US20120159982A1 - Ternary compositions for low-capacity refrigeration - Google Patents

Ternary compositions for low-capacity refrigeration Download PDF

Info

Publication number
US20120159982A1
US20120159982A1 US13/393,640 US201013393640A US2012159982A1 US 20120159982 A1 US20120159982 A1 US 20120159982A1 US 201013393640 A US201013393640 A US 201013393640A US 2012159982 A1 US2012159982 A1 US 2012159982A1
Authority
US
United States
Prior art keywords
hfc
weight
tetrafluoropropene
composition
heat
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.)
Abandoned
Application number
US13/393,640
Other languages
English (en)
Inventor
Wissam Rached
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.)
Arkema France SA
Original Assignee
Arkema France SA
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 Arkema France SA filed Critical Arkema France SA
Assigned to ARKEMA FRANCE reassignment ARKEMA FRANCE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RACHED, WISSAM
Publication of US20120159982A1 publication Critical patent/US20120159982A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
    • C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • 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
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
    • F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
    • F25B13/00—Compression machines, plants or systems, with reversible cycle
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2207/00—Foams characterised by their intended use
    • C08J2207/04—Aerosol, e.g. polyurethane foam spray
    • 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
    • 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
    • C09K2205/22—All components of a mixture being fluoro compounds
    • 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
    • C09K2205/40—Replacement mixtures

