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WO2025174926A1 - Purification de e-1,1,1,4,4,4-hexafluoro-2-butène par adsorption - Google Patents

Purification de e-1,1,1,4,4,4-hexafluoro-2-butène par adsorption

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Publication number
WO2025174926A1
WO2025174926A1 PCT/US2025/015666 US2025015666W WO2025174926A1 WO 2025174926 A1 WO2025174926 A1 WO 2025174926A1 US 2025015666 W US2025015666 W US 2025015666W WO 2025174926 A1 WO2025174926 A1 WO 2025174926A1
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WO
WIPO (PCT)
Prior art keywords
butene
hexafluoro
chloro
adsorbent
1336mzz
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Pending
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PCT/US2025/015666
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English (en)
Inventor
Xuehui Sun
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Chemours Co FC LLC
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Chemours Co FC LLC
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Publication of WO2025174926A1 publication Critical patent/WO2025174926A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids

Definitions

  • This invention relates to methods for removing impurities in fluorinated organic compounds, especially methods for removing unsaturated impurities included in fluorinated olefins, and even more particularly to methods for removing impurities included in E-1,1,1,4,4,4-hexafluoro-2-butene.
  • HFOs hydrofluoroolefins
  • tetrafluoropropenes including 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), and 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze)
  • hexafluorobutenes such as Z- and E-1,1,1,4,4,4-hexafluoro-2- butene (Z- and E-HFO-1336mzz, respectively
  • refrigerants heat transfer media
  • propellants foaming agents, blowing agents, gaseous dielectrics, sterilant carriers, polymerization media, particulate removal fluids, carrier fluids, buffing abrasive agents, displacement drying agents and power cycle working fluids.
  • the removing agent is an adsorbent and the adsorbent is alumina.
  • the alumina is loaded with sodium oxide.
  • the adsorbent is activated carbon.
  • washing with water is found to remove particular impurities from E-1336mzz.
  • the alumina can be an alumina loaded with alkali metal oxide, such as sodium oxide (Na2O).
  • the mixture to be treated typically comprises at least 98% or at least 99% or at least 99.5% or at least 99.8% or at least 99.9% of E-1336mzz, based on the total weight of said mixture.
  • the process of contacting may be performed by simply combining the mixture comprising E-1336mzz and at least one impurity with a removing agent in any suitable vessel at any suitable temperature and pressure. Conveniently the contacting step may be performed at room temperature in a suitable vessel such as a cylinder. It should be recognized that the boiling point of E-1336mzz is about 7.4°C.
  • the adsorbent comprises molecular sieves. In one embodiment, the adsorbent comprises alumina. In one embodiment, the adsorbent comprises high surface nickel. In one embodiment, the adsorbent comprises silica gel. In one embodiment, the adsorbent comprises activated carbon. [0022] In one embodiment, the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1-difluoroethylene.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and 1,1-dichloro-1,4,4,4-tetrafluoro-2-butene.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and E-1,1,1,2,4,4,4-heptafluorobut-2-ene.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4-hexafluoro-2-butene.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3-trifluoropropene.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1,1-trifluoroethane.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves is 13X, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2- butene and 2-chloro-1,1,1-trifluoroethane.
  • the adsorbent comprises molecular sieves, wherein the molecular sieves are chosen from 4A, 5A and 13X, and the mixture comprises E- 1,1,1,4,4,4-hexafluoro-2-butene and 2,2-dichloro-1,1,1-trifluoroethane.
  • the molecular sieves comprise molecular sieve 4A.
  • the molecular sieves comprise molecular sieve 5A. In one embodiment the molecular sieves comprise molecular sieve 13X.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 3,3,3-trifluoro-2-(trifluoromethyl)-1- propene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and vinyl chloride.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3-trifluoropropene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 1,1,3,3,3-pentafluoro-2-methyl-1- propene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1-difluoroethylene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 1,1-dichloro-1,4,4,4-tetrafluoro-2- butene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and E-1,1,1,2,4,4,4-heptafluorobut-2- ene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4-hexafluoro-2-butene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3-trifluoropropene.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1,1-trifluoroethane.
