EP2938692A1 - Composition comprenant du 1,1,-difluoroethane et du 3,3,3-trifluoropropene - Google Patents

Composition comprenant du 1,1,-difluoroethane et du 3,3,3-trifluoropropene

Info

Publication number
EP2938692A1
EP2938692A1 EP13815070.1A EP13815070A EP2938692A1 EP 2938692 A1 EP2938692 A1 EP 2938692A1 EP 13815070 A EP13815070 A EP 13815070A EP 2938692 A1 EP2938692 A1 EP 2938692A1
Authority
EP
European Patent Office
Prior art keywords
mole
trifluoropropene
difluoroethane
heat transfer
composition according
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.)
Withdrawn
Application number
EP13815070.1A
Other languages
German (de)
English (en)
Inventor
Dominique Deur-Bert
Laurent Wendlinger
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
Publication of EP2938692A1 publication Critical patent/EP2938692A1/fr
Withdrawn legal-status Critical Current

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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
    • C09K3/00—Materials not provided for elsewhere
    • 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
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F9/00—Compounds to be used as driers, i.e. siccatives
    • 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
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/56—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances gases
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/142—Halogenated saturated hydrocarbons, e.g. H3C-CF3
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/16—Unsaturated hydrocarbons
    • C08J2203/162—Halogenated unsaturated hydrocarbons, e.g. H2C=CF2
    • 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
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/18—Binary blends of expanding agents
    • C08J2203/182—Binary blends of expanding agents of physical blowing agents, e.g. acetone and butane
    • 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
    • C09K2205/122—Halogenated 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
    • C09K2205/10—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
    • C09K2205/10—Components
    • C09K2205/13—Inert gases
    • 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
    • C09K2205/32—The mixture being azeotropic

Definitions

  • compositions comprising 1,1-difluoroethane and 3,3,3-trifluoropropene useful in many fields of application.
  • Halocarbon-based fluids have thus found many applications in various industrial fields, in particular as heat transfer fluid, propellants, foaming agents, blowing agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, agents for abrasives, drying agents and fluids for power generation units.
  • azeotropic or quasi-azeotropic fluids do not fractionate during evaporation processes and act (almost) as a pure body. However, it is difficult to identify new fluids that meet these characteristics, since azeotropes are not predictable.
  • the subject of the present invention is an azeotropic or quasi-azeotropic composition comprising the compounds 1, 1 -difluoroethane and 3,3,3-trifluoropropene.
  • near-azeotropic has a broad meaning and is meant to include compositions that are strictly azeotropic and those that behave as an azeotropic mixture.
  • a mixture is azeotropic when the pressure at the dew point is equal to that at the point of bubble formation, which means that the vapor composition is equal to that of the condensed liquid.
  • the composition according to the invention comprises, preferably consisting essentially of from 10% to 80% by mole of 1,1-difluoroethane and from 90% to 20% by mole of 3,3,3- trifluoropropene.
  • the composition according to the invention preferably comprises essentially from 20% to 70% by mole of 1,1-difluoroethane and from 80% to 30% by mole of 3,3,3-trifluoropropene. .
  • the composition according to the invention preferably comprises essentially from 25% to 65% by mole of 1,1-difluoroethane and from 75% to 35% by mole of 3,3 , 3-trifluoropropene and has a boiling point between -25 ° C to 25 ° C at a pressure between 1 and 6 bar.
  • composition according to the invention further comprises hydrogen fluoride.
  • compositions according to the invention comprise, preferably consisting essentially of from 20% to 55% by mole of HF, 30% to 40% by mole of 1,1-difluoroethane and 30% to 40% by mole of HF. mole% 3,3,3-trifluoropropene.
  • the invention also relates to the use of a fluid comprising the composition according to the invention as a heat transfer fluid, propellants, foaming agents, swelling agents, gaseous dielectrics, polymerization medium or monomer, carrier fluids, agents for abrasives, drying agents and fluids for power generation unit.
  • the invention relates to the use of a fluid comprising the composition according to the invention as heat transfer fluid in a refrigeration plant or heat pump.
  • the invention also relates to a heat transfer installation comprising a vapor compression circuit containing a fluid comprising a composition according to the invention as a heat transfer fluid or containing a heat transfer fluid as described above. .
  • the installation is selected from mobile or stationary heat pump heating, air conditioning, and especially automotive air conditioning or stationary centralized air conditioning, refrigeration, freezing and Rankine cycles; and which is preferably an air conditioning installation.
  • the invention also relates to a method for heating or cooling a fluid or a body by means of a vapor compression circuit containing a heat transfer fluid, said method comprising successively evaporation of the heat transfer fluid, compression of the heat transfer fluid, condensation of the heat fluid and expansion of the heat transfer fluid, wherein the heat transfer fluid is a fluid comprising a composition according to the invention.
  • heat transfer fluid is meant a fluid, capable of absorbing heat by evaporating at low temperature and low pressure and of rejecting heat by condensing at high temperature and high pressure, in a circuit steam compression.
  • a heat transfer fluid optionally comprises one or more additives that are not heat transfer compounds for the intended application.
  • the additives may especially be chosen from lubricants, nanoparticles, stabilizers, surfactants, tracer agents, fluorescent agents, odorants and solubilizing agents, as are well known to those skilled in the art.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

