JP2018515574A - SbF5による1233xfの244bbへのフッ化水素処理 - Google Patents
SbF5による1233xfの244bbへのフッ化水素処理 Download PDFInfo
- Publication number
- JP2018515574A JP2018515574A JP2017560782A JP2017560782A JP2018515574A JP 2018515574 A JP2018515574 A JP 2018515574A JP 2017560782 A JP2017560782 A JP 2017560782A JP 2017560782 A JP2017560782 A JP 2017560782A JP 2018515574 A JP2018515574 A JP 2018515574A
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- hydrofluoroalkane
- olefin
- trifluoropropene
- tetrafluoropropane
- 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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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims description 30
- 229910000040 hydrogen fluoride Inorganic materials 0.000 title claims description 25
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 title abstract 2
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000000460 chlorine Substances 0.000 claims abstract description 39
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 37
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 36
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims abstract description 35
- 239000011737 fluorine Chemical group 0.000 claims abstract description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 claims abstract description 23
- 239000007791 liquid phase Substances 0.000 claims abstract description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 18
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 47
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 23
- 229910018287 SbF 5 Inorganic materials 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical group CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 claims description 15
- 239000012808 vapor phase Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 6
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims description 5
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical group CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 4
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical group FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 3
- XTRPJEPJFXGYCI-UHFFFAOYSA-N 3-chloro-1,1,1,2,2-pentafluoropropane Chemical group FC(F)(F)C(F)(F)CCl XTRPJEPJFXGYCI-UHFFFAOYSA-N 0.000 claims description 2
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical group FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 claims description 2
- HXNJCCYKKHPFIO-UHFFFAOYSA-N 3-chloro-1,1,2,3-tetrafluoroprop-1-ene Chemical compound FC(Cl)C(F)=C(F)F HXNJCCYKKHPFIO-UHFFFAOYSA-N 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- 238000003682 fluorination reaction Methods 0.000 description 15
- -1 gold-lined Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 229910001507 metal halide Inorganic materials 0.000 description 10
- 150000005309 metal halides Chemical class 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000011651 chromium Substances 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 229910001026 inconel Inorganic materials 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 229910000423 chromium oxide Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910001092 metal group alloy Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 229910016569 AlF 3 Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012025 fluorinating agent Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical group CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 1
