[go: up one dir, main page]

WO2025136893A1 - Système de pompe à chaleur à haute température et procédé d'utilisation - Google Patents

Système de pompe à chaleur à haute température et procédé d'utilisation Download PDF

Info

Publication number
WO2025136893A1
WO2025136893A1 PCT/US2024/060441 US2024060441W WO2025136893A1 WO 2025136893 A1 WO2025136893 A1 WO 2025136893A1 US 2024060441 W US2024060441 W US 2024060441W WO 2025136893 A1 WO2025136893 A1 WO 2025136893A1
Authority
WO
WIPO (PCT)
Prior art keywords
hfo
hthp
distillation column
heat
working fluid
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/US2024/060441
Other languages
English (en)
Inventor
Mark Ernest JENKINS
David Matthew Snyder
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 WO2025136893A1 publication Critical patent/WO2025136893A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/007—Energy recuperation; Heat pumps
    • 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
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-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
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials 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
    • C09K5/044—Materials 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
    • C09K5/045—Materials 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/126—Unsaturated fluorinated hydrocarbons

Definitions

  • a method for conducting chemical separations is by continuous fractional distillation which involves the input of heat at a reboiler to create vapors at the bottom of a tower containing surfaces where liquid and vapor contact.
  • the column typically contains one or more condensers where heat is removed causing vapors to condense with some or all the resulting liquid returned to the column as reflux.
  • a large amount of energy is required for the heat input in the form of fossil-fuel derived heat such as steam to the distillation and the amount of heat rejected from the distillation at the condenser are similar and continuous.
  • the rejected heat at the condenser is often removed using a cooling tower or refrigeration machine with little or no recovery of the heat input.
  • the instant invention solves problems associated with conventional systems and methods by providing a HTHP and distillation column integration.
  • the instant invention can reduce steam inputs in chemical manufacturing, recover heat as well as reduce energy consumption.
  • One aspect of the invention relates to recovering waste heat (for example, heat conventionally rejected to cooling tower water) and upgrade the recovered heat as an input at a column reboiler.
  • the process temperature lift or upgrade can be at least 40oC, at least 50oC and, in some cases greater than 80oC and, in turn supply heat, at a temperature of at least 90oC, at least 100oC and, in some cases greater than 200oC.
  • the electrical energy required to operate the heat pump is less than the energy value of the resultant heat (for example, approximately about 0.55 MW electricity is used while 2.4 MW is produced).
  • the integration of the HTHP to a distillation column reduces the energy consumption for heating of this unit operation (for example, by approximately 50%, 65% and in some cases at least 77%).
  • External heat will typically only be used to start-up the distillation column from ambient temperature.
  • the use of an electrically driven HTHP to provide all the energy input provides the capability for this unit operation to be performed with renewable energy while reducing cooling tower load. External heat can be applied to the distillation column to assist with startup or supplement the heat pump.
  • Environmental and safety requirements include zero ozone depletion potential, low GWP, low to no-flammability, and low to no-toxicity.
  • Performance metrics include high efficiency at the proposed conditions, high volumetric capacity, oil solubility, thermal stability with oil, and refrigerant-oil material compatibility.
  • the working fluid should not cause significant issues should a leak into the process occur.
  • the working fluid needs to have balance of operating pressures, efficiency, and volumetric capacity that equate to economical equipment component sizing (compressor, condenser, evaporator), low electrical consumption, and subsequent operating cost.
  • the inventive system and method also solves the undesirable toxicity and flammability dangers caused by ammonia and hydrocarbons.
  • the inventive system and method are free of ammonia and hydrocarbon.
  • One aspect of the invention relates to working fluids comprising at least one fluoroolefin.
  • fluoroolefin is meant any compound containing carbon, fluorine and optionally, hydrogen or oxygen that also contains at least one double bond.
  • fluoroolefins may be linear, branched or cyclic.
  • Fluoroolefins have a variety of utilities in working fluids, which include use as foaming agents, blowing agents, fire extinguishing agents, heat transfer mediums (such as heat transfer fluids and refrigerants for use in refrigeration systems, refrigerators, air-conditioning systems, heat pumps, chillers, and the like), to name a few.
  • the working fluid may comprise fluoroolefins comprising at least one compound with 2 to 12 carbon atoms, in another embodiment, the fluoroolefins comprise compounds with 3 to 10 carbon atoms, and in yet another embodiment the fluoroolefins comprise compounds with 3 to 7 carbon atoms.
