JP2018538347A5 - - Google Patents
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- Publication number
- JP2018538347A5 JP2018538347A5 JP2018533080A JP2018533080A JP2018538347A5 JP 2018538347 A5 JP2018538347 A5 JP 2018538347A5 JP 2018533080 A JP2018533080 A JP 2018533080A JP 2018533080 A JP2018533080 A JP 2018533080A JP 2018538347 A5 JP2018538347 A5 JP 2018538347A5
- Authority
- JP
- Japan
- Prior art keywords
- dichloro
- chloro
- methyl
- tetrafluoropropane
- tetrafluoro
- 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.)
- Granted
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- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-Difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 54
- RFCAUADVODFSLZ-UHFFFAOYSA-N Chloropentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 claims description 53
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-Tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 36
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (E)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 239000004340 Chloropentafluoroethane Substances 0.000 claims description 26
- 235000019406 chloropentafluoroethane Nutrition 0.000 claims description 26
- 239000012535 impurity Substances 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- JARKCYVAAOWBJS-UHFFFAOYSA-N Hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 8
- PYOKUURKVVELLB-UHFFFAOYSA-N Trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims 8
- 229960004132 diethyl ether Drugs 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- -1 (methyleneamino) Ethylenediamine Chemical compound 0.000 claims 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-Butanol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 4
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims 4
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-Methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 4
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 4
- UAOMVDZJSHZZME-UHFFFAOYSA-N Diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 4
- NKDDWNXOKDWJAK-UHFFFAOYSA-N Dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N M-Xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N Pentylamine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims 4
- PJGSXYOJTGTZAV-UHFFFAOYSA-N Pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N Propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 4
- DCKVNWZUADLDEH-UHFFFAOYSA-N Sec-Butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims 4
- WMOVHXAZOJBABW-UHFFFAOYSA-N Tert-Butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M caproate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N ethylene glycol monomethyl ether Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 4
- 229940011051 isopropyl acetate Drugs 0.000 claims 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims 4
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N methyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 4
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 claims 4
- RMOUBSOVHSONPZ-UHFFFAOYSA-N propan-2-yl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 4
- 239000001893 (2R)-2-methylbutanal Substances 0.000 claims 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 claims 2
- HIILBTHBHCLUER-IWQZZHSRSA-N (Z)-1,2,3-trichloroprop-1-ene Chemical compound ClC\C(Cl)=C\Cl HIILBTHBHCLUER-IWQZZHSRSA-N 0.000 claims 2
- ZHJBJVPTRJNNIK-UPHRSURJSA-N (Z)-1,2-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(\Cl)=C\Cl ZHJBJVPTRJNNIK-UPHRSURJSA-N 0.000 claims 2
