WO2022138176A1 - ハイドロハロオレフィン組成物 - Google Patents
ハイドロハロオレフィン組成物 Download PDFInfo
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- WO2022138176A1 WO2022138176A1 PCT/JP2021/045200 JP2021045200W WO2022138176A1 WO 2022138176 A1 WO2022138176 A1 WO 2022138176A1 JP 2021045200 W JP2021045200 W JP 2021045200W WO 2022138176 A1 WO2022138176 A1 WO 2022138176A1
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- WIPO (PCT)
- Prior art keywords
- hydrohaloolefin
- composition
- composition according
- hfo
- hcfo
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 18
- WGGQACQXYLQPKW-UHFFFAOYSA-N 1,1,2,3-tetrafluorobutane Chemical compound CC(F)C(F)C(F)F WGGQACQXYLQPKW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 17
- 239000011347 resin Substances 0.000 claims description 17
- 239000012459 cleaning agent Substances 0.000 claims description 15
- 239000012530 fluid Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000443 aerosol Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000003380 propellant Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- DKSYJUPLFVFPRY-UHFFFAOYSA-N 2,4,4,4-tetrafluorobut-1-ene Chemical compound FC(=C)CC(F)(F)F DKSYJUPLFVFPRY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 239000005555 hypertensive agent Substances 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- GDPWRLVSJWKGPJ-UHFFFAOYSA-N 1-chloro-2,3,3,3-tetrafluoroprop-1-ene Chemical group ClC=C(F)C(F)(F)F GDPWRLVSJWKGPJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000000428 dust Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000014593 oils and fats Nutrition 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
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- 239000003921 oil Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 13
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- 239000006260 foam Substances 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 10
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 7
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 6
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- 239000001257 hydrogen Substances 0.000 description 6
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- 238000000354 decomposition reaction Methods 0.000 description 5
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- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 4
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 4
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- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- -1 fluorocarbons (FCs) Chemical class 0.000 description 4
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- 239000002994 raw material Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 3
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 3
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- WMCLYSGSAJGCJY-UHFFFAOYSA-N 3-chloro-1,1,2,2-tetrafluoropropane Chemical compound FC(F)C(F)(F)CCl WMCLYSGSAJGCJY-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 2
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 2
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 2
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 2
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 2
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 description 2
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 2
- FQAMAOOEZDRHHB-UHFFFAOYSA-N 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl FQAMAOOEZDRHHB-UHFFFAOYSA-N 0.000 description 2
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
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- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 description 2
- JODPGPKOJGDHSV-UHFFFAOYSA-N 1-chloro-1,1,2,3,3,3-hexafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)Cl JODPGPKOJGDHSV-UHFFFAOYSA-N 0.000 description 2
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- DCWQLZUJMHEDKD-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoropropane Chemical compound CC(Cl)(Cl)C(F)(F)F DCWQLZUJMHEDKD-UHFFFAOYSA-N 0.000 description 2
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- JYNCTFQDWJMJDI-UHFFFAOYSA-N 2-chloro-1,1,1,3,3-pentafluoropropane Chemical compound FC(F)C(Cl)C(F)(F)F JYNCTFQDWJMJDI-UHFFFAOYSA-N 0.000 description 2
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- PUFSJRPTJJPPJP-UHFFFAOYSA-N 3-chloro-1,1,1,2,2,3-hexafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)F PUFSJRPTJJPPJP-UHFFFAOYSA-N 0.000 description 2
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- GATVIKZLVQHOMN-UHFFFAOYSA-N Chlorodibromomethane Chemical compound ClC(Br)Br GATVIKZLVQHOMN-UHFFFAOYSA-N 0.000 description 2
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- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000010731 rolling oil Substances 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IHZAEIHJPNTART-UHFFFAOYSA-N tribromofluoromethane Chemical compound FC(Br)(Br)Br IHZAEIHJPNTART-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/048—Boiling liquids as heat transfer materials
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02803—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
- C23G5/02825—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine containing hydrogen
- C23G5/02841—Propanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/56—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances gases
-
- C—CHEMISTRY; METALLURGY
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/10—Objects to be cleaned
- C11D2111/14—Hard surfaces
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
- C11D7/30—Halogenated hydrocarbons
Definitions
- the present disclosure relates to hydrohaloolefin compositions.
- hydrohaloolefins such as hydrofluoroolefins (HFOs) and hydrochlorofluoroolefins (HCFOs), which have low global warming potentials, are expected as alternatives to Freon.
- Hydrohaloolefins may be decomposed over time, and their stability is not sufficient. When acid is generated by decomposition, it may cause corrosion of metal.
- Patent Document 1 a small amount of 1-chloro-2,2,3,3-tetrafluoropropane (HCFC-244ca) is added to 1-chloro-2,3,3-trifluoro-1-propene (HCFO-1233yd).
- Patent Documents 1 and 2 disclose HCFC-244ca or water as a compound that contributes to stability, but further enrichment of technology is required.
- the present disclosure is intended to provide a hydrohaloolefin composition having good stability.
- the disclosure includes the following aspects: [1]
- the main component is hydrohaloolefin, which further contains 1,1,2,3-tetrafluorobutane, and the content of 1,1,2,3-tetrafluorobutane with respect to the total amount of organic compounds.
