JP5081225B2 - ハイドロフルオロオレフィンの併産 - Google Patents
ハイドロフルオロオレフィンの併産 Download PDFInfo
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- JP5081225B2 JP5081225B2 JP2009503070A JP2009503070A JP5081225B2 JP 5081225 B2 JP5081225 B2 JP 5081225B2 JP 2009503070 A JP2009503070 A JP 2009503070A JP 2009503070 A JP2009503070 A JP 2009503070A JP 5081225 B2 JP5081225 B2 JP 5081225B2
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- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 32
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 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 claims description 13
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 8
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 claims description 6
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 238000005796 dehydrofluorination reaction Methods 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 12
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 12
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 12
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 11
- 229910052725 zinc Inorganic materials 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000011261 inert gas Substances 0.000 description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 9
- 239000003575 carbonaceous material Substances 0.000 description 9
- 239000011651 chromium Substances 0.000 description 9
- 229910052804 chromium Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910000856 hastalloy Inorganic materials 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910000990 Ni alloy Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 229910052746 lanthanum Inorganic materials 0.000 description 5
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 4
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000003507 refrigerant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910052779 Neodymium Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052777 Praseodymium Inorganic materials 0.000 description 3
- 229910052772 Samarium Inorganic materials 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 3
- 229910000423 chromium oxide Inorganic materials 0.000 description 3
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 229910001512 metal fluoride Inorganic materials 0.000 description 3
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 229910052727 yttrium Inorganic materials 0.000 description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 3
- SUAMPXQALWYDBK-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoropropane Chemical compound FCC(F)(F)C(F)(F)F SUAMPXQALWYDBK-UHFFFAOYSA-N 0.000 description 2
- 229910021193 La 2 O 3 Inorganic materials 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012025 fluorinating agent Substances 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 229910017768 LaF 3 Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- VFZCPZOOBHMUBZ-UHFFFAOYSA-N [Mg].FOF Chemical compound [Mg].FOF VFZCPZOOBHMUBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 bone Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BYMUNNMMXKDFEZ-UHFFFAOYSA-K trifluorolanthanum Chemical compound F[La](F)F BYMUNNMMXKDFEZ-UHFFFAOYSA-K 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
-
- 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
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78784006P | 2006-03-31 | 2006-03-31 | |
| US60/787,840 | 2006-03-31 | ||
| PCT/US2007/008202 WO2007117391A1 (en) | 2006-03-31 | 2007-03-29 | Coproduction of hydrofluoroolefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009532365A JP2009532365A (ja) | 2009-09-10 |
| JP2009532365A5 JP2009532365A5 (enExample) | 2010-04-02 |
| JP5081225B2 true JP5081225B2 (ja) | 2012-11-28 |
Family
ID=38362853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009503070A Expired - Fee Related JP5081225B2 (ja) | 2006-03-31 | 2007-03-29 | ハイドロフルオロオレフィンの併産 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7687670B2 (enExample) |
| EP (1) | EP2001828B1 (enExample) |
| JP (1) | JP5081225B2 (enExample) |
| CN (1) | CN101415664B (enExample) |