  • the adsorbent comprises alumina, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2,2-dichloro-1,1,1-trifluoroethane.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 3,3,3- trifluoro-2-(trifluoromethyl)-1-propene (HFIB).
  • HFIB 3,3,3- trifluoro-2-(trifluoromethyl)-1-propene
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and vinyl chloride.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro- 3,3,3-trifluoropropene.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 1,1,3,3,3- pentafluoro-2-methyl-1-propene.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and E- 1,1,1,2,4,4,4-heptafluorobut-2-ene.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and Z- 1,1,1,4,4,4-hexafluoro-2-butene.
  • the adsorbent comprises alumina loaded with sodium oxide, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2,2- dichloro-1,1,1-trifluoroethane.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 3,3,3-trifluoro-2- (trifluoromethyl)-1-propene (HFIB).
  • HFIB trifluoromethyl-1-propene
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and vinyl chloride.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 1,1-dichloro-1,4,4,4- tetrafluoro-2-butene.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and E-1,1,1,2,4,4,4- heptafluorobut-2-ene.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4- hexafluoro-2-butene.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3- trifluoropropene.
  • the adsorbent comprises high surface area nickel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1,1- trifluoroethane.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3-trifluoropropene.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 1,1,3,3,3-pentafluoro-2-methyl-1- propene.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1-difluoroethylene.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and Z-1,1,1,4,4,4-hexafluoro-2-butene.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-3,3,3-trifluoropropene.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2-chloro-1,1,1-trifluoroethane.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2,2-dichloro-1,1,1-trifluoroethane.
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 3,3,3-trifluoro-2-(trifluoromethyl)-1- propene .
  • the adsorbent comprises silica gel, and the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and vinyl chloride.
  • the adsorbent comprises silica gel
  • the mixture comprises E-1,1,1,4,4,4-hexafluoro-2-butene and 2,2-dichloro-1,1,1-trifluoroethane.
  • the amount of removing agent can be any amount suitable to achieve the desired reduction in the impurities present in the mixture comprising E-1336mzz.
  • the ratio of the mixture to the removing agent is typically in the range of 0.01:1 to 2:1, preferably 0.05:1 to 1:1, more preferably 0.1:1 to 0.8:1.
  • compositions comprising at least 99% of E-1336mzz and less than 0.00005% (0.1 ppm) of VCM. In another embodiment of this invention is provided a composition comprising at least 99.8% of E-1336mzz and less than 0.00001% (0.1 ppm) of VCM. In another embodiment of this invention is provided a composition comprising at least 99.9% of E-1336mzz and less than 0.00001% (0.1 ppm) of VCM. [0105] In another embodiment of this invention is provided a composition comprising at least 99% of E-1336mzz and less than 0.02% (200 ppm) of 133a.
  • the process provides a product comprising E-1336mzz and less than 0.001% or less than 0.0005% or less than 0.0001 or less than 0.00005% or less than 0.00001% or non-detectable concentration (less than 0.1 ppm) of VCM.
  • Materials Molecular sieves (13X, 4A and 5A), silica gel, and alumina are commercially available, from multiple suppliers. HF-200XP alumina is available from BASF. E474 NI is a high surface area nickel, available from BASF. Carbon Example 1. Reduction of HFIB concentration in E-1336mzz.
  • HFIB HFIB Removing Agent h ours concentration removed /E1336 weight ratio 2 .5 0.2257% 0.0028% Mol sieve 13X 2 3 0.2148% 0.0137% 10/50 M ol Sieve 4A 1 0.2185% 0.0100% 10/50 1.6 0.2133% 0.0152% Mol Sieve 5A 7 2 0.2099% 0.0186% 10/50 5 0.2038% 0.0247% HF200XP alumina 2 4 0.1960% 0.0325% 10/50 2 .8 0.1903% 0.0382% E474 Ni 7 2 0.1689% 0.0596% 10/50 1 0.2029% 0.0256% Silica Gel 6 7 0.2014% 0.0271% 10/50 1 .5 0.2187% 0.0098% Water 7 0 0.21% 0.0181% 200/30 [0110] As can be seen from Table 2a, all removing agents were effective at reducing the concentration of HFIB as
  • Example 1b HFIB reduction in E-1336mzz using Activated Carbon (removing agent)
  • Samples of E-1336mzz containing 0.1566% of HFIB were mixed with the commercially available activated carbons for use as removing agent (adsorbent) as recited in Table 2b, at the recited weight ratios in a carbon steel cylinder which was pre-loaded with a activated carbon. The mixtures were shaken well then maintained at room temperature for the times recited in Table 2b.
  • the liquid phase of E- 1336mzz in the test cylinder was analyzed by GC-MS-FID. The results are presented in GC-FID area%.