La présente invention concerne des compositions comprenant du 1,1- difluoroethane et du 3,3,3-trifluoropropene, utiles dans de nombreux domaines d'applications.

Description

COMPOSITION COMPRENANT DU 1 ,1 -DIFLUOROETHANE ET DU 3,3,3-
TRIFLUOROPROPENE
La présente invention concerne des compositions comprenant du 1 ,1 - difluoroethane et du 3,3,3-trifluoropropene, utiles dans de nombreux domaines d'applications.
Les fluides à bases d'halogénocarbones ont trouvés ainsi de nombreuses applications dans des domaines industrielles variés, notamment en tant que fluide de transfert de chaleur, propulseurs, agents moussants, agents gonflants, diélectriques gazeux, milieu de polymérisation ou monomère, fluides supports, agents pour abrasifs, agents de séchage et fluides pour unité de production d'énergie.
Une importance particulière est donnée aux fluides ayant un faible impact sur l'environnement.
L'avantage d'utiliser des fluides azéotropiques ou quasi-azéotropiques est qu'ils ne fractionnent pas lors de processus d'évaporation et agissent (quasiment) comme un corps pur. Cependant il est difficile d'identifier de nouveaux fluides répondant à ces caractéristiques, puisque les azéotropes ne sont pas prévisibles.
La présente invention a pour objet une composition azéotropique ou quasi- azéotropique comprenant les composés 1 ,1 -difluoroethane et 3,3,3-trifluoropropene.
Dans ce qui suit, les composés suivants représentent :
- 1 ,1 -difluoroethane : HFC-152a ou 152a
- 3,3,3-trifluoropropene : HFO-1243zf ou 1243zf
L'expression « quasi-azéotropique » a un sens large et est destinée à inclure les compositions qui sont strictement azéotropique et celles qui se comportent comme un mélange azéotropique.
Un mélange est azéotropique lorsque la pression au point de rosée est égale à celle au point de formation de bulles, ce qui signifie que la composition de vapeur est égale à celle du liquide condensée.
Un mélange est considéré comme quasi-azéotropique lorsque la différence de pression entre la pression au point de rosée et la pression au point de formation de bulles est inférieure ou égale à 5 %, sur la base de la pression au point de formation de bulles. Selon un mode de mise œuvre, la composition selon l'invention comprend, préférentiellement consistant essentiellement en, de 10 % à 80 % en mole de 1 , 1 - difluoroethane et de 90 % à 20 % en mole de 3,3,3-trifluoropropene.
Selon un mode de réalisation, la composition selon l'invention comprend, préférentiellement consistant essentiellement en, de 20 % à 70 % en mole de 1 , 1 - difluoroethane et de 80 % à 30 % en mole de 3,3,3-trifluoropropene.
Selon un mode de mise en œuvre particulièrement préféré, la composition selon l'invention comprend, préférentiellement consistant essentiellement en, de 25 % à 65 % en mole de 1 , 1 -difluoroethane et de 75 % à 35 % en mole de 3,3,3- trifluoropropene et a une température d'ébullition comprise entre -25 °C à 25 °C à une pression comprise entre 1 et 6 bars.
Selon un autre mode de réalisation, la composition selon l'invention comprend en outre du fluorure d'hydrogène.
Selon un mode de mise en œuvre, la compositions selon l'invention comprend, préférentiellement consistant essentiellement en , de 20 % à 55 % en mole de HF, 30 % à 40 % en mole de 1 , 1 -difluoroethane et 30 % à 40 % en mole de 3,3,3- trifluoropropene .
L'invention concerne également l'utilisation d'un fluide comprenant la composition selon l'invention en tant que fluide de transfert de chaleur, propulseurs, agents moussants, agents gonflants, diélectriques gazeux, milieu de polymérisation ou monomère, fluides supports, agents pour abrasifs, agents de séchage et fluides pour unité de production d'énergie.
De préférence, l'invention concerne l'utilisation d'un fluide comprenant la composition selon l'invention en tant que fluide de transfert de chaleur dans une installation de réfrigération ou pompe à chaleur.
L'invention concerne également une installation de transfert de chaleur comprenant un circuit de compression de vapeur contenant un fluide comprenant une composition selon l'invention en tant que fluide de transfert de chaleur ou contenant un fluide de transfert de chaleur tel que décrit ci-dessus.
Selon un mode de réalisation, l'installation est choisie parmi les installations mobiles ou stationnaires de chauffage par pompe à chaleur, de climatisation, et notamment de climatisation automobile ou de climatisation stationnaire centralisée, de réfrigération, de congélation et les cycles de Rankine ; et qui est de préférence une installation de climatisation.
L'invention concerne également un procédé de chauffage ou de refroidissement d'un fluide ou d'un corps au moyen d'un circuit de compression de vapeur contenant un fluide de transfert de chaleur, ledit procédé comprenant successivement l'évaporation du fluide de transfert de chaleur, la compression du fluide de transfert de chaleur, la condensation du fluide de chaleur et la détente du fluide de transfert de chaleur, dans lequel le fluide de transfert de chaleur est un fluide comprenant une composition selon l'invention.
Par « fluide de transfert de chaleur », on entend un fluide, susceptible d'absorber de la chaleur en s'évaporant à basse température et basse pression et de rejeter de la chaleur en se condensant à haute température et haute pression, dans un circuit de compression de vapeur.
Un fluide de transfert de chaleur comprend éventuellement un ou plusieurs additifs qui ne sont pas des composés de transfert de chaleur pour l'application envisagée. Les additifs peuvent notamment être choisis parmi les lubrifiants, les nanoparticules, les stabilisants, les tensioactifs, les agents traceurs, les agents fluorescents, les agents odorants et les agents de solubilisation, tel que bien connus de l'homme du métier.
Tableau 1
Pression : 1 bar absolu Pression 3 bar absolu
Température Mole (%) Mole (%) Température Mole (%) Mole (%)
Azéotrope
(°C) 152a 1243zf °C 152a 1243zf
152a / 1243zf -25 29 71 3 60 40