Definitions

  • the present invention relates to compositions containing 2,3,3,3-tetrafluoropropene and uses thereof as heat-transfer fluids, blowing agents, solvents and aerosols.
  • HFCs hydrofluorocarbons
  • HFC-134a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a) refrigerant which is less harmful to the ozone layer.
  • CFC-12 chlorofluorocarbon
  • HFC-134a hydrofluorocarbon (1,1,1,2-tetrafluoroethane: HFC-134a) refrigerant which is less harmful to the ozone layer.
  • the contribution to the greenhouse effect of a fluid is quantified by a criterion, the GWP (global warming potential) which indexes the warming potential by taking a reference value of 1 for carbon dioxide.
  • carbon dioxide Since carbon dioxide is non-toxic and non-flammable and has a very low GWP, it has been proposed as a refrigerant in air-conditioning systems as a replacement for HFC-134a. However, the use of carbon dioxide has several drawbacks, in particular linked to the very high pressure at which it is used as a refrigerant in the existing apparatuses and technologies.
  • compositions comprising at least one fluoroalkene having three or four carbon atoms, in particular pentafluoropropene and tetrafluoropropene, preferably having a GWP at most of 150, as heat-transfer fluids.
  • Document WO 2005/105947 teaches the addition to tetrafluoropropene, preferably 1,3,3,3-tetrafluoropropene, of a blowing coagent such as difluoromethane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoropropane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water and carbon dioxide.
  • a blowing coagent such as difluoromethane, pentafluoroethane, tetrafluoroethane, difluoroethane, heptafluoropropane, hexafluoropropane, pentafluoropropane, pentafluorobutane, water and carbon dioxide.
  • Quaternary mixtures comprising 1,1,1,2,3-pentafluoro-propene (HFO-1225ye) in combination with difluoromethane, 2,3,3,3-tetrafluoropropene and HFC-134a were disclosed in this document. However, 1,1,1,2,3-pentafluoropropene is toxic.
  • CF 3 I Quaternary mixtures comprising 2,3,3,3-tetrafluoropropene in combination with iodotrifluoromethane (CF 3 I), HFC-32 and HFC-134a have also been disclosed in document WO 2006/094303.
  • CF 3 I has a non-zero ODP and poses stability and corrosion problems.
  • compositions used as heat-transfer fluid in the present invention have values for the temperatures at the compressor outlet, and pressure levels, equivalent to the values given by HFC-134a.
  • the compression ratios are lower. These compositions can replace HFC-134a without changing compressor technology.
  • compositions used as a heat-transfer fluid in the present invention have volume capacities which are greater than the volume capacity of HFC-134a (between 116 and 133%). By virtue of these properties, these compositions can use smaller compressors and have the same heating or cooling capacity.
  • compositions according to the present invention are characterized in that they essentially contain from 10 to 90% by weight of 2,3,3,3-tetrafluoropropene, from 5 to 80% by weight of HFC-134a and from 5 to 10% by weight of HFC-32.
  • compositions essentially contain from 10 to 45% by weight of 2,3,3,3-tetrafluoropropene, from 50 to 80% by weight of HFC-134a and from 5 to 10% by weight of HFC-32.
  • compositions according to the present invention can be used as heat-transfer fluids, preferably in compression systems and advantageously with exchangers operating in counterflow mode or in cross-flow mode with counterflow tendency. They are particularly suitable for systems of low-capacity refrigeration per unit volume swept by the compressor.
  • heat-transfer fluids In compression systems, the heat exchange between the refrigerant and the heat sources takes place by means of heat-transfer fluids. These heat-transfer fluids are in the gaseous state (the air in air-conditioning and direct expansion refrigeration), liquid state (the water in domestic heat pumps, glycolated water) or two-phase state.
  • compositions according to the present invention are advantageously used in stationary air conditioning and heat pumps, preferably as a replacement for HFC-134a.
  • compositions according to the present invention can be stabilized.
  • the stabilizer preferably represents at most 5% by weight relative to the total composition.
  • nitromethane ascorbic acid, terephthalic acid, azoles such as tolutriazole or benzotriazole, phenolic compounds such as tocopherol, hydroquinone, t-butyl hydroquinone or 2,6-di-tert-butyl-4-methylphenol, epoxides (alkyl, optionally fluorinated or perfluorinated, or alkenyl or aromatic) such as n-butyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether or butylphenyl glycidyl ether, phosphites, phosphates, phosphonates, thiols and lactones.
  • epoxides alkyl, optionally fluorinated or perfluorinated, or alkenyl or aromatic
  • compositions according to the present invention as a heat-transfer agent, can be employed in the presence of lubricants such as mineral oil, alkylbenzene, polyalkylene glycol and polyvinyl ether.
  • compositions according to the present invention can also be used as blowing agents, aerosols and solvents.
  • the RK-Soave equation is used for calculating the densities, enthalpies, entropies and liquid/vapor equilibrium data of the mixtures.
  • the use of this equation requires knowledge of the properties of the pure bodies used in the mixtures in question and also the interaction coefficients for each binary mixture.
  • HFC-32, HFC-134a
  • the data of the temperature-pressure curve for HFO-1234yf are measured by the static method.
  • the critical temperature and the critical pressure are measured using a C80 calorimeter sold by Setaram.
  • the densities, at saturation as a function of temperature, are measured using the vibrating tube densitometer technology developed by the laboratories of the autoimmune des Mines of Paris.
  • the RK-Soave equation uses binary interaction coefficients to represent the behavior of the products in mixtures.
  • the coefficients are calculated as a function of the experimental liquid/vapor equilibrium data.
  • the technique used for the liquid/vapor equilibrium measurements is the static-cell analytical method.
  • the equilibrium cell comprises a sapphire tube and is equipped with two electromagnetic ROLSITM samplers. It is immersed in a cryothermostat bath (HUBER HS40). A magnetic stirrer with a field drive rotating at varying speed is used to accelerate reaching the equilibria.
  • the analysis of the samples is carried out by gas chromatography (HP5890 series II) using a katharometer (TCD).
  • the liquid/vapor equilibrium data for the binary mixture HFC-134a/HFC-32 are available from Refprop. Two isotherms ( ⁇ 20° C. and 20° C.) and one isobar (30 bar) are used to calculate the interaction coefficients for this binary mixture.
  • a compression system equipped with a counterflow condenser and evaporator, with a screw compressor and with an expansion valve is considered.
  • the system operates with 15° C. of overheat and 5° C. of undercooling.
  • the minimum temperature difference between the secondary fluid and the refrigerant is considered to be about 5° C.
  • the isentropic efficiency of the compressors depends on the compression ratio. This efficiency is calculated according to the following equation:
  • ⁇ isen a - b ⁇ ( ⁇ - c ) 2 - d ⁇ - e . ( 1 )
  • the % CAP is the percentage of the ratio of the volumetric capacity supplied by each product over the capacity of HFC-134a.
  • the coefficient of performance is defined as being the useful power supplied by the system over the power provided or consumed by the system.
  • the Lorenz coefficient of performance (COPLorenz) is a reference coefficient of performance. It is a function of temperatures and is used for comparing the COPs of various fluids.
  • the Lorenz coefficient of performance is defined as follows:
  • T average condenser T inlet condenser ⁇ T outlet condenser (2)
  • T average evaporator T outlet evaporator ⁇ T inlet evaporator (3)
  • the Lorenz COP in the case of air-conditioning and refrigeration is:
  • the Lorenz COP in the case of heating is:
  • the coefficient of performance of the Lorenz cycle is calculated as a function of the corresponding temperatures.
  • the %COP/COPLorenz is the ratio of the COP of the system relative to the COP of the corresponding Lorenz cycle.
  • the compression system In heating mode, the compression system operates between a temperature for inlet of the refrigerant into the evaporator of ⁇ 5° C. and a temperature for inlet of the refrigerant into the condenser of 50° C.
  • the system supplies heat at 45° C.
  • compositions according to the invention under the heating mode operating conditions are given in table 1.
  • values of the constituents (HFO-1234yf, HFC-32, HFC-134a) for each composition are given as percentage by weight.
  • the compression system In cooling mode, the compression system operates between a temperature for inlet of the refrigerant into the evaporator of ⁇ 5° C. and a temperature for inlet of the refrigerant into the condenser of 50° C.
  • the system supplies refrigeration at 0° C.
  • compositions according to the invention under the cooling mode operating conditions are given in table 2.
  • values of the constituents (HFO-1234yf, HFC-32, HFC-134a) for each composition are given as percentage by weight.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US13/393,640 2009-09-11 2010-08-20 Ternary compositions for low-capacity refrigeration Abandoned US20120159982A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0956249A FR2950071B1 (fr) 2009-09-11 2009-09-11 Compositions ternaires pour refrigeration basse capacite
FR0956249 2009-09-11
PCT/FR2010/051747 WO2011030032A1 (fr) 2009-09-11 2010-08-20 Compositions ternaires pour refrigeration basse capacite