| ES (1) | ES2392591T3 (enExample) |
| WO (1) | WO2007117391A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US7722781B2 (en) | 2006-06-27 | 2010-05-25 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| EP2046704A2 (en) * | 2006-06-27 | 2009-04-15 | E.I. Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| US7803975B2 (en) * | 2006-07-13 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Process for separating a fluoroolefin from HF by liquid-liquid extraction |
| US8232435B2 (en) | 2006-09-05 | 2012-07-31 | E I Du Pont De Nemours And Company | 1,2,3,3,3-pentafluoropropene production processes |
| KR101394583B1 (ko) | 2006-10-03 | 2014-05-12 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| US8013194B2 (en) | 2008-03-14 | 2011-09-06 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
| TW200831446A (en) * | 2006-11-15 | 2008-08-01 | Du Pont | Processes for producing pentafluoropropenes and certain azeotropes comprising HF and certain halopropenes of the formula C3HCIF4 |
| GB0625214D0 (en) | 2006-12-19 | 2007-01-24 | Ineos Fluor Holdings Ltd | Process |
| ES2400365T3 (es) | 2007-12-27 | 2013-04-09 | Arkema France | Procedimiento para la producción de 1,1,1,2-tetrafluorpropeno |
| US8710282B2 (en) * | 2008-03-14 | 2014-04-29 | Honeywell International Inc. | Integrated process for the manufacture of fluorinated olefins |
| FR2929272B1 (fr) * | 2008-03-28 | 2010-04-09 | Arkema France | Procede pour la preparation du 2,3,3,3-tetrafluoro-1-propene |
| FR2929271B1 (fr) * | 2008-03-28 | 2010-04-16 | Arkema France | Procede pour la preparation du 1,2,3,3,3-pentafluoropropene- 1 |
| FR2929273B1 (fr) * | 2008-03-28 | 2017-05-26 | Arkema France | Procede de preparation de composes fluores. |
| JP5701205B2 (ja) * | 2008-05-07 | 2015-04-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | ２，３−ジクロロ−１，１，１−トリフルオロプロパン、２−クロロ−１，１，１−トリフルオロプロペン、２−クロロ−１，１，１，２−テトラフルオロプロパンまたは２，３，３，３−テトラフルオロプロペンを含む組成物 |
| AU2014208303B2 (en) * | 2008-05-07 | 2017-08-31 | The Chemours Company Fc, Llc. | Compositions comprising 1,1,1,2,3-pentafluoropropane or 2,3,3,3-tetrafluoropropene |
| CN102015956B (zh) | 2008-05-07 | 2014-06-11 | 纳幕尔杜邦公司 | 包含1,1,1,2,3-五氟丙烷或2,3,3,3-四氟丙烯的组合物 |
| GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
| US8053612B2 (en) * | 2008-05-30 | 2011-11-08 | Honeywell International Inc. | Process for dehydrochlorinating 1,1,1,2-tetrafluoro-2-chloropropane to 2,3,3,3-tetrafluoropropene in the presence of an alkali metal-doped magnesium oxyfluoride catalyst and methods for making the catalyst |
| KR20110086037A (ko) * | 2008-10-13 | 2011-07-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 염화된 및/또는 불화된 프로펜의 제조 방법 |
| BR112012007913A2 (pt) | 2009-10-09 | 2019-09-24 | Dow Global Technologies Llc | reator adiabático de fluxo pistonado, processo para produzir um prpeno clorado ou fluorado, processo para preparar um produto a jusante e processo para preparar 2,3,3,3-tetrafluoroprop-1-eno (hfo-123yf) ou 1,3,3,3-tetrafluoroprop-1-eno (hfo-123ze) |
| CN102686544B (zh) | 2009-10-09 | 2017-02-15 | 蓝立方知识产权公司 | 用于生产氯化和/或氟化丙烯和高级烯烃的方法 |
| WO2011044447A2 (en) * | 2009-10-09 | 2011-04-14 | Dow Global Technologies, Inc | Process for the production of chlorinated and/or fluorinated propenes |
| KR20120091192A (ko) | 2009-10-09 | 2012-08-17 | 다우 글로벌 테크놀로지스 엘엘씨 | 등온 다중튜브 반응기 및 이를 도입한 방법 |
| US9012702B2 (en) | 2011-02-21 | 2015-04-21 | E. I. Du Pont De Nemours And Company | Catalytic dehydrochlorination of hydrochlorofluorocarbons |
| WO2012166394A1 (en) | 2011-05-31 | 2012-12-06 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| US8907149B2 (en) | 2011-05-31 | 2014-12-09 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| WO2012170239A1 (en) | 2011-06-08 | 2012-12-13 | Dow Agrosciences, Llc | Process for the production of chlorinated and/or fluorinated propenes |
| CN103717557A (zh) | 2011-08-07 | 2014-04-09 | 陶氏环球技术有限责任公司 | 生产氯化的丙烯的方法 |
| US8907148B2 (en) | 2011-08-07 | 2014-12-09 | Dow Global Technologies Llc | Process for the production of chlorinated propenes |