- UOORRWUZONOOLO-UPHRSURJSA-N (Z)-1,3-dichloropropene Chemical compound ClC\C=C/Cl UOORRWUZONOOLO-UPHRSURJSA-N 0.000 claims 2
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-Dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 claims 2
- UVWPNDVAQBNQBG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-icosafluorononane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UVWPNDVAQBNQBG-UHFFFAOYSA-N 0.000 claims 2
- ZQTIKDIHRRLSRV-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluorobutane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)F ZQTIKDIHRRLSRV-UHFFFAOYSA-N 0.000 claims 2
- NOPJRYAFUXTDLX-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)(F)F NOPJRYAFUXTDLX-UHFFFAOYSA-N 0.000 claims 2
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims 2
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 claims 2
- SRCNPEKLEHSVCL-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2-fluoroethane Chemical compound FC(Cl)C(Cl)(Cl)Cl SRCNPEKLEHSVCL-UHFFFAOYSA-N 0.000 claims 2
- LWLBLAAPXGGJGY-UHFFFAOYSA-N 1,1,1,2-tetrachloro-3,3,3-trifluoropropane Chemical compound FC(F)(F)C(Cl)C(Cl)(Cl)Cl LWLBLAAPXGGJGY-UHFFFAOYSA-N 0.000 claims 2
- VCARXVNAFDSAFZ-UHFFFAOYSA-N 1,1,1,3-tetrachloro-2,2,3-trifluoropropane Chemical compound FC(Cl)C(F)(F)C(Cl)(Cl)Cl VCARXVNAFDSAFZ-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-Trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims 2
- LJPLFJPOUHWADA-UHFFFAOYSA-N 1,1,1-trichloro-2,2,3,3-tetrafluoropropane Chemical compound FC(F)C(F)(F)C(Cl)(Cl)Cl LJPLFJPOUHWADA-UHFFFAOYSA-N 0.000 claims 2
- HXUSPOJBFARDNS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,3-trifluoropropane Chemical compound FCC(F)(F)C(Cl)(Cl)Cl HXUSPOJBFARDNS-UHFFFAOYSA-N 0.000 claims 2
- RDTZCQIUXDONLZ-UHFFFAOYSA-N 1,1,1-trichloro-2,2-difluoroethane Chemical compound FC(F)C(Cl)(Cl)Cl RDTZCQIUXDONLZ-UHFFFAOYSA-N 0.000 claims 2
- GVWSTOIEDDREHS-UHFFFAOYSA-N 1,1,1-trichloro-3-fluoropropane Chemical compound FCCC(Cl)(Cl)Cl GVWSTOIEDDREHS-UHFFFAOYSA-N 0.000 claims 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims 2
- OHLVGBXMHDWRRX-UHFFFAOYSA-N 1,1,1-trifluoro-2-methoxyethane Chemical compound COCC(F)(F)F OHLVGBXMHDWRRX-UHFFFAOYSA-N 0.000 claims 2
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 claims 2
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 claims 2
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 claims 2
- COWKRCCNQSQUGJ-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropan-1-ol Chemical compound OC(F)(F)C(F)(F)CF COWKRCCNQSQUGJ-UHFFFAOYSA-N 0.000 claims 2
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 claims 2
- IJURQEZAWYGJDB-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-(1,1,2,2-tetrafluorobutoxy)butane Chemical compound CCC(F)(F)C(F)(F)OC(F)(F)C(F)(F)CC IJURQEZAWYGJDB-UHFFFAOYSA-N 0.000 claims 2
- YQQHEHMVPLLOKE-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-methoxyethane Chemical compound COC(F)(F)C(F)F YQQHEHMVPLLOKE-UHFFFAOYSA-N 0.000 claims 2
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 claims 2
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 claims 2
- ORMSTDJYMPIZAO-UHFFFAOYSA-N 1,1,2-trichloro-2-fluoroethane Chemical compound FC(Cl)C(Cl)Cl ORMSTDJYMPIZAO-UHFFFAOYSA-N 0.000 claims 2
- GRSQYISVQKPZCW-UHFFFAOYSA-N 1,1,2-trichloropropane Chemical compound CC(Cl)C(Cl)Cl GRSQYISVQKPZCW-UHFFFAOYSA-N 0.000 claims 2