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2010/051747 A-371-Of-International WO2011030032A1 (fr) 2009-09-11 2010-08-20 Compositions ternaires pour refrigeration basse capacite

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/335,281 Continuation US9175203B2 (en) 2009-09-11 2014-07-18 Ternary compositions for low-capacity refrigeration

Publications (1)

Publication Number Publication Date
US20120159982A1 true US20120159982A1 (en) 2012-06-28

Family

ID=42077109

Family Applications (3)

Application Number Title Priority Date Filing Date
US13/393,640 Abandoned US20120159982A1 (en) 2009-09-11 2010-08-20 Ternary compositions for low-capacity refrigeration
US14/335,281 Expired - Fee Related US9175203B2 (en) 2009-09-11 2014-07-18 Ternary compositions for low-capacity refrigeration
US14/873,891 Expired - Fee Related US9505968B2 (en) 2009-09-11 2015-10-02 Ternary compositions for low-capacity refrigeration

Family Applications After (2)

Application Number Title Priority Date Filing Date
US14/335,281 Expired - Fee Related US9175203B2 (en) 2009-09-11 2014-07-18 Ternary compositions for low-capacity refrigeration
US14/873,891 Expired - Fee Related US9505968B2 (en) 2009-09-11 2015-10-02 Ternary compositions for low-capacity refrigeration

Country Status (9)

Country Link
US (3) US20120159982A1 (enrdf_load_stackoverflow)
EP (1) EP2475733B1 (enrdf_load_stackoverflow)
JP (2) JP2013504644A (enrdf_load_stackoverflow)
CN (2) CN102482556B (enrdf_load_stackoverflow)
BR (1) BR112012005096A2 (enrdf_load_stackoverflow)
FR (1) FR2950071B1 (enrdf_load_stackoverflow)
PT (1) PT2475733T (enrdf_load_stackoverflow)
RU (1) RU2554180C2 (enrdf_load_stackoverflow)
WO (1) WO2011030032A1 (enrdf_load_stackoverflow)