| CN102989489B (zh) | 2011-09-14 | 2015-04-22 | 中化蓝天集团有限公司 | 一种制备2,3,3,3-四氟丙烯的方法 |
| JP6050372B2 (ja) | 2011-11-21 | 2016-12-21 | ブルー キューブ アイピー エルエルシー | クロロアルカンの製造方法 |
| US9199899B2 (en) | 2011-12-02 | 2015-12-01 | Blue Cube Ip Llc | Process for the production of chlorinated alkanes |
| CA2856717A1 (en) | 2011-12-02 | 2013-06-06 | Dow Global Technologies Llc | Process for the production of chlorinated alkanes |
| JP6170068B2 (ja) | 2011-12-13 | 2017-07-26 | ブルー キューブ アイピー エルエルシー | 塩素化プロパン及びプロペンの製造方法 |
| CN104011000A (zh) | 2011-12-22 | 2014-08-27 | 陶氏环球技术有限责任公司 | 生产四氯甲烷的方法 |
| EP2794521B1 (en) | 2011-12-23 | 2016-09-21 | Dow Global Technologies LLC | Process for the production of alkenes and/or aromatic compounds |
| US9598334B2 (en) | 2012-09-20 | 2017-03-21 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| US9321707B2 (en) | 2012-09-20 | 2016-04-26 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| EP2900364B1 (en) | 2012-09-30 | 2018-06-13 | Blue Cube IP LLC | Weir quench and processes incorporating the same |
| CA2887559A1 (en) | 2012-10-26 | 2014-05-01 | Dow Global Technologies Llc | Mixer and reactor and process incorporating the same |
| WO2014100066A1 (en) | 2012-12-18 | 2014-06-26 | Dow Global Technologies, Llc | Process for the production of chlorinated propenes |
| US9475740B2 (en) | 2012-12-19 | 2016-10-25 | Blue Cube Ip Llc | Process for the production of chlorinated propenes |
| EP2961722A2 (en) | 2013-02-27 | 2016-01-06 | Blue Cube IP LLC | Process for the production of chlorinated propenes |
| US9403741B2 (en) | 2013-03-09 | 2016-08-02 | Blue Cube Ip Llc | Process for the production of chlorinated alkanes |
| CN104069878B (zh) * | 2014-07-07 | 2016-03-02 | 浙江师范大学 | 一种用于HFC-245fa裂解制备HFO-1234yf的催化剂及其制备方法 |
| CN119118781A (zh) | 2018-06-06 | 2024-12-13 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| CN112264035B (zh) * | 2020-10-09 | 2024-09-20 | 南北兄弟药业投资有限公司 | 1,1-二氟乙烷气相脱除氟化氢制备氟乙烯的催化剂 |
| CN120590235A (zh) * | 2025-08-07 | 2025-09-05 | 泉州宇极新材料科技有限公司 | 联产HFC-236ea、Z-HFO-1225ye、E-HFO-1225ye和HFO-1234yf的工艺 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766260A (en) | 1987-07-07 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| SU1706690A1 (ru) | 1988-04-19 | 1992-01-23 | Всесоюзный Научно-Исследовательский Институт Технического Углерода | Пористый углеродный материал |
| US4902838A (en) | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| US5136113A (en) | 1991-07-23 | 1992-08-04 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenolysis |
| US5268122A (en) | 1991-08-28 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions |
| BR9306493A (pt) | 1992-06-05 | 1998-09-15 | Daikin Ind Ltd | Método para a manufatura de 1,1,1,2,3-pentafluoropropeno e método para a manufatura de 1,1,1,2,3-pentafluoropropano |
| US5396000A (en) | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
| EP0958265B1 (en) | 1997-01-31 | 2003-04-02 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of pentafluoropropenes |
| US6031141A (en) * | 1997-08-25 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Fluoroolefin manufacturing process |
| WO1999062849A1 (en) | 1998-06-02 | 1999-12-09 | E.I. Du Pont De Nemours And Company | Process for the production of hexafluoropropylene from cc1f2cc1fcf3 and azeotropes of cc1f2cc1fcf3 with hf |
| US6548719B1 (en) | 2001-09-25 | 2003-04-15 | Honeywell International | Process for producing fluoroolefins |
| US7897823B2 (en) * | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| WO2007019358A2 (en) | 2005-08-05 | 2007-02-15 | E. I. Du Pont De Nemours And Company | Process for the preparation of 1,3,3,3-tetrafluoropropene and/or 1,1,3,3,3-pentafluoropropene |
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| EP2001828B1 (en) | 2012-08-22 |
| WO2007117391A1 (en) | 2007-10-18 |
| CN101415664A (zh) | 2009-04-22 |
| US7687670B2 (en) | 2010-03-30 |
| JP2009532365A (ja) | 2009-09-10 |
| EP2001828A1 (en) | 2008-12-17 |
| US20090018375A1 (en) | 2009-01-15 |
| CN101415664B (zh) | 2012-05-30 |
| ES2392591T3 (es) | 2012-12-12 |
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