  • the fluoroolefins of Formula II have at least about 3 carbon atoms in the molecule. In another embodiment, the fluoroolefins of Formula II have at least about 4 carbon atoms in the molecule. In yet another embodiment, the fluoroolefins of Formula II have at least about 5 carbon atoms in the molecule.
  • Representative cyclic fluoroolefins of Formula II are listed in Table 2. TABLE 2 Cyclic f luoroolefins Structure Chemical name [00 compound of Formula I or formula II, for example, one of the compounds in Table 1 or Table 2, or may comprise a combination of compounds of Formula I or formula II.
  • fluoroolefins may comprise those compounds listed in Table 3.
  • E/Z-HFO-1132 CFH CHF E/Z-1,2-difluoroethylene
  • HFO-1327ye CHF CFCF2CF3 1,2,3,3,4,4,4-heptafluoro-1-butene e e
  • FC-141-10myy CF3CF CFCF2CF3 1,1,1,2,3,4,4,5,5,5-decafluoro-2- t
  • fluoroethers include but are not limited to nonafluoromethoxybutane (C4F9OCH3, any or all possible isomers or mixtures thereof); nonafluoroethoxybutane (C 4 F 9 OC 2 H 5 , any or all possible isomers or mixtures thereof); 2-difluoromethoxy-1,1,1,2-tetrafluoroethane (HFOC-236eaE ⁇ , or CHF 2 OCHFCF 3 ); 1,1-difluoro-2-methoxyethane (HFOC- 272fbE ⁇ , or CH3OCH2CHF2); 1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane (HFOC-347mmzE ⁇ , or CH 2 FOCH(CF 3 ) 2 ); 1,1,1,3,3,3-hexafluoro-2-methoxypropane (HFOC-356mmzE ⁇ , or CH3OCH(CH3)2); 1,1,1,2,2-pentaflu
  • working fluids may further comprise hydrocarbons comprising compounds having only carbon and hydrogen.
  • hydrocarbons comprising compounds having only carbon and hydrogen.
  • Hydrocarbons are commercially available through numerous chemical suppliers. Representative hydrocarbons include but are not limited to propane, n-butane, isobutane, cyclobutane, n-pentane, 2- methylbutane, 2,2-dimethylpropane, cyclopentane, n-hexane, 2-methylpentane, 2,2- dimethylbutane, 2,3-dimethylbutane, 3-methylpentane, cyclohexane, n-heptane, and cycloheptane.
  • the working fluid may comprise hydrocarbons containing heteroatoms, such as dimethylether (DME, CH 3 OCH 3 ).
  • working fluids may further comprise carbon dioxide (CO2), which is commercially available from various sources or may be prepared by methods known in the art.
  • CO2 carbon dioxide
  • working fluids may further comprise ammonia (NH3), which is commercially available from various sources or may be prepared by methods known in the art.
  • the working fluid comprises at least one of the compounds defined in Table 4.
  • Table 4 TABLE 4 C ode Structure Chemical name CH2 ⁇ CH2 Ethylene
  • One aspect of the invention relates to manufacturing HFOs that utilize distillation to separate components obtained during the manufacturing process.
  • One specific embodiment of the invention relates to using the instant invention in an HFO- 1234yf manufacturing process that recovers heat employed for separating, for example, HCFC-244bb from HCFO-1233xf.
  • Another specific embodiment of the invention relates to using the instant invention in the HFO-1234yf manufacturing processes described in U.S. Patent Nos.10214669 and 8147709; and HFO-1234ze manufacturing processes described in U.S.
  • Patent Nos.7189884 and 9255046 the disclosure of the foregoing US Patents is hereby incorporated by reference in their entirety.
  • inventive system and method can be used for making a wide range of compounds including HFOs.
  • Another aspect of the invention relates to any combination of the foregoing aspects and a system for separating at least two compounds comprising a distillation column and an integrated HTHP, wherein the HTHP receives and provides heat to the distillation column.
  • Another aspect of the invention relates to any combination of the foregoing aspects and a system for separating at least two compounds of a mixture, the system comprising a distillation column and an integrated HTHP, wherein the HTHP receives and provides heat to the distillation column and wherein the mixture comprises any of the compounds of Table 1, Table 2, Table 3 and/or Table 4.
  • the present invention relates to a system for separating at least two compounds of a mixture, the system comprising a distillation column and an integrated HTHP, wherein the HTHP receives and provides heat to the distillation column and wherein the mixture includes a.
  • a further aspect of the invention relates to any combination of the foregoing aspects wherein the temperature of the heat provided to the distillation column is greater than the temperature of the heat received by the HTHP.
  • High coefficient of performance (COP) and energy efficiency is achieved by coupling, more particularly integrating, the HTHP(s) with distillation process equipment, and provides flexibility in the choice of refrigerant and equipment design while maintaining high reliability required for a continuous operation.
  • one or more HTHP units associated with process heat exchangers providing cooling and heating, especially in energy intensive unit operations such as reactors, provide additional heat recovery beyond what is achievable with direct process-to-process heat exchange or heat exchange with a common utility.
  • 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).
  • 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 process and/or HTHP equipment disclosed herein should be constructed of materials resistant to the reactants and or product produced.
  • the reactors and components are made of an acid resistant alloy, e.g., nickel, a nickel-based alloys (e.g., Hastelloy ® , available from Special Metals Corp.), nickel-chromium alloys commercially available under the trade name of Inconel ® (hereafter "Inconel ® "), or nickel-copper alloys marketed under the trade name Monel ® .
