US20040089839A1 - Fluorinated alkene refrigerant compositions - Google Patents

Fluorinated alkene refrigerant compositions Download PDF

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Publication number
US20040089839A1
US20040089839A1 US10/695,212 US69521203A US2004089839A1 US 20040089839 A1 US20040089839 A1 US 20040089839A1 US 69521203 A US69521203 A US 69521203A US 2004089839 A1 US2004089839 A1 US 2004089839A1
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US
United States
Prior art keywords
fluoroalkene
composition
lubricant
refrigerant
polyalkylene glycol
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
US10/695,212
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English (en)
Inventor
Raymond Thomas
Rajiv Singh
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34549972&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20040089839(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to US10/695,212 priority Critical patent/US20040089839A1/en
Assigned to HONEYWELL INTERNATIONAL INC. reassignment HONEYWELL INTERNATIONAL INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SINGH, RAJIV R., THOMAS, RAYMOND H.
Priority to US10/837,525 priority patent/US7279451B2/en
Publication of US20040089839A1 publication Critical patent/US20040089839A1/en
Priority to PT04817445T priority patent/PT1725628E/pt
Priority to ES10011589T priority patent/ES2784188T3/es
Priority to KR1020127011477A priority patent/KR101335358B1/ko
Priority to EP10010521.2A priority patent/EP2275509B1/en
Priority to TR2017/08747T priority patent/TR201708747T4/tr
Priority to EP19218149.3A priority patent/EP3680308A1/en
Priority to PCT/US2004/035132 priority patent/WO2005042663A1/en
Priority to PL04817445T priority patent/PL1725628T3/pl
Priority to PL08011766T priority patent/PL2009075T3/pl
Priority to CN201410138436.7A priority patent/CN103923723B/zh
Priority to HUE10010520A priority patent/HUE032542T2/en
Priority to PT100115898T priority patent/PT2277976T/pt
Priority to PT100105212T priority patent/PT2275509T/pt
Priority to CN201310062932.4A priority patent/CN103215013B/zh
Priority to EP10010520.4A priority patent/EP2277970B1/en
Priority to EP08011766.6A priority patent/EP2009075B1/en
Priority to ES08011766.6T priority patent/ES2546024T3/es
Priority to SI200432490T priority patent/SI2277976T1/sl
Priority to SI200432481T priority patent/SI2275509T1/sl
Priority to CN200480039094.8A priority patent/CN1898353B/zh
Priority to SI200431900T priority patent/SI1725628T1/sl
Priority to DK10011589.8T priority patent/DK2277976T3/da
Priority to DK04817445.2T priority patent/DK1725628T3/da
Priority to CN201410138211.1A priority patent/CN103923611B/zh
Priority to JP2006538130A priority patent/JP2007510039A/ja
Priority to PL10010521T priority patent/PL2275509T3/pl
Priority to ES10010520.4T priority patent/ES2628746T3/es
Priority to PT100105204T priority patent/PT2277970T/pt
Priority to CN201410137429.5A priority patent/CN103923610B/zh
Priority to DE08011766T priority patent/DE08011766T1/de
Priority to PL10011589T priority patent/PL2277976T3/pl
Priority to DK10010521.2T priority patent/DK2275509T3/da
Priority to PL10010520T priority patent/PL2277970T3/pl
Priority to ES10010521T priority patent/ES2748910T3/es
Priority to HUE10010521A priority patent/HUE046570T2/hu
Priority to EP10011589.8A priority patent/EP2277976B1/en
Priority to KR1020067010510A priority patent/KR101335360B1/ko
Priority to CN201310572027.3A priority patent/CN103642461B/zh
Priority to EP04817445A priority patent/EP1725628B1/en
Priority to ES04817445T priority patent/ES2385650T3/es
Priority to US11/385,259 priority patent/US9631129B2/en
Priority to US11/475,605 priority patent/US9005467B2/en
Priority to US11/773,959 priority patent/US20080121837A1/en
Priority to US12/426,948 priority patent/US8033120B2/en
Priority to US12/511,954 priority patent/US20120097885A9/en
Priority to US13/394,289 priority patent/US8962707B2/en
Priority to US12/890,143 priority patent/US20110037016A1/en
Priority to JP2013110268A priority patent/JP2013166962A/ja
Priority to US14/188,346 priority patent/US20140166923A1/en
Priority to US14/245,406 priority patent/US9708537B2/en
Priority to JP2014119442A priority patent/JP2014159604A/ja
Priority to US14/538,335 priority patent/US9657208B2/en
Priority to US14/630,166 priority patent/US20150231527A1/en
Priority to JP2016038691A priority patent/JP2016104886A/ja
Priority to US15/200,268 priority patent/US20160310922A1/en
Priority to US15/367,825 priority patent/US9988567B2/en
Priority to US15/389,697 priority patent/US20170233624A1/en
Priority to US15/419,622 priority patent/US20170137682A1/en
Priority to US15/490,413 priority patent/US20180094179A1/en
Priority to JP2017104404A priority patent/JP2017197753A/ja
Priority to US15/675,024 priority patent/US10975007B2/en
