US20080111100A1 - Use of low gwp refrigerants comprising cf3i with stable lubricants - Google Patents

Use of low gwp refrigerants comprising cf3i with stable lubricants Download PDF

Info

Publication number
US20080111100A1
US20080111100A1 US11/937,267 US93726707A US2008111100A1 US 20080111100 A1 US20080111100 A1 US 20080111100A1 US 93726707 A US93726707 A US 93726707A US 2008111100 A1 US2008111100 A1 US 2008111100A1
Authority
US
United States
Prior art keywords
composition
iodocarbon
hydrofluoroalkene
hydrogen atoms
refrigerant
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
US11/937,267
Other languages
English (en)
Inventor
Raymond H. Thomas
Rajiv R. Singh
George J. Samuels
Ian Shankland
David P. Wilson
Roy P. Robinson
Michael Van Der Puy
John L. Welch
Gregory J. Shafer
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
Individual
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 to US11/937,267 priority Critical patent/US20080111100A1/en
Application filed by Individual filed Critical Individual
Priority to PCT/US2007/084515 priority patent/WO2008061083A2/en
Priority to CN201310038914.2A priority patent/CN103173191B/zh
Priority to EP07864326A priority patent/EP2087078A2/en
Priority to CN2007800497667A priority patent/CN101583700B/zh
Priority to JP2009537310A priority patent/JP2010509489A/ja
Assigned to HONEYWELL INTERNATIONAL INC reassignment HONEYWELL INTERNATIONAL INC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HULSE, RYAN, ROBINSON, ROY P., SAMUELS, GEORGE J., SINGH, RAJIV R., SPATZ, MARK W., THOMAS, RAYMOND H., VAN DER PUY, MICHAEL, WELCH, JOHN L., WILSON, DAVID P., SHAFER, GREGORY J., SHANKLAND, IAN
Publication of US20080111100A1 publication Critical patent/US20080111100A1/en
Priority to US13/022,902 priority patent/US9920230B2/en
Priority to US13/419,071 priority patent/US9175201B2/en
Priority to US14/929,916 priority patent/US20160215191A1/en
Priority to US15/896,777 priority patent/US20180171195A1/en
Priority to US16/048,025 priority patent/US20190136108A1/en
Priority to US17/116,381 priority patent/US20210095177A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-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
    • C09K5/02Materials undergoing a change of physical state when used
    • C09K5/04Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041Materials 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
    • C09K5/044Materials 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
    • C09K5/045Materials 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10Components
    • C09K2205/12Hydrocarbons
    • C09K2205/122Halogenated hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/30Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention pertains to heat transfer compositions. More particularly the invention relates to automobile refrigerants comprising a hydrofluoroalkene, an iodocarbon, and at least one lubricant having hydrogen atoms and carbon atoms, wherein no more than 17% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms.
  • compositions containing iodocarbon compounds have been disclosed as being particularly useful as heat transfer fluids.
  • international application PCT/US05/46982 filed Dec. 21, 2005, which is incorporated herein by reference, discloses compositions containing one or more fluoroolefins and the iodocarbon trifluoroiodomethane (CF 3 I) for use as refrigerants in applications such as automotive air conditioning systems.
  • CF 3 I iodocarbon trifluoroiodomethane
  • compositions comprising iodinated compounds and in particular compositions comprising trifluoroiodomethane, are that such compositions may be used as replacements for various other chlorinated and/or fluorinated compounds which have previously been used widely in refrigeration applications but which have tended to cause potential environmental damage as a result of such use.
  • iodinated compounds such as trifluoroiodomethane, tend to be relatively unstable, and often significantly less stable than certain CFCs, HCFCs and HFCs, especially under conditions that tend to occur in heat transfer systems in general and in refrigeration/air conditioning systems in particular.
  • compositions containing iodocarbons, and in particular CF 3 I can have substantial advantages when used in heat transfer applications, the use of such compositions presents heretofore unencountered and/or unrecognized problems.
  • compositions comprising iodocarbons particularly compositions which comprise fluorinated olefins and iodocarbons, are frequently involved in a relatively complex chemical system under conditions of use, particularly as heat transfer fluids, that can cause unexpected results.
  • the refrigerant which comprises iodocarbon, such as CF 3 I results in such a compound being exposed to certain of the metallic components of the refrigeration system at temperatures and under other conditions which promote the formation of iodine, iodide ions, organic radicals, and iodine containing inorganic acids.
  • the stabilizing agent can contribute to unwanted and/or undesirable reactions in heat transfer systems.
  • Applicants have come to appreciate that the use of refrigerants containing iodocarbons in accordance with conventional techniques, and even the prior techniques described by some of the present inventors in the patent application indicated above, leaves the need in many embodiments for yet further improvements in the refrigerant compositions and/or the refrigeration system.
  • compositions which are suitable for use as heat transfer compositions which comprise a hydrofluoroalkene, an iodocarbon, and at least one lubricant having hydrogen atoms and carbon atoms, wherein no more than 17% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms.
  • the invention provides a composition comprising a composition comprising a hydrofluoroalkene, an iodocarbon, and at least one lubricant having hydrogen atoms and carbon atoms, wherein no more than 17% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms.
  • the composition first comprises a hydrofluoroalkene.
  • Useful hydrofluoroalkene especially for use in connection with heat transfer applications such as automotive air conditioning systems include C 2 -C 5 hydrofluoroalkenes, preferably C 2 -C 4 hydrofluoroalkenes, and more preferably C 2 -C 4 hydrofluoroalkene with at least two, and preferably at least three fluorine substituents.
  • hydrofluoroalkenes are tetrafluoroalkenes and pentafluoroalkenes such as tetrafluoropropenes and pentafluoropropenes, particularly 1,1,1,2-tetrafluoropropene (HFO-1234yf); trans-1,3,3,3-tetrafluoropropene (trans-HFO-1234ze); 1,1,3,3,3-pentafluoropropene, (HFO 1225zc) and 1,2,3,3,3-pentafluoropropene (HFO-1225ye).
  • the composition comprises from about 60% to about 80% by weight of C 2 -C 4 hydrofluoroalkene, and even more preferably from about 65% to about 75% of hydrofluoroalkene, based on the total weight of the composition.
  • the composition then contains an iodocarbon.
  • an iodocarbon Of particular use are C 1 -C 6 iodocarbons, preferably a C 1 -C 3 iodofluorocarbon, and more preferably C 1 -C 2 iodocarbons.
  • the iodocarbon comprises an iodofluorocarbon such as trifluoroiodomethane (CF 3 I), that are surprisingly stable and can be used advantageously in a variety of applications, including as refrigerants in various cooling systems such as automobile air conditioning systems.
  • CF 3 I trifluoroiodomethane
  • compositions of the present invention are stable and suitable for use in many systems, apparatus and methods.
  • one aspect of the present invention provides systems, apparatus and methods that comprise the compositions of the present invention being included as a heating or cooling fluid (based on latent heat transfer and/or sensible heat transfer), such as in refrigeration applications, including particularly automotive air conditioning applications.
  • Trifluoroiodomethane is readily available from a variety of commercial sources, including Matheson TriGas, Inc.
  • trifluoroiodomethane prepared via any of a variety of conventional methods may be used.
  • An example of one such conventional method of preparing trifluoroiodomethane is disclosed in JACS 72, 3806 (1950), “The Degradation of Silver Trifluoroacetate to Trifluoroiodomethane” by Albert L. Henne and William G. Finnegan, which is incorporated herein by reference.
  • the iodocarbon compounds may be present in the compositions in widely ranging amounts, depending on numerous factors, including for example the particular intended conditions of use of the compound.
  • the iodocarbon compound is usually present in the present composition in amounts, based on weight, of from about 10% to less than about 100%, preferably from about 20% to less than about 100%, more preferably from about 15% to about 50%, still more preferably from about 20% to about 40%, and even more preferably from about 25% to about 35%.
  • the iodocarbon compounds is present in the present composition in amounts, based on weight, of from about 35% to about 95%, more preferably from about 45% to about 95%, and more preferably from about 65% to about 95%.
  • the composition then contains a at least one lubricant having hydrogen atoms and carbon atoms, wherein no more than 17% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms.
  • the lubricant has less than 1% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms, and more preferably has no tertiary hydrogen atoms, that is wherein about 0% of the total number of hydrogen atoms which are attached to a carbon atom are tertiary hydrogen atoms. It preferably also has a relatively low percentage of oxygen, and preferably no oxygen in the molecule.
  • a lubricant or oil having little inherent concentration of polar solvent, particularly water is also generally preferred.
  • An important requirement for the lubricant is that there must be enough lubricant returning to the compressor of the system such that the compressor is lubricated.
  • suitability of the lubricant is determined partly by the refrigerant/lubricant characteristics and partly by the system characteristics.
  • suitable lubricants include mineral oil, alkyl benzenes, including polyalkylene glycols, polyvinyl ethers (PVEs), and the like.
  • Preferred lubricants include a naphthenic mineral oil, a paraffinic mineral oil, an ester oil, a polyalkylene glycol, a polyvinyl ether, an alkyl benzene, a polyalphaolefin, a polyester, a polyol ester, or combinations thereof.
  • Mineral oil which comprises paraffin oil or naphthenic oil, is commercially available.
  • Commercially available mineral oils include Witco LP 250 (registered trademark) from Witco, Zerol 300 (registered trademark) from Scheve Chemical, Sunisco 3GS from Witco, and Calumet R015 from Calumet.
  • Commercially available alkyl benzene lubricants include Zerol 150 (registered trademark).
  • 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. Such combination may therefore be advantageous.
  • 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. Mixtures of different lubricants may be used.
  • a lubricant comprising in major proportion by weight, and even more preferably at least about 75% by weight of alkyl benzene-based compounds, mineral oil compounds, and combinations of these.
  • alkyl benzene applicants have found that such compounds are preferred from among the numerous other lubricant compounds which have heretofore been available due to the relatively high level of miscibility in the preferred refrigerant compositions and the relatively high level of stability that such molecules exhibit in the heat transfer compositions and the heat transfer systems of the present invention.
  • Another preferred molecule for use in connection with the present invention is referred to herein, by way of convenience but not by way of limitation, as ethylene oxide/propylene oxide (EO/PO) molecules.
  • EO/PO ethylene oxide/propylene oxide
  • EO/PO molecules which are also referred to herein as “dual capped EO/PO molecules” due to the presence of the methyl radical on each end of the molecule, or alternatively other relatively low chain length alkyl group” can provide the ability to adjust, to suit each particular application, the n and the m values.
  • a lubricant molecule can be selected to achieve a highly advantageous combination of miscibility and stability.
  • U.S. Pat. No. 4,975,212 which is incorporated herein by reference, discloses techniques for capping molecules of this type. Although it is not generally preferred, is also possible to combine the preferred lubricants of the present invention with one or more conventional lubricants.
  • Suitable polyol ester lubricants suitable for air conditioning or refrigeration use are typically prepared by the condensation of a poly alcohol or polyol compound such as pentaerythritol, dipentaerythritol, neopentyl glycol or trimethylpropanol with either pure or mixed, linear or branched aliphatic carboxylic acids such as a linear or branched monocarboxylic acid having from about 4 to about 10 carbon atoms.
  • Polyol ester base stocks polyols are available from Hatco Corporation. For example Hatcol 3307 is a pure polyol ester basestock based on neopentyl glycol.
  • Hatcol 3329 and Hatcol 3504 are a pure polyol ester refrigeration base stocks based on pentaerythritol mixed fatty acids esters.
  • Hatcol 3316 is a polyol ester of dipentaerythritol and short chain fatty acids.
  • Other examples of such polyol ester lubricant formulations include the Cognis ProEcOTM line of Polyol ester refrigeration lubricants, ICI's EMKARATE RL line of polyol esters, as well as polyol ester lubricants provided by Lubrizol subsidiary CPI Engineering Services, Inc. such as Solest.
  • Preferred compositions according to the invention include a lubricant in amounts of from about 20 wt. % to about 50 wt. %, preferably from about 20 wt. %to about 30 wt. % by weight of the composition.
  • compositions may include additionally stabilizers, such as but not limited to phenols, epoxides, phosphites and phosphates, and combinations of these, which are disclosed in co-pending U.S. patent application Ser. No. 11/109,575 filed Apr. 18, 2005, which is incorporated herein by reference.
  • stabilizers such as but not limited to phenols, epoxides, phosphites and phosphates, and combinations of these, which are disclosed in co-pending U.S. patent application Ser. No. 11/109,575 filed Apr. 18, 2005, which is incorporated herein by reference.
  • aromatic epoxides and fluorinated alkyl epoxides are preferred additional stabilizers.
  • phenol compounds are suitable for use as optional stabilizer in the present compositions. While applicants do not wish to be bound by or to any theory of operation, it is believed that the present phenols act as radical scavengers in the present compositions and thereby tend to increase the stability of such compositions.
  • phenol compound refers generally to any substituted or unsubstituted phenol.
  • Suitable phenol compounds include 4,4′-methylenebis(2,6-di-tert-butylphenol); 4,4′-bis(2,6-di-tert-butylphenol); 2,2- or 4,4-biphenyldiols including 4,4′-bis(2-methyl-6-tert-butylphenol); derivatives of 2,2- or 4,4-biphenyldiols; 2,2′-methylenebis(4-ethyl-6-tertbutylpheol); 2,2′-methylenebis(4-methyl-6-tert-butylphenol); 4,4,-butylidenebis(3-methyl-6-tert-butylphenol); 4,4,-isopropylidenebis(2,6-di-tert-butylphenol); 2,2′-methylenebis(4-methyl-6-nonylphenol); 2,2′-isobutylidenebis(4,6-dimethylphenol); 2,2′-methylenebis(4-methyl-6-cyclo
  • Suitable phenols include tocopherol, hydroquinone; t-butyl hydroquinone; and other derivatives of hydroquinone; and the like.
  • Certain preferred phenols include tocopherol, BHT, hydroquinone and the like.
  • Certain particularly preferred phenols include tocopherol and the like.
  • Most phenols are commercially available such as the Irganox compounds from Ciba. A single phenol compound and/or mixtures of two or more phenols may be used in the present compositions.
  • epoxides are suitable for use in the compositions of the present invention. While applicants do not wish to be bound by or to any theory of operation, it is believed that the epoxides of the present invention act as acid scavengers in the CF 3 I compositions and thereby tend to increase the stability of such compositions.
  • suitable aromatic epoxides include those defined by the Formula I below:
  • R is hydrogen, alkyl, fluoroalkyl, aryl, fluoroaryl, or
  • Ar is a substituted or unsubstituted phenylene or naphthylene moiety.
  • Certain preferred aromatic epoxides of Formula I include: butylphenylglycidyl ether; pentylphenylglycidyl ether; hexylphenylglycidyl ether; heptylphenylglycidyl ether; octylphenylglycidyl ether; nonylphenylglycidyl ether; decylphenylglycidyl ether; glycidyl methyl phenyl ether; 1,4-diglycidyl phenyl diether and derivatives thereof; 1,4-diglycidyl naphthyl diether and derivatives thereof; and 2,2′[[[5-heptadecafluorooctyl]1,3phenylene]bis[[2,2,2trifluorome thyl]ethylidene]
  • aromatic epoxides include naphthyl glycidyl ether, 4-methoxyphenyl glycidyl ether, and derivatives of naphthyl glycidyl ether; and the like. Certain more preferred aromatic epoxides include butylphenyl glycidyl ether, and the like. A single aromatic epoxide and/or mixtures of two or more aromatic epoxides may be used in the present compositions.
  • alkyl and/or alkenyl epoxides are suitable for use in the present compositions.
  • suitable alkyl and alkenyl epoxides include those of Formula II:
  • R alk is a substituted or unsubstituted alkyl or alkenyl group.
  • R alk is a substituted or unsubstituted alkyl or alkenyl group having from about 1 to about 10 carbon atoms, more preferably from about 1 to about 6 carbon atoms.
  • Certain preferred alkyl epoxides of Formula II include n-butyl glycidyl ether, isobutyl glycidyl ether, hexanediol diglycidyl ether, and the like, as well as, fluorinated and perfluorinated alkyl epoxides.
  • More preferred alkyl epoxides include hexanediol diglycidyl ether.
  • Certain preferred alkenyl epoxides of Formula II include allyl glycidyl ether, fluorinated and perfluorinated alkenyl epoxides, and the like. More preferred alkenyl epoxides include allyl glycidyl ether and the like.
  • composition may optionally contain additional components. These may include:
  • Hydrocarbons substituted and un-substituted, particularly C 2 -C 6 hydrocarbons
  • Alcohols substituted and un-substituted, particularly C 2 -C 6 alcohols
  • Ketones substituted and un-substituted, particularly C 2 -C 5 ketones
  • Aldehydes substituted and un-substituted, particularly C 2 -C 5 aldehydes
  • Ethers/Diethers substituted and un-substituted, particularly C 2 -C 5 ethers
  • Fluoroethers substituted and un-substituted, particularly C 2 -C 5 fluoroethers
  • Fluoroalkenes (substituted and un-substituted, particularly C 2 -C 6 fluoroalkenes);
  • HFC particularly C 2 -C 5 HFCs
  • HCC particularly C 2 -C 5 HCCs
  • Haloalkenes including preferably fluoroalkenes (substituted and un-substituted, particularly C 2 -C 6 fluoroalkenes);
  • HBrFO (particularly C 2 -C 5 HBrFOs).
  • the composition may optionally further comprises one or more hydrofluorocarbons.
  • Preferred hydrofluorocarbons comprise a C 1 -C 4 hydrofluorocarbon, preferably C 1 -C 3 hydrofluorocarbon, and even more preferably C 1 -C 2 hydrofluorocarbon.
  • Preferred hydrofluorocarbons include hydrofluoroalkane such as pentafluoroethane, 1,1,1,2-tetrafluoroethane, trifluorethane or combinations thereof.
  • a hydrofluorocarbon is employed It is preferably present in the overall composition in an amount of from about 1% to about 50% and more preferably from about 5% to about 35% of hydrofluorocarbon, based on the total weight of the composition.
  • HFO means compounds that consist of atoms of carbon, fluorine and hydrogen, and no other atoms, and in which there is at least one carbon-carbon double bond
  • HClFO means compounds that consist of atoms of carbon, chlorine, fluorine and hydrogen, and no other atoms, and in which there is at least one carbon-carbon double bond
  • HBrFO means compounds that consist of atoms of carbon, bromine, fluorine and hydrogen, and no other atoms, and in which there is at least one carbon-carbon double bond
  • the designations C 2 -C 5 and like usages refer to compounds having at least one carbon atom and up to about five carbon atoms, etc.
  • HFC-32 difluoromethane
  • HFC-125 pentafluoroethane
  • HFC-134 1,1,2,2-tetrafluoroethane
  • HFC-134a 1,1,1,2-tetrafluoroethane
  • HFC-143a trifluorethane
  • difluoroethane (HFC-152a) 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea); 1,1,1,3,3,3-hexafluoropropane (HFC-236fa); 1,1,1,3,3-pentafluoropropane (HFC-245fa); and 1,1,1,3,3-pentafluorobutane (HFC-365mfc).
  • compositions comprise one or more C 3 or C 4 fluoroalkenes, preferably compounds having the formula as follows:
  • X is a C 2 or a C 3 unsaturated, substituted or unsubstituted, alkyl radical, each R is independently Cl, F, Br, I or H, and z is 1 to 3.
  • fluoroethenes, fluorpropenes; fluorobutenes; chlorofluorethenes; chlorofluoropropenes; and chlorofluorobutenes are particularly preferred among the following compounds: fluoroethenes, fluorpropenes; fluorobutenes; chlorofluorethenes; chlorofluoropropenes; and chlorofluorobutenes.
  • composition then optionally contains a compound comprising trifluoromethane, methyl iodide, heptafluorobutane or propene.
  • a compound comprising trifluoromethane, methyl iodide, heptafluorobutane or propene.
  • the latter is usually present in an amount of from greater than zero to about 1% by weight of the composition, more usually from about 0.01% to about 1% by weight of the composition.
  • compositions of the present invention are believed to be adaptable for use in many of such systems, either with or without system modification.
  • the compositions of the present invention may provide an advantage as a replacement in systems, which are currently based on refrigerants having a relatively high capacity.
  • embodiments where it is desired to use a lower capacity refrigerant composition of the present invention for reasons of cost for example, to replace a refrigerant of higher capacity, such embodiments of the present compositions provide a potential advantage.
  • compositions of the present invention particularly compositions comprising a substantial proportion of, and in some embodiments comprising a major proportion of HFO-1234yf, as a replacement for existing refrigerants, such as HFC-134a.
  • the refrigerants of the present invention potentially permit the beneficial use of larger displacement compressors, thereby resulting in better energy efficiency than other refrigerants, such as HFC-134a. Therefore the refrigerant compositions of the present invention, particularly compositions comprising HFO-1234yf, provide the possibility of achieving a competitive advantage on an energy basis for refrigerant replacement applications.
  • the present methods, systems and compositions are thus adaptable for use in connection with automotive air conditioning systems and devices, commercial refrigeration systems and devices, chillers, residential refrigerator and freezers, general air conditioning systems, heat pumps, ORCs, CRCs and the like.
  • 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, preferably by changing the phase of the composition and/or by sensible heat transfer.
  • the present methods provide cooling by absorbing heat from a fluid or article, 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 temperature, high pressure vapor at least a portion of the heat added by the evaporation and compression steps.
  • 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.
  • 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. Such methods, as mentioned hereinbefore, frequently are reverse cycles to the refrigeration cycle described above.
  • the present compositions have a Global Warming Potential (GWP) of not greater than about 1000, more preferably not greater than about 500, and even more preferably not greater than about 150, and in certain cases of not greater than about 100. In certain embodiments, the GWP of the present compositions is not greater than about 75.
  • GWP Global Warming Potential
  • “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.
  • compositions preferably also having an Ozone Depleting Potential (ODP) of not greater than about 0.05, more preferably not greater than about 0.02 and even more preferably about zero.
  • ODP Ozone Depleting Potential
  • “ODP” is 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 invention also provides a heat transfer system comprising:
  • the invention also contemplates a method of transferring heat to or from a fluid or body comprising contacting the fluid or body with a heat transfer composition comprising the above composition.
  • the invention further contemplates a method of replacing an existing refrigerant contained in a refrigerant system comprising replacing at least a portion of said existing refrigerant from said system and replacing at least a portion of said existing refrigerant by introducing into said system a refrigerant composition comprising the above composition.
  • a standard test used by the industry for evaluation of thermal stability of refrigeration systems is the Sealed Tube Stability Test (ASHRAE 97-99).
  • refrigerant and lubricant typically in the weight ratio of 1:1, are sealed into an evacuated glass tube containing samples of selected metals, copper, steel, and aluminum immersed in the liquid.
  • the tube is then maintained at 175° C. for 14 days, cooled, and the contents removed for analysis.
  • the refrigerant is analyzed by gas chromatography for degradation; the lubricating oil is analyzed for changes in total acid number, TAN, and the presence of metals and halide ions; and the metal samples are evaluated for corrosion.
  • This accelerated test simulates the interaction between the lubricant and the refrigerant in the presence of the mixed metals of construction. A good refrigeration lubricant will not cause degradation of the refrigerant or corrosion of the metals.
  • Lubricant Property “Di-capped”PAG Mineral Oil Alkyl Benzene Change in TAN 13.7 0.4 0.2 Iodide (ppm) 2020 ⁇ 5 ⁇ 5 Fluoride (ppm) 2801 7.0 3.7 Color Dark Clear Very Pale Yellow

Landscapes

  • 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)
US11/937,267 2004-12-21 2007-11-08 Use of low gwp refrigerants comprising cf3i with stable lubricants Abandoned US20080111100A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US11/937,267 US20080111100A1 (en) 2006-11-14 2007-11-08 Use of low gwp refrigerants comprising cf3i with stable lubricants
PCT/US2007/084515 WO2008061083A2 (en) 2006-11-14 2007-11-13 Use of low gwp refrigerants comprising cf3i with stable lubricants
CN201310038914.2A CN103173191B (zh) 2006-11-14 2007-11-13 包含cf3i以及稳定润滑剂的低gwp制冷剂的用途
EP07864326A EP2087078A2 (en) 2006-11-14 2007-11-13 Use of low gwp refrigerants comprising cf3i with stable lubricants
CN2007800497667A CN101583700B (zh) 2006-11-14 2007-11-13 包含cf3i以及稳定润滑剂的低gwp制冷剂的用途
JP2009537310A JP2010509489A (ja) 2006-11-14 2007-11-13 安定な潤滑剤とともにcf3iを含む低地球温暖化係数の冷媒の使用
US13/022,902 US9920230B2 (en) 2004-12-21 2011-02-08 Use of low GWP refrigerants comprising CF3I with stable lubricants
US13/419,071 US9175201B2 (en) 2004-12-21 2012-03-13 Stabilized iodocarbon compositions
US14/929,916 US20160215191A1 (en) 2004-12-21 2015-11-02 Stabilized iodocarbon compositions
US15/896,777 US20180171195A1 (en) 2004-12-21 2018-02-14 Use of low gwp refrigerants comprising cf3i with stable lubricants
US16/048,025 US20190136108A1 (en) 2004-12-21 2018-07-27 Stabilized iodocarbon compositions
US17/116,381 US20210095177A1 (en) 2004-12-21 2020-12-09 Stabilized iodocarbon compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86565906P 2006-11-14 2006-11-14
US11/937,267 US20080111100A1 (en) 2006-11-14 2007-11-08 Use of low gwp refrigerants comprising cf3i with stable lubricants

Related Parent Applications (4)

Application Number Title Priority Date Filing Date
PCT/US2005/046982 Continuation-In-Part WO2006069362A2 (en) 2004-12-21 2005-12-21 Stabilized iodocarbon compositions
US11/795,779 Continuation-In-Part US20080157022A1 (en) 2004-12-21 2005-12-21 Stabilized Iodocarbon Compositions
US79577908A Continuation-In-Part 2004-12-21 2008-03-10
US14/929,916 Continuation US20160215191A1 (en) 2004-12-21 2015-11-02 Stabilized iodocarbon compositions

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US79577908A Continuation 2004-12-21 2008-03-10
US13/022,902 Continuation US9920230B2 (en) 2004-12-21 2011-02-08 Use of low GWP refrigerants comprising CF3I with stable lubricants

Publications (1)

Publication Number Publication Date
US20080111100A1 true US20080111100A1 (en) 2008-05-15

Family

ID=39368344

Family Applications (3)

Application Number Title Priority Date Filing Date
US11/937,267 Abandoned US20080111100A1 (en) 2004-12-21 2007-11-08 Use of low gwp refrigerants comprising cf3i with stable lubricants
US13/022,902 Expired - Lifetime US9920230B2 (en) 2004-12-21 2011-02-08 Use of low GWP refrigerants comprising CF3I with stable lubricants
US15/896,777 Abandoned US20180171195A1 (en) 2004-12-21 2018-02-14 Use of low gwp refrigerants comprising cf3i with stable lubricants

Family Applications After (2)

Application Number Title Priority Date Filing Date
US13/022,902 Expired - Lifetime US9920230B2 (en) 2004-12-21 2011-02-08 Use of low GWP refrigerants comprising CF3I with stable lubricants
US15/896,777 Abandoned US20180171195A1 (en) 2004-12-21 2018-02-14 Use of low gwp refrigerants comprising cf3i with stable lubricants

Country Status (5)

Country Link
US (3) US20080111100A1 (enExample)
EP (1) EP2087078A2 (enExample)
JP (1) JP2010509489A (enExample)
CN (2) CN103173191B (enExample)
WO (1) WO2008061083A2 (enExample)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100012882A1 (en) * 2008-07-16 2010-01-21 Sherman John W Refrigerant compositions including silyl terminated polyalkylene glycols as lubricants and methods for making the same
US20100038582A1 (en) * 2007-02-27 2010-02-18 Yuji Shimomura Refrigerator oil and working fluid composition for refrigerator
US20100154419A1 (en) * 2008-12-19 2010-06-24 E. I. Du Pont De Nemours And Company Absorption power cycle system
WO2011048722A1 (ja) * 2009-10-19 2011-04-28 パナソニック株式会社 空気調和機及び空気調和機の設置方法
US20130099154A1 (en) * 2010-07-06 2013-04-25 Beatrice Boussand Compositions of tetrafluoropene and polyol ester lubricants
US8715521B2 (en) 2005-02-04 2014-05-06 E I Du Pont De Nemours And Company Absorption cycle utilizing ionic liquid as working fluid
EP2743325A3 (en) * 2009-02-26 2014-09-10 Daikin Industries, Ltd. Method for evaluating a refrigerant composition comprising hydrofluoropropene with low global warming potential
US8992793B2 (en) 2009-02-04 2015-03-31 Panasonic Intellectual Property Management Co., Ltd. Refrigeration apparatus
US9347446B2 (en) 2013-04-17 2016-05-24 Mitsubishi Electric Corporation Refrigerant compressor including a polymerization inhibitor contained therein
US9435575B2 (en) * 2014-06-26 2016-09-06 Hudson Technologies, Inc. System and method for retrofitting a refrigeration systems from HCFC to HFC refrigerant
EP2989187A4 (en) * 2013-04-22 2016-12-21 Basf Se SEALING COMPATIBILITY ADDITIVE FOR IMPROVING THE FLUORPOLYMER SEALING COMPATIBILITY OF LUBRICANT COMPOSITIONS
EP2342302B1 (fr) 2008-11-03 2017-04-26 Arkema France Procede de chauffage et/ou climatisation d'un vehicule
US10066186B2 (en) 2013-04-22 2018-09-04 Basf Se Lubricating oil compositions containing a halide seal compatibility additive and a second seal compatibility additive

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190136108A1 (en) * 2004-12-21 2019-05-09 Honeywell International Inc. Stabilized iodocarbon compositions
JP5226242B2 (ja) * 2007-04-18 2013-07-03 出光興産株式会社 冷凍機用潤滑油組成物
JP5669343B2 (ja) * 2008-06-16 2015-02-12 三菱電機株式会社 冷凍サイクル装置
JP2010024410A (ja) 2008-07-24 2010-02-04 Sanden Corp 冷凍回路
FR2941890B1 (fr) * 2009-02-09 2011-09-09 Valeo Systemes Thermiques Dispositif de stockage presentant un moyen destine a provoquer des turbulences.
EP2531785B1 (en) * 2010-02-01 2017-01-11 Panasonic Corporation Refrigeration apparatus
IT1406472B1 (it) 2010-12-22 2014-02-28 Nuovo Pignone Spa Prova per similitudine di prestazione di compressore
CN104592943B (zh) * 2014-12-24 2018-03-27 巨化集团技术中心 一种含氟碘代烃组合物的制备方法
CN106705472A (zh) * 2015-07-24 2017-05-24 珠海格力节能环保制冷技术研究中心有限公司 工作介质及应用其的制冷装置
US11162720B2 (en) * 2015-08-11 2021-11-02 Trane International Inc. Refrigerant recovery and repurposing
JP7060287B2 (ja) * 2017-08-08 2022-04-26 出光興産株式会社 冷凍機油組成物
TWI843706B (zh) * 2017-09-19 2024-06-01 美商哈尼威爾國際公司 傳熱方法、系統和組成物
FR3082841B1 (fr) 2018-06-25 2021-01-08 Arkema France Stabilisation du trifluoroiodomethane
CN118048126A (zh) * 2018-12-31 2024-05-17 霍尼韦尔国际公司 经稳定的热传递组合物、方法和系统
US11945989B2 (en) 2019-03-04 2024-04-02 The Chemours Company Fc, Llc Heat transfer compositions comprising R-1225ye(E), HFO-1234yF, R-32, R-125 and CO2
JP7094443B2 (ja) * 2019-04-02 2022-07-01 三菱電機株式会社 熱源側ユニットおよび冷凍サイクル装置
CN110878194B (zh) * 2019-10-16 2020-11-17 珠海格力电器股份有限公司 一种含r13i1的环保混合制冷剂及换热系统
MX2022006623A (es) 2019-12-12 2022-06-27 Chemours Co Fc Llc Composiciones refrigerantes que comprenden difluorometano (r-32), 1,1,1,2-tetrafluoroetano (r-134a) y trifluoroyodometano (cf3i).
US11883706B2 (en) 2020-02-14 2024-01-30 Kidde Technologies, Inc. Fire suppression blends of CF31 and 2-BTP
US12415108B2 (en) 2020-02-14 2025-09-16 Kidde Technologies, Inc. Fire suppression blends of CF3I, HCFOs and CO2
CN113388372A (zh) * 2021-07-12 2021-09-14 国节新辉科技(浙江)有限公司 一种替代r410的制冷剂及其制备方法和应用、制冷设备

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183661B1 (en) * 1989-10-25 2001-02-06 Imperial Chemical Industries Plc Composition comprising a hydrofluoroalkane or hydrochlorofluoroalkane and a polyether lubricant
US20050233934A1 (en) * 2004-04-16 2005-10-20 Honeywell International, Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE536296A (enExample) 1954-03-22
BE538608A (enExample) 1954-06-10
US2846458A (en) 1956-05-23 1958-08-05 Dow Corning Organosiloxane ethers
US2889379A (en) 1957-02-06 1959-06-02 Dow Chemical Co Preparation of 3, 3, 3-trifluoropropene
NL121693C (enExample) 1959-05-22
GB1587907A (en) 1976-12-23 1981-04-15 Hercules Inc Perfumed fluorocarbon compositions
US4465786A (en) 1982-09-27 1984-08-14 General Electric Company Catalyst composition for the preparation of 3,3,3-trifluoropropene
US4755316A (en) 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
US4798818A (en) 1987-11-27 1989-01-17 Dow Corning Corporation Catalyst composition and process for its preparation
ES2152282T3 (es) * 1988-12-06 2001-02-01 Idemitsu Kosan Co Aceite lubricante para refrigerador por compresion.
AU1665392A (en) 1991-04-05 1992-11-02 Allied-Signal Inc. Stabilized dichlorotrifluoroethane refrigeration compositions
JPH04323294A (ja) 1991-04-22 1992-11-12 Daikin Ind Ltd 熱伝達用流体
DE4116274C2 (de) 1991-05-17 1998-03-19 Forschungszentrum Fuer Kaeltet Kältemittel
US5611210A (en) 1993-03-05 1997-03-18 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
DE69506550D1 (de) 1994-07-14 1999-01-21 Du Pont Kühlzusammensetzungen
JPH08277389A (ja) 1995-04-06 1996-10-22 Matsushita Electric Ind Co Ltd 混合作動流体およびそれを用いたヒートポンプ装置
JPH0959612A (ja) 1995-08-30 1997-03-04 Matsushita Electric Ind Co Ltd トリフルオロイオドメタンを含む混合作動流体およびそれを用いた冷凍サイクル装置
JPH09111230A (ja) 1995-10-13 1997-04-28 Matsushita Electric Ind Co Ltd トリフルオロイオドメタンを含む混合作動流体およびそれを用いた冷凍サイクル装置
WO1997015637A1 (en) 1995-10-20 1997-05-01 Tsinghua University Refrigerant
US6086782A (en) 1996-07-02 2000-07-11 Advanced Fluid Technologies, Inc. Heat transfer fluid compositions for low temperature applications
TW492999B (en) 1997-01-31 2002-07-01 Showa Denko Kk Process for preparing mixed cooling-media
US6270689B1 (en) 1998-03-26 2001-08-07 Ikon Corporation Blend compositions of trifluoroiodomethane, tetrafluoroethane and difluoroethane
US6124510A (en) 1998-07-21 2000-09-26 Elf Atochem North America, Inc. 1234ze preparation
AU769440B2 (en) 1998-12-12 2004-01-29 Solvay (Societe Anonyme) Compositions comprising 1,1,1,3,3-pentafluorobutane and use of said compositions
GB9828737D0 (en) 1998-12-29 1999-02-17 Star Refrigeration Vaporisable composition
US6100230A (en) 1999-03-15 2000-08-08 Alliedsignal Inc. Azeotrope-like compositions of pentafluoropropane, hydrocarbons and water
JP2000309789A (ja) 1999-04-26 2000-11-07 Sanyo Electric Co Ltd 着火爆発性のない混合作動流体およびそれを用いた冷凍装置
US6589355B1 (en) 1999-10-29 2003-07-08 Alliedsignal Inc. Cleaning processes using hydrofluorocarbon and/or hydrochlorofluorocarbon compounds
KR20020019682A (ko) 2000-09-06 2002-03-13 권오석 고온용 혼합 냉매 조성물
US6516837B2 (en) 2000-09-27 2003-02-11 Honeywell International Inc. Method of introducing refrigerants into refrigeration systems
DE10056606A1 (de) 2000-11-15 2002-05-23 Solvay Fluor & Derivate Verwendung von Gemischen,die 1,1,1,3,3-Pentafluorbutan enthalten, als Kältemittel oder Wärmerträger
CN106753250A (zh) 2002-10-25 2017-05-31 霍尼韦尔国际公司 含有氟取代烯烃的组合物
US7230146B2 (en) 2003-10-27 2007-06-12 Honeywell International Inc. Process for producing fluoropropenes
KR101150177B1 (ko) * 2004-04-16 2012-05-29 허니웰 인터내셔널 인코포레이티드 테트라플루오로프로펜과 트리플루오로요오드메탄으로 이루어진 공비-성 조성물
US7341984B2 (en) * 2004-04-16 2008-03-11 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane
US7074751B2 (en) * 2004-04-16 2006-07-11 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane
WO2005103189A1 (en) * 2004-04-16 2005-11-03 Honeywell International, Inc. Azeotrope-like compositions of difluoromethane and trifluoroiodomethane
US7413674B2 (en) * 2004-04-16 2008-08-19 Honeywell International Inc. Azeotrope-like trifluoroiodomethane compositions
US20060033072A1 (en) 2004-04-16 2006-02-16 Honeywell International Inc. Stabilized trifluoroiodomethane compositions
KR20070090939A (ko) * 2004-12-21 2007-09-06 허니웰 인터내셔널 인코포레이티드 안정화된 요오드카본 조성물
US20060243944A1 (en) * 2005-03-04 2006-11-02 Minor Barbara H Compositions comprising a fluoroolefin
US8535556B2 (en) * 2006-03-30 2013-09-17 E I Du Pont De Nemours And Company Compositions comprising iodotrifluoromethane and stabilizers
TW200930801A (en) * 2007-10-31 2009-07-16 Du Pont Compositions comprising iodotrifluoromethane and uses thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183661B1 (en) * 1989-10-25 2001-02-06 Imperial Chemical Industries Plc Composition comprising a hydrofluoroalkane or hydrochlorofluoroalkane and a polyether lubricant
US20050233934A1 (en) * 2004-04-16 2005-10-20 Honeywell International, Inc. Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8715521B2 (en) 2005-02-04 2014-05-06 E I Du Pont De Nemours And Company Absorption cycle utilizing ionic liquid as working fluid
US9321948B2 (en) * 2007-02-27 2016-04-26 Nippon Oil Corporation Refrigerator oil and working fluid composition for refrigerator
US20100038582A1 (en) * 2007-02-27 2010-02-18 Yuji Shimomura Refrigerator oil and working fluid composition for refrigerator
US10214671B2 (en) 2007-02-27 2019-02-26 Jx Nippon Oil & Energy Corporation Refrigerator oil and working fluid composition for refrigerator
US20100012882A1 (en) * 2008-07-16 2010-01-21 Sherman John W Refrigerant compositions including silyl terminated polyalkylene glycols as lubricants and methods for making the same
EP2342302B1 (fr) 2008-11-03 2017-04-26 Arkema France Procede de chauffage et/ou climatisation d'un vehicule
US20100154419A1 (en) * 2008-12-19 2010-06-24 E. I. Du Pont De Nemours And Company Absorption power cycle system
US8992793B2 (en) 2009-02-04 2015-03-31 Panasonic Intellectual Property Management Co., Ltd. Refrigeration apparatus
EP2743325A3 (en) * 2009-02-26 2014-09-10 Daikin Industries, Ltd. Method for evaluating a refrigerant composition comprising hydrofluoropropene with low global warming potential
EP2492616A4 (en) * 2009-10-19 2015-08-12 Panasonic Corp AIR CONDITIONING AND METHOD FOR INSTALLING AN AIR-CONDITIONING SYSTEM
WO2011048722A1 (ja) * 2009-10-19 2011-04-28 パナソニック株式会社 空気調和機及び空気調和機の設置方法
US10132541B2 (en) 2009-10-19 2018-11-20 Panasonic Intellectual Property Management Co., Ltd. Air conditioner and installing method of the air conditioner
US20130099154A1 (en) * 2010-07-06 2013-04-25 Beatrice Boussand Compositions of tetrafluoropene and polyol ester lubricants
US9347446B2 (en) 2013-04-17 2016-05-24 Mitsubishi Electric Corporation Refrigerant compressor including a polymerization inhibitor contained therein
US10066186B2 (en) 2013-04-22 2018-09-04 Basf Se Lubricating oil compositions containing a halide seal compatibility additive and a second seal compatibility additive
US10106759B2 (en) 2013-04-22 2018-10-23 Basf Se Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions
EP2989187A4 (en) * 2013-04-22 2016-12-21 Basf Se SEALING COMPATIBILITY ADDITIVE FOR IMPROVING THE FLUORPOLYMER SEALING COMPATIBILITY OF LUBRICANT COMPOSITIONS
US20170131009A1 (en) * 2014-06-26 2017-05-11 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from hcfc to hfc refrigerant
US10094603B2 (en) * 2014-06-26 2018-10-09 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant
US9435575B2 (en) * 2014-06-26 2016-09-06 Hudson Technologies, Inc. System and method for retrofitting a refrigeration systems from HCFC to HFC refrigerant

Also Published As

Publication number Publication date
WO2008061083A2 (en) 2008-05-22
US20110126558A1 (en) 2011-06-02
US9920230B2 (en) 2018-03-20
CN103173191B (zh) 2016-04-13
US20180171195A1 (en) 2018-06-21
CN101583700B (zh) 2013-10-30
CN101583700A (zh) 2009-11-18
WO2008061083A3 (en) 2008-09-18
CN103173191A (zh) 2013-06-26
EP2087078A2 (en) 2009-08-12
JP2010509489A (ja) 2010-03-25

Similar Documents

Publication Publication Date Title
US9920230B2 (en) Use of low GWP refrigerants comprising CF3I with stable lubricants
US20080111099A1 (en) Heat transfer compositions with a hydrofluoroalkene, an iodocarbon and additives
US20080157023A1 (en) Fluorocarbon stabilizers
EP1725628B1 (en) Fluorinated alkene refrigerant compositions
CN1965049A (zh) 稳定的三氟碘甲烷组合物
US20060033072A1 (en) Stabilized trifluoroiodomethane compositions
US20080116417A1 (en) Iodine and iodide removal method
US20080110833A1 (en) Iodine removal with activated carbon

Legal Events

Date Code Title Description
AS Assignment

Owner name: HONEYWELL INTERNATIONAL INC, NEW JERSEY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:THOMAS, RAYMOND H.;SINGH, RAJIV R.;SAMUELS, GEORGE J.;AND OTHERS;REEL/FRAME:020400/0502;SIGNING DATES FROM 20070116 TO 20080115

STCB Information on status: application discontinuation

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