  • containers, piping, or reactors fabricated from less corrosive- resistant metals such as stainless steel or carbon steel may be lined with a fluoropolymer such as poly(tetrafluoroethylene).
  • the preheaters and vaporizers, heat exchangers, feed, transfer and effluent lines, units associated with mass transfer, contacting vessels (pre-mixers), distillation columns, and valving associated with reactors, heat exchangers, vessels, columns, and units that are used in the processes of various embodiments disclosed herein should be constructed of materials resistant to corrosion.
  • the condenser and evaporator tube side materials of construction would be the corrosion resistant materials such as the nickel-based alloys listed above.
  • the remainder of the refrigerant circuit would be standard carbon steel and stainless steel.
  • FIG. 1 exemplifies an HTHP unit that is to be integrated with a chemical manufacturing process, as shown in for example FIG.3, to provide heating with the highest efficiency possible, while providing the stable and reliable heat input required to operate the process.
  • Integration of the one or more HTHP units with one or more distillation columns reduces energy intensity for heating of the distillation processes. More particularly, integrating one or more HTHP units with one or more distillation columns can reduce total steam consumption for not only the distillation process, but the overall chemical manufacturing process. [0063] For example, in some embodiments, integrating one or more HTHP units with one or more distillation columns can reduce total steam consumption for the manufacturing process by at least about 10%, 20%, 30% or higher or any amount between 10% and 100%, depending on the process and the upper limit of steam reduction, possibly limited by, e.g., design footprint and/or process economics. [0064] The HTHP can be integrated to any suitable distillation column, for example, a column with over 50 theoretical separation stages.
  • the HTHP can employ an independent PLC control package that will be integrated into the process DCS (distributed control system) and safety system.
  • DCS distributed control system
  • the inventive system and method achieve a high coefficient of performance (COP) by coupling the heat pump to the distillation process, and provides flexibility in the choice of refrigerant and equipment design while maintaining high reliability required for a continuous operation.
  • Fig. 1 illustrate an exemplary HTHP unit to be coupled to a distillation column to form the integrated system of the present invention.
  • the HTHP system 100 includes a closed loop 110 filled with a working fluid connected with and providing fluid communication to and from the compressor 120, condenser 130 (process reboiler), economizer 140, evaporator 150 (process condenser), flow valves 160, 170 and 180 associated with a control system (not shown).
  • Closed loop 110 includes flow lines 190 and 192, and valved lines 194, 196 and 198.
  • the loop 110 may be filled with any working fluid, including but not limited to, for example, HFO-1234yf, E/Z-HFO-1234ze, HFO-1233zd, E/Z-HFO-1336mzz, and blends thereof including R-514A, R-515B, R-476A and R-471A, but preferably a refrigerant that has sufficient volumetric capacity to keep compressor and equipment sizes reasonable, exhibits low flammability or is non-flammable, low to no PFAS, an azeotrope/near azeotrope/or single component fluid that is suitable for use in flooded systems, and/or has positive pressures at the desired evaporating condition and reasonable pressures at the desired condensing condition.
  • HFO-1234yf E/Z-HFO-1234ze
  • HFO-1233zd E/Z-HFO-1336mzz
  • blends thereof including R-514A, R-515B, R-476A and R-471A
  • a refrigerant that has sufficient volumetric capacity
  • suction gas enters the suction side of the compressor (P-1) and the refrigerant pressure and temperature are elevated as the working fluid (e.g., refrigerant) travels through the compressor in what could be multiple stages of compression.
  • Point P-4 is depicting a point within the compressor between suction and discharge where working fluid vapor from the economizer is introduced as a side load. The working fluid travels further along the path of compression and is discharged at point P-5 in the form (“state”) of a superheated vapor.
  • the superheated vapor working fluid travels through the discharge piping 190 and into a heat exchanger 130 (process reboiler) where a process fluid (e.g., air, water and the like) is used to condense the superheated vapor working fluid to a liquid.
  • a process fluid e.g., air, water and the like
  • Saturated or subcooled liquid working fluid exits the condenser at point P-6, passes through line 194, valve 170 and point P-7 to an economizer 140, e.g., one or more expansion devices for an expansion process.
  • the working fluid pressure can be dropped in an isenthalpic expansion process. Flash gas from this expansion process is sent via flow line 198 and valve 160 to the compressor (along point P-2 and P-3 to point P- 4).
  • FIG. 2 reflects a typical enthalpy cycle for the HTHP of Fig. 1.
  • suction gas enters the compressor, and the refrigerant pressure and temperature are elevated as the refrigerant travels through the compressor in what could be multiple stages of compression.
  • State 4 is within the compressor between suction and discharge where refrigerant vapor from the economizer is introduced as a side load.
