HCC, HFO, and HCFO, of which at least one of is an HCC or HCFO compound present in an amount of less than 500 ppm by weight, and further including reduced moisture in an amount of less than 100 ppm by weight and reduced NCG in an amount of less than 5 vol %, and wherein one of E-HFO1336mzz and Z-HFO-1336mzz is present in an amount of at least 99% based on the total amount of the composition. 33. The composition of claim 32 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO-1336mzz(Z)), 2-chloro- 1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 1-chloro-3,3,3- trifluoropropene (HCFO-1233zd), Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z), 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz), and 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft).
34. The composition of claim 32 wherein the additional compounds are selected from at least one of 1,1,1,4,4,4-hexafluorobutene (HFO-1336mzz(E)), 2-chloro- 1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf), 1,1,1,4,4,4-hexafluorobutane (HFC-356mff), 1,1-dichloroethene (HCO-1130a), Z-2-chloro-1,1,1,4,4,4- hexafluoro -2-butene (HCFO-1326mxz(Z), E-2-chloro-1,1,1,4,4,4-hexafluoro-2- butene (HCFO-1326mxz(E)), and 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO- 1327mz). 35. The composition of claims 33 or 34 wherein the total amount of additional compounds is selected from between: greater than 0 and less than 0.5 percent, greater than 0 and less than 0.4 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than 0.2 percent, greater than 0 and less than about 0.1 percent, or greater than 0 and less than about 0.01 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%, and/or (2) the amount of an additional compound/member is selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 mole, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100% and/or (3) the respective amount of an additional compound/member is independently selected from one of greater than 0 and less than about 0.2 percent, greater than 0 and less than about 0.1 percent, greater than 0 and less than about 0.01 percent, greater than 0 and less than about 0.001 based, or greater than 0 and less than about 0.0001 percent based on the total amount of the composition, with the proviso that the total amount of the composition is 100%. 36. The composition of claim 32 wherein the additional compounds are selected from at least one of: a. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, b. 1,1,1,3,3-pentafluoropropane (HFC-245fa) in an amount greater than 0 and less than about 0.1 percent, c. 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in an amount greater than 0 and less than about 0.05 percent, d. 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) in an amount greater than 0 and less than about 0.05 percent, e. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount greater than 0 and less than about 0.05 percent, f. 1,1,1,2,4,4,4-heptafluoro-2-butene (HFO-1327mz) in an amount greater than 0 and less than about 0.1 percent, and g. 3,3,3-trifluoro-2-(trifluoromethyl)-1-propene (HFO-1336ft) in an amount greater than 0 and less than about 0.1 percent. 37. The composition of claim 32 wherein the additional compounds are selected from at least one of: a. 2-chloro-1,1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) in an amount greater than 0 and less than about 0.05 percent, b. 1,1,1,4,4,4-hexafluorobutane (HFC-356mff) in an amount greater than 0 and less than about 0.1 percent, c. 1,1-dichloroethene (HCO-1130a) in an amount greater than 0 and less than about 0.05 percent, d. Z-2-chloro-1,1,1,4,4,4-hexafluoro -2-butene (HCFO-1326mxz(Z) in an amount greater than 0 and less than about 0.05 percent, e. E-2-chloro-1,1,1,4,4,4-hexafluoro-2-butene (HCFO-1326mxz(E)) in an amount greater than 0 and less than about 0.05 percent, and f. 1,1,1,2,4,4,4-hexafluoro-2-butene (HFO-1327mz) in an amount greater than 0 and less than about 0.1 percent. 38. The composition of claims 36 or 37 wherein the total amount of chlorinated compounds is less than 0.01 percent. 39. The composition of claims 36 or 37 wherein the total amount of chlorinated compounds is less than 0.005 percent.
40. The composition of claim 38 wherein moisture is present in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight. 41. The composition of claim 39 wherein moisture is present in an amount selected from one of between 0 and less than 500 ppm by weight, less than 100 or less than 50 ppm by weight. 42. The composition of claim 38 wherein non-condensable gases (NCG) are present in an amount selected from one of less than 5 vol%, less than 4 vol%, less than 3 vol%, less than 1.5 vol%. 43. The composition of claim 39 wherein non-condensable gases (NCG) are present in an amount selected from one of less than 5 vol%, less than 4 vol%, less than 3 vol%, or less than 1.5 vol%. 44. A pressurized container filed with the compositions of claim 40. 45. A pressurized container filed with the compositions of claim 41. 46. A pressurized container filed with the compositions of claim 42. 47. A pressurized container filed with the compositions of claim 43. 48. Any of the processes of claims 27-29 and 31 wherein the compositions contacts an absorbent to reduce moisture to less than one of 500ppm by weight, 100ppm by weight or 20 ppm by weight by weight. 49. A composition according to any of claims 1-25 and 32-43, wherein the compositions have been pretreated with an absorbent to reduce moisture to less than one of 500ppm by weight, 100 ppm by weight or 20 ppm by weight. 50. A composition according to any of claims 3 or 4 wherein the compositions have been pretreated to reduce moisture to reduce NCGs below 5 vol % or 3 vol %. 51. A composition according to any of claims 3 or 4 wherein the compositions have been pretreated with an absorbent to reduce moisture to less than one of 500ppm by weight, 100ppm by weight or 20 ppm by weight. 52. A composition according to any of claims 3 or 4 wherein the compositions have been treated to reduce the presence of chlorinated HCC, HCFC, HCO and HCFO compounds to levels below one of 1000ppm by weight, 750 ppm by weight, 500 ppm by weight, 100 ppm by weight or 50 ppm by weight by weight. 53. A composition according to any of claims 1-4, and 21 having one of an acidity of < 1 ppm by weight by weight and chloride of < 3 ppm by weight by weight. 54. A composition according to any of claims 1-25 comprising E-HFO-1336mzz or Z- HFO-1336mzz, wherein, when the composition comprises E-HFO-1336mzz the amount of Z-HFO-1336mzz is not detectable (zero percent) or when the composition comprises Z-HFO-1336mzz the amount of E-HFO-1336mzz is not detectable (zero percent).
PCT/US2024/038689 2023-07-20 2024-07-19 Hexafluoro-2-butene compositions, storage and handling Pending WO2025019749A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363527882P 2023-07-20 2023-07-20
US63/527,882 2023-07-20