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120151958A1 (en) * 2009-09-11 2012-06-21 Arkema France Use of ternary compositions
US20120151959A1 (en) * 2009-09-11 2012-06-21 Arkema France Binary refrigerating fluid
US20120298909A1 (en) * 2009-08-28 2012-11-29 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20130025299A1 (en) * 2010-04-16 2013-01-31 E I Du Pont De Nemours And Company Composition comprising 2,3,3,3-tetrafluoropropene and 1,1,1,2-tetrafluoroethane, chillers containing same and methods of producing cooling therein
US20130055738A1 (en) * 2010-05-11 2013-03-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US20130096218A1 (en) * 2010-06-22 2013-04-18 Arkema Inc. Heat transfer compositions of hydrofluorocarbons and a hydrofluoroolefin
US8940180B2 (en) 2012-11-21 2015-01-27 Honeywell International Inc. Low GWP heat transfer compositions
US9011711B2 (en) 2009-09-11 2015-04-21 Arkema France Heat transfer fluid replacing R-410A
US9028706B2 (en) 2011-02-10 2015-05-12 Arkema France Binary compositions of 2,3,3,3-tetrafluoropropene and of ammonia
US9039922B2 (en) 2009-09-11 2015-05-26 Arkema France Low-temperature and average-temperature refrigeration
US9074115B2 (en) 2009-08-28 2015-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US9175203B2 (en) 2009-09-11 2015-11-03 Arkema France Ternary compositions for low-capacity refrigeration
US9267064B2 (en) 2009-09-11 2016-02-23 Arkema France Ternary compositions for high-capacity refrigeration
US9315708B2 (en) 2011-05-04 2016-04-19 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US9512343B2 (en) 2010-09-20 2016-12-06 Arkema France Composition based on 2,3,3,3-tetrafluoropropene
US9599381B2 (en) 2008-10-08 2017-03-21 Arkema France Heat transfer fluid
US9650551B2 (en) 2012-12-26 2017-05-16 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US9650553B2 (en) 2012-12-26 2017-05-16 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US9683156B2 (en) 2013-09-11 2017-06-20 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US9683157B2 (en) 2009-09-11 2017-06-20 Arkema France Heat transfer method
US9683155B2 (en) 2012-12-26 2017-06-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US9752069B2 (en) 2012-11-20 2017-09-05 Arkema France Refrigerant composition
US9783721B2 (en) 2012-08-20 2017-10-10 Honeywell International Inc. Low GWP heat transfer compositions
US9908828B2 (en) 2015-03-18 2018-03-06 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US9982180B2 (en) 2013-02-13 2018-05-29 Honeywell International Inc. Heat transfer compositions and methods
US10023780B2 (en) 2013-07-11 2018-07-17 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
US10119055B2 (en) 2010-07-09 2018-11-06 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US10252913B2 (en) 2013-03-20 2019-04-09 Arkema France Composition comprising HF and 2,3,3,3-tetrafluoropropene
US10308853B2 (en) 2009-12-18 2019-06-04 Arkema France Heat-transfer fluids having reduced flammability
US10450488B2 (en) 2012-01-26 2019-10-22 Arkema France Heat transfer compositions having improved miscibility with lubricating oil
US10808157B2 (en) 2008-11-03 2020-10-20 Arkema France Vehicle heating and/or air conditioning method
US10858561B2 (en) 2008-10-16 2020-12-08 Arkema France Heat transfer method
US10954467B2 (en) 2016-10-10 2021-03-23 Arkema France Use of tetrafluoropropene based compositions
US11001546B2 (en) 2018-02-05 2021-05-11 Arkema France Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane
US11053420B2 (en) 2017-09-12 2021-07-06 Arkema France Composition on the basis of hydrochlorofluoroolefin and mineral oil
US11306232B2 (en) 2016-10-10 2022-04-19 Arkema France Tetrafluoropropene-based azeotropic compositions
US11359122B2 (en) 2017-03-21 2022-06-14 Arkema France Method for heating and/or air-conditioning in a vehicle
US11370948B2 (en) 2017-03-21 2022-06-28 Arkema France Tetrafluoropropene-based composition
US11629278B2 (en) 2018-02-15 2023-04-18 Arkema France Heat transfer compositions as replacement for R-134A

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104955926B (zh) 2012-11-16 2018-06-22 巴斯夫欧洲公司 用于改进氟聚合物密封剂相容性的包括环氧化物化合物的润滑剂组合物
CN106350017A (zh) * 2016-08-26 2017-01-25 北方工业大学 三元混合制冷剂及制备方法
KR102599222B1 (ko) * 2016-10-31 2023-11-08 한화오션 주식회사 가변 주파수 드라이브의 냉각 장치 및 그를 이용한 냉각 방법
US11209196B2 (en) 2018-10-26 2021-12-28 The Chemours Company Fc, Llc HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions
CN118978892A (zh) * 2024-08-06 2024-11-19 浙江巨化新材料研究院有限公司 传热组合物及其应用

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080230738A1 (en) * 2005-03-04 2008-09-25 Barbara Haviland Minor Compositions comprising a fluoroolefin
US20090120619A1 (en) * 2007-05-11 2009-05-14 E. I. Du Pont De Nemours And Company Method for exchanging heat in vapor compression heat transfer systems
WO2011023923A1 (en) * 2009-08-28 2011-03-03 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20110258147A1 (en) * 2008-12-02 2011-10-20 Mexichem Amanco Holdings S.A. De C.V. Heat Transfer Compositions
US8070977B2 (en) * 2008-06-11 2011-12-06 Arkema France Hydrofluoroolefin compositions
US20120097885A9 (en) * 2003-10-27 2012-04-26 Honeywell International Inc. Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US20120126187A1 (en) * 2009-04-16 2012-05-24 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20120153213A1 (en) * 2009-09-11 2012-06-21 Arkema France Ternary compositions for high-capacity refrigeration
US20120151958A1 (en) * 2009-09-11 2012-06-21 Arkema France Use of ternary compositions
US20120255316A1 (en) * 2009-12-18 2012-10-11 Arkema France Heat-transfer fluids having reduced flammability
US20130055739A1 (en) * 2010-05-11 2013-03-07 Arkema France Heat-transfer fluids and use thereof in countercurrent heat exchangers
US20130055733A1 (en) * 2010-05-11 2013-03-07 Arkema France Heat-transfer fluids and use thereof in countercurrent heat exchangers
US20130096218A1 (en) * 2010-06-22 2013-04-18 Arkema Inc. Heat transfer compositions of hydrofluorocarbons and a hydrofluoroolefin
US20130145778A1 (en) * 2009-05-08 2013-06-13 Honeywell International Inc. Heat transfer compositions and methods