- VSPRXIMPHWEJMN-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1,2,2-trifluoropropane Chemical compound ClC(Cl)C(F)(F)C(F)(Cl)Cl VSPRXIMPHWEJMN-UHFFFAOYSA-N 0.000 claims 2
- IAHLQJBJZKIZIQ-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1-fluoropropane Chemical compound FC(Cl)(Cl)CC(Cl)Cl IAHLQJBJZKIZIQ-UHFFFAOYSA-N 0.000 claims 2
- LYNCQSNLMRUIRI-UHFFFAOYSA-N 1,1,3-trichloro-1,2,2,3-tetrafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(Cl)Cl LYNCQSNLMRUIRI-UHFFFAOYSA-N 0.000 claims 2
- CPHFUGPCSJJMOI-UHFFFAOYSA-N 1,1,3-trichloro-1,2,2-trifluoropropane Chemical compound ClCC(F)(F)C(F)(Cl)Cl CPHFUGPCSJJMOI-UHFFFAOYSA-N 0.000 claims 2
- PJJNYNCHHJISIH-UHFFFAOYSA-N 1,1,3-trichloro-2,2,3-trifluoropropane Chemical compound FC(Cl)C(F)(F)C(Cl)Cl PJJNYNCHHJISIH-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-Dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 claims 2
- JXMGZLBGSDLPKN-UHFFFAOYSA-N 1,1-dichloro-1,2,2,3,3-pentafluoropropane Chemical compound FC(F)C(F)(F)C(F)(Cl)Cl JXMGZLBGSDLPKN-UHFFFAOYSA-N 0.000 claims 2
- CUQVBEQXNAJKNB-UHFFFAOYSA-N 1,1-dichloro-1,2,2,3-tetrafluoropropane Chemical compound FCC(F)(F)C(F)(Cl)Cl CUQVBEQXNAJKNB-UHFFFAOYSA-N 0.000 claims 2
- GELJRWJPYZKUPR-UHFFFAOYSA-N 1,1-dichloro-2,2,3-trifluoropropane Chemical compound FCC(F)(F)C(Cl)Cl GELJRWJPYZKUPR-UHFFFAOYSA-N 0.000 claims 2
- NWVBAOKYACOFKR-UHFFFAOYSA-N 1,1-dichloro-2,2-difluoro-1-methoxyethane Chemical compound COC(Cl)(Cl)C(F)F NWVBAOKYACOFKR-UHFFFAOYSA-N 0.000 claims 2
- VLIDBBNDBSNADN-UHFFFAOYSA-N 1,1-dichloro-2,2-difluoroethane Chemical compound FC(F)C(Cl)Cl VLIDBBNDBSNADN-UHFFFAOYSA-N 0.000 claims 2
- RGZHHTKDHXSAQQ-UHFFFAOYSA-N 1,1-dichloro-2-fluoroethane Chemical compound FCC(Cl)Cl RGZHHTKDHXSAQQ-UHFFFAOYSA-N 0.000 claims 2
- WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 claims 2
- MBNMGGKBGCIEGF-UHFFFAOYSA-N 1,1-diethoxypropane Chemical compound CCOC(CC)OCC MBNMGGKBGCIEGF-UHFFFAOYSA-N 0.000 claims 2
- DLWHXAYXTKNIBW-UHFFFAOYSA-N 1,2,2,3,3-pentachloro-1,1-difluoropropane Chemical compound FC(F)(Cl)C(Cl)(Cl)C(Cl)Cl DLWHXAYXTKNIBW-UHFFFAOYSA-N 0.000 claims 2
- HFHVCPIWDWKEOX-UHFFFAOYSA-N 1,2,2,3-tetrachloro-1,1-difluoropropane Chemical compound FC(F)(Cl)C(Cl)(Cl)CCl HFHVCPIWDWKEOX-UHFFFAOYSA-N 0.000 claims 2
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Description
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Claims (8)
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ã¢ã»ããããªã«ãïŒïŒïŒâãžããã¢ãããã³ãïŒâããã¿ã³ã¢ãã³ãïŒïŒïŒïŒïŒâããªã¯ãããããã³ãïŒïŒïŒïŒïŒâããªã¡ãã«ã·ã¯ããããµã³ãïŒïŒïŒâãžã¡ãã«ãã¿ããŒã«ãïŒâãšããã·ãããµã³ãïŒâã¯ããâïŒâããã¢ãããã³ããã«ãã«ãªãâïœâãã«ã³ãïŒâãã«ãã©ãŒã«ãïœïŒïœâãžãšãã«ãšãã¬ã³ãžã¢ãã³ãïŒïŒïŒâãžã¡ãã«ããªãžã³ãïŒïŒïŒïŒïŒïŒïŒâããã©ã¯ããâïŒâãã«ãªããããã³ãïŒâã¡ãã«âïŒâãããµãã³ãïŒïŒïŒâãžã¡ãã«ãã³ãŒã³ãïŒïŒïŒïŒïŒïŒïŒïŒïŒâãã³ã¿ã¯ããâïŒïŒïŒâãžãã«ãªããããã³ãïŒâã¡ããã·âïŒâã¢ã»ããã·ãããã³ãïŒïŒïŒïŒïŒâããªãšããã·ãšã¿ã³ãã¹ãã¬ã³ãïŒâã¡ãã«ããªãžã³ãïœïŒïœââãžãšãã«âïŒïŒïŒâãšã¿ã³ãžã¢ãã³ãïŒïŒïŒâãžã¡ãã«ã¢ã«ããªã³ãïŒâãšãã«âïŒâãã¿ããŒã«ãïŒïŒïŒâãžã¯ãããã³ã¿ã³ãïŒâã¡ãã«âïŒâãã³ã¿ããŒã«ãã¡ãã« ãããµããšãŒããïŒâããããã·ãšã¿ããŒã«ããžã¡ãã«ãšã¿ããŒã«ã¢ãã³åã³ïŒâããããã·âïŒâãããããŒã«ãããªã矀ããéžæãããããšãç¹åŸŽãšãããçµæç©ã - åèšææ©æœåºå€ãããšãã«ã¢ãã³ãã€ãœãããã«ã¢ãã³ããžãšãã«ãšãŒãã«ããšããã·ãšãã³ããžã¡ããã·ã¡ã¿ã³ãïœâãããã«ã¢ãã³ãã¡ãã« ïœâããã«ãšãŒãã«ããžãšãã«ã¢ãã³ãããããã³ãé ¢é žã¡ãã«ãã€ãœãã¿ããŒã«ãããã©ããããã©ã³ãã®é žã€ãœãããã«ããžã€ãœãããã«ãšãŒãã«ãïŒâãšããã·âïŒâã¡ãã«ãããã³ãé ¢é žãšãã«ããã¿ãã³ããžãšããã·ã¡ã¿ã³ãé ¢é žã€ãœãããã«ãïŒâãã³ãã«ã¢ãã³ãïŒâã¡ããã·ãšã¿ã³ã¢ãã³ãïœïœ ïœïœâããã«ã¢ã»ããŒãããžãªããµã³ãïŒâãã³ã¿ãã³ãïŒïŒïŒâãžãšããã·ãšã¿ã³ãïŒâãã³ã¿ãã³ãããªã¡ããã·ã¡ã¿ã³ãïœâãã³ãã«ã¢ãã³ãïŒïŒïŒâãžãªããµã³ãïŒïŒïŒâãžã¡ãã«âïŒâãã¿ãã³ãïœïœ ïœâããã«ã¢ã»ããŒããïŒâã¡ãã«âïŒâãã³ã¿ãã³ãïŒïŒïŒâãžã¢ãããšã¿ã³ãïŒâã¡ããã·ïŒâãããããŒã«ãçé žãžãšãã«ãïœâããã«ã¢ã»ããŒããïŒâãšããã·âïŒâãããããŒã«åã³ãããµããŒã«ãããªã矀ããéžæãããããšãç¹åŸŽãšãããè«æ±é ïŒã«èšèŒã®çµæç©ã