  • the refrigerant travels further along the path of compression and is discharged at state 5 in the form of a superheated vapor.
  • the refrigerant travels through the discharge piping and into a heat exchanger where a process media is used to condense the superheated vapor refrigerant to a liquid.
  • the HTHP unit/system (such as, for example, the HTHP of Figs.1 and 2 as described above) is integrated with a distillation column.
  • Process streams include, but are not limited to, final product stream mixtures, crude product steam mixtures, intermediate product stream mixtures and the like.
  • the stream or mixture to be separated for example process streams generated from the reactor system (not shown), in the form of a liquid is introduced into the distillation column 302 through, e.g., line 301.
  • Overhead 302a is selectively conveyed directly to CTW (cooling tower water) condenser 305 and/or through line 302c to and through the tube side of heat pump chiller 350 to reflux tank 306 along with discharge from CTW condenser 305.
  • Discharge from reflux tank 306 is transferred via pump 304 to either a recycle line or through line 302b back to the distillation column 302.
  • Bottoms 302d from column 302 are selectively transferred by appropriate valving (not shown) through line 302e to the tube side of a HTHP condenser 330 (process reboiler), through line 302f to a reboiler 303.
  • Heat is provided via the reboiler 303 and HTHP condenser 330 at a location below the entry location of the material for separation 301 in distillation column 302.
  • Heat recovered from the overhead of the distillation column 302 is provided through line 302a to the HTHP condenser 330, which upgrades or lifts (increases the temperature) the heat produced thereby, and the generated heat, in turn, is provided to the distillation column 302.
  • the working fluid is circulated through the closed loop system, which includes, in addition to the components specifically discussed in detail above, the shell side of heat pump chiller 350 (process condenser), compressor 340, shell side of condenser 330, valve 370 which controls flow from the HTHP condenser 330 to at least the shell side of the economizer 340, valve 360 which controls flow from at least the tube side of the economizer 340 and to compressor 320.
  • Fig. 4 there is shown a system and process according to an embodiment of the present invention which includes a multiple component HTHP system 400, and more particularly an integrated system 400 which includes multiple HTHP units for coupling to one or more distillation columns (not shown).
  • the multicomponent HTHP system 400 comprises first and second compressors 420, 421; first, second and third condensers 430, 431 and 432 (process reboilers); one or more economizers 440; and first, second and third evaporators 450, 450 and 451 (process condensers). It will be understood by those skilled in the art that the systems are not limited to only two compressors, three condensers, or three evaporators. Instead, more or less of each type of process equipment may be utilized.
  • the inventive system and method can be used in connection with manufacturing any suitable material, in one embodiment, the invention can be employed for reducing heat required for manufacturing a refrigerant, such as HFO-1234yf.
  • a refrigerant such as HFO-1234yf
  • one step for making a refrigerant, such as HFO-1234yf may comprise separating two compounds from each other. The inventive system can reduce the amount of heat required for the separation.
  • the need for and use of fossil-fuel derived steam is reduced, if not completely eliminated. This is because the energy produced is greater than the energy input needed to operate the compressor.
  • the heat recovery may occur by installing a suitable evaporator (such as a flooded evaporator) with the refrigerant on the shell-side and the distillation column overhead vapors condensing in the tube-side of the heat pump evaporator.
  • the integration of the heat pump into the distillation column with a specific refrigerant working fluid is done so that the refrigerant pressure is maintained higher than the process, in order to provide a predictable leak path, and the chosen refrigerant is compatible with the process if a leak were to occur.
  • Example 1 [0074] The system depicted in Fig. 3 is employed for separating HCFC-244bb from HCFO-1233xf during manufacture of HFO-1234yf, thereby reducing the heat required for manufacturing HFO-1234yf.
  • the amount of heat required for the separation of HCFC-244bb from HCFO-1233xf i.e., the energy intensity for heating of the distillation step
  • the HTHP fluid vapor is condensed with one or more the heat exchangers, such as related distillation reboilers as described herein, used to purify HFO-1243zf and HFO-1234yf, and distill HF that is recycled in the process.
  • the recovered heat is transferred with heat exchangers that condense the heat pump fluid while boiling the distillation liquid either directly or with an intermediate working fluid.
  • Example 3 [0076] An integrated HTHP/distillation system is applied where heat is recovered from the process cooling tower water return for the manufacture of HFO-1243zf, HCFO-1233xf, HCFC-244bb, and HFO-1234yf using a large heat exchanger by evaporating the heat pump working fluid.
  • Example 4 [0077] A thermodynamic model using NIST Reference Fluid Thermodynamic and Transport Properties (REFPROP) version 10.0.0.98b for refrigerant properties was used to compare heat pump system performance between heat pump working fluids, in accordance with the integrated system of the present invention.