  • Adsorbent Molecular Sieves 13X, treatment for 2 hours, 24 hours, 7 days C omponent Starting material 2 hours 24 hours 7 days E-1327mzy 0.00420% 0.00420% 0.00420% 0.00400% E-1336mzz 99.97490% 99.97490% 99.98360% 99.98310% 1345cm 0.00040% 0.00040% 0.00020% 0.00020% Z-1336mzz 0.00280% 0.00280% 0.00032% 0.00018% VCM 0.00092% 0.00092% 0.00040% 0.00031% 1233xf 0.01130% 0.01130% 0.00780% 0.00740% [0115] As can be seen from Tables 3a, 3b, and 3c, the GC results show VCM was efficiently reduced by molecular sieves 4A, 5A and 13X when used as adsorbents / removing agents.
  • Molecular sieve 13X also reduced Z-1336mzz and 1233xf from E- 1336mzz.
  • Example 3 HCFC-133a removal from E-1336mzz by adsorption using molecular sieves [0116] In this Example, it was found that certain adsorbents can be used as removing agents to selectively adsorb HCFC-133a from E-1336mzz to reduce the HCFC-133a concentration. [0117] For each molecular sieve adsorbent, 50 g of E-1336mzz containing HCFC- 133a and other impurities was mixed with 5 g molecular sieves in a dried cylinder, the mixture was shaken well then maintained at room temperature.
  • Adsorbent Molecular Sieves 13X, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0044% 0.0045% E-1336mzz 99.8513% 99.9470% 99.9601% 356mff 0.0009% 0.0007% 0.0005% 1122 0.0005% 0.0004% 0.0003% 1345cm 0.0066% 0.0042% 0.0038% 1334mzz 0.0003% 0.0004% Z-1336mzz 0.0796% 0.0205% 0.0094% 133a 0.0218% 0.0091% 0.0079% VCM 0.0002% 0.0004% 0.0003% 1233xf 0.0104% 0.0080% 0.0081% 1233zd 0.0036% 0.0034% 0.0034% 1112 0.0005% 0.0005% 0.0005% 123 0.0012% 0.0007% 0.0008% Table 4b.
  • Adsorbent Molecular Sieves 5A, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0045% 0.0044% E-1336mzz 99.8513% 99.8586% 99.8667% 356mff 0.0009% 0.0012% 0.0012% 1122 0.0005% ND ND 1345cm 0.0066% 0.0077% 0.0068% 1334mzz 0.0003% ND ND Z-1336mzz 0.0796% 0.0893% 0.0865% 133a 0.0218% 0.0222% 0.0187% VCM 0.0002% ND ND 1233xf 0.0104% 0.0111% 0.0109% 1233zd 0.0036% 0.0035% 0.0030% 1112 0.0005% 0.0006% 0.0005% 123 0.0012% 0.0014% 0.0012% Table 4c.
  • Adsorbent Molecular Sieves 4A, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0042% 0.0045% E-1336mzz 99.8513% 99.8694% 99.8618% 356mff 0.0009% 0.0013% 0.0013% 1122 0.0005% 0.0005% 0.0005% 1345cm 0.0066% 0.0073% 0.0077% 1334mzz 0.0003% 0.0005% 0.0004% Z-1336mzz 0.0796% 0.0812% 0.0854% 133a 0.0218% 0.0200% 0.0218% VCM 0.0002% 0.0003% 0.0001% 1233xf 0.0104% 0.0102% 0.0108% 1233zd 0.0036% 0.0035% 0.0037% 1112 0.0005% 0.0005% 0.0005% 123 0.0012% 0.0012% 0.0013% [0118] As can be seen from Table 4a, the GC results showed molecular sieve 13X can be used as a removing agent to efficiently
  • molecular sieve 5A also reduced VCM, 1334mzz and 1122 from E-1336mzz when used as an adsorbent (removing agent).
  • 13X molecular sieves are preferred over 4A and 5A sieves to reduce concentrations of 133a.
  • Example 4. Purification of E-1336mzz by adsorption using Alumina with and without Na2O [0120] Several types of alumina were used as removing agents (adsorbents). For each alumina adsorbent, 50 g of E-1336mzz containing impurities was mixed with 5 g alumina adsorbent in a dried cylinder. The mixture was shaken well then maintained at room temperature.
  • Adsorbent JM PuraspecTM 6259, Na2O/Al2O3, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0042% 0.0043% E-1336mzz 99.8513% 99.9480% 99.9635% 356mff 0.0009% 0.0010% 0.0005% 1122 0.0005% 0.0004% 0.0004% 1345cm 0.0066% 0.0038% 0.0036% 1334mzz 0.0003% 0.0004% 0.0004% Z-1336mzz 0.0796% 0.0148% 0.0077% 133a 0.0218% 0.0079% 0.0070% VCM 0.0002% 0.0003% 0.0002% 1233xf 0.0104% 0.0076% 0.0077% 1233zd 0.0036% 0.0033% 0.0033% 1112 0.0005% 0.0005% 0.0006% 123 0.0012% 0.0007% 0.0007% Table 5b.
  • Adsorbent BASF CL 750, Na2O/Al2O3, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0039% 0.0027% E-1336mzz 99.8513% 99.8814% 99.8717% 356mff 0.0009% 0.0011% 0.0012% 1122 0.0005% 0.0005% 0.0005% 0.0005% 1345cm 0.0066% 0.0069% 0.0074% 1334mzz 0.0003% 0.0004% 0.0005% Z-1336mzz 0.0796% 0.0744% 0.0792% 133a 0.0218% 0.0162% 0.0204% VCM 0.0002% 0.0004% 0.0004% 1233xf 0.0104% 0.0097% 0.0105% 1233zd 0.0036% 0.0034% 0.0036% 1112 0.0005% 0.0002% 123 0.0012% 0.0011% 0.0010% Table 5c.
  • Adsorbent JM PuraspecTM 3110 Na2O/Al2O3, treatment for 24.5 hours C omponent Starting material 24.5 hours E-1327mzy 0.0042% 0.0024% E-1336mzz 99.8513% 99.8637% 356mff 0.0009% 0.0012% 1122 0.0005% 0.0004% 1345cm 0.0066% 0.0075% 1334mzz 0.0003% 0.0005% Z-1336mzz 0.0796% 0.0865% 133a 0.0218% 0.0210% VCM 0.0002% 0.0003% 1233xf 0.0104% 0.0109% 1233zd 0.0036% 0.0038% 1112 0.0005% 0.0004% 123 0.0012% 0.0013% Table 5d.
  • Adsorbent BASF CL 850 Al2O3, treatment for 2 hours, 24 hours C omponent Starting material 2 hours 24 hours E-1327mzy 0.0042% 0.0051% 0.0041% E-1336mzz 99.8513% 99.9516% 99.9774% 356mff 0.0009% 0.0006% 0.0001% 1122 0.0005% 0.0005% 0.0003% 1345cm 0.0066% 0.0030% 0.0011% 1334mzz 0.0003% 0.0007% 0.0004% Z-1336mzz 0.0796% 0.0155% 0.0023% 133a 0.0218% 0.0087% 0.0038% VCM 0.0002% 0.0004% 0.0002% 1233xf 0.0104% 0.0083% 0.0062% 1233zd 0.0036% 0.0040% 0.0032% 1112 0.0005% 0.0010% 0.0005% 123 0.0012% 0.0006% 0.0004% [0121] Note to Tables 5a-5d: Z-1327mzy was present as shoulder peak to the right side of E-1336mzz.