Priority to US15/711,431 priority patent/US10781152B2/en
Priority to US15/889,702 priority patent/US10435342B2/en
Priority to US15/995,751 priority patent/US20190136107A1/en
Priority to US16/051,765 priority patent/US20190153281A1/en
Priority to JP2018212825A priority patent/JP2019048996A/ja
Priority to US16/281,577 priority patent/US10676656B2/en
Priority to US16/589,770 priority patent/US20200208034A1/en
Priority to US17/221,314 priority patent/US20210300846A1/en
Abandoned legal-status Critical Current

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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • 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
    • C09K2205/24—Only one single fluoro component present
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C10M2207/2895—Partial esters containing free hydroxy groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C10M2211/063—Perfluorinated compounds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/097—Refrigerants
    • C10N2020/101—Containing Hydrofluorocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to compositions used as refrigeration fluids in compression refrigeration, air-conditioning and heat pump systems.
  • chlorine-containing refrigerants such as chlorofluorocarbons (CFC's), hydrochlorofluorocarbons (HCF's) and the like
  • CFC's chlorofluorocarbons
  • HCF's hydrochlorofluorocarbons
  • any of the replacement materials In order for any of the replacement materials to be useful in connection with refrigeration compositions, the materials must be compatible with the lubricant utilized in the compressor.
  • many non-chlorine-containing refrigeration fluids including 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 In order for a refrigeration fluid-lubricant combination to work efficiently within a compression refrigeration, air-conditioning or heat pump system, the lubricant must be sufficiently soluble in the refrigeration liquid over a wide range of operating temperatures.
  • solubility lowers the viscosity of the lubricant and allows it to flow more easily throughout the system. In the absence of such solubility, lubricants tend to become lodged in the coils of the compression refrigeration, air-conditioning or heat pump system evaporator, as well as other parts of the system, and thus reduce the system efficiency.
  • Polyalkylene glycol, esterified polyalkylene glycol, and polyol ester lubricating oils have been developed as misicible lubricants for HFC refrigeration liquids.
  • Polyalkylene glycol refrigeration lubricants are disclosed by U.S. Pat. Nos. 4,755,316; 4,971,712, and 4,975,212.
  • Polyalkylene glycol esters are disclosed by U.S. Pat. No. 5,008,028.
  • the polyalkylene glycol and polyalkylene glycol ester lubricating oils are disclosed as being misicible in fluoroalkanes containing one or two carbon atoms and no double bonds.
  • Compression refrigeration generally involves changing the refrigerant from the liquid to the vapor phase through heat adsorption at a lower pressure and then from the vapor to the liquid phase through heat removal at an elevated pressure.
  • fluoro-olefin-based materials fluoroalkenes
  • HFC's fluoroalkanes
  • Flammability is another important property for many applications. That is, it is considered either important or essential in many applications, including particularly in heat transfer applications, to use compositions which are non-flammable. Thus, it is frequently beneficial to use in such compositions compounds which are nonflammable.
  • nonflammable refers to compounds or compositions which are determined to be nonflammable in accordance with ASTM standard E-681, dated 2002, which is incorporated herein by reference. Unfortunately, many HFC's which might otherwise be desirable for used in refrigerant compositions are not nonflammable.
  • fluoroalkane difluoroethane HFC-152a
  • fluoroalkene 1,1,1-trifluoropropene HFO-1243zf
  • 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.
  • compositions, and particularly fluid transfer compositions that are potentially useful in numerous applications, including vapor compression heating and cooling systems and methods, while avoiding one or more of the disadvantages noted above.
  • compositions comprising one or more C3 or C4 fluoroalkenes, preferably compounds having Formula I as follows:
  • compositions also preferably include one or more lubricants in combination with one or more of the compounds of the present invention.
  • the present invention provides also methods and systems which utilize the heat transfer compositions of the present invention.
  • the present invention is directed to compositions comprising at least one fluoroalkene containing from 3 to 4 carbon atoms and at least one carbon-carbon double bond.