Publications (1)

Publication Number Publication Date
WO2025019749A1 true WO2025019749A1 (en) 2025-01-23

Family

ID=92301212

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/038689 Pending WO2025019749A1 (en) 2023-07-20 2024-07-19 Hexafluoro-2-butene compositions, storage and handling

Country Status (1)

Country Link
WO (1) WO2025019749A1 (en)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150108176A1 (en) 2012-04-12 2015-04-23 E I Du Pont De Nemours And Company Can tap
US10131486B2 (en) 2012-07-27 2018-11-20 The Chemours Company Fc, Llc Can tap
US20190248719A1 (en) 2014-02-07 2019-08-15 The Chemours Company Fc, Llc Integrated process for the production of z-1,1,1,4,4,4-hexafluoro-2-butene
US10479745B2 (en) 2015-08-07 2019-11-19 The Chemours Company Fc, Llc Catalytic isomerization of Z-1,1,1,4,4,4-hexafluoro-2-butene to E-1,1,1,4,4,4-hexafluoro-2-butene
EP3929264A1 (en) * 2015-02-06 2021-12-29 The Chemours Company FC, LLC Compositions comprising e-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof
US20220136748A1 (en) 2019-03-08 2022-05-05 The Chemours Company Fc, Llc. Methods and containers for transporting, transferring, storing and using refrigerants
US20220194882A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same
EP4083164A1 (en) * 2015-02-06 2022-11-02 The Chemours Company FC, LLC Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150108176A1 (en) 2012-04-12 2015-04-23 E I Du Pont De Nemours And Company Can tap
US10131486B2 (en) 2012-07-27 2018-11-20 The Chemours Company Fc, Llc Can tap
US20190248719A1 (en) 2014-02-07 2019-08-15 The Chemours Company Fc, Llc Integrated process for the production of z-1,1,1,4,4,4-hexafluoro-2-butene
EP3929264A1 (en) * 2015-02-06 2021-12-29 The Chemours Company FC, LLC Compositions comprising e-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof
EP4083164A1 (en) * 2015-02-06 2022-11-02 The Chemours Company FC, LLC Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof
US10479745B2 (en) 2015-08-07 2019-11-19 The Chemours Company Fc, Llc Catalytic isomerization of Z-1,1,1,4,4,4-hexafluoro-2-butene to E-1,1,1,4,4,4-hexafluoro-2-butene
US20220136748A1 (en) 2019-03-08 2022-05-05 The Chemours Company Fc, Llc. Methods and containers for transporting, transferring, storing and using refrigerants
US20220194882A1 (en) * 2019-04-05 2022-06-23 The Chemours Company Fc, Llc Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WILHELMSEN SHIPS SERVICES: "Refrigerant Handling Guide", 1 January 2021 (2021-01-01), XP093211801, Retrieved from the Internet <URL:https://www.wilhelmsen.com/globalassets/ships-service/refrigeration-solutions/documents/refrigerant-handling-guide-062020.pdf> *

Similar Documents

Publication Publication Date Title
US11512239B2 (en) Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene
EP3959188B1 (en) Hfo-1234ze, hfo-1225zc and hfo-1234yf containing compositions
EP4400489B1 (en) Compositions comprising 2,3,3,3 tetrafluoropropene and methods for making and using the compositions
US20240336823A1 (en) Refrigerant compositions comprising z-1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof
WO2025019749A1 (en) Hexafluoro-2-butene compositions, storage and handling
WO2025072100A2 (en) A process of coproducing e/z-1,2-difluoroethylene and compositions thereof
WO2025096370A2 (en) Compositions comprising 1,3,3,3-tetrafluoropropene, methods of making same, and uses thereof

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24754808

Country of ref document: EP

Kind code of ref document: A1