Landscapes

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

Abstract

L'invention concerne des systèmes et des procédés d'utilisation de pompes à chaleur à haute température pour récupérer de la chaleur d'un processus chimique et, en particulier, faire fonctionner une pompe à chaleur intégrée dans un processus de distillation continue.
PCT/US2024/060441 2023-12-18 2024-12-17 Système de pompe à chaleur à haute température et procédé d'utilisation Pending WO2025136893A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363611456P 2023-12-18 2023-12-18
US63/611,456 2023-12-18

Publications (1)

Publication Number Publication Date
WO2025136893A1 true WO2025136893A1 (fr) 2025-06-26

Family

ID=94384076

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/060441 Pending WO2025136893A1 (fr) 2023-12-18 2024-12-17 Système de pompe à chaleur à haute température et procédé d'utilisation

Country Status (1)

Country Link
WO (1) WO2025136893A1 (fr)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3436021A1 (de) * 1984-03-07 1985-09-12 Linde Ag, 6200 Wiesbaden Verfahren und vorrichtung zur rektifizierung und/oder strippung
KR100499650B1 (ko) * 1996-10-09 2005-09-16 술저 켐테크 악티엔게젤샤프트 증류플랜트
US7189884B2 (en) 2004-04-29 2007-03-13 Honeywell International Processes for synthesis of tetrafluoropropene
US8147709B2 (en) 2008-05-07 2012-04-03 E. I. Du Pont De Nemours And Company Compositions comprising 3,3,3-trifluoropropyne
CN103017411B (zh) * 2012-11-28 2014-11-05 西安交通大学 一种蒸馏用高温热泵系统
US9255046B2 (en) 2003-07-25 2016-02-09 Honeywell International Inc. Manufacturing process for HFO-1234ze
US10214669B2 (en) 2008-05-07 2019-02-26 The Chemours Company Fc, Llc 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
US10287469B2 (en) * 2013-06-04 2019-05-14 The Chemours Company Fc, Llc Use of alkyl perfluoroalkene ethers and mixtures thereof in high temperature heat pumps
JP2023508643A (ja) * 2019-12-03 2023-03-03 ヴェオリア・ウォーター・テクノロジーズ・イタリア・エッセ・ピ・ア・コン・ソシオ・ウニコ 汚水処理機
US20230235930A1 (en) * 2007-05-11 2023-07-27 The Chemours Company Fc, Llc Method for exchanging heat in vapor compression heat transfer systems and vapor compression heat transfer systems comprising intermediate heat exchangers with dual-row evaporators or condensers