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH549772A (de) * 1972-04-29 1974-05-31 Bertrams Ag Hch Kreuzgegenstromwaermeaustauscher und verfahren zu seiner herstellung.
FR2256381A1 (en) * 1973-12-27 1975-07-25 Tour Agenturer Ab Arrangement for heating or cooling a flow medium - part of air currents diverted to a circuit containing e.g. ammonia in a heat exchanger
JPS58104466A (ja) 1981-12-16 1983-06-21 松下電器産業株式会社 熱ポンプ装置
US20090253820A1 (en) 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
DK2258784T3 (en) * 2002-10-25 2017-08-28 Honeywell Int Inc Compositions containing fluorine-substituted olefins
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
JP4705157B2 (ja) 2005-03-18 2011-06-22 キャリア・コマーシャル・リフリージレーション・インコーポレーテッド 複数要素からなる熱交換器
DE202007008291U1 (de) 2006-06-17 2007-10-18 Ineos Fluor Holdings Ltd., Runcorn Wärmeübertragungszusammensetzungen
WO2008009923A2 (en) * 2006-07-17 2008-01-24 Ineos Fluor Holdings Limited Heat transfer compositions
GB0614080D0 (en) 2006-07-17 2006-08-23 Ineos Fluor Holdings Ltd Heat transfer compositions
JP2010513827A (ja) * 2006-09-01 2010-04-30 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 閉ループ・サイクル中の選択された伝熱流体の循環方法
CN101529219B (zh) * 2006-09-15 2012-08-29 纳幕尔杜邦公司 检测氟烯烃组合物泄漏的方法及其所用的传感器
WO2008157757A1 (en) * 2007-06-21 2008-12-24 E. I. Du Pont De Nemours And Company Method for leak detection in heat transfer system
FR2932493B1 (fr) 2008-06-11 2010-07-30 Arkema France Compositions a base d'hydrofluoroolefines
WO2010002023A1 (en) * 2008-07-01 2010-01-07 Daikin Industries, Ltd. REFRIGERANT COMPOSITION COMPRISING DIFLUOROMETHANE (HFC32), 2,3,3,3-TETRAFLUOROPROPENE (HFO1234yf) AND 1,1,1,2-TETRAFLUOROETHANE (HFC134a)
FR2936806B1 (fr) 2008-10-08 2012-08-31 Arkema France Fluide refrigerant
FR2937906B1 (fr) 2008-11-03 2010-11-19 Arkema France Procede de chauffage et/ou climatisation d'un vehicule.
BRPI0916022A2 (pt) 2008-11-19 2015-11-10 Du Pont composições, composição inflamável, processo para produzir resfriamento, processo para produzir aquecimento, método, equipamento de refrigeração e sistema de refrigeração estacionário
FR2938550B1 (fr) 2008-11-20 2010-11-12 Arkema France Composition comprenant du 2,3,3,3-tetrafluoropropene procede de chauffage et/ou climatisation d'un vehicule
FR2938551B1 (fr) 2008-11-20 2010-11-12 Arkema France Procede de chauffage et/ou climatisation d'un vehicule
FR2942237B1 (fr) 2009-02-13 2013-01-04 Arkema France Procede de chauffage et/ou climatisation d'un vehicule
US9074115B2 (en) * 2009-08-28 2015-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
FR2950067B1 (fr) 2009-09-11 2011-10-28 Arkema France Fluide de transfert de chaleur en remplacement du r-410a
FR2950071B1 (fr) 2009-09-11 2012-02-03 Arkema France Compositions ternaires pour refrigeration basse capacite
FR2950065B1 (fr) * 2009-09-11 2012-02-03 Arkema France Fluide refrigerant binaire
FR2950068B1 (fr) 2009-09-11 2012-05-18 Arkema France Procede de transfert de chaleur
FR2950066B1 (fr) 2009-09-11 2011-10-28 Arkema France Refrigeration basse et moyenne temperature
FR2962130B1 (fr) 2010-06-30 2012-07-20 Arkema France Composition a base de 2,3,3,3-tetrafluoropropene
FR2962442B1 (fr) 2010-07-09 2016-02-26 Arkema France Composition stable de 2,3,3,3-tetrafluoropropene
FR2964975B1 (fr) 2010-09-20 2012-08-24 Arkema France Composition a base de 2,3,3,3-tetrafluoropropene
FR2971512B1 (fr) 2011-02-10 2013-01-18 Arkema France Compositions binaires de 2,3,3,3-tetrafluoropropene et d'ammoniac
FR2974812B1 (fr) 2011-05-04 2014-08-08 Arkema France Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification
FR2986007B1 (fr) 2012-01-25 2015-01-23 Arkema France Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification
FR2986236B1 (fr) 2012-01-26 2014-01-10 Arkema France Compositions de transfert de chaleur presentant une miscibilite amelioree avec l'huile de lubrification
FR3000096B1 (fr) 2012-12-26 2015-02-20 Arkema France Composition comprenant du 2,3,3,3-tetrafluoropropene
FR3000095B1 (fr) 2012-12-26 2015-02-20 Arkema France Composition comprenant du 2,3,3,3-tetrafluoropropene et du 1,2-difluoroethylene
FR3000093B1 (fr) 2012-12-26 2015-07-17 Arkema France Composition azeotropique ou quasi-azeotropique de chloromethane
FR3003565B1 (fr) 2013-03-20 2018-06-29 Arkema France Composition comprenant hf et 2,3,3,3-tetrafluoropropene
KR102382714B1 (ko) * 2013-10-10 2022-04-06 더 케무어스 컴퍼니 에프씨, 엘엘씨 다이플루오로메탄, 펜타플루오로에탄, 테트라플루오로에탄, 및 테트라플루오로프로펜을 포함하는 조성물 및 그의 용도