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PCT/EP2016/080946 WO2017108520A1 (fr) | 2015-12-23 | 2016-12-14 | Procede de production et de purification du 2,3,3,3-tetrafluoro-1-propene |
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US4902838A (en) | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
US5874657A (en) | 1996-11-01 | 1999-02-23 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,1-difluoroethane |
DE69807962T2 (de) | 1997-03-11 | 2003-01-30 | Central Glass Co., Ltd. | Verfahren zur Reinigung von rohem 1,1,1,3,3-Pentafluorpropan |
EP0939071B1 (en) | 1998-02-26 | 2003-07-30 | Central Glass Company, Limited | Method for producing fluorinated propane |
US7060165B2 (en) | 2002-02-14 | 2006-06-13 | Pcbu Services, Inc. | Processes for purification and production of fluorocarbons |
EP2546223B1 (en) | 2006-01-03 | 2016-08-10 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
ES2447037T3 (es) * | 2006-09-05 | 2014-03-11 | E.I. Du Pont De Nemours And Company | Procedimiento de fabricación de 2,3,3,3-tetrafluoropropeno |
WO2008040969A2 (en) | 2006-10-03 | 2008-04-10 | Ineos Fluor Holdings Limited | Dehydrogenationhalogenation process for the production of c3-c6-(hydro)fluoroalkenes |
EP2091897B2 (en) | 2006-10-31 | 2021-12-01 | The Chemours Company FC, LLC | Processes for the production of fluoropropanes and halopropenes |
BRPI0906015A2 (pt) * | 2008-02-21 | 2015-06-30 | Du Pont | "processo de separação de uma mistura que compreende o hf e hfc-1234ze, processo para a separação de um e-hfc-1234ze a partir de uma mistura que inclui o fluoreto de hidrogênio e dito e-hfc-1234ze, processo para a separação do fluoreto de hidrogênio a partir de uma mistura contendo fluoreto de hidrogênio e e-hfc-1234ze, processo para a purificação de um e-hfc-1234ze a partir de uma mistura de e-hfc-1234ze e hf, processo para a purificação do hf a partir de uma mistura que compreende e-hfc-1234ze e hf, processo para a separação do e-hfc-1234ze de uma mistura de e-hfc-1234ze, hf e pelo menos um dos hfc-245fa ou hfc-245eb e processo para a separação do hfc-1234yf do hfc-1234ze" |
US20110001080A1 (en) * | 2008-03-07 | 2011-01-06 | Arkema Inc. | Stable formulated systems with chloro-3,3,3-trifluoropropene |
FR2929271B1 (fr) | 2008-03-28 | 2010-04-16 | Arkema France | Procede pour la preparation du 1,2,3,3,3-pentafluoropropene- 1 |
FR2948678B1 (fr) * | 2009-07-28 | 2011-10-14 | Arkema France | Procede de transfert de chaleur |
US8900417B2 (en) * | 2010-07-23 | 2014-12-02 | Daikin Industries, Ltd. | Purification method of 2,3,3,3-tetrafluoropropene |
FR3000096B1 (fr) * | 2012-12-26 | 2015-02-20 | Arkema France | Composition comprenant du 2,3,3,3-tetrafluoropropene |
FR3033791B1 (fr) * | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
FR3046165B1 (fr) * | 2015-12-23 | 2019-12-13 | Arkema France | Procede de production et de purification du 2,3,3,3-tetrafluoro-1-propene |
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- 2016-12-14 JP JP2018533080A patent/JP6970092B2/ja active Active
- 2016-12-14 EP EP16809095.9A patent/EP3394014B1/fr active Active
- 2016-12-14 WO PCT/EP2016/080946 patent/WO2017108520A1/fr active Application Filing
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