  • the fluoroalkene compounds of the present invention are sometimes referred to herein for the purpose of convenience as hydrofluoro-olefins or “HFOs.” Although it is contemplated that the HFOs of the present invention may contain two carbon—carbon double bonds, such compounds at the present time are not considered to be preferred.
  • compositions comprise one or compounds in accordance with Formula I.
  • compositions include compounds of Formula II below:
  • each R is independently Cl, F, Br, I or H; R′ is (CR 2 ) n Y; Y is CRF 2 and n is 0 or 1. In highly preferred embodiments, Y is CF 3 , n is 0 and at least one of the remaining R's is F.
  • a relatively low toxicity level is associated with compounds of Formula II, preferably wherein Y is CF 3 , wherein at least one R on the unsaturated terminal carbon is H, and at least one of the remaining R's is F. It is believed also that all structural, geometric and stereoisomers of such compounds are effective and of beneficially low toxicity.
  • compositions of the present invention comprise one or more compounds selected from the group consisting of trifluorpropene (HFC -1243), tetrafluoropropenes (HFO-1234), pentafluoropropenes (HFO-1225) and combinations of these.
  • the trans-1234 isomer has a boiling point of approximately ⁇ 19° C. and the cis isomer has a boiling point of approximately +9° C.
  • the trans isomer is particularly useful as a refrigerant and as an aersol propellent.
  • the compounds of the present invention are the tetrafluoroprpoene and pentafluoropropene compounds in which the unsaturated terminal carbon has not more than one F substituent, specifically: 1, 3, 3, 3-tetrafluoropropene (HFO-1234ze); 2, 3, 3, 3-tetrafluoropropene (HFO-1234yf); and 1,2,3,3,3-pentafluoropropene (HFO-1225ye), and any and all stereoisomers of each of these. It has been discovered that such compounds have a very acute low toxicity level, as measured by inhalation exposure to mice and rats.
  • a relatively high degree of toxicity may be associated with certain compounds adaptable for use with the present compositions, namely, those compounds which have more than one F on the terminal unsaturated carbon, or which do not have at least one H on the terminal unsaturated carbon.
  • HFO-1225zc 1,1,3,3,3-pentafluoropropene exhibits an unacceptably high degree of toxicity, as measured by inhalation exposure to mice and rats.
  • HFO-1225 and HFO-1234 are known materials and are listed in Chemical Abstracts databases.
  • HFO-1225 is commercially available, for example from Syntex Chemical Co. Futhermore, methods are described generally in the patent literature for producing fluoroalkenes.
  • 5,532,419 which is also incorporated herein by reference, discloses a vapor phase catalytic process for the preparation of fluoroalkene using a chloro- or bromo-halofluorocarbon and H.
  • EP 974,571 also incorporated herein by reference, discloses the preparation of 1,1,1,3-tetrafluoro-propene by contacting 1,1,1,3,3-pentafluoropropane (HFC-245fa) in the vapor phase with a chromium-based catalyst at elevated temperature, or in the liquid phase with an alcoholic solution of KOH, NaOH, Ca(OH) 2 or Mg(OH) 2 .
  • the present compositions are believed to possess properties that are advantageous for a number of important reasons. For example, applicants believe, based at least in part on mathematical modeling, that the fluoroolefins of the present invention will not have a substantial negative affect on atmospheric chemistry, being negligible contributors to ozone depletion in comparison to some other halogenated species.
  • the preferred compositions of the present invention thus have the advantage of not contributing substantially to ozone depletion.
  • the preferred compositions also do not contribute substantially to global warming compared to many of the hydrofluoroalkanes presently in use.
  • compositions of the present invention may include the compounds of the present invention in widely ranging amounts
  • refrigerant compositions of the present invention comprise compound(s) in accordance with Formula I, and even more preferably Formula II, in an amount that is at least about 50% by weight, and even more preferably at least about 70% by weight, of the composition.
  • compound(s) in accordance with Formula I, and even more preferably Formula II are present in an amount that is at least about 5% by weight, and even more preferably at least about 15% by weight, of the composition.
  • 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.
  • refrigerant compositions according to the present invention especially those used in vapor compression systems, include a lubricant, generally in amounts of from about 30 to about 50 percent by weight of the composition.
  • the present compositions may also include a 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.
  • Combinations of surfactants and solubilizing agents may also be added to the present compositions to aid oil solubility, as disclosed by U.S. Pat. No. 6,516,837, the disclosure of which is incorporated by reference.
  • Commonly used refrigeration lubricants such as Polyol Esters (POEs), Poly Alkylene Glycols (PAGs) and esterified Poly Alkylene Glycols that are used in refrigeration machinery with hydrofluorocarbon (HFC) refrigerants may be used with the refrigerant compositions of the present invention.