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120097885A9 (en) * 2003-10-27 2012-04-26 Honeywell International Inc. Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US20080230738A1 (en) * 2005-03-04 2008-09-25 Barbara Haviland Minor Compositions comprising a fluoroolefin
US20090120619A1 (en) * 2007-05-11 2009-05-14 E. I. Du Pont De Nemours And Company Method for exchanging heat in vapor compression heat transfer systems
US8252198B2 (en) * 2008-06-11 2012-08-28 Arkema France Hydrofluoroolefin compositions
US8070977B2 (en) * 2008-06-11 2011-12-06 Arkema France Hydrofluoroolefin compositions
US20120049104A1 (en) * 2008-06-11 2012-03-01 Arkema France Hydrofluoroolefin compositions
US20110258147A1 (en) * 2008-12-02 2011-10-20 Mexichem Amanco Holdings S.A. De C.V. Heat Transfer Compositions
US20120126187A1 (en) * 2009-04-16 2012-05-24 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20130145778A1 (en) * 2009-05-08 2013-06-13 Honeywell International Inc. Heat transfer compositions and methods
US20120298909A1 (en) * 2009-08-28 2012-11-29 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
WO2011023923A1 (en) * 2009-08-28 2011-03-03 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20120151958A1 (en) * 2009-09-11 2012-06-21 Arkema France Use of ternary compositions
US20120153213A1 (en) * 2009-09-11 2012-06-21 Arkema France Ternary compositions for high-capacity refrigeration
US20120255316A1 (en) * 2009-12-18 2012-10-11 Arkema France Heat-transfer fluids having reduced flammability
US20130055739A1 (en) * 2010-05-11 2013-03-07 Arkema France Heat-transfer fluids and use thereof in countercurrent heat exchangers
US20130055733A1 (en) * 2010-05-11 2013-03-07 Arkema France Heat-transfer fluids and use thereof in countercurrent heat exchangers
US20130096218A1 (en) * 2010-06-22 2013-04-18 Arkema Inc. Heat transfer compositions of hydrofluorocarbons and a hydrofluoroolefin