Claims

REVENDICATIONS
1 . Composition azéotropique ou quasi-azéotropique comprenant les composés 1 , 1 -difluoroethane et 3,3,3-trifluoropropene.
2. Composition selon la revendication 1 caractérisée en ce qu'elle comprend, préférentiellement consistant essentiellement en, de 10 % à 80 % en mole de 1 , 1 - difluoroethane et de 90 % à 20 % en mole de 3,3,3-trifluoropropene.
3. Composition selon la revendication 1 ou la revendication 2 caractérisée en ce qu'elle comprend, préférentiellement consistant essentiellement en, de 20 % à 70 % en mole de 1 , 1 -difluoroethane et de 80 % à 30 % en mole de 3,3,3-trifluoropropene.
4. Compositions selon l'une quelconque des revendications précédentes caractérisée en ce qu'elle comprend, préférentiellement consistant essentiellement en, de 25 % à 65 % en mole de 1 , 1 -difluoroethane et de 75 % à 35 % en mole de 3,3,3- trifluoropropene à une température comprise entre -25 °C à 25 °C et une pression comprise entre 1 et 6 bars.
5. Composition selon l'une quelconque des revendications précédentes caractérisée en ce qu'elle comprend au moins du fluorure d'hydrogène.
6. Composition selon l'une quelconque des revendications précédentes caractérisée en ce que qu'elle comprend, préférentiellement consistant essentiellement en, de 20 % à 55 % en mole de HF, 30 % à 40 % en mole de 1 , 1 -difluoroethane et 30 % à 40 % en mole de 3,3,3-trifluoropropene.
EP13815070.1A 2012-12-26 2013-12-06 Composition comprenant du 1,1,-difluoroethane et du 3,3,3-trifluoropropene Withdrawn EP2938692A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1262764A FR3000094B1 (fr) 2012-12-26 2012-12-26 Composition comprenant du 1,1-difluoroethane et du 3,3,3-trifluoropropene
PCT/FR2013/052971 WO2014102476A1 (fr) 2012-12-26 2013-12-06 Composition comprenant du 1,1,-difluoroethane et du 3,3,3-trifluoropropene