  • 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.
  • 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 by changing the phase of the composition.
  • the present methods provide cooling by absorbing heat from a fluid or article, preferably by condensing a refrigerant comprising the present compositions and thereafter evaporating the refrigerant in the vicinity of the body or fluid to be cooled.
  • the step of compressing the refrigerant vapor usually with a rotary compressor or similar equipment, is also included as part of the refrigeration cycle. Such a step is then sometimes followed by an intermediate cooling step to remove at least a portion of the heat added to the refrigerant composition of the present invention by the compression step.
  • This intermediate cooling step is then preferably followed by a nominally isoenthalpic reduction of the pressure of the cooled, high pressure refrigerant vapor to cause at least a portion of the vapor to condense to a relatively cold liquid phase.
  • this reduced temperature refrigerant liquid which is then vaporized by heat transferred from the body or fluid to be cooled.
  • 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 and thereafter evaporating the refrigerant.
  • a method for producing heating comprises condensing a refrigerant comprising the compositions in the vicinity of a liquid or body to be heated and thereafter evaporating the refrigerant.
  • a method for producing refrigeration is provided by condensing a fluoroalkene containing from 2 to 5 carbon atoms and at least 1 but no more than 2 double bonds and thereafter evaporating the fluoroalkene in the vicinity of a body to be cooled. Fluoroalkenes containing 3 carbon atoms and 1 double bond are preferred.
  • a method for producing heating by condensing a fluoroalkene containing from 2 to 5 carbon atoms and at least 1 but no more than 2 double bonds in the vicinity of a body to be heated and thereby evaporating the fluoroalkene.
  • fluoroalkenes containing 3 carbon atoms and 1 double bond are preferred.
  • a liquid composition for use in compression refrigeration, air-conditioning and heat pump systems in which a fluoroalkene containing from 2 to 5 carbon atoms and at least 1 but no more than 2 double bonds is combined with a sufficient amount to provide lubrication of an essentially miscible organic lubricant selected from polyalkylene glycol, polyalkylene glycol ester and polyol ester lubricants for compression refrigeration, air-conditioning and heat pump systems.
  • the lubricants of this invention are organic compounds which are comprised of carbon, hydrogen and oxygen with a ratio of oxygen to carbon sufficient to provide a degree of miscibility with the fluoroalkene such the when about 1 to 5 weight percent of the lubricant is added to the refrigerant fluid the mixture has one liquid phase.
  • the mixture has one liquid phase when 1 to 20 weight percent of the lubricant is present in the mixture.
  • the mixture is one liquid phase in all proportions of the components of mixture.
  • This solubility or miscibility preferably exists at at least one temperature from about ⁇ 40° C. and 70° C, and more preferably over essentially the entire temperature range.
  • refrigeration system refers to any system or apparatus, or any part or portion of such a system or apparatus, which employs a refrigeration liquid or refrigerant to provide cooling.
  • refrigeration systems include, for example, air-conditioners, electric refrigerators, chillers, transport refrigeration systems, commercial refrigeration systems, and the like.
  • the present invention substitutes HFO's for HFC's, which, despite being safe for the ozone layer, are suspected of contributing to global warming. At least certain of the preferred HFO's according to the present invention have physical characteristics that allow for their substitution for HFC's with only a minimum of equipment changes.
  • the polyalkylene glycol lubricants suitable for use with the present invention typically containing from about 5 to 50 oxylakylene repeating units that contain from 1 to 5 carbon atoms.
  • the polyalkylene glycol can be straight chain or branched and can be a homopolymer or co-polymer of 2, 3 or more oxyethylene, oxypropylene, oxybutylene or oxypentylene groups or combinations thereof in any proportions.
  • Preferred polyalkylene glycols contain at least 50% oxypropylene groups.
  • Compositions according to the present invention may contain one or more polyalkylene glycols as the lubricant, one or more polyalkylene glycol esters as the lubricant, one or more polyol esters as the lubricant, or a mixture of one of more polyalkylene glycols, one or more polyalkylene glycol esters and one or more polyol esters.
  • Vinyl ethers are also useful in this invention.
  • Suitable polyalkylene glycols include the polyalkylene glycols of U.S. Pat. No. 4, 971,712 and the polyalkylene glycol having hydroxy groups at each terminus disclosed by U.S. Pat. No. 4,755,316. The disclosures of both patents are incorporated herein by reference.
  • suitable polyalkylene glycols include glycols terminating at each end with a hydroxyl group
  • other suitable HFO lubricants include polyalkylene glycols in which either or both terminal hydroxyl group is capped.