Cited By (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11130893B2 (en) 2008-10-08 2021-09-28 Arkema France Heat transfer fluid
US9599381B2 (en) 2008-10-08 2017-03-21 Arkema France Heat transfer fluid
US10858561B2 (en) 2008-10-16 2020-12-08 Arkema France Heat transfer method
US10808157B2 (en) 2008-11-03 2020-10-20 Arkema France Vehicle heating and/or air conditioning method
US8894874B2 (en) * 2009-08-28 2014-11-25 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US20120298909A1 (en) * 2009-08-28 2012-11-29 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US9074115B2 (en) 2009-08-28 2015-07-07 Mexichem Amanco Holding S.A. De C.V. Heat transfer compositions
US10358592B2 (en) 2009-09-11 2019-07-23 Arkema France Heat transfer method
US9663697B2 (en) 2009-09-11 2017-05-30 Arkema France Use of ternary compositions
US20120151959A1 (en) * 2009-09-11 2012-06-21 Arkema France Binary refrigerating fluid
US9011711B2 (en) 2009-09-11 2015-04-21 Arkema France Heat transfer fluid replacing R-410A
US10858562B2 (en) 2009-09-11 2020-12-08 Arkema France Binary refrigerating fluid
US9039922B2 (en) 2009-09-11 2015-05-26 Arkema France Low-temperature and average-temperature refrigeration
US20120151958A1 (en) * 2009-09-11 2012-06-21 Arkema France Use of ternary compositions
US10316231B2 (en) 2009-09-11 2019-06-11 Arkema France Low-temperature and average-temperature refrigeration
US9127191B2 (en) 2009-09-11 2015-09-08 Arkema France Use of ternary compositions
US9133379B2 (en) * 2009-09-11 2015-09-15 Arkema France Binary refrigerating fluid
US9175203B2 (en) 2009-09-11 2015-11-03 Arkema France Ternary compositions for low-capacity refrigeration
US9267064B2 (en) 2009-09-11 2016-02-23 Arkema France Ternary compositions for high-capacity refrigeration
US10125296B2 (en) 2009-09-11 2018-11-13 Arkema France Binary refrigerating fluid
US10035938B2 (en) 2009-09-11 2018-07-31 Arkema France Heat transfer fluid replacing R-134a
US9399726B2 (en) 2009-09-11 2016-07-26 Arkema France Use of ternary compositions
US9884984B2 (en) 2009-09-11 2018-02-06 Arkema France Binary refrigerating fluid
US9505968B2 (en) 2009-09-11 2016-11-29 Arkema France Ternary compositions for low-capacity refrigeration
US8808569B2 (en) * 2009-09-11 2014-08-19 Arkema France Use of ternary compositions
US9683157B2 (en) 2009-09-11 2017-06-20 Arkema France Heat transfer method
US10308853B2 (en) 2009-12-18 2019-06-04 Arkema France Heat-transfer fluids having reduced flammability
US11352533B2 (en) 2009-12-18 2022-06-07 Arkema France Heat-transfer fluids having reduced flammability
US20130025299A1 (en) * 2010-04-16 2013-01-31 E I Du Pont De Nemours And Company Composition comprising 2,3,3,3-tetrafluoropropene and 1,1,1,2-tetrafluoroethane, chillers containing same and methods of producing cooling therein
US8765004B2 (en) * 2010-04-16 2014-07-01 E I Du Pont De Nemours And Company Composition comprising 2,3,3,3-tetrafluoropropene and 1,1,1,2-tetrafluoroethane, chillers containing same and methods of producing cooling therein
US20130055738A1 (en) * 2010-05-11 2013-03-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US9488398B2 (en) 2010-05-11 2016-11-08 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US9057010B2 (en) * 2010-05-11 2015-06-16 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US9359540B2 (en) 2010-05-11 2016-06-07 Arkema France Ternary heat-transfer fluids comprising difluoromethane, pentafluoroethane and tetrafluoropropene
US20130096218A1 (en) * 2010-06-22 2013-04-18 Arkema Inc. Heat transfer compositions of hydrofluorocarbons and a hydrofluoroolefin
US10119055B2 (en) 2010-07-09 2018-11-06 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US10662357B2 (en) 2010-07-09 2020-05-26 Arkema France Stable 2,3,3,3-tetrafluoropropene composition
US9512343B2 (en) 2010-09-20 2016-12-06 Arkema France Composition based on 2,3,3,3-tetrafluoropropene
US9028706B2 (en) 2011-02-10 2015-05-12 Arkema France Binary compositions of 2,3,3,3-tetrafluoropropene and of ammonia
US9676984B2 (en) 2011-05-04 2017-06-13 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US9315708B2 (en) 2011-05-04 2016-04-19 Arkema France Heat-transfer compositions exhibiting improved miscibility with the lubricating oil
US10450488B2 (en) 2012-01-26 2019-10-22 Arkema France Heat transfer compositions having improved miscibility with lubricating oil
US9783721B2 (en) 2012-08-20 2017-10-10 Honeywell International Inc. Low GWP heat transfer compositions
US9752069B2 (en) 2012-11-20 2017-09-05 Arkema France Refrigerant composition
US8940180B2 (en) 2012-11-21 2015-01-27 Honeywell International Inc. Low GWP heat transfer compositions
US9969918B2 (en) 2012-12-26 2018-05-15 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US9683155B2 (en) 2012-12-26 2017-06-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US10131829B2 (en) 2012-12-26 2018-11-20 Arkema France Composition containing 2,3,3,3-tetrafluoropropene and 1,2-difluoroethylene
US9650551B2 (en) 2012-12-26 2017-05-16 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US10604690B2 (en) 2012-12-26 2020-03-31 Arkema France Composition including 2,3,3,3-tetrafluoropropene
US9650553B2 (en) 2012-12-26 2017-05-16 Arkema France Azeotropic or quasi-azeotropic composition of chloromethane
US9982180B2 (en) 2013-02-13 2018-05-29 Honeywell International Inc. Heat transfer compositions and methods
US10252913B2 (en) 2013-03-20 2019-04-09 Arkema France Composition comprising HF and 2,3,3,3-tetrafluoropropene
US10377935B2 (en) 2013-07-11 2019-08-13 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US10023780B2 (en) 2013-07-11 2018-07-17 Arkema France 2,3,3,3-tetrafluoropropene compositions having improved miscibility
US9683156B2 (en) 2013-09-11 2017-06-20 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US10113093B2 (en) 2013-09-11 2018-10-30 Arkema France Heat transfer fluids comprising difluoromethane, pentafluoroethane, tetrafluoropropene and optionally propane
US9908828B2 (en) 2015-03-18 2018-03-06 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US10618861B2 (en) 2015-03-18 2020-04-14 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US10399918B2 (en) 2015-03-18 2019-09-03 Arkema France Stabilization of 1-chloro-3,3,3-trifluoropropene
US10954467B2 (en) 2016-10-10 2021-03-23 Arkema France Use of tetrafluoropropene based compositions
US11306232B2 (en) 2016-10-10 2022-04-19 Arkema France Tetrafluoropropene-based azeotropic compositions
US11359122B2 (en) 2017-03-21 2022-06-14 Arkema France Method for heating and/or air-conditioning in a vehicle
US11370948B2 (en) 2017-03-21 2022-06-28 Arkema France Tetrafluoropropene-based composition
US11053420B2 (en) 2017-09-12 2021-07-06 Arkema France Composition on the basis of hydrochlorofluoroolefin and mineral oil
US11001546B2 (en) 2018-02-05 2021-05-11 Arkema France Ternary azeotropic or quasi-azeotropic composition comprising HF, 2,3,3,3-tetrafluoropropene and 1,1,1,2,2-pentafluoropropane
US11629278B2 (en) 2018-02-15 2023-04-18 Arkema France Heat transfer compositions as replacement for R-134A