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Abstract

L'invention concerne un procédé pour éliminer au moins une impureté d'un mélange comprenant du E-1,1,1,4,4,4-hexafluoro-2-butène et ladite impureté, le procédé comprenant : la mise en contact du ou des agents d'élimination, l'agent d'élimination étant de l'eau ou comprenant au moins un adsorbant pour réduire la concentration de la ou des impuretés.
PCT/US2025/015666 2024-02-16 2025-02-13 Purification de e-1,1,1,4,4,4-hexafluoro-2-butène par adsorption Pending WO2025174926A1 (fr)

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Publication number Priority date Publication date Assignee Title
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
US10611709B2 (en) 2017-09-11 2020-04-07 The Chemours Company Fc, Llc Liquid phase process for preparing (E)-1,1,1,4,4,4-hexafluorobut-2-ene
US20210188743A1 (en) 2017-12-04 2021-06-24 The Chemours Company Fc, Llc Process and Intermediates for Preparing (E)-1,1,1,4,4,4-hexafluorobut-2-ene
AU2019294496A1 (en) * 2018-06-28 2020-11-12 The Chemours Company Fc, Llc Refrigerant blends having low global warming potential
WO2020206335A1 (fr) 2019-04-05 2020-10-08 The Chemours Company Fc, Llc Procédés de production de z-1,1,1,4,4,4-hexafluorobut-2-ène et intermédiaires pour leur production
WO2020206247A1 (fr) 2019-04-05 2020-10-08 The Chemours Company Fc, Llc Procédé de production de 1,1,1,4,4,4-hexafluorobut-2-ène
WO2023205374A1 (fr) * 2022-04-22 2023-10-26 The Chemours Company Fc, Llc Compositions comprenant du tétrafluoropropène et de l'hexafluorobutène
WO2023205375A1 (fr) * 2022-04-22 2023-10-26 The Chemours Company Fc, Llc Compositions de fluorobutène comprenant du e-1,1,1,4,4,4-hexafluoro-2-butène et leurs utilisations
KR20230159298A (ko) * 2022-05-13 2023-11-21 (주)후성 1,1,1,4,4,4-헥사플루오로-2-부텐의 제조방법

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