  • the hydroxyl group may be capped with alkyl groups containing from 1 to 10 carbon atoms, 1 to 10 carbon atom alkyl groups containing heteroatoms such as nitrogen, the fluoroalkyl groups described by U.S. Pat. No. 4,975,212, the disclosure of which is incorporated herein by reference, and the like.
  • the same type or a combination of two different types of terminal capping groups can be used.
  • Either or both hydroxyl groups can also be capped by forming the ester thereof with a carboxylic acid as disclosed by U.S. Pat. No. 5,008,028, the disclosure of which is also incorporated herein by reference.
  • the lubricating oils of this patent are referred to as polyol esters and polyalkylene glycol esters.
  • the carboxylic acid can also be fluorinated.
  • polyalkylene glycol lubricants include Goodwrench Refrigeration Oil for HFC-134a systems from General Motors and MOPAR-56 from Daimler-Chrysler, which is a polyalkylene glycol that is bis-capped by acetyl groups.
  • commercially available polyalkylene glycol esters include Mobil EAL 22 cc available from Exxon-Mobil and Solest 120 available from CPI Engineering Services, Inc. A wide variety of polyalkylene glycol lubricants are also available from Dow Chemical.
  • the lubricants of this invention have viscosities of from about 1 to 1000 centistokes at about 37° C., more preferably in the range of from about 10 to about 200 centistokes at about 37° C. and even more preferably of from about 30 to about 150 centistokes.
  • compositions according to the present invention can include other additives or materials of the type used in refrigeration, air-conditioning and heat pump compositions to enhance their performance.
  • the compositions can also include extreme pressure and anti-wear additives, oxidation and thermal stability improvers, pour and floc point depressants, anti-foaming agents, other lubricants soluble in HFO's, and the like. Examples of such additives are disclosed in U.S. Pat. No. 5,254,280, the disclosure of which is incorporated herein by reference.
  • Compositions of the present invention can thus further include a quantity of mineral oil lubricant that would not otherwise be misicible or soluble with the HFO but is at least partially misicible or partially soluble when added to the HFO in combination with a polyalkylene glycol, polyalkylene glycol ester or polyol ester. Typically, this is a quantity up to about 5-20 weight %.
  • a surfactant may also be added to compatibilize the mineral oil with the polyalkylene glycol, polyalkylene glycol ester or polyol ester and the HFO, as disclosed in U.S. Pat. No. 6,516,837, the disclosure of which is incorporated herein by reference.
  • any of a wide range of methods for introducing the refrigeration compositions of the present invention to a compression refrigeration, air-conditioning or heat pump system can be used from the present invention.
  • one method comprises attaching a refrigerant container to the low-pressure side of a refrigeration system and turning on the refrigeration system compressor to pull the refrigeration composition into the system.
  • the refrigerant container may be placed on a scale such that the amount of refrigeration composition entering the system can be monitored.
  • charging is stopped.
  • a wide range of charging tools known to those skilled in the art, are commercially available. Accordingly, in light of the above disclosure, those of skill in the art will be readily able to introduce the HFO refrigerant and refrigeration compositions of the present invention into compression refrigeration, air-conditioning and heat pump systems without undue experimentation.
  • the coefficient of performance is a universally accepted measure of refrigerant performance, especially useful in representing the relative thermodynamic efficiency of a refrigerant in a specific heating or cooling cycle involving evaporation or condensation of the refrigerant. In refrigeration engineering, this term expresses the ratio of useful refrigeration to the energy applied by the compressor in compressing the vapor.
  • the capacity of a refrigerant represents the volumetric efficiency of the refrigerant and provides some measure of the capability of a compressor to pump quantities of heat for a given volumetric flow rate of refrigerant. In other words, given a specific compressor, a refrigerant with a higher capacity will deliver more cooling or heating power.
  • thermodynamic properties of the refrigerant is from the thermodynamic properties of the refrigerant using standard refrigeration cycle analysis techniques (see for example, R. C. Downing, FLUOROCARBON REFRIGERANTS HANDBOOK, Chapter 3, Prentice-Hall, 1988).
  • a refrigeration/air conditioning cycle system where the condenser temperature is about 150° F. and the evaporator temperature is about ⁇ 35° F. under nominally isentropic compression with a compressor inlet temperature of about 50° F.
  • COP is determined for several compositions of the present invention over a range of condenser and evaporator temperatures and reported in Table I below, based upon HFC-134a having a COP value of 1.00, a capacity value of 1.00 and a discharge temperature of 175° F.
  • the miscibility of HFO-1225ye and HFO-1234ze with various refrigeration lubricants is tested.
