EP2958972A1 - Compositions contenant des oléfines substituées par du difluorométhane et par du fluor - Google Patents

Compositions contenant des oléfines substituées par du difluorométhane et par du fluor

Info

Publication number
EP2958972A1
EP2958972A1 EP14753578.5A EP14753578A EP2958972A1 EP 2958972 A1 EP2958972 A1 EP 2958972A1 EP 14753578 A EP14753578 A EP 14753578A EP 2958972 A1 EP2958972 A1 EP 2958972A1
Authority
EP
European Patent Office
Prior art keywords
composition
refrigerant
systems
hfo
present
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Withdrawn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
EP14753578.5A
Other languages
German (de)
English (en)
Other versions
EP2958972A4 (fr
Inventor
Samuel F. Yana Motta
Mark W. Spatz
Ryan Hulse
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.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
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
Priority claimed from US14/188,346 external-priority patent/US20140166923A1/en
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of EP2958972A1 publication Critical patent/EP2958972A1/fr
Publication of EP2958972A4 publication Critical patent/EP2958972A4/fr
Withdrawn legal-status Critical Current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
    • 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

  • This invention relates to heat transfer compositions, methods and systems and more particularly to composition and methods well adapted for use in stationary refrigeration and air conditioning equipment.
  • Fluorocarbon based fluids have found widespread use in many commercial and industrial applications, including as the working fluid in systems such as air conditioning, heat pump and refrigeration systems, among other uses such as aerosol propellants, as blowing agents, and as gaseous dielectrics.
  • Heat transfer fluids to be commercially viable, must satisfy certain very specific and in certain cases very stringent combinations of physical, chemical and economic properties. Moreover, there are many different types of heat transfer systems and heat transfer equipment, and in many cases it is important that the heat transfer fluid used in such systems possess a particular combination of properties that match the needs of the individual system. For example, systems based on the vapor compression cycle usually involve the phase change of the refrigerant from the liquid to the vapor phase through heat absorption at a relatively low pressure and compressing the vapor to a relatively elevated pressure, condensing the vapor to the liquid phase through heat removal at this relatively elevated pressure and temperature, and then reducing the pressure to start the cycle over again. For example, certain fluorocarbons have been a preferred component in many heat exchange fluids, such as refrigerants, for many years in many applications.
  • Fluoroalkanes such as chlorofluoromethanes and chlorofluoroethanes
  • many of the refrigerants commonly utilized in vapor compression systems are either single
  • chlorine-containing compositions such as chlorofluorocarbons (CFCs), hydrochlorofluorocarbons (HCFCs) and the like
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbons
  • HFCs hydrofluorocarbons
  • GWP global warming potential
  • R-410 has a Global Warming Potential of 2088. While this refrigerant has proven effective in many respects, it has become increasingly less preferred since it is frequently undesirable to use materials having GWPs greater than about 1000. A need exists, therefore, for more environmentally friendly substitutes for high GWP refrigerants in general and R-410A in particular refrigerants having undesirable GWPs.
  • any potential substitute refrigerant must also possess those properties present in many of the most widely used fluids, such as excellent heat transfer properties, chemical stability, low- or no- toxicity, low or non-flammability and lubricant compatibility, among others.
  • efficiency in use it is important to note that a loss in refrigerant thermodynamic performance or energy efficiency may have secondary environmental impacts through increased fossil fuel usage arising from an increased demand for electrical energy.
  • refrigerant substitutes it is generally considered desirable for refrigerant substitutes to be effective without major engineering changes to conventional vapor compression technology currently used with existing refrigerants, such as CFC-containing
  • lubricant compatibility is of particular importance in many of applications. More particularly, it is highly desirably for refrigeration fluids to be compatible with the lubricant utilized in the compressor unit, used in most refrigeration systems.
  • non-chlorine-containing refrigeration fluids including HFC's
  • HFC's are relatively insoluble and/or immiscible in the types of lubricants used traditionally with CFC's and HFC's, including, for example, mineral oils, alkylbenzenes or poly(alpha-olefins).
  • the lubricant should be sufficiently soluble in the refrigeration liquid over a wide range of operating
  • nonflammable refers to compounds or compositions which are determined to be nonflammable as determined in accordance with AST standard E-681 , dated 2002, which is incorporated herein by reference.