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3436021A1 (de) * 1984-03-07 1985-09-12 Linde Ag, 6200 Wiesbaden Verfahren und vorrichtung zur rektifizierung und/oder strippung
KR100499650B1 (ko) * 1996-10-09 2005-09-16 술저 켐테크 악티엔게젤샤프트 증류플랜트
US9255046B2 (en) 2003-07-25 2016-02-09 Honeywell International Inc. Manufacturing process for HFO-1234ze
US7189884B2 (en) 2004-04-29 2007-03-13 Honeywell International Processes for synthesis of tetrafluoropropene
US20230235930A1 (en) * 2007-05-11 2023-07-27 The Chemours Company Fc, Llc Method for exchanging heat in vapor compression heat transfer systems and vapor compression heat transfer systems comprising intermediate heat exchangers with dual-row evaporators or condensers
US8147709B2 (en) 2008-05-07 2012-04-03 E. I. Du Pont De Nemours And Company Compositions comprising 3,3,3-trifluoropropyne
US10214669B2 (en) 2008-05-07 2019-02-26 The Chemours Company Fc, Llc 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
CN103017411B (zh) * 2012-11-28 2014-11-05 西安交通大学 一种蒸馏用高温热泵系统
US10287469B2 (en) * 2013-06-04 2019-05-14 The Chemours Company Fc, Llc Use of alkyl perfluoroalkene ethers and mixtures thereof in high temperature heat pumps
JP2023508643A (ja) * 2019-12-03 2023-03-03 ヴェオリア・ウォーター・テクノロジーズ・イタリア・エッセ・ピ・ア・コン・ソシオ・ウニコ 汚水処理機

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"14th IEA Heat Pump Conference", 15 May 2023, article "Integration of High-Temperature Heat Pumps in Swiss Industrial Processes (HTHP-CH"
JIANG JIATONG ET AL: "A review and perspective on industry high-temperature heat pumps", RENEWABLE AND SUSTAINABLE ENERGY REVIEWS, ELSEVIERS SCIENCE, NEW YORK, NY, US, vol. 161, 10 March 2022 (2022-03-10), XP087030061, ISSN: 1364-0321, [retrieved on 20220310], DOI: 10.1016/J.RSER.2022.112106 *

Similar Documents

Publication Publication Date Title
US12287129B2 (en) Method for exchanging heat in vapor compression heat transfer systems and vapor compression heat transfer systems comprising intermediate heat exchangers with dual-row evaporators or condensers
CN102686957B (zh) 具有氟烯烃制冷剂的阶式制冷系统
US10035938B2 (en) Heat transfer fluid replacing R-134a
JP5936604B2 (ja) 熱伝達流体と、その向流熱交換器での使用
US20110088418A1 (en) Compositions comprising ionic liquids and fluoroolefins and use thereof in absorption cycle systems
US20150152306A1 (en) Heat transfer fluid replacing r-410a
WO2025136893A1 (fr) Système de pompe à chaleur à haute température et procédé d'utilisation
KR20210143272A (ko) 트리플루오로에틸렌을 포함하는 공비 또는 유사 공비 조성물
US20250289987A1 (en) Air conditioner
HK1150366A (en) Method for exchanging heat in a vapor compression heat transfer system and a vapor compression heat transfer system comprising an intermediate heat exchanger with a dual-row evaporator or condenser
HK1158676A (en) Compositions comprising ionic liquids and fluoroolefins and use thereof in absorption cycle systems

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: 24846797

Country of ref document: EP

Kind code of ref document: A1