KR20140019399A - 열 전달 유체로서의 플루오르화 옥시란 - Google Patents
열 전달 유체로서의 플루오르화 옥시란 Download PDFInfo
- Publication number
- KR20140019399A KR20140019399A KR1020137027755A KR20137027755A KR20140019399A KR 20140019399 A KR20140019399 A KR 20140019399A KR 1020137027755 A KR1020137027755 A KR 1020137027755A KR 20137027755 A KR20137027755 A KR 20137027755A KR 20140019399 A KR20140019399 A KR 20140019399A
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- KR
- South Korea
- Prior art keywords
- heat transfer
- oxirane
- fluorinated
- temperature
- semiconductor
- 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.)
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- 150000002924 oxiranes Chemical class 0.000 title claims abstract description 53
- 238000012546 transfer Methods 0.000 title claims abstract description 52
- 239000012530 fluid Substances 0.000 title description 23
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000013529 heat transfer fluid Substances 0.000 claims abstract description 24
- 230000007246 mechanism Effects 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 239000004065 semiconductor Substances 0.000 claims description 31
- 238000012360 testing method Methods 0.000 claims description 27
- 238000001816 cooling Methods 0.000 claims description 13
- -1 fluorinated oxirane compound Chemical class 0.000 claims description 10
- 238000005476 soldering Methods 0.000 claims description 9
- 239000012808 vapor phase Substances 0.000 claims description 8
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 claims description 7
- 230000035939 shock Effects 0.000 claims description 5
- 238000009826 distribution Methods 0.000 claims description 4
- 239000000446 fuel Substances 0.000 claims description 3
- 229910000679 solder Inorganic materials 0.000 claims description 3
- 229910001416 lithium ion Inorganic materials 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 239000012071 phase Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 12
- 238000005194 fractionation Methods 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 230000007613 environmental effect Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 239000010702 perfluoropolyether Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005057 refrigeration Methods 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PQMAKJUXOOVROI-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(trifluoromethyl)morpholine Chemical compound FC(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F PQMAKJUXOOVROI-UHFFFAOYSA-N 0.000 description 3
- DLXDAPOINQCHSK-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-3-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C1(F)OC1(F)C(F)(F)F DLXDAPOINQCHSK-UHFFFAOYSA-N 0.000 description 3
- NOESGFSFSJKFIF-UHFFFAOYSA-N 2-fluoro-2-(1,1,2,2,2-pentafluoroethyl)-3,3-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1(F)OC1(C(F)(F)F)C(F)(F)F NOESGFSFSJKFIF-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PBVZTJDHQVIHFR-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)F.FC(F)=C(F)C(F)(F)F PBVZTJDHQVIHFR-UHFFFAOYSA-N 0.000 description 2
- ZWSICHXNVFXDHH-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6-decafluoro-7-oxabicyclo[4.1.0]heptane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C1(F)O2 ZWSICHXNVFXDHH-UHFFFAOYSA-N 0.000 description 2
- ZFFLXJVVPHACEG-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F ZFFLXJVVPHACEG-UHFFFAOYSA-N 0.000 description 2
- PCGUNVYNJIFBQT-UHFFFAOYSA-N 2,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pentan-1-ol Chemical compound OCC(F)(C(F)(F)F)C(F)C(F)(C(F)(F)F)C(F)(F)F PCGUNVYNJIFBQT-UHFFFAOYSA-N 0.000 description 2
- SVENBAIZELMMEQ-UHFFFAOYSA-N 2,3-difluoro-2,3-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(F)OC1(F)C(F)(F)F SVENBAIZELMMEQ-UHFFFAOYSA-N 0.000 description 2
- IFSMQHYHIPUYBH-UHFFFAOYSA-N 2-[1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propyl]-2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(F)(F)C1(C(F)(F)F)CO1 IFSMQHYHIPUYBH-UHFFFAOYSA-N 0.000 description 2