  • HFC- 152a the fluoroalkane difluoroethane
  • HFO-1243zf the fluoroalkene 1 ,1 ,1-trifluorpropene
  • fluorinated olefins described in Smutny may have some level of effectiveness in heat transfer applications, it is believed that such compounds may also have certain disadvantages. For example, some of these compounds may tend to attack substrates, particularly general-purpose plastics such as acrylic resins and ABS resins. Furthermore, the higher olefinic compounds described in Smutny may also be undesirable in certain applications because of the potential level of toxicity of such compounds which may arise as a result of pesticide activity noted in Smutny. Also, such compounds may have a boiling point which is too high to make them useful as a refrigerant in certain applications.
  • refrigerant compositions comprising, and in certain preferred embodiments consisting essentially of, from about 61 % by weight to about 69% by weight of difluoromethane (R- 32) and from about 31% by weight to about 39% by weight of tetrafluoropropene, more preferably 1 ,1 ,1 ,3-tetrafluoropropene (HFO-1234ze), and even more preferably trans ,1 ,1 ,3-tetrafluoropropene (transHFO-1234ze or HFO-1234ze(E)).
  • HFO-1234 is used herein to refer to all tetrafluoropropenes. Among the tetrafluoropropenes are included 1 ,1 ,1 ,2-tetrafluoropropene (HFO-1234yf) and both cis- and trans-1 , 1 , 1 , 3-tetrafluoropropene (HFO-1234ze).
  • HFO-1234ze is used herein generically to refer to 1 , 1 ,1 , 3-tetrafluoropropene, independent of whether it is the cis- or trans- form.
  • cisHFO-1234ze and “transHFO-1234ze” are used herein to describe the cis- and trans- forms of 1 , 1 , 1 , 3-tetrafluoropropene respectively.
  • HFO-1234ze therefore includes within its scope cisHFO- 1234ze, transHFO-1234ze, and all combinations and mixtures of these.
  • the present invention provides also methods and systems which utilize the refrigerant compositions of the present invention, in refrigeration systems, including particularly and preferably in systems and methods which have heretofore used the refrigerant R-410A, including particularly stationary refrigeration systems, including residential and commercial air conditioning equipment.
  • Other aspects of the invention include methods and systems for replacing R-410A in an existing heat transfer system with a refrigerant of the present invention.
  • the refrigerant compositions of the present invention include difluoromethane (R-32) and tetrafluoropropene.
  • R-32 difluoromethane
  • tetrafluoropropene The relative amount of HFC-32 and the tetrafluoropropene in the refrigerant composition of the present invention is critically important to the provision of the properties and features provided by the preferred aspects of the present invention. More specifically, and as explained in detail in the examples here of, refrigerant compositions comprising the components in the amounts as required by the present claims produce a highly desirable but unexpected
  • the tetrafluoropropene of the present invention comprises, and in many preferred embodiment consists essentially of (trans)HFO- 1234ze.
  • HFO-1234ze(E) has a normal boiling point of -19° C.
  • (cis)HFO-1234ze has a normal boiling point of +9° C.
  • relatively small amounts, for example, up to 5% by weight of the composition, of the cis- and trans- isomers, and perhaps other tetrafluoropropenes such as HFO-1234yf will be acceptable and/or preferred in many embodiments.
  • the tetrafluoride are, and according to the present invention consists essentially of, and even more preferably in certain embodiments consists of, HFO-1234ze(E).
  • Another advantage of certain embodiments of the present invention is the provision of compositions having exceptional flammability properties while retaining other important properties in the desirable range.
  • Applicants have come to appreciate that both R-32 and HFO-1234yf have measurable flame limits at room temperature.
  • the flame hazard of the preferred compositions of the present invention based upon HFO-1234ze compare favorably to other HFCs such as R-152a and HCs such as R-290.
  • One way of ranking the flammability of these materials is to measure the flame speed of each compound.
  • the maximum flame speed of R-32, R-152a and R-290 have been reported (Jabbour) to be 6.7, 23.0 and 38.5 cm/s, respectively.
  • the refrigerant compositions of the present invention have a flame speed of less than 6.7 cm/s.
  • the refrigerant compositions of the present invention also have a Global Warming Potential (GWP) of not greater than about 1600, more preferably not greater than about 1000, and even more preferably not greater than about 500.
  • the GWP is not greater than about 150, more preferably not greater than about 100 and even more preferably not greater than about 75.
  • GWP is measured relative to that of carbon dioxide and over a 100 year time horizon, as defined in "The Scientific Assessment of Ozone Depletion, 2002, a report of the World Meteorological Association's Global Ozone Research and Monitoring Project," which is incorporated herein by reference.