  • the lubricants tested are mineral oil (C3), alkyl benzene (Zerol 150), ester oil (Mobil EAL 22 cc and Solest 120), polyalkylene glycol (PAG) oil (Goodwrench Refrigeration Oil for 134a systems), and a poly(alpha-olefin) oil (CP-6005-100).
  • C3 mineral oil
  • alkyl benzene Zerol 150
  • ester oil Mobil EAL 22 cc and Solest 120
  • PAG polyalkylene glycol
  • CP-6005-100 poly(alpha-olefin) oil
  • the lubricant compositions are placed in heavy-walled glass tubes.
  • the tubes are evacuated, the refrigerant compound in accordance with the present invention is added, and the tubes are then sealed.
  • the tubes are then put into an air bath environmental chamber, the temperature of which is varied from about ⁇ 50° C. to 70° C. At roughly 10° C. intervals, visual observations of the tube contents are made for the existence of one or more liquid phases. In a case where more than one liquid phase is observed, the mixture is reported to be immiscible. In a case where there is only one liquid phase observed, the mixture is reported to be miscible. In those cases where two liquid phases were observed, but with one of the liquid phases occupying only a very small volume, the mixture is reported to be partially miscible.
  • the polyalkylene glycol and ester oil lubricants were judged to be miscible in all tested proportions over the entire temperature range, except that for the HFO-1225ye mixtures with polyalkylene glycol, the refrigerant mixture was found to be immiscible over the temperature range of ⁇ 50° C. to ⁇ 30° C. and to be partially miscible over from 20 to 50° C. At 50 weight percent concentration of the PAG in refrigerant and at 60°, the refrigerant/PAG mixture was miscible. At 70° C., it was miscible from 5 weight percent lubricant in refrigerant to 50 weight percent lubricant in refrigerant.
  • Aluminum, copper and steel coupons are added to heavy walled glass tubes. Two grams of oil are added to the tubes. The tubes are then evacuated and one gram of refrigerant is added. The tubes are put into an oven at 350° F. for one week and visual observations are made. At the end of the exposure period, the tubes are removed.
  • Example 3 Aluminum, copper and steel coupons are added to a heavy walled glass tube with mineral oil and CFC-12 and heated for one week at 350° C., as in Example 3. At the end of the exposure period, the tube is removed and visual observations are made. The liquid contents are observed to turn black, indicating there is severe decomposition of the contents of the tube.
  • CFC-12 and mineral oil have heretofore been the combination of choice in many refrigerant systems and methods.
  • the refrigerant compounds and compositions of the present invention possess significantly better stability with many commonly used lubricating oils than the widely-used prior art refrigerant-lubricating oil combination.

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US10/695,212 2002-10-25 2003-10-27 Fluorinated alkene refrigerant compositions Abandoned US20040089839A1 (en)

Priority Applications (71)

Application Number Priority Date Filing Date Title
US10/695,212 US20040089839A1 (en) 2002-10-25 2003-10-27 Fluorinated alkene refrigerant compositions
US10/837,525 US7279451B2 (en) 2002-10-25 2004-04-29 Compositions containing fluorine substituted olefins
PT04817445T PT1725628E (pt) 2003-10-27 2004-10-25 Compostos refrigerantes de alquenos fluoretados
ES10011589T ES2784188T3 (es) 2003-10-27 2004-10-25 Composiciones que comprenden HFC-1234ZE y lubricante
KR1020127011477A KR101335358B1 (ko) 2003-10-27 2004-10-25 플루오르화 알켄 냉매 조성물
EP10010521.2A EP2275509B1 (en) 2003-10-27 2004-10-25 Use of fluorinated alkene refrigerant compositions
TR2017/08747T TR201708747T4 (tr) 2003-10-27 2004-10-25 Florlaştırılan alken soğutkan bileşimleri.
EP19218149.3A EP3680308A1 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant compositions
PCT/US2004/035132 WO2005042663A1 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant compositions
PL04817445T PL1725628T3 (pl) 2003-10-27 2004-10-25 Fluorowane, alkenowe kompozycje czynników chłodniczych
PL08011766T PL2009075T3 (pl) 2003-10-27 2004-10-25 Fluorowane, alkenowe kompozycje czynników chłodniczych
CN201410138436.7A CN103923723B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
HUE10010520A HUE032542T2 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant preparations
PT100115898T PT2277976T (pt) 2003-10-27 2004-10-25 Composições que compreendem hfc-1234ze e lubrificante
PT100105212T PT2275509T (pt) 2003-10-27 2004-10-25 Uso de compostos refrigerantes de alquenos fluoretados.
CN201310062932.4A CN103215013B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
EP10010520.4A EP2277970B1 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant compositions
EP08011766.6A EP2009075B1 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant compositions
ES08011766.6T ES2546024T3 (es) 2003-10-27 2004-10-25 Composiciones refrigerantes de alquenos fluorados
SI200432490T SI2277976T1 (sl) 2003-10-27 2004-10-25 Sestavki, ki vsebujejo HFC-1234ZE in mazivo
SI200432481T SI2275509T1 (sl) 2003-10-27 2004-10-25 Uporaba hladilnih sestavkov fluoriranega alkena
CN200480039094.8A CN1898353B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
SI200431900T SI1725628T1 (sl) 2003-10-27 2004-10-25 Hladilni sestavki fluoriniranega alkena
DK10011589.8T DK2277976T3 (da) 2003-10-27 2004-10-25 Sammensætninger omfattende hfc-1234ze og smøremiddel
DK04817445.2T DK1725628T3 (da) 2003-10-27 2004-10-25 Kølemiddelsammensætninger med fluorineret alken
CN201410138211.1A CN103923611B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
JP2006538130A JP2007510039A (ja) 2003-10-27 2004-10-25 フッ素化アルケン冷媒組成物
PL10010521T PL2275509T3 (pl) 2003-10-27 2004-10-25 Zastosowanie kompozycji czynników chłodniczych na bazie fluorowanych alkenów
ES10010520.4T ES2628746T3 (es) 2003-10-27 2004-10-25 Composiciones refrigerantes de alquenos fluorados
PT100105204T PT2277970T (pt) 2003-10-27 2004-10-25 Composições refrigerantes de alquenos fluoretados
CN201410137429.5A CN103923610B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
DE08011766T DE08011766T1 (de) 2003-10-27 2004-10-25 Kühlzusammensetzungen mit fluorinierten Alkenen
PL10011589T PL2277976T3 (pl) 2003-10-27 2004-10-25 Kompozycje zawierające HFC-1234ZE i smar
DK10010521.2T DK2275509T3 (da) 2003-10-27 2004-10-25 Anvendelse af kølemiddelsammensætninger med fluorineret alken
PL10010520T PL2277970T3 (pl) 2003-10-27 2004-10-25 Fluorowane alkenowe kompozycje czynników chłodniczych
ES10010521T ES2748910T3 (es) 2003-10-27 2004-10-25 Uso de composiciones refrigerantes de alquenos fluorados
HUE10010521A HUE046570T2 (hu) 2003-10-27 2004-10-25 Fluorozott alkén hûtõközeg kompozíciók alkalmazása
EP10011589.8A EP2277976B1 (en) 2003-10-27 2004-10-25 Compositions comprising hfc-1234ze and lubricant
KR1020067010510A KR101335360B1 (ko) 2003-10-27 2004-10-25 플루오르화 알켄 냉매 조성물
CN201310572027.3A CN103642461B (zh) 2003-10-27 2004-10-25 氟代烯烃制冷剂组合物
EP04817445A EP1725628B1 (en) 2003-10-27 2004-10-25 Fluorinated alkene refrigerant compositions
ES04817445T ES2385650T3 (es) 2003-10-27 2004-10-25 Composiciones refrigerantes de alquenos fluorados
US11/385,259 US9631129B2 (en) 2002-10-25 2006-03-20 Fluorinated alkene refrigerant compositions
US11/475,605 US9005467B2 (en) 2003-10-27 2006-06-26 Methods of replacing heat transfer fluids
US11/773,959 US20080121837A1 (en) 2003-10-27 2007-07-06 Compositions containing fluorine substituted olefins
US12/426,948 US8033120B2 (en) 2002-10-25 2009-04-20 Compositions and methods containing fluorine substituted olefins
US12/511,954 US20120097885A9 (en) 2003-10-27 2009-07-29 Compositions Containing Difluoromethane and Fluorine Substituted Olefins
US13/394,289 US8962707B2 (en) 2003-10-27 2010-09-08 Monochlorotrifluoropropene compounds and compositions and methods using same
US12/890,143 US20110037016A1 (en) 2003-10-27 2010-09-24 Fluoropropene compounds and compositions and methods using same
JP2013110268A JP2013166962A (ja) 2003-10-27 2013-05-24 フッ素化アルケン冷媒組成物
US14/188,346 US20140166923A1 (en) 2002-10-25 2014-02-24 Compositions containing difluoromethane and fluorine substituted olefins
US14/245,406 US9708537B2 (en) 2002-10-25 2014-04-04 Compositions containing fluorine substituted olefins and methods and systems using same
JP2014119442A JP2014159604A (ja) 2003-10-27 2014-06-10 フッ素化アルケン冷媒組成物
US14/538,335 US9657208B2 (en) 2003-10-27 2014-11-11 Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
US14/630,166 US20150231527A1 (en) 2003-10-27 2015-02-24 Monochlorotrifluoropropene compounds and compositions and methods using same
JP2016038691A JP2016104886A (ja) 2003-10-27 2016-03-01 フッ素化アルケン冷媒組成物
US15/200,268 US20160310922A1 (en) 2003-10-27 2016-07-01 Fluoropropene compounds and compositions and methods using same
US15/367,825 US9988567B2 (en) 2003-10-27 2016-12-02 Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons
US15/389,697 US20170233624A1 (en) 2002-10-25 2016-12-23 Fluorinated alkene refrigerant compositions
US15/419,622 US20170137682A1 (en) 2003-10-27 2017-01-30 Compositions containing difluoromethane and fluorine substituted olefins
US15/490,413 US20180094179A1 (en) 2002-10-25 2017-04-18 Fluorinated alkene refrigerant compositions
JP2017104404A JP2017197753A (ja) 2003-10-27 2017-05-26 フッ素化アルケン冷媒組成物
US15/675,024 US10975007B2 (en) 2002-10-25 2017-08-11 Aerosol compositions containing fluorine substituted olefins and methods and systems using same
US15/711,431 US10781152B2 (en) 2002-10-25 2017-09-21 Heat transfer compositions, methods and systems
US15/889,702 US10435342B2 (en) 2002-10-25 2018-02-06 Heat transfer methods
US15/995,751 US20190136107A1 (en) 2003-10-27 2018-06-01 Azeotrope-Like Compositions of Tetrafluoropropene And Hydrofluorocarbons
US16/051,765 US20190153281A1 (en) 2003-10-27 2018-08-01 Compositions containing difluoromethane and fluorine substituted olefins
JP2018212825A JP2019048996A (ja) 2003-10-27 2018-11-13 フッ素化アルケン冷媒組成物
US16/281,577 US10676656B2 (en) 2003-10-27 2019-02-21 Compositions containing difluoromethane and fluorine substituted olefins
US16/589,770 US20200208034A1 (en) 2002-10-25 2019-10-01 Fluorinated alkene refrigerant compositions
US17/221,314 US20210300846A1 (en) 2002-10-25 2021-04-02 Aerosol compositions containing fluorine substituted olefins and methods and systems using same

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US10/695,212 US20040089839A1 (en) 2002-10-25 2003-10-27 Fluorinated alkene refrigerant compositions

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US10/694,272 Continuation-In-Part US7230146B2 (en) 2002-10-25 2003-10-27 Process for producing fluoropropenes
US10/694,273 Continuation-In-Part US7534366B2 (en) 2002-10-25 2003-10-27 Compositions containing fluorine substituted olefins

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US10/694,272 Continuation-In-Part US7230146B2 (en) 2002-10-25 2003-10-27 Process for producing fluoropropenes
US10/694,263 Continuation-In-Part US7255784B2 (en) 2001-11-30 2003-10-27 Polishing method and electropolishing apparatus
US10/694,273 Continuation-In-Part US7534366B2 (en) 2002-10-25 2003-10-27 Compositions containing fluorine substituted olefins
US10/837,521 Continuation-In-Part US7655610B2 (en) 2003-10-27 2004-04-29 Blowing agent compositions comprising fluorinated olefins and carbon dioxide
US10/837,525 Continuation-In-Part US7279451B2 (en) 2002-10-25 2004-04-29 Compositions containing fluorine substituted olefins
US11/385,259 Continuation US9631129B2 (en) 2002-10-25 2006-03-20 Fluorinated alkene refrigerant compositions
US11/385,259 Continuation-In-Part US9631129B2 (en) 2002-10-25 2006-03-20 Fluorinated alkene refrigerant compositions
US11/475,605 Continuation-In-Part US9005467B2 (en) 2002-10-25 2006-06-26 Methods of replacing heat transfer fluids

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US15/389,697 Abandoned US20170233624A1 (en) 2002-10-25 2016-12-23 Fluorinated alkene refrigerant compositions
US15/490,413 Abandoned US20180094179A1 (en) 2002-10-25 2017-04-18 Fluorinated alkene refrigerant compositions
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US15/490,413 Abandoned US20180094179A1 (en) 2002-10-25 2017-04-18 Fluorinated alkene refrigerant compositions
US16/589,770 Abandoned US20200208034A1 (en) 2002-10-25 2019-10-01 Fluorinated alkene refrigerant compositions

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