Publications (1)

Publication Number Publication Date
EP2938692A1 true EP2938692A1 (fr) 2015-11-04

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EP13815070.1A Withdrawn EP2938692A1 (fr) 2012-12-26 2013-12-06 Composition comprenant du 1,1,-difluoroethane et du 3,3,3-trifluoropropene

Country Status (7)

Country Link
US (2) US9663692B2 (fr)
EP (1) EP2938692A1 (fr)
JP (2) JP2016505684A (fr)
KR (1) KR20150102012A (fr)
CN (1) CN104837950B (fr)
FR (1) FR3000094B1 (fr)
WO (1) WO2014102476A1 (fr)

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Publication number Priority date Publication date Assignee Title
FR3000094B1 (fr) * 2012-12-26 2019-10-18 Arkema France Composition comprenant du 1,1-difluoroethane et du 3,3,3-trifluoropropene

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AT213644B (de) 1959-05-15 1961-02-27 Franz Aumueller Spielautomat
JP2005162738A (ja) * 2003-11-10 2005-06-23 Showa Denko Kk １，１−ジフルオロエタンの精製方法およびその用途
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US20060243945A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
CA2681872C (fr) * 2007-03-29 2015-06-09 Arkema Inc. Composition d'agent d'expansion a base d'hydrochlorofluoroolefine et d'hydrofluoroolefine
WO2009047535A2 (fr) * 2007-10-12 2009-04-16 Ineos Fluor Holdings Limited Compositions de transfert de chaleur
US8101672B2 (en) * 2007-12-13 2012-01-24 Honeywell International Inc. Azeotrope-like compositions of 1,1,2,3,3-pentafluoropropene
US7629307B2 (en) * 2008-01-17 2009-12-08 3M Innovative Properties Company Ternary azeotropic-like compositions with 1,1,1,2,3,3-hexafluoro-3-methoxy-propane and trans-1,2-dichloroethylene
CA2717216A1 (fr) * 2008-02-21 2009-08-27 Jeffrey P. Knapp Compositions azeotropique composee de 3,3,3-trifluoropropene et de fluorure d'hydrogene et procedes de separation
JP5592597B2 (ja) * 2008-03-17 2014-09-17 Ｊｘ日鉱日石エネルギー株式会社 冷凍機油及び冷凍機用作動流体組成物
US8075797B2 (en) * 2009-01-29 2011-12-13 Honeywell International Inc. Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hydrogen fluoride
FR2959997B1 (fr) * 2010-05-11 2012-06-08 Arkema France Fluides de transfert de chaleur et leur utilisation dans des echangeurs de chaleur a contre-courant
JP2012127519A (ja) * 2010-12-13 2012-07-05 Panasonic Corp 空気調和機
FR3000094B1 (fr) * 2012-12-26 2019-10-18 Arkema France Composition comprenant du 1,1-difluoroethane et du 3,3,3-trifluoropropene

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Also Published As

Publication number Publication date
KR20150102012A (ko) 2015-09-04
JP2019031681A (ja) 2019-02-28
US20170081577A1 (en) 2017-03-23
CN104837950B (zh) 2017-08-08
WO2014102476A1 (fr) 2014-07-03
JP2016505684A (ja) 2016-02-25
FR3000094A1 (fr) 2014-06-27
CN104837950A (zh) 2015-08-12
US10023779B2 (en) 2018-07-17
FR3000094B1 (fr) 2019-10-18
US9663692B2 (en) 2017-05-30
US20150344757A1 (en) 2015-12-03

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