  • the present compositions also preferably have an Ozone Depletion Potential (ODP) of not greater than 0.05, more preferably not greater than 0.02 and even more preferably about zero.
  • ODP Ozone Depletion Potential
  • the refrigerant compositions of the present invention are generally adaptable for use in heat transfer applications, that is, as a heating and/or cooling medium, including as evaporative cooling agents.
  • compositions of the present invention may include other components for the purpose of enhancing or providing certain functionality to the composition, or in some cases to reduce the cost of the composition.
  • heat transfer compositions of the present invention include the present refrigerant compositions and a lubricant, with the lubricant in preferred embodiments being present in the heat transfer composition in amounts of from about 30 to about 50 percent by weight of the heat transfer composition.
  • the present compositions may also include a co- refrigerant, or compatibilzer, such as propane, for the purpose of aiding compatibility and/or solubility of the lubricant.
  • compatibilizers including propane, butanes and pentanes, are preferably present in amounts of from about 0.5 to about 5 percent by weight of the composition.
  • compatibilizers may be replaced with one or more of the additional components (e.g. fluorinated alkanes) discussed herein.
  • Combinations of surfactants and solubilizing agents may also be added to the present compositions to aid oil solubility, as disclosed by U.S. Patent No. 6,516,837, the disclosure of which is incorporated by reference.
  • Commonly used refrigeration lubricants such as Polyol Esters (POEs) and Poly Alkylene Glycols (PAGs), PAG oils, silicone oil, mineral oil, alkyl benzenes (ABs) and poly(alpha-olefin) (PAO) that are used in refrigeration machinery with hydrofluorocarbon (HFC) refrigerants may be used with the refrigerant compositions of the present invention.
  • mineral oils include Witco LP 250 (registered trademark) from Witco, Zerol 300 (registered trademark) from Shrieve Chemical, Sunisco 3GS from Witco, and Calumet R015 from Calumet.
  • Commercially available alkyl benzene lubricants include Zerol 150 (registered trademark).
  • Commercially available esters include neopentyl glycol dipelargonate, which is available as Emery 2917 (registered trademark) and Hatcol 2370 (registered trademark). Other useful esters include phosphate esters, dibasic acid esters, and fluoroesters.
  • hydrocarbon based oils are have sufficient solubility with the refrigerant that is comprised of an iodocarbon, the combination of the iodocarbon and the hydrocarbon oil might more stable than other types of lubricant.
  • Preferred lubricants include polyalkylene glycols and esters.
  • Polyalkylene glycols are highly preferred in certain embodiments because they are currently in use in particular applications such as mobile air- conditioning. Of course, different mixtures of different types of lubricants may be used.
  • compositions of the present invention are thus adaptable for use in connection with a wide variety of heat transfer systems in general and refrigeration systems in particular, such as air-conditioning (including both stationary and mobile air conditioning systems), refrigeration, heat-pump systems, and the like.
  • air-conditioning including both stationary and mobile air conditioning systems
  • refrigeration heat-pump systems
  • the compositions of the present invention are used in stationary refrigeration systems, such as stationary air conditioning units and stationary
  • compositions of the present invention tend to exhibit many of the desirable characteristics of these existing refrigerants, including a GWP that is as low, or lower than the existing refrigerant and a capacity that is as high or higher than such refrigerants and a capacity that is
  • GWPs global warming potentials
  • compositions of the present invention are believed to be adaptable for use in many of such systems, either with or without system
  • the preferred heat transfer compositions of the present invention are not azeotropic over much, and potentially over the entire, range of temperatures and pressures of use. That is, the mixtures of the components produce a liquid with a non- constant boiling temperature, therefore producing what is know as a "temperature glide" in the evaporator and condenser.
  • the "temperature glide” is the change in temperature that occurs as a zeotropic material condenses or evaporates. This glide is preferably considered in connection with the method and composition aspects of the present invention in order to provide a composition which most effectively matches the refrigerant composition being replaced.
  • the present refrigerant compositions produce a temperature glide of not greater than about 8°C under conditions of actual or contemplated use.
  • compositions are also believed to be suitable as replacements for many compositions that are currently used in other applications, such as aerosols, blowing agents and the like, as explained elsewhere herein.
  • compositions of the present invention are described below.
  • the preferred refrigerant compositions of the present invention comprise HFC-32 in amount of from greater than about 61 wt.% to less than about 70%, more preferably from about 62 wt.% to less than about 69%, and even more preferably from about 65 wt.% to less than about 69%, with an amount of about 68% by weight being preferred in certain embodiments.
  • HFO-1234ze preferably transHFO-1234ze
  • the amount of HFO-1234ze is provided in the composition from an amount preferably from about 30 wt% to about 39 wt% percent, more preferably from about 31 wt% to about 38 wt%, and even more preferably from about 31 wt% to about 35 wt% by weight, with an amount of about 32 wt% in certain preferred embodiments.
  • the amount of HFO-1234ze particularly and preferably in connection with embodiments in which the composition is intended or used as a replacement or alternative to R-410A or R-404A.
  • compositions within this range provide refrigerant fluids that have a global warming potential (GWP) that is much less than many standard refrigerants, including R-410A, while at the same time exhibiting performance parameters that are commercially comparable to or improved with respect to such previously used refrigerants, including particularly R404A, R410A and R-22.
  • GWP global warming potential
  • compositions of the present invention comprising the preferred concentrations of components described herein are capable of providing an excellent match in the parameter of discharge temperature for refrigerants such as R-410A while still achieving acceptable or improved performance parameters in connection with capacity and efficiency.
  • compositions of the present invention are useful in connection with numerous methods and systems, including as heat transfer fluids in methods and systems for transferring heat, such as refrigerants used in refrigeration, air conditioning and heat pump systems.
  • HEAT TRANSFER METHODS AND SYSTEMS are useful in connection with numerous methods and systems, including as heat transfer fluids in methods and systems for transferring heat, such as refrigerants used in refrigeration, air conditioning and heat pump systems.
  • the preferred heat transfer methods generally comprise providing a composition of the present invention and causing heat to be transferred to or from the composition, either by sensible heat transfer, phase change heat transfer, or a combination of these.
  • the present methods provide
  • refrigeration systems comprising a refrigerant of the present invention and methods of producing heating or cooling by condensing and/or evaporating a composition of the present invention.
  • the methods for cooling including cooling of other fluid either directly or indirectly or a body directly or indirectly, comprise condensing a refrigerant composition comprising a composition of the present invention and thereafter evaporating said refrigerant composition in the vicinity of the article to be cooled.
  • body is intended to refer not only to inanimate objects but also to living tissue, including animal tissue in general and human tissue in particular.
  • certain aspects of the present invention involve application of the present composition to human tissue for one or more therapeutic purposes, such as a pain killing technique, as a preparatory anesthetic, or as part of a therapy involving reducing the temperature of the body being treated.
  • the application to the body comprises providing the present compositions in liquid form under pressure, preferably in a pressurized container having a one-way discharge valve and/or nozzle, and releasing the liquid from the pressurized container by spraying or otherwise applying the composition to the body. As the liquid evaporates from the surface being sprayed, the surface cools.
  • Certain preferred methods for heating a fluid or body comprise condensing a refrigerant composition comprising a composition of the present invention in the vicinity of the fluid or body to be heated and thereafter evaporating said refrigerant composition.
  • a refrigerant composition comprising a composition of the present invention in the vicinity of the fluid or body to be heated and thereafter evaporating said refrigerant composition.
  • the present invention provides retrofitting methods which comprise replacing the heat transfer fluid (such as a refrigerant) in an existing system with a composition of the present invention, without substantial modification of the system.
  • the replacement step is a drop-in replacement in the sense that no substantial redesign of the system is required and no major item of equipment needs to be replaced in order to accommodate the composition of the present invention as the heat transfer fluid.
  • the methods comprise a drop-in replacement in which the capacity of the system is at least about 70%, preferably at least about 85%, and even more preferably at least about 95% of the system capacity prior to replacement.
  • the methods comprise a drop- in replacement in which the efficiency of the system is at least about 99%, preferably at least about 100% of the system efficiency prior to replacement.
  • the methods comprise a drop-in replacement in which the suction pressure and/or the discharge pressure of the system, and even more preferably both, is/are at least about 70%, more preferably at least about 90% and even more preferably at least about 95% of the suction pressure and/or the discharge pressure prior to replacement , and preferably not greater than about 130%, even more preferably less than about 115, and even more preferably less than about 110%.
  • the methods comprise a drop-in replacement in which the mass flow of the system is at least about 80%, and even more preferably at least 90% of the mass flow prior to replacement, and preferably not greater than about 130%, even more preferably less than about 115, and even more preferably less than about 110%.
  • the present invention provides cooling by absorbing heat from a fluid or body, preferably by evaporating the present refrigerant composition in the vicinity of the body or fluid to be cooled to produce vapor comprising the present composition.
  • the methods include the further step of compressing the refrigerant vapor, usually with a compressor or similar equipment to produce vapor of the present composition at a relatively elevated pressure.
  • the step of compressing the vapor results in the addition of heat to the vapor, thus causing an increase in the temperature of the relatively high pressure vapor.
  • the present methods include removing from this relatively high
  • the heat removal step preferably includes condensing the high temperature, high pressure vapor while the vapor is in a relatively high pressure condition to produce a relatively high pressure liquid comprising a composition of the present invention.
  • This relatively high pressure liquid preferably then undergoes a nominally isoenthalpic reduction in pressure to produce a relatively low temperature, low pressure liquid. In such embodiments, it is this reduced
  • compositions of the invention may be used in a method for producing heating which comprises condensing a refrigerant comprising the compositions in the vicinity of a liquid or body to be heated.
  • a method for producing heating which comprises condensing a refrigerant comprising the compositions in the vicinity of a liquid or body to be heated.
  • a representative air-to-air reversible heat pump designed for R410A was tested.
  • This ducted unit was tested in Honeywell's Buffalo, New York application laboratory.
  • the ducted unit is a 3-ton (10.5 kW cooling capacity) 13 SEER (3.8 cooling seasonal performance factor, SPF) with a heating capacity of 10.1 kW and an HSPF of 8.5 (rated heating SPF of -2.5), equipped with a scroll compressor.
  • SPF cooling seasonal performance factor
  • This system has tube-and-fin heat exchangers, reversing valves and thermostatic expansion valves for each operating mode. Due to the different pressures and densities of the refrigerants tested, some of the tests required the use of Electronic Expansion Valves (EEV) to reproduce the same degrees of superheat observed with the original refrigerants.
  • EEV Electronic Expansion Valves
  • Tests were performed using standard (AHRI, 2008) operating conditions. All tests were performed inside environmental chambers equipped with instrumentation to measure both air-side and refrigerant-side parameters. Refrigerant flow was measured using a coriolis flow meter while air flow and capacity was measured using an air- enthalpy tunnel designed according to industry standards (ASHRAE, 1992). All primary measurement sensors were calibrated to ⁇ 0.25°C for temperatures and ⁇ 0.25 psi for pressure. Experimental uncertainties for capacity and efficiency were on average ⁇ 5%. Capacity values represent the air-side measurements, which were carefully calibrated using the reference fluid (R-410A).
  • the test result reported in Table A illustrates that, for drop-in replacements, the capacity of the tested fluids increased as the amount of R-32 is increased. That is, the capacity of a fluid having 60 wt.% HFC-32 and 40 wt. % 1234ze was 89% in a cooling application, 88% with a Heat Rating conducted according to AHRI H1 , and 83% with Heat Testing at low temperatures in accordance with AHRI H4.
  • the amount of R- 32 is increased from 60 wt% to 68 wt. %, the capacity rose in all three tests -- i.e. to 95% for a cooling application; 93% for the AHRI H1 Heat Rating and 90% for AHRIH4 Heat Testing at low temperatures.
  • the developmental blend, L-41 was tested in this heat pump in both cooling and heating modes along with the baseline refrigerant R-410A.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention porte sur des compositions qui renferment du HFO-1234ze(E) et du HFC-32. Lesdites compositions sont utilisées, en particulier, dans les équipements fixes de réfrigération et de conditionnement d'air.
EP14753578.5A 2013-02-25 2014-02-25 Compositions contenant des oléfines substituées par du difluorométhane et par du fluor Withdrawn EP2958972A4 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361769179P 2013-02-25 2013-02-25
US14/188,346 US20140166923A1 (en) 2002-10-25 2014-02-24 Compositions containing difluoromethane and fluorine substituted olefins
PCT/US2014/018160 WO2014130983A1 (fr) 2013-02-25 2014-02-25 Compositions contenant des oléfines substituées par du difluorométhane et par du fluor

Publications (2)

Publication Number Publication Date
EP2958972A1 true EP2958972A1 (fr) 2015-12-30
EP2958972A4 EP2958972A4 (fr) 2016-10-19

Family

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Application Number Title Priority Date Filing Date
EP14753578.5A Withdrawn EP2958972A4 (fr) 2013-02-25 2014-02-25 Compositions contenant des oléfines substituées par du difluorométhane et par du fluor

Country Status (4)

Country Link
EP (1) EP2958972A4 (fr)
JP (1) JP2016513166A (fr)
CN (1) CN105189689A (fr)
WO (1) WO2014130983A1 (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107739594B (zh) * 2008-07-30 2023-07-25 霍尼韦尔国际公司 含有二氟甲烷和氟取代的烯烃的组合物
US20100122545A1 (en) * 2008-11-19 2010-05-20 E. I. Du Pont De Nemours And Company Tetrafluoropropene compositions and uses thereof
DE202009019199U1 (de) * 2008-11-19 2018-10-15 The Chemours Company Fc, Llc Tetrafluorpropen-Zusammensetzungen und ihre Verwendungen
US20120119136A1 (en) * 2010-11-12 2012-05-17 Honeywell International Inc. Low gwp heat transfer compositions
CN103108936B (zh) * 2010-11-30 2015-12-16 大金工业株式会社 具有改善滑动性的hfo制冷剂组合物
BR112013028071A2 (pt) * 2011-05-02 2020-08-04 Honeywell International Inc. composição para transparência de calor, método para substituir um fluido para transferência de calor existente contido no sistema para transferência de calor, e sistema para transferência de calor
US9187682B2 (en) * 2011-06-24 2015-11-17 Emerson Climate Technologies, Inc. Refrigeration compressor lubricant
GB2493395B (en) * 2011-08-05 2014-07-23 Mexichem Amanco Holding Sa Heat transfer compositions

Also Published As

Publication number Publication date
CN105189689A (zh) 2015-12-23
JP2016513166A (ja) 2016-05-12
EP2958972A4 (fr) 2016-10-19
WO2014130983A1 (fr) 2014-08-28

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