- the hydrohaloolefin composition is 0.001 to 0.1% by mass.
- the hydrohaloolefin contains 2,4,4,4-tetrafluoro-1-butene, and the 1,1,2,3-tetrafluorobutane and the above 2 are relative to the total amount of the organic compound.
- 4,4,4-The hydrohaloolefin composition of [1] having a total content of tetrafluoro-1-butene of more than 0.001 to 0.4% by mass.
- the application is one or more selected from the group consisting of a working fluid, a foaming agent, a diluting solvent, a detergent, a propellant, a fire extinguishing agent, a gaseous dielectric, an etching gas, and a molten metal cover gas, [1. ] To [4].
- the hydrohaloolefin composition according to [5] which is in the form of an aerosol.
- the cleaning agent is at least one cleaning agent selected from the group consisting of carbon, oils and fats, and dust adhering through them. ..
- the cleaning agent is a cleaning agent for articles made of metal, resin, rubber, glass, ceramics, natural fibers, synthetic fibers, or a composite material having two or more of these materials.
- hydrohaloolefin composition according to [5] wherein the propellant contains at least one selected from the group consisting of a pressor agent and a spray agent.
- the gas dielectric contains at least one selected from the group consisting of a liquefied gas and a compressed gas.
- hydrohaloolefin composition having good stability can be obtained.
- the hydrohaloolefin is a general term for unsaturated hydrocarbon compounds containing a hydrogen atom and one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- the organic compound is a compound containing a carbon atom and is a general term for compounds excluding carbon oxides and metal carbonates.
- the main component of the composition means that the content mass is the largest with respect to the total mass of the composition.
- the abbreviation or alias of the compound may be written in parentheses after the name of the compound. The abbreviation or alias may be used instead of the compound name.
- the hydrohaloolefin composition of the present disclosure (hereinafter, also referred to as the present composition) contains two or more kinds of organic compounds, and the main component is hydrohaloolefin.
- the content of the main component with respect to the total mass of the present composition is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 80% by mass or more, particularly preferably 90% by mass or more, and 99% by mass or more. Is extremely preferable.
- hydrohaloolefin examples include hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), and hydrochloroolefin (HCO).
- HFO hydrofluoroolefin
- HCFO hydrochlorofluoroolefin
- HCO hydrochloroolefin
- the hydrohaloolefin may be used alone or in combination of two or more.
- hydrofluoroolefins as main components include 1,1,2-trifluoroethylene (HFO-1123), 1-fluoropropene (HFO-1261ze), and 1,2-difluoropropene (HFO-).
- hydrochlorofluoroolefin as a main component include 1-chloro-2,3,3,3-tetrafluoropropene (HCFO-1224yd) and 1-chloro-2,3,3-trifluoro.
- HCFO-1233yd 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2-chloro-1,1,3-trifluoropropene (HCFO-1233xc), 2-chloro-1 , 3,3-Trifluoropropene (HCFO-1233xe), 1-chloro-1,2,3-trifluoropropene (HCFO-1233yb), 1-chloro-1,3,3-trifluoropropene (HCFO-1233zb) ), 3-Chloro-1,1,3-trifluoropropene (HCFO-1233zc), 3-chloro-1,3,3-trifluoropropene (HCFO-1233ze), 1-chloro-3,3,3- Trifluoropropene (HCFO-1233zd), 2,3,3-trichloro-3-fluoropropene (HCFO-1231xf), 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf),
- hydrochloroolefin as a main component include chloroethylene and 1,2-dichloroethylene.
- the main component of this composition is preferably hydrochlorofluoroolefin (HCFO), more preferably HCFO-1224yd.
- HCFO-1224yd may be HCFO-1224yd (Z), HCFO-1224yd (E), or a mixture thereof.
- the Z / E ratio representing the mass ratio of the Z-form content and the E-form content in HCFO-1224yd may be 100/0 to 0/100, preferably 99.9 / 0.1 to 50/50. 99.9 / 0.1 to 70/30 is more preferable, and 99.9 / 0.1 to 99.0 / 1.0 is even more preferable.
- This composition contains 1,1,2,3-tetrafluorobutane (HFC-374pee) in addition to the main component hydrohaloolefin.
- the content of HFC-374pee is 0.001 to 0.1% by mass, preferably 0.001 to 0.05% by mass, preferably 0.001 to 0, based on the total mass of the organic compounds in the present composition. 0.01% by mass is more preferable. Within the above range, the stability of the present composition is excellent.
- the hydrohaloolefin may contain 2,4,4,4-tetrafluoro-1-butene (HFO-1354yf), and when it contains HFO-1354yf, it is based on the total mass of the organic compound in the present composition.
- the total content of HFC-374pee and HFO-1354yf is preferably more than 0.001 to 0.4% by mass, more preferably 0.001 to 0.2% by mass, and 0.01 to 0.1% by mass. Is even more preferable. Within the above range, the stability of the present composition is excellent.
- the present composition contains HFO-1354yf, the main component is a hydrohaloolefin other than HFO-1354yf.
- the present composition may contain one or more organic compounds other than the main component hydrohaloolefin (which may contain HFO-1354yf) and HFC-374pee.
- organic compounds include chlorofluoroolefin (CFO), fluoroolefin, chloroolefin, olefin, hydrofluorocarbon (HFC) excluding HFC-374pee, hydrochlorocarbon (HCC), hydrochlorofluorocarbon (HCFC), chlorofluorocarbon ( Examples thereof include CFCs), chlorocarbons, fluorocarbons (FCs), hydrocarbons (HCs), hydrofluoroethers (HFEs), chlorofluoroalkynes, alcohols, ethers, ketones, organic acids, and saturated hydrocarbons.
- methane halide containing at least one selected from the group consisting of a bromine atom and an iodine atom may be contained.
- chlorofluoroolefin examples include 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO-1214ya), 1,1,2-trichloro-2-fluoroethylene, 1, Included are 1,2-trifluoro-2-chloroethylene (HCFO-1113) and 2-chloro-1,1,3,3,3-pentafluoro-1-propene (CFO-1215xc).
- fluoroolefins include hexafluoropropene (FO-1216) and octafluoro-2-butene (FO-1318my).
- chloroolefin examples include tetrachlorethylene.
- olefins include ethylene and propylene.
- hydrofluorocarbons (HFCs) other than HFC-374pee include 1,1,1,3,3-pentafluoropropane (HFC-245fa) and 1,1,1,2,2-pentafluoropropane (HFC).
- hydrochlorocarbon examples include chloroform, 1,1,1,2,3-pentachloropropane (HCC-240db), and 2-chloropropane.
- hydrochlorofluorocarbon examples include chlorodifluoromethane (HCFC-22), chlorofluoromethane (HCFC-31), trichlorodifluoroethane (HCFC-122), 1,1,2-trichloro-1,2-.
- HCFC-122a Difluoroethane
- HCFC-122b 1,1,1-trichloro-2,2-difluoroethane
- HCFC-122b 2,2-dichloro-1,1,1-trifluoroethane
- HCFC-124 2-chloro -1,1,1,2-tetrafluoroethane
- HCFC-124a 2-chloro-1,1,2,2-tetrafluoroethane
- HCFC-124a 2-chloro-1,1,1-tri Fluoroethane
- HCFC-133a 1,1-dichloro-1-fluoroethane
- HCFC-141b 1,1-difluoro-2-chloroethane
- HCFC-142 1-chloro-1,2-difluoroethane (HCFC) -142a)
- chlorofluorocarbon examples include trichlorofluoromethane (CFC-11), dichlorodifluoromethane (CFC-12), chlorotrifluoromethane (CFC-13), trichlorotrifluoroethane (CFC-113), 1, 1,1-Trichloro-2,2,2-trifluoroethane (CFC-113a), 1,2-dichloro-1,1,2,2-tetrafluoroethane (CFC-114), 1,1-dichloro- 1,2,2,2-tetrafluoroethane (CFC-114a), chloropentafluoroethane (CFC-115), dichlorohexafluoropropane (CFC-216), 2,2,3,3-tetrachlorohexafluorobutane (CFC-316) and dichlorooctafluorobutane (CFC-318).
- CFC-11 trichlorofluoromethane
- CFC-12 dichlorodi
- chlorocarbon examples include dichloromethane (methylene chloride) and trichloroethane.
- FC fluorocarbons
- FC-116 1,1,1,2,2,2-hexafluoroethane
- FC-218 octafluoropropane
- FC-227ca 1,1,1,2,2. , 3,3-Heptafluoropropane
- hydrocarbon (HC) examples include methane, ethane, propane, n-butane, isobutane, n-pentane, isopentane, neopentane, cyclopentane, n-hexane, isohexane, and heptane.
- hydrofluoroether examples include CHF 2 -O-CHF 2 , CHF 2 -O-CH 2 F, CH 2 F-O-CH 2 F, CH 2 F-O-CH 3 , and cyclo-.
- chlorofluoroalkynes include 1-chloro-3,3,3-trifluoro-1-propine (CF 3 -C ⁇ CCl).
- alcohol examples include methanol, ethanol, propanol, and isopropanol.
- ethers include dimethyl ether, methyl ethyl ether, diethyl ether, methyl propyl ether, methyl isopropyl ether, ethyl propyl ether, ethyl isopropyl ether, dipropyl ether, diisopropyl ether, dimethoxymethane, diethoxyethane, and dipropoxymethane. And dibutoxymethane.
- ketone examples include ketone, methyl ethyl ketone, methyl isobutyl ketone, and perfluoroethyl isopropyl ketone.
- organic acids include methyl formate, ethyl formate, and formic acid.
- saturated hydrocarbons include methane, ethane, propane, butane, isobutane, pentane, isopentane, cyclopentane, and hexane.
- halogenated methane containing one or more selected from the group consisting of a bromine atom and an iodine atom include (mono) iodomethane (CH 3 I), diiodomethane (CH 2 I 2 ), and dibromomethane (CH 2 Br 2 ). ), Bromomethane (CH 3 Br), dichloromethane (CH 2 Cl 2 ), chloroiodomethane (CH 2 ClI), dibromochloromethane (CHBr 2 Cl), methane iodide (CI 4 ), carbon tetrabromide (CBr).
- bromotrichloromethane CBrCl 3
- dibromodiio dichloromethane CBr 2 Cl 2
- tribromofluoromethane CBr 3 F
- fluorodiiodomethane CHFI 2
- difluorodiiodomethane CF 2 I 2
- Examples thereof include dibromodifluoromethane (CBr 2 F 2 ) and trifluoroiodomethane (CF 3 I).
- the content of the other organic compounds is preferably 1.5% by mass or less, more preferably 1.0% by mass or less, still more preferably 0.5% by mass or less, based on the total mass of the organic compounds in the present composition. ..
- the present composition may contain an inert gas in addition to the organic compound.
- the inert gas include carbon dioxide, nitrogen, oxygen, air (nitrogen: about 80% by volume, oxygen: about 20% by volume), argon, and helium.
- the inert gas may be 20% by volume or less, preferably 15% by volume or less, more preferably 10% by volume or less, and 5% by volume, based on the total volume of the gas phase portion when the present composition is filled in a closed container. The following is more preferable, and 1.5% by volume or less is particularly preferable.
- This composition may contain water in addition to the organic compound.
- the water content may be 200% by mass or less, preferably 150% by mass or less, more preferably 100% by mass, still more preferably 20% by mass, based on the total amount of the organic compounds in the composition.
- the hydrohaloolefin contained in this composition can be produced by a known production method.
- HCFO-1224yd is obtained as an intermediate in the step of reducing CFO-1214ya with hydrogen in the presence of a catalyst (hydrogen reduction reaction) to obtain HFO-1234yf.
- CFO-1214ya which is a raw material, is, for example, a method of using HCFC-225ca as a raw material and reacting with an alkaline aqueous solution such as potassium hydroxide aqueous solution in the presence of a phase transfer catalyst such as tetrabutylammonium bromide, or chromium.
- It can be produced by a method of performing a defluorinated hydrogen reaction by a gas phase reaction in the presence of a catalyst such as iron, copper or activated carbon.
- the reaction solution obtained by the hydrogen reduction reaction was distilled using a usual distillation method or the extraction distillation method described in International Publication No. 2017/146190 to obtain unreacted CFO-1214ya and HFO-1234yf. Separation from HCFO-1224yd gives a purified composition containing HCFO-1224yd at a high concentration. This purified composition may contain by-products produced by the hydrogen reduction reaction.
- the HFC-374pee contained in the present composition may be contained in a purified composition obtained by producing and purifying a hydrohaloolefin, may be added separately, or may be a combination thereof.
- the HFO-1354yf which may be contained in the present composition may be contained in the purified composition of hydrohaloolefin, may be added separately, or may be a combination thereof.
- the type and content of the organic compound contained in the present composition can be analyzed and identified using a GC-MS system.
- the composition containing hydrohaloolefin as a main component contains HFC-374pee
- the decomposition of hydrohaloolefin is suppressed and the stability is improved.
- HFC-374pee has properties as an HFC and also has an action of capturing radicals, although it is not always clear. It is considered that the action acts as a stabilizer that suppresses and stabilizes the decomposition of hydrohaloolefins such as HCFO-1224yd.
- This composition has good stability and can be used for known uses as hydrohaloolefins. Further, the present composition does not easily corrode the metal even if it comes into contact with the metal, and can be applied to applications in which the metal comes into contact with the metal. Examples of applications for this composition include working fluids, foaming agents, diluent solvents, detergents, propellants, fire extinguishing agents, dielectrics, etching gases, and molten metal cover gases.
- the present composition may be used for one kind or two or more kinds.
- the present composition may be used in the form of an aerosol or the like.
- Working fluids using this composition include refrigerants for refrigerating machines, refrigerants for air conditioning equipment, working fluids for power generation systems (waste heat recovery power generation, etc.), working fluids for latent heat transport devices (heat pipes, etc.), secondary cooling media, etc.
- the working fluid for the heat cycle of is exemplified.
- thermoplastic resin foam examples include polycarbonate resin, polystyrene resin, polyphenylene ether resin, acrylonitrile-butadiene-styrene resin, polyolefin resin, polyvinyl chloride resin, (meth) acrylic resin, and polyester resin.
- thermosetting resin foam examples include polyurethane foam, polyisocyanurate foam, and phenol resin foam.
- polyurethane foam include a rigid urethane foam, a soft urethane foam, a semi-rigid urethane foam, and an integral skin foam.
- a lubricant sicone-based lubricant, fluorine-based lubricant, etc.
- a rust preventive mineral oil, synthetic oil, etc.
- a moisture-proof coating agent for applying a water-repellent treatment
- an antifouling agent a lubricant
- the functional component such as the antifouling coating agent (fingerprint removal adhesion inhibitor) for applying the treatment
- the functional component such as the insecticide, the insect repellent, and the preservative.
- the functional component such as the insecticide, the insect repellent, and the preservative.
- examples thereof include a solvent, a diluting solvent for a chemical process (extraction solvent, a polymerization solvent), and the like.
- the diluting solvent can be used in the form of an aerosol or the like.
- Cleaning agents using this composition include degreasing cleaning, flux cleaning, precision cleaning, dry cleaning cleaning agents, pipe cleaning, glass cleaners, heat exchanger cleaners for refrigerating and air conditioning equipment, oil stain cleaning, flux cleaning, precision cleaning, etc. Examples thereof include cleaning for removing hydrophobic substances such as dry cleaning, and cleaning agents for removing stains from clothes and the like.
- the cleaning agent can be used in the form of an aerosol or the like.
- the stains to be cleaned and removed include carbon, oils and fats adhering to various objects to be cleaned, and dust adhering through them.
- fats and oils include fluxes, processing oils, mold release agents, sebum, food oils, and cosmetics.
- processing oil include cutting oil, quenching oil, rolling oil, lubricating oil, machine oil, press processing oil, punching oil, drawing oil, assembly oil, drawing oil, brake fluid and the like.
- cosmetics include manicure and lipstick. Two or more of the above-mentioned stains may be attached to various objects to be cleaned. Since the solvent composition of the present disclosure is superior in solubility in these oils as compared with conventional solvent compositions such as HFC and HFE, it is preferable to use it for cleaning stains composed of these oils.
- the material of the article to which the cleaning agent using this composition can be applied examples include metal, resin, rubber, glass, ceramics, natural fiber, and synthetic fiber.
- the article may be an article made of a composite material having these two or more kinds of materials. Examples of the composite material include a laminate of metal and resin.
- the solvent composition of the present disclosure can also be used for articles containing rubber materials such as SBR and resin materials affected by HCFO-1224yd.
- the propellant using this composition may be mixed with one or more selected from the group consisting of a pressor agent and a spray agent as a functional component.
- the pressor agent is a compressed gas
- the spray agent is an insecticide, a deodorant, a lubricant, a rust preventive agent, an antistatic agent, an extreme pressure agent, an antifogging agent, a penetrant, a wetting agent, and a paint.
- examples thereof include detergents, cosmetic amounts, external medicines, dyes, antifouling agents, water repellents, and oil repellents.
- the propellant can be used in the form of an aerosol or the like.
- the gas dielectric using this composition may be mixed with one or more selected from the group consisting of liquefied gas and compressed gas and used in an electric device.
- the electric device include a circuit breaker, a current cutoff facility, a gas-insulated transmission line, a gas-insulated transformer, a gas-insulated substation, a gas-insulated switch, a gas-insulated disconnector, and a gas-insulated load switch.
- a step of forming a circuit pattern of a semiconductor integrated circuit can be exemplified.
- a gas covering the molten metal (protective atmosphere) can be exemplified in order to prevent oxidation and evaporation of the molten metal in the crucible.
- the acid content contained in the hydrohaloolefin composition to be tested is determined as the HCl-equivalent concentration. Based on the determined acid content (HCl-equivalent concentration), the stability is evaluated according to the following criteria. S (excellent): Acid content is less than 1 mass ppm. A (good): Acid content is 1 mass ppm or more and less than 5 mass ppm. B (slightly defective): Acid content is 5 mass ppm or more.
- Example 1 is a comparative example, and Examples 2 to 5 are Examples.
- Examples 1 to 5 Using HCFC-225ca as a raw material, it was mixed with a metal hydroxide aqueous solution in the presence of an interphase transfer catalyst and reacted with hydrogen fluoride to obtain CFO-1214ya. Using the obtained CFO-1214ya as a raw material, hydrogen and nitrogen are brought into contact with a catalyst in which palladium is carried on activated carbon or a metal oxide in the gas phase to undergo a hydrogen reduction reaction, and a reaction containing HFO-1234yf and HCFO-1224yd is carried out. Obtained liquid.
- the obtained reaction solution was distilled and purified to obtain a purified composition containing HCFO-1224yd at a high concentration.
- the obtained purified composition was used as a hydrohaloolefin composition.
- HFC-374pee was added to the obtained purified composition to obtain the hydrohaloolefin composition shown in Table 1.
- the composition of the resulting hydrohaloolefin composition was analyzed using a GC-MS system. Content of HCFO-1224yd (Z), HCFO-1224yd (E), HFC-374pee, HFO-1354yf, and other organic compounds relative to the total mass of organic compounds in the hydrohaloolefin composition (unit:% by weight). Is shown in Table 1. In Table 1, " ⁇ 0.001" means that it is below the detection limit.
- the obtained hydrohaloolefin composition was used as a test subject, and the stability and metal corrosion resistance were evaluated by the above method. The results are shown in Table 1.
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Abstract
Description
ハイドロハロオレフィンは時間の経過等により分解が生じることがあり、安定性が充分とは言えない。分解によって酸が発生すると金属の腐食を引き起こす場合もある。
特許文献1には、1-クロロ-2,3,3-トリフルオロ-1-プロペン(HCFO-1233yd)に1-クロロ-2,2,3,3-テトラフルオロプロパン(HCFC-244ca)を少量加えると、保存中の分解が抑制された例が記載されている。
特許文献2には、2,3,3,3-テトラフルオロプロペン(HFO-1234yf)又は1,3,3,3-テトラフルオロプロペン(HFO-1234ze)と酸素を含む組成物に水を少量加えると、保存中の分解が抑制された例が記載されている。
本開示は、安定性が良好なハイドロハロオレフィン組成物の提供を目的とする。
[1] 主成分がハイドロハロオレフィンであり、さらに1,1,2,3-テトラフルオロブタンを含み、有機化合物の総量に対して、前記1,1,2,3-テトラフルオロブタンの含有量が0.001~0.1質量%である、ハイドロハロオレフィン組成物。
[2] 前記ハイドロハロオレフィンは、2,4,4,4-テトラフルオロ-1-ブテンを含み、前記有機化合物の総量に対して、前記1,1,2,3-テトラフルオロブタンと前記2,4,4,4-テトラフルオロ-1-ブテンとの合計の含有量が0.001超~0.4質量%である、[1]のハイドロハロオレフィン組成物。
[3] 前記主成分が、ハイドロクロロフルオロオレフィンである、[1]又は[2]のハイドロハロオレフィン組成物。
[4] 前記主成分が、1-クロロ-2,3,3,3-テトラフルオロプロペンである、[3]のハイドロハロオレフィン組成物。
[5] 用途が、作動流体、発泡剤、希釈溶媒、洗浄剤、噴射剤、消火剤、気体誘電体、エッチングガス、及び溶融金属カバーガスからなる群から選ばれる1種以上である、[1]~[4]のいずれかのハイドロハロオレフィン組成物。
[6] エアゾールの形態である、[5]に記載のハイドロハロオレフィン組成物。
[7] 前記作動流体が、熱サイクル用の作動流体である、[5]に記載のハイドロハロオレフィン組成物。
[8] 前記洗浄剤が、カーボン、油脂、及びこれらを介して付着した塵埃からなる群から選択される少なくとも1種の除去用の洗浄剤である、[5]に記載のハイドロハロオレフィン組成物。
[9] 前記洗浄剤が、金属、樹脂、ゴム、ガラス、セラミックス、天然繊維、合成繊維、又は、これらの2種以上の材料を有する複合材料からなる物品用の洗浄剤である、[5]に記載のハイドロハロオレフィン組成物。
[10] 前記噴射剤は、昇圧剤及び噴霧薬剤からなる群から選ばれる1種以上を含む、[5]に記載のハイドロハロオレフィン組成物。
[11] 前記気体誘電体は、液化ガス及び圧縮ガスからなる群から選ばれる1種以上を含む、[5]に記載のハイドロハロオレフィン組成物。
ハイドロハロオレフィンとは、水素原子と、フッ素原子、塩素原子、臭素原子及びヨウ素原子からなる群から選ばれる1種以上とを含む不飽和炭化水素化合物の総称である。
有機化合物とは、炭素原子を含む化合物であって、炭素の酸化物及び金属の炭酸塩を除く化合物の総称である。
組成物の主成分とは、組成物の総質量に対する含有質量が最も多いことを意味する。
化合物の名称の後の括弧内にその化合物の略称又は別名を記すことがある。化合物名に代えてその略称又は別名を用いることがある。
不飽和炭化水素化合物において、二重結合を有する炭素に結合された置換基の位置により、幾何異性体であるZ体(シス体)とE体(トランス体)が存在する。Z体とE体が存在する化合物について、特に断らずに化合物名や化合物の略称を用いた場合は、Z体もしくはE体、またはZ体とE体の任意の割合の混合物であることを意味する。化合物名や化合物の略称の後ろに(Z)または(E)を付した場合は、それぞれの化合物のZ体またはE体であることを示す。
「~」で表した数値範囲は、~の前後の数値を下限値及び上限値とする数値範囲を意味する。段階的に記載されている数値範囲において、一つの数値範囲で記載された上限値または下限値は、他の段階的な記載の数値範囲の上限値または下限値に置き換えてもよい。また、数値範囲において、その数値範囲の上限値または下限値は、実施例に示されている値に置き換えてもよい。
(メタ)アクリルとは、アクリル又はメタクリルを意味する。
本開示のハイドロハロオレフィン組成物(以下、本組成物ともいう。)は2種以上の有機化合物を含み、主成分はハイドロハロオレフィンである。
本組成物の総質量に対して主成分の含有量は50質量%以上が好ましく、70質量%以上がより好ましく、80質量%以上がさらに好ましく、90質量%以上が特に好ましく、99質量%以上が極めて好ましい。
ハイドロハロオレフィンとしては、ハイドロフルオロオレフィン(HFO)、ハイドロクロロフルオロオレフィン(HCFO)、及びハイドロクロロオレフィン(HCO)が例示できる。ハイドロハロオレフィンは1種単独で用いても、2種以上併用してもよい。
HCFO-1224ydは、HCFO-1224yd(Z)でもよく、HCFO-1224yd(E)でもよく、これらの混合物でもよい。HCFO-1224ydにおけるZ体の含有量とE体の含有量の質量比を表すZ/E比は、100/0~0/100でよく、99.9/0.1~50/50が好ましく、99.9/0.1~70/30がより好ましく、99.9/0.1~99.0/1.0がさらに好ましい。
本組成物中の有機化合物の総質量に対して、HFC-374peeの含有量は0.001~0.1質量%であり、0.001~0.05質量%が好ましく、0.001~0.01質量%がより好ましい。上記範囲内であると本組成物の安定性に優れる。
ハイドロハロオレフィンは2,4,4,4-テトラフルオロ-1-ブテン(HFO-1354yf)を含んでもよく、HFO-1354yfを含む場合には、本組成物中の有機化合物の総質量に対して、HFC-374peeとHFO-1354yfとの合計の含有量は0.001超~0.4質量%が好ましく、0.001~0.2質量%がより好ましく、0.01~0.1質量%がさらに好ましい。上記範囲内であると本組成物の安定性に優れる。
なお、本組成物がHFO-1354yfを含む場合、主成分はHFO-1354yf以外のハイドロハロオレフィンである。
他の有機化合物としては、クロロフルオロオレフィン(CFO)、フルオロオレフィン、クロロオレフィン、オレフィン、HFC-374peeを除くハイドロフルオロカーボン(HFC)、ハイドロクロロカーボン(HCC)、ハイドロクロロフルオロカーボン(HCFC)、クロロフルオロカーボン(CFC)、クロロカーボン、フルオロカーボン(FC)、ハイドロカーボン(HC)、ハイドロフルオロエーテル(HFE)、クロロフルオロアルキン、アルコール、エーテル、ケトン、有機酸、及び飽和炭化水素が例示できる。
さらに、臭素原子及びヨウ素原子からなる群から選ばれる1種以上を含むハロゲン化メタンを必要に応じて含んでもよい。
本組成物を密閉容器に充填した際の気相部の合計体積に対して、不活性ガスは20体積%以下でよく、15体積%以下が好ましく、10体積%以下がより好ましく、5体積%以下がさらに好ましく、1.5体積%以下が特に好ましい。
本組成物に含まれるハイドロハロオレフィンは公知の製法で製造できる。
例えば、HCFO-1224ydは、CFO-1214yaを、触媒存在下で、水素を用いて還元(水素還元反応)してHFO-1234yfを得る工程において、中間体として得られる。
原料であるCFO-1214yaは、例えば、HCFC-225caを原料とし、臭化テトラブチルアンモニウム等の相間移動触媒存在下、水酸化カリウム水溶液等のアルカリ水溶液で脱フッ化水素反応させる方法、又はクロム、鉄、銅、活性炭等の触媒存在下に気相反応で脱フッ化水素反応させる方法で製造できる。
前記水素還元反応で得られた反応液を、通常の蒸留法又は国際公開第2017/146190号に記載の抽出蒸留法を用いて蒸留することにより、未反応のCFO-1214ya及びHFO-1234yfと、HCFO-1224ydとを分離して、HCFO-1224ydを高濃度で含む精製組成物が得られる。この精製組成物は、前記水素還元反応で生成した副生物を含んでもよい。
本組成物に含まれるHFC-374peeは、ハイドロハロオレフィンを製造し、精製して得られる精製組成物に含まれるものでもよく、別途添加してもよく、これらの組み合わせでもよい。
本組成物に含まれてもよいHFO-1354yfは、ハイドロハロオレフィンの精製組成物に含まれるものでもよく、別途添加してもよく、これらの組み合わせでもよい。
本組成物に含まれる有機化合物の種類及びその含有量は、GC-MSシステムを用いて分析して同定できる。
HFC-374peeは、HFCとしての性質を有するとともに、必ずしも明確ではないがラジカルを捕捉する作用を有すると推定される。その作用により、HCFO-1224ydのようなハイドロハロオレフィンの分解を抑制して安定化させる、安定剤としての機能を発揮すると考えられる。
本組成物は安定性が良好であり、ハイドロハロオレフィンの用途として公知の用途に使用できる。また本組成物は、金属と接触しても金属を腐食させ難く、金属と接触する用途に適用できる。
本組成物の用途の例として、作動流体、発泡剤、希釈溶媒、洗浄剤、噴射剤、消火剤、気体誘電体、エッチングガス、及び溶融金属カバーガスが挙げられる。本組成物の用途は1種でもよく、2種以上でもよい。本組成物は、エアゾールの形態等で使用してもよい。
熱可塑性樹脂発泡体に含まれる熱可塑性樹脂の具体例として、ポリカーボネート樹脂、ポリスチレン樹脂、ポリフェニレンエーテル樹脂、アクリロニトリル-ブタジエン-スチレン樹脂、ポリオレフィン樹脂、ポリ塩化ビニル樹脂、(メタ)アクリル樹脂、ポリエステル樹脂、変性ポリフェニレンエーテル樹脂、ポリアセタール樹脂、ポリエーテルイミド樹脂、ポリエーテルサルフォン樹脂、ポリアミド樹脂、ポリサルフォン樹脂、ポリエーテルエーテルケトン樹脂、及びポリエーテルケトン樹脂が挙げられる。
熱硬化性樹脂発泡体の具体例としては、ポリウレタン発泡体、ポリイソシアヌレート発泡体、及びフェノール樹脂発泡体が挙げられる。
ポリウレタン発泡体の具体例として、硬質ウレタン発泡体、軟質ウレタン発泡体、半硬質ウレタン発泡体、及びインテグラルスキンフォームが挙げられる。
<評価方法>
[安定性試験・金属耐食試験]
SS400製、Cu製、及びAl製の金属片(一辺の長さ20mm×30mm、厚さ2mm)を各1枚、合計3枚用意する。
容量200mLのステンレス鋼製耐圧容器に前記金属片を3枚入れて密閉する。真空排気し、試験対象のハイドロハロオレフィン組成物60gを充填する。
次いで、密閉した耐圧容器を175℃の恒温槽内で14日間保存した後、室温(25℃)になるまで静置する。
抽出後の吸収瓶内の水は、耐圧容器に近い側から1本目と2本目を合わせて指示薬(BTB:ブロモチモールブルー)を1滴加え、1/100NのNaOHアルカリ標準液を用いて滴定し、測定値とする。また、3本目及び4本目の吸収瓶の水を合わせて同様に滴定し、測定ブランクとする。これら測定値と測定ブランクの値から、試験対象のハイドロハロオレフィン組成物に含まれる酸分をHCl換算濃度として求める。
求めた酸分(HCl換算濃度)の値に基づいて、下記の基準で安定性を評価する。
S(優良):酸分が1質量ppm未満。
A(良):酸分が1質量ppm以上5質量ppm未満。
B(やや不良):酸分が5質量ppm以上。
S(優良):3枚の金属片の全部が未使用品と同等の光沢を有し、錆が発生したものは無い。
A(良):光沢が失われた金属片が1枚以上あるが、錆が発生したものは無い。
B(やや不良):表面がわずかに錆びたものが1枚以上あるが、全面が錆びたものは無い。
<例1~5>
HCFC-225caを原料とし、相間異動触媒存在下、金属水酸化物水溶液と混合し、脱フッ化水素反応し、CFO-1214yaを得た。得られたCFO-1214yaを原料とし、気相で水素及び窒素と、活性炭又は金属酸化物にパラジウムを担持させた触媒に接触させることで水素還元反応し、HFO-1234yf及びHCFO-1224ydを含む反応液を得た。得られた反応液を蒸留して精製し、HCFO-1224ydを高濃度で含む精製組成物を得た。例1では得られた精製組成物をハイドロハロオレフィン組成物とした。例2~5では、得られた精製組成物にHFC-374peeを添加して、表1に示すハイドロハロオレフィン組成物を得た。
得られたハイドロハロオレフィン組成物の組成はGC-MSシステムを用いて分析した。ハイドロハロオレフィン組成物中の有機化合物の総質量に対する、HCFO-1224yd(Z)、HCFO-1224yd(E)、HFC-374pee、HFO-1354yf、及び他の有機化合物の含有量(単位:質量%)を表1に示す。表1において「<0.001」は検出限界未満であることを意味する。
得られたハイドロハロオレフィン組成物を試験対象とし、上記の方法で安定性と金属耐食性を評価した。結果を表1に示す。
本明細書に記載された全ての文献、特許出願、及び技術規格は、個々の文献、特許出願、及び技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書中に援用されて取り込まれる。
Claims (11)
- 主成分がハイドロハロオレフィンであり、さらに1,1,2,3-テトラフルオロブタンを含み、有機化合物の総量に対して、前記1,1,2,3-テトラフルオロブタンの含有量が0.001~0.1質量%である、ハイドロハロオレフィン組成物。
- 前記ハイドロハロオレフィンは、2,4,4,4-テトラフルオロ-1-ブテンを含み、前記有機化合物の総量に対して、前記1,1,2,3-テトラフルオロブタンと前記2,4,4,4-テトラフルオロ-1-ブテンとの合計の含有量が0.001超~0.4質量%である、請求項1に記載のハイドロハロオレフィン組成物。
- 前記主成分が、ハイドロクロロフルオロオレフィンである、請求項1又は2に記載のハイドロハロオレフィン組成物。
- 前記主成分が、1-クロロ-2,3,3,3-テトラフルオロプロペンである、請求項3に記載のハイドロハロオレフィン組成物。
- 用途が、作動流体、発泡剤、希釈溶媒、洗浄剤、噴射剤、消火剤、気体誘電体、エッチングガス、及び溶融金属カバーガスからなる群から選ばれる1種以上である、請求項1~4のいずれか一項に記載のハイドロハロオレフィン組成物。
- エアゾールの形態である、請求項5に記載のハイドロハロオレフィン組成物。
- 前記作動流体が、熱サイクル用の作動流体である、請求項5に記載のハイドロハロオレフィン組成物。
- 前記洗浄剤が、カーボン、油脂、及びこれらを介して付着した塵埃からなる群から選択される少なくとも1種の除去用の洗浄剤である、請求項5に記載のハイドロハロオレフィン組成物。
- 前記洗浄剤が、金属、樹脂、ゴム、ガラス、セラミックス、天然繊維、合成繊維、又は、これらの2種以上の材料を有する複合材料からなる物品用の洗浄剤である、請求項5に記載のハイドロハロオレフィン組成物。
- 前記噴射剤は、昇圧剤及び噴霧薬剤からなる群から選ばれる1種以上を含む、請求項5に記載のハイドロハロオレフィン組成物。
- 前記気体誘電体は、液化ガス及び圧縮ガスからなる群から選ばれる1種以上を含む、請求項5に記載のハイドロハロオレフィン組成物。
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