- LJEQTMAJLCLERP-UHFFFAOYSA-N 3,3,4,5,5,5-hexafluoro-2,4-bis(trifluoromethyl)pent-1-ene Chemical compound FC(F)(F)C(=C)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F LJEQTMAJLCLERP-UHFFFAOYSA-N 0.000 description 2
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- WCTKUENARPWTAY-UHFFFAOYSA-N ac1l9mss Chemical compound OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- WCTKUENARPWTAY-UHFFFAOYSA-M chlorosulfite Chemical compound [O-]S(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-M 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000003754 machining Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- WSJULBMCKQTTIG-OWOJBTEDSA-N (e)-1,1,1,2,3,4,4,4-octafluorobut-2-ene Chemical compound FC(F)(F)C(/F)=C(\F)C(F)(F)F WSJULBMCKQTTIG-OWOJBTEDSA-N 0.000 description 1
- VVMQLAKDFBLCHB-UHFFFAOYSA-N 1,1,1,2,3,4,4,5,5,5-decafluoropent-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(F)C(F)(F)F VVMQLAKDFBLCHB-UHFFFAOYSA-N 0.000 description 1
- SAPOZTRFWJZUFT-UHFFFAOYSA-N 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)pent-2-ene Chemical class FC(F)(F)C(F)=C(F)C(F)(C(F)(F)F)C(F)(F)F SAPOZTRFWJZUFT-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LOUICXNAWQPGSU-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxirane Chemical compound FC1(F)OC1(F)F LOUICXNAWQPGSU-UHFFFAOYSA-N 0.000 description 1
- ZEZAFHZIZCXHGO-UHFFFAOYSA-N 2,2,3-trifluoro-3-(1,1,2,2,2-pentafluoroethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1(F)OC1(F)F ZEZAFHZIZCXHGO-UHFFFAOYSA-N 0.000 description 1
- NYZSKEULTVZUAW-UHFFFAOYSA-N 2,2-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(C(F)(F)F)CO1 NYZSKEULTVZUAW-UHFFFAOYSA-N 0.000 description 1
- DMILFILPEIMZDC-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1OC1C(F)(F)F DMILFILPEIMZDC-UHFFFAOYSA-N 0.000 description 1
- JDJXXAGSIYOKAR-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,2,2,2-pentafluoroethyl)-3-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1(F)OC1(F)C(F)(F)F JDJXXAGSIYOKAR-UHFFFAOYSA-N 0.000 description 1
- LFUODFBQLVQAOS-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,2,2,3,3,3-heptafluoropropyl)-3-(1,1,2,2,2-pentafluoroethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(F)OC1(F)C(F)(F)C(F)(F)F LFUODFBQLVQAOS-UHFFFAOYSA-N 0.000 description 1
- BKPQIBGQPWNQOU-UHFFFAOYSA-N 2,3-difluoro-2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-3-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC1(F)C(F)(F)F BKPQIBGQPWNQOU-UHFFFAOYSA-N 0.000 description 1
- BDGDPAGJMXESQU-UHFFFAOYSA-N 2-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)-2,3,3-tris(trifluoromethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(C(F)(F)F)C1(C(F)(F)F)OC1(C(F)(F)F)C(F)(F)F BDGDPAGJMXESQU-UHFFFAOYSA-N 0.000 description 1
- YCUAEPBEOFDHTN-UHFFFAOYSA-N 2-(1,1,2,2,2-pentafluoroethyl)-3-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1OC1C(F)(F)C(F)(F)F YCUAEPBEOFDHTN-UHFFFAOYSA-N 0.000 description 1
- VQWGFENTQFTYAN-UHFFFAOYSA-N 2-(1,1,2,2,2-pentafluoroethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1CO1 VQWGFENTQFTYAN-UHFFFAOYSA-N 0.000 description 1
- YXVLDWFJBCGDJY-UHFFFAOYSA-N 2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-3-(1,1,2,2,2-pentafluoroethyl)oxirane Chemical compound FC(F)(F)C(F)(F)C1OC1C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YXVLDWFJBCGDJY-UHFFFAOYSA-N 0.000 description 1
- QHHCBVYZWRKFLZ-UHFFFAOYSA-N 2-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1CO1 QHHCBVYZWRKFLZ-UHFFFAOYSA-N 0.000 description 1
- XLLHDUOEQXDROH-UHFFFAOYSA-N 2-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1CO1 XLLHDUOEQXDROH-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- AQZRARFZZMGLHL-UHFFFAOYSA-N 2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1CO1 AQZRARFZZMGLHL-UHFFFAOYSA-N 0.000 description 1
- DHGQMHOMRCABJL-UHFFFAOYSA-N 2-fluoro-2-(trifluoromethyl)oxirane Chemical compound FC(F)(F)C1(F)CO1 DHGQMHOMRCABJL-UHFFFAOYSA-N 0.000 description 1
- ULFHADFFJVZYKF-UHFFFAOYSA-N 2-fluoro-3-(trifluoromethyl)oxirane Chemical compound FC1OC1C(F)(F)F ULFHADFFJVZYKF-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 229910000980 Aluminium gallium arsenide Inorganic materials 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- 241001167556 Catena Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910000661 Mercury cadmium telluride Inorganic materials 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910007709 ZnTe Inorganic materials 0.000 description 1
- RRMWLBOQVDUJQX-UHFFFAOYSA-L [I+].S([O-])(O)=O.[Na+].S([O-])(O)=O Chemical compound [I+].S([O-])(O)=O.[Na+].S([O-])(O)=O RRMWLBOQVDUJQX-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K7/00—Constructional details common to different types of electric apparatus
- H05K7/20—Modifications to facilitate cooling, ventilating, or heating
- H05K7/20218—Modifications to facilitate cooling, ventilating, or heating using a liquid coolant without phase change in electronic enclosures
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Epoxy Compounds (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
- Secondary Cells (AREA)
Applications Claiming Priority (3)
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| US201161467432P | 2011-03-25 | 2011-03-25 | |
| US61/467,432 | 2011-03-25 | ||
| PCT/US2012/029649 WO2012134860A1 (en) | 2011-03-25 | 2012-03-19 | Fluorinated oxiranes as heat transfer fluids |
Publications (1)
| Publication Number | Publication Date |
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| KR20140019399A true KR20140019399A (ko) | 2014-02-14 |
Family
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Family Applications (1)
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|---|---|
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| EP (1) | EP2688973A1 (https=) |
| JP (1) | JP2014515048A (https=) |
| KR (1) | KR20140019399A (https=) |
| CN (1) | CN103443238A (https=) |
| TW (1) | TW201245430A (https=) |
| WO (1) | WO2012134860A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015095285A1 (en) | 2013-12-20 | 2015-06-25 | 3M Innovative Properties Company | Fluorinated olefins as working fluids and methods of using same |
| WO2018165623A1 (en) * | 2017-03-10 | 2018-09-13 | The Chemours Company Fc, Llc | Uses of fluorinated epoxides and novel mixtures thereof |
| JP6971253B2 (ja) * | 2017-03-21 | 2021-11-24 | スリーエム イノベイティブ プロパティズ カンパニー | 熱伝達流体及び同流体の使用方法 |
| US20200255714A1 (en) * | 2017-10-24 | 2020-08-13 | 3M Innovative Properties Company | Hydrofluoroepoxide containing compositions and methods for using same |
| CN113242876A (zh) * | 2018-12-21 | 2021-08-10 | 霍尼韦尔国际公司 | 包含1,2,2-三氟-1-三氟甲基环丁烷的发泡剂组合物及发泡方法 |
| JP7833891B2 (ja) * | 2019-03-18 | 2026-03-23 | サイエンスコ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | 低いgwpを有するフッ素化化合物を使用する熱交換方法 |
| JP7829486B2 (ja) * | 2019-12-31 | 2026-03-13 | スリーエム イノベイティブ プロパティズ カンパニー | 塩素化フルオロ芳香族及びその使用方法 |
| CN112928182B (zh) * | 2021-01-22 | 2022-05-31 | 徐州中辉光伏科技有限公司 | 一种散热性能好的太阳能光伏刻蚀装置 |
| CN112812747A (zh) * | 2021-01-25 | 2021-05-18 | 浙江诺亚氟化工有限公司 | 一种适用于it设备的全浸没式单相液冷剂及其应用 |
| CN114106787B (zh) * | 2021-12-02 | 2024-01-23 | 中国石油化工股份有限公司 | 一种冷却介质组合物及其制备方法 |
| CN114539986A (zh) * | 2022-02-15 | 2022-05-27 | 浙江诺亚氟化工有限公司 | 一种含全氟醚化合物的组合物作为热传递介质的应用 |
| US12534657B2 (en) | 2022-03-23 | 2026-01-27 | Nano And Advanced Materials Institute Limited | Two-phase immersion cooling |
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| DE2557655C3 (de) * | 1975-12-20 | 1981-08-27 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Hexafluorpropylenoxid |
| US4721578A (en) * | 1986-10-06 | 1988-01-26 | E. I. Du Pont De Nemours And Company | Perfluorinated polypropylene oxide compounds for vapor phase heat transfer processes |
| US4960951A (en) * | 1989-01-30 | 1990-10-02 | E. I. Du Pont De Nemours And Company | Novel perfluoropolyethers |
| DE3902803A1 (de) * | 1989-01-31 | 1990-08-02 | Hoechst Ag | Verfahren zur reinigung und stabilisierung von perfluorpolyethern |
| US5084146A (en) * | 1990-04-09 | 1992-01-28 | E. I. Du Pont De Nemours And Company | Method for preparing perfluoropolyethers |
| DE4025348A1 (de) * | 1990-08-10 | 1992-02-13 | Hoechst Ag | Verfahren und vorrichtung fuer die thermoschock-pruefung |
| US5254774A (en) | 1992-12-28 | 1993-10-19 | Minnesota Mining And Manufacturing Company | Preparation of hexafluoropropene oligomers |
| AU4811800A (en) * | 1999-05-04 | 2000-11-17 | E.I. Du Pont De Nemours And Company | Polyfluorinated epoxides and associated polymers and processes |
| US6705506B1 (en) * | 2000-05-08 | 2004-03-16 | William Sund | Inert atmosphere soldering apparatus |
| 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 |
| US6913076B1 (en) * | 2002-07-17 | 2005-07-05 | Energent Corporation | High temperature heat pump |
| US7128133B2 (en) | 2003-12-16 | 2006-10-31 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| KR101150177B1 (ko) * | 2004-04-16 | 2012-05-29 | 허니웰 인터내셔널 인코포레이티드 | 테트라플루오로프로펜과 트리플루오로요오드메탄으로 이루어진 공비-성 조성물 |
| US7428816B2 (en) * | 2004-07-16 | 2008-09-30 | Honeywell International Inc. | Working fluids for thermal energy conversion of waste heat from fuel cells using Rankine cycle systems |
| JP2008531975A (ja) * | 2005-03-04 | 2008-08-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | エンジン排ガス駆動タービンを動力源とする冷凍/空気調節装置 |
| US20070172666A1 (en) * | 2006-01-24 | 2007-07-26 | Denes Ferencz S | RF plasma-enhanced deposition of fluorinated films |
| US8791254B2 (en) | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| US20100025619A1 (en) * | 2006-07-12 | 2010-02-04 | Solvay Fluor Gmbh | Method for heating and cooling using fluoroether compounds, compositions suitable therefore and their use |
| CN104017544B (zh) * | 2006-09-01 | 2017-04-12 | 纳幕尔杜邦公司 | 氟烯烃用的环氧化物和氟化环氧化物稳定剂 |
| EP2090572A1 (en) * | 2006-10-24 | 2009-08-19 | Daikin Industries, Ltd. | Process for production of hexafluoropropylene oxide |
| US20080157023A1 (en) * | 2006-11-14 | 2008-07-03 | Samuels George J | Fluorocarbon stabilizers |
| US8193397B2 (en) | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US7807074B2 (en) * | 2006-12-12 | 2010-10-05 | Honeywell International Inc. | Gaseous dielectrics with low global warming potentials |
| WO2008157757A1 (en) * | 2007-06-21 | 2008-12-24 | E. I. Du Pont De Nemours And Company | Method for leak detection in heat transfer system |
| WO2009042855A1 (en) * | 2007-09-28 | 2009-04-02 | E. I. Du Pont De Nemours And Company | Ionic liquid stabilizer compositions |
| JP5163659B2 (ja) | 2008-01-30 | 2013-03-13 | ダイキン工業株式会社 | 含フッ素エポキシドの製造方法 |
| US7988877B2 (en) | 2008-11-03 | 2011-08-02 | 3M Innovative Properties Company | Methods of making fluorinated ethers, fluorinated ethers, and uses thereof |
| WO2012134803A2 (en) * | 2011-03-25 | 2012-10-04 | 3M Innovative Properties Company | Fluorinated oxiranes as organic rankine cycle working fluids and methods of using same |
| EP2660547A1 (de) * | 2012-05-03 | 2013-11-06 | Siemens Aktiengesellschaft | Metallurgische Anlage |
| GB201208771D0 (en) * | 2012-05-17 | 2012-07-04 | Atalla Naji A | Improved heat engine |
| US20140000261A1 (en) * | 2012-06-29 | 2014-01-02 | General Electric Company | Triple expansion waste heat recovery system and method |
| JP6021526B2 (ja) * | 2012-08-30 | 2016-11-09 | 三菱日立パワーシステムズ株式会社 | 冷却水供給システムおよびこれを備えたバイナリ発電装置 |
| US20150089949A1 (en) * | 2013-10-01 | 2015-04-02 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Closed loop supercritical carbon dioxide power cycle |
| JP6213194B2 (ja) * | 2013-11-29 | 2017-10-18 | セントラル硝子株式会社 | 熱エネルギーを機械エネルギーへ変換する方法、有機ランキンサイクル装置、及び作動流体を置換える方法 |
-
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- 2012-03-19 EP EP12716148.7A patent/EP2688973A1/en not_active Withdrawn
- 2012-03-19 KR KR1020137027755A patent/KR20140019399A/ko not_active Withdrawn
- 2012-03-19 CN CN2012800150192A patent/CN103443238A/zh active Pending
- 2012-03-19 JP JP2014501168A patent/JP2014515048A/ja active Pending
- 2012-03-19 WO PCT/US2012/029649 patent/WO2012134860A1/en not_active Ceased
- 2012-03-19 US US14/007,041 patent/US20140009887A1/en not_active Abandoned
- 2012-03-23 TW TW101110243A patent/TW201245430A/zh unknown
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| Publication number | Publication date |
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| TW201245430A (en) | 2012-11-16 |
| US20140009887A1 (en) | 2014-01-09 |
| CN103443238A (zh) | 2013-12-11 |
| JP2014515048A (ja) | 2014-06-26 |
| WO2012134860A1 (en) | 2012-10-04 |
| EP2688973A1 (en) | 2014-01-29 |
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