Also Published As

Publication number Publication date
EP2475733B1 (fr) 2019-10-02
US9505968B2 (en) 2016-11-29
PT2475733T (pt) 2019-11-05
JP2016194077A (ja) 2016-11-17
JP6546563B2 (ja) 2019-07-17
RU2554180C2 (ru) 2015-06-27
HK1211610A1 (en) 2016-05-27
FR2950071B1 (fr) 2012-02-03
US20140326017A1 (en) 2014-11-06
CN105018034A (zh) 2015-11-04
RU2012114163A (ru) 2013-10-20
FR2950071A1 (fr) 2011-03-18
BR112012005096A2 (pt) 2016-05-03
JP2013504644A (ja) 2013-02-07
CN102482556B (zh) 2015-07-29
US20160024363A1 (en) 2016-01-28
CN105018034B (zh) 2018-05-25
CN102482556A (zh) 2012-05-30
WO2011030032A1 (fr) 2011-03-17
EP2475733A1 (fr) 2012-07-18
US9175203B2 (en) 2015-11-03

Similar Documents

Publication Publication Date Title
US9505968B2 (en) Ternary compositions for low-capacity refrigeration
US9663697B2 (en) Use of ternary compositions
US9267064B2 (en) Ternary compositions for high-capacity refrigeration
US10358592B2 (en) Heat transfer method
US10035938B2 (en) Heat transfer fluid replacing R-134a
US9011711B2 (en) Heat transfer fluid replacing R-410A
US9133379B2 (en) Binary refrigerating fluid
US20120144857A1 (en) Low-temperature and average-temperature refrigeration
HK1211610B (zh) 用於低容量制冷的三元组合物

Legal Events

Date Code Title Description
AS Assignment

Owner name: ARKEMA FRANCE, FRANCE

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:RACHED, WISSAM;REEL/FRAME:027797/0161

Effective date: 20120221

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION