JP2008539311A - ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびヒドロフルオロカーボンを含む伝熱および冷媒組成物 - Google Patents
３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびヒドロフルオロカーボンを含む伝熱および冷媒組成物 Download PDFInfo
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- JP2008539311A JP2008539311A JP2008509029A JP2008509029A JP2008539311A JP 2008539311 A JP2008539311 A JP 2008539311A JP 2008509029 A JP2008509029 A JP 2008509029A JP 2008509029 A JP2008509029 A JP 2008509029A JP 2008539311 A JP2008539311 A JP 2008539311A
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- JP
- Japan
- Prior art keywords
- weight percent
- nonafluoro
- hexene
- composition
- difluorobutane
- Prior art date
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- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 168
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 title claims abstract description 67
- 239000003507 refrigerant Substances 0.000 title claims description 75
- 238000012546 transfer Methods 0.000 title claims description 12
- 238000005057 refrigeration Methods 0.000 claims abstract description 49
- -1 aliphatic hydrocarbylene radical Chemical class 0.000 claims description 84
- 239000002904 solvent Substances 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 43
- 229930195733 hydrocarbon Natural products 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 239000013529 heat transfer fluid Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000007850 fluorescent dye Substances 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000000975 dye Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000001816 cooling Methods 0.000 claims description 16
- 150000002596 lactones Chemical class 0.000 claims description 16
- 238000001704 evaporation Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- XRKOOHTZZDPJNE-UHFFFAOYSA-N 1,1,1-trifluorohexane Chemical compound CCCCCC(F)(F)F XRKOOHTZZDPJNE-UHFFFAOYSA-N 0.000 claims description 10
- GQSMEOJGQJMOHA-UHFFFAOYSA-N 1,1,3-trifluoropropane Chemical compound FCCC(F)F GQSMEOJGQJMOHA-UHFFFAOYSA-N 0.000 claims description 10
- VHJOGNLCVJAXFE-UHFFFAOYSA-N 1,2-difluorobutane Chemical compound CCC(F)CF VHJOGNLCVJAXFE-UHFFFAOYSA-N 0.000 claims description 10
- OLURRGJWZJYRIM-UHFFFAOYSA-N 1,3-difluoro-2-methylpropane Chemical compound FCC(C)CF OLURRGJWZJYRIM-UHFFFAOYSA-N 0.000 claims description 10
- JFGBHUQZXJIATI-UHFFFAOYSA-N 1,3-difluorobutane Chemical compound CC(F)CCF JFGBHUQZXJIATI-UHFFFAOYSA-N 0.000 claims description 10
- OOLOYCGJRJFTPM-UHFFFAOYSA-N 1,3-difluoropropane Chemical compound FCCCF OOLOYCGJRJFTPM-UHFFFAOYSA-N 0.000 claims description 10
- CXHPKSYTQFAXIN-UHFFFAOYSA-N 1,4-difluorobutane Chemical compound FCCCCF CXHPKSYTQFAXIN-UHFFFAOYSA-N 0.000 claims description 10
- QSWGSLWFQDIXSH-UHFFFAOYSA-N 2,2-difluoropentane Chemical compound CCCC(C)(F)F QSWGSLWFQDIXSH-UHFFFAOYSA-N 0.000 claims description 10
- GRELHMBELDGGLT-UHFFFAOYSA-N 2,3-difluorobutane Chemical compound CC(F)C(C)F GRELHMBELDGGLT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 230000006835 compression Effects 0.000 claims description 10
- 238000007906 compression Methods 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 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 claims description 9
- CONTVCYXDSFGMN-UHFFFAOYSA-N 1,1,1-trifluoro-3-methylbutane Chemical compound CC(C)CC(F)(F)F CONTVCYXDSFGMN-UHFFFAOYSA-N 0.000 claims description 9
- GENRYAJRHIWOJI-UHFFFAOYSA-N 1,1,1-trifluoropentane Chemical compound CCCCC(F)(F)F GENRYAJRHIWOJI-UHFFFAOYSA-N 0.000 claims description 9
- AKQMZZOTFNLAQJ-UHFFFAOYSA-N 1,1,2,2-tetrafluorocyclobutane Chemical compound FC1(F)CCC1(F)F AKQMZZOTFNLAQJ-UHFFFAOYSA-N 0.000 claims description 9
- PSSHQAXMSKKIBE-UHFFFAOYSA-N 1,1-difluoropentane Chemical compound CCCCC(F)F PSSHQAXMSKKIBE-UHFFFAOYSA-N 0.000 claims description 9
- JKYLNUHIUDXCMN-UHFFFAOYSA-N 1,2-difluoropentane Chemical compound CCCC(F)CF JKYLNUHIUDXCMN-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229920001774 Perfluoroether Polymers 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052731 fluorine Chemical group 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- CUKJWRYRLCTJNJ-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluoro-2,3-bis(trifluoromethyl)but-2-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(C(F)(F)F)C(F)(F)F CUKJWRYRLCTJNJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 150000008378 aryl ethers Chemical class 0.000 claims description 6
- 239000002516 radical scavenger Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 5
- 230000000873 masking effect Effects 0.000 claims description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 5
- VWCLQNINSPFHFV-UHFFFAOYSA-N 10-oxapentacyclo[12.8.0.02,11.04,9.015,20]docosa-1(14),2(11),4,6,8,12,15,17,19,21-decaene Chemical compound C1=CC=C2C3=CC=C4OC5=CC=CC=C5CC4=C3C=CC2=C1 VWCLQNINSPFHFV-UHFFFAOYSA-N 0.000 claims description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 4
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 230000004907 flux Effects 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002905 orthoesters Chemical group 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims 1
- 238000004378 air conditioning Methods 0.000 abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 150000003254 radicals Chemical class 0.000 description 18
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229940123457 Free radical scavenger Drugs 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 3
- 238000005238 degreasing Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/505—Mixtures of (hydro)fluorocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
- C09K2205/12—Hydrocarbons
- C09K2205/126—Unsaturated fluorinated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/22—All components of a mixture being fluoro compounds
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Thermal Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
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- Cleaning By Liquid Or Steam (AREA)
- Cleaning Or Drying Semiconductors (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67482505P | 2005-04-26 | 2005-04-26 | |
| US11/410,559 US7264745B2 (en) | 2005-04-26 | 2006-04-25 | Heat transfer and refrigerant compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and a hydrofluorocarbon |
| PCT/US2006/015580 WO2006116371A1 (en) | 2005-04-26 | 2006-04-25 | Heat transfer and refrigerant compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and a hydrofluorocarbon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008539311A true JP2008539311A (ja) | 2008-11-13 |
| JP2008539311A5 JP2008539311A5 (https=) | 2009-05-07 |
Family
ID=36754585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008509029A Pending JP2008539311A (ja) | 2005-04-26 | 2006-04-25 | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびヒドロフルオロカーボンを含む伝熱および冷媒組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7264745B2 (https=) |
| EP (1) | EP1874887A1 (https=) |
| JP (1) | JP2008539311A (https=) |
| CN (1) | CN101166805B (https=) |
| AR (1) | AR054351A1 (https=) |
| WO (1) | WO2006116371A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2642570T3 (es) * | 2006-02-28 | 2017-11-16 | The Chemours Company Fc, Llc | Composiciones azeotrópicas que comprenden compuestos fluorados para aplicaciones de limpieza |
| CN102227395A (zh) * | 2008-11-13 | 2011-10-26 | 苏威氟有限公司 | 氢氟烯烃、氢氟烯烃的制造以及使用氢氟烯烃的方法 |
| WO2015095285A1 (en) | 2013-12-20 | 2015-06-25 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| WO2018116159A1 (en) * | 2016-12-21 | 2018-06-28 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
| CN108335759B (zh) * | 2018-02-06 | 2019-11-12 | 华中科技大学 | 基于蒸发冷却原理的用于托卡马克装置偏滤器的冷却系统 |
| CN111337460B (zh) * | 2018-12-18 | 2021-09-17 | 中国科学院大连化学物理研究所 | 一种高稳定性Halo-tag探针及其合成和生物应用 |
| CN111793475B (zh) * | 2019-07-17 | 2021-11-02 | 泉州宇极新材料科技有限公司 | 一种热传递装置及方法 |
| CN111792985B (zh) * | 2019-07-17 | 2022-10-14 | 泉州宇极新材料科技有限公司 | 一种含氟传热流体及其制备方法和应用 |
| WO2021124032A1 (en) | 2019-12-19 | 2021-06-24 | 3M Innovative Properties Company | Fluorinated coumarins |
| ES3038726T3 (en) * | 2021-02-24 | 2025-10-15 | Castrol Ltd | Dielectric thermal management fluids and methods for using them |
| CN115572579B (zh) * | 2022-10-12 | 2023-10-13 | 澳江(无锡)网络能源有限公司 | 一种液冷用全氟化合物组合物及其在浸没式冷却中的应用 |
| CN115466601B (zh) * | 2022-11-01 | 2023-03-24 | 北京宇极科技发展有限公司 | 一种含氟电子冷却液 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5037573A (en) * | 1990-10-03 | 1991-08-06 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1-dichloro-1-fluoroethane and n-perfluorobutylethylene |
| JPH04227803A (ja) * | 1990-02-20 | 1992-08-17 | Elf Atochem Sa | （パーフルオロアルキル）エチレンの洗浄剤又は乾燥剤としての適用、及びその目的に使用し得る組成物 |
| US5458800A (en) * | 1990-02-20 | 1995-10-17 | Societe Atochem | Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose |
| WO2003091305A1 (en) * | 2002-04-25 | 2003-11-06 | Daikin Industries, Ltd. | Process for producing synthetic resin foam, blowing agent, and premix |
| JP2004525879A (ja) * | 2000-12-22 | 2004-08-26 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | パーフルオロブチルエチレン含有の共沸混合物 |
| JP2005502770A (ja) * | 2001-09-07 | 2005-01-27 | スリーエム イノベイティブ プロパティズ カンパニー | 共沸様組成物およびその使用 |
| JP2008539312A (ja) * | 2005-04-26 | 2008-11-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびフルオロエーテルを含む伝熱および冷媒組成物 |
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| US4054036A (en) * | 1976-12-21 | 1977-10-18 | Allied Chemical Corporation | Constant boiling mixtures of 1,1,2-trichlorotrifluoroethane and cis-1,1,2,2-tetrafluorocyclobutane |
| US5039445A (en) | 1990-10-03 | 1991-08-13 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions of N-perfluorobutylethylene and cis-1,2-dichloroethylene with methanol or ethanol or isopropanol |
| KR0180613B1 (en) * | 1994-09-07 | 1999-05-15 | Matsushita Electric Industrial Co Ltd | Thermal insulating foamed material and method for manufacturing the same |
| FR2760463B1 (fr) * | 1997-03-04 | 2000-12-08 | Atochem Elf Sa | Compositions pour le sechage de surfaces solides |
| US6793840B2 (en) | 2000-12-22 | 2004-09-21 | E. I. Du Pont De Nemours And Company | Azeotrope mixtures with perfluorobutylethylene |
| CN100465204C (zh) | 2001-11-13 | 2009-03-04 | 大金工业株式会社 | 合成树脂发泡体的制造方法 |
| FR2850114B1 (fr) * | 2003-01-17 | 2005-02-18 | Atofina | Nouvelles compositions contenant des hydrocarbures fluores et des solvants oxygenes |
| WO2005008819A2 (en) * | 2003-07-23 | 2005-01-27 | Dupont Canada Inc. | Evaporative coolants having low dielectric constant for use in fuel cells & other electrochemical reactor stacks |
| JP2007517971A (ja) | 2004-01-14 | 2007-07-05 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ヒドロフルオロカーボンを含む１，１，１，３，３−ペンタフルオロブタン冷媒または伝熱流体組成物およびその使用 |
| US7276177B2 (en) | 2004-01-14 | 2007-10-02 | E.I. Dupont De Nemours And Company | Hydrofluorocarbon refrigerant compositions and uses thereof |
| EP1711577A2 (en) * | 2004-01-14 | 2006-10-18 | E.I. du Pont de Nemours and Company | Hydrofluorocarbon refrigerant compositions and uses thereof |
-
2006
- 2006-04-25 EP EP06751342A patent/EP1874887A1/en not_active Withdrawn
- 2006-04-25 JP JP2008509029A patent/JP2008539311A/ja active Pending
- 2006-04-25 CN CN200680014341.8A patent/CN101166805B/zh not_active Expired - Fee Related
- 2006-04-25 US US11/410,559 patent/US7264745B2/en not_active Expired - Fee Related
- 2006-04-25 WO PCT/US2006/015580 patent/WO2006116371A1/en not_active Ceased
- 2006-04-25 AR ARP060101655A patent/AR054351A1/es not_active Application Discontinuation
-
2007
- 2007-07-11 US US11/776,054 patent/US20080042097A1/en not_active Abandoned
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| JPH04227803A (ja) * | 1990-02-20 | 1992-08-17 | Elf Atochem Sa | （パーフルオロアルキル）エチレンの洗浄剤又は乾燥剤としての適用、及びその目的に使用し得る組成物 |
| US5458800A (en) * | 1990-02-20 | 1995-10-17 | Societe Atochem | Use of (perfluoroalkyl) ethylenes as cleaning or drying agents, and compositions which can be used for this purpose |
| US5037573A (en) * | 1990-10-03 | 1991-08-06 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1-dichloro-1-fluoroethane and n-perfluorobutylethylene |
| JP2004525879A (ja) * | 2000-12-22 | 2004-08-26 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | パーフルオロブチルエチレン含有の共沸混合物 |
| JP2005502770A (ja) * | 2001-09-07 | 2005-01-27 | スリーエム イノベイティブ プロパティズ カンパニー | 共沸様組成物およびその使用 |
| WO2003091305A1 (en) * | 2002-04-25 | 2003-11-06 | Daikin Industries, Ltd. | Process for producing synthetic resin foam, blowing agent, and premix |
| JP2008539312A (ja) * | 2005-04-26 | 2008-11-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ３，３，４，４，５，５，６，６，６−ノナフルオロ−１−ヘキセンおよびフルオロエーテルを含む伝熱および冷媒組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR054351A1 (es) | 2007-06-20 |
| US20060255312A1 (en) | 2006-11-16 |
| EP1874887A1 (en) | 2008-01-09 |
| CN101166805B (zh) | 2011-06-08 |
| US7264745B2 (en) | 2007-09-04 |
| WO2006116371A1 (en) | 2006-11-02 |
| CN101166805A (zh) | 2008-04-23 |
| US20080042097A1 (en) | 2008-02-21 |
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