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 1
- LLJWABOOFANACB-UHFFFAOYSA-N 1-chloro-1,1,3,3,3-pentafluoropropane Chemical compound FC(F)(F)CC(F)(F)Cl LLJWABOOFANACB-UHFFFAOYSA-N 0.000 description 1
- LOCOMRPWMOCMPV-UHFFFAOYSA-N 2,3-dichloro-1,1,1,2-tetrafluoropropane Chemical group FC(F)(F)C(F)(Cl)CCl LOCOMRPWMOCMPV-UHFFFAOYSA-N 0.000 description 1
- IRCLJRMKYIULFK-UHFFFAOYSA-N 2,3-dichloro-1,1,1,3-tetrafluoropropane Chemical compound FC(Cl)C(Cl)C(F)(F)F IRCLJRMKYIULFK-UHFFFAOYSA-N 0.000 description 1
- AWRHGKKFIUAKHZ-UHFFFAOYSA-N 3,3-dichloro-1,1,2,3-tetrafluoroprop-1-ene Chemical compound FC(F)=C(F)C(F)(Cl)Cl AWRHGKKFIUAKHZ-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910000934 Monel 400 Inorganic materials 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001349 alkyl fluorides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 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 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OANFWJQPUHQWDL-UHFFFAOYSA-N copper iron manganese nickel Chemical compound [Mn].[Fe].[Ni].[Cu] OANFWJQPUHQWDL-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/18—Arsenic, antimony or bismuth
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- 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
- C07C17/42—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
(i)(CQ2=CCl−CH2Q又は、CQ3−CCl=CH2又は、CQ3−CHCl−CH2Q)+HF−>2−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233xf又は1233xf)+固体触媒で充填した蒸気相反応器中のHCl
(ii)2−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233xf)+HF−>液体フッ化水素処理触媒で充填した液相反応器中の2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb又は244bb)、および、
(iii)2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)−>蒸気相反応器中の2,3,3,3,−テトラフルオロプロペン(HFO−1234yf)
ここで、少なくとも一つのQはフッ素ではないという条件で、Qは独立して、F,Cl,Br,およびIから選択される。
X,Y,およびZは、それぞれ独立して同じであるか又は異なり、H,F,Cl,Br及び、塩素若しくはフッ素若しくは臭素で一部又は全部置換されたC1−C6アルキルからなる群から選択され、及び、Rは、塩素若しくはフッ素若しくは臭素で一部又は全部置換されたC1−C6アルキルであり、液相中で、SbF5の存在下、約−30℃〜約65℃の範囲の温度で、フルオロオレフィンと、HFとを反応させる方法に関するものである。
(i)(CQ2=CCl−CH2Q又は、CQ3−CCl=CH2又は、CQ3−CHCl−CH2Q)+HF−>2−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233xf)+固体触媒で充填した蒸気相反応器中のHCl
(ii)2−クロロ−3,3,3−トリフルオロプロペン(HCFO−1233xf)+HF−>液体フッ化水素処理触媒で充填した液相反応器中の2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)、および、
(iii)2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)−>蒸気相反応器中の2,3,3,3,−テトラフルオロプロペン(HFO−1234yf)
(実施例1)
30℃で、SbF5触媒とHFによる1233xfのフッ化水素処理
10℃で、SbF5触媒とHFによる1233xfのフッ化水素処理
30℃で、SbF5触媒とHFによる1233xfのフッ化水素処理
80℃で、フッ化SbCl5触媒とHFによる1233xf-244bb平衡
Claims (25)
- 式RCXFCHYZのハイドロフルオロアルカンを調製する方法であって、
液相中、SbF5の存在下、約−30℃〜約65℃の範囲の温度で、式RCX=CYZのオレフィンと、HFとを反応させ、ハイドロフルオロアルカンを製造する工程を含み、
X,Y,およびZは、それぞれ独立して同じであるか又は異なり、H,F,Cl,Br又は、塩素若しくはフッ素若しくは臭素で一部又は全部置換されたC1−C6アルキルであり、Rは、塩素若しくはフッ素若しくは臭素で一部又は全部置換されたC1−C6アルキルであることを特徴とする方法。 - X,Y,およびZは、それぞれ独立して、H,F,Cl,又はBrである請求項1に記載の方法。
- Rは、1−6の炭素原子を有するフッ素化アルキル、又は、1−6の炭素原子を有する塩素化アルキルである請求項1又は2に記載の方法。
- Rは、フッ素化アルキルである請求項3に記載の方法。
- Rは、過フッ素化アルキルである請求項3に記載の方法。
- Rは、CF3又はC2F5である請求項4に記載の方法。
- HF対オレフィンの比率が、1〜10の範囲である請求項1に記載の方法。
- HF対オレフィンの比率が、1〜5の範囲である請求項7に記載の方法。
- 触媒が、重量比で1%〜50%の量で存在する請求項1に記載の方法。
- 触媒が、重量比で2%〜30%の量で存在する請求項9に記載の方法。
- 触媒が、重量比で3%〜20%の量で存在する請求項10に記載の方法。
- オレフィンが、2−クロロ−3,3,3−トリフルオロプロペン、1−クロロ−3,3,3−トリフルオロプロペン、クロロテトラフルオロプロペン、2,3,3,3−テトラフルオロプロペン、1,3,3,3−テトラフルオロプロペン、または、3,3,3−トリフルオロプロペンである請求項1に記載の方法。
- ハイドロフルオロアルカンが、2−クロロ−1,1,1,2−テトラフルオロプロパンである請求項1に記載の方法。
- オレフィンが、2−クロロ−3,3,3−トリフルオロプロペンであり、且つ、ハイドロフルオロアルカンが、2−クロロ−1,1,1,2−テトラフルオロプロパンである請求項1に記載の方法。
- オレフィンが、(Z)又は(E)−1−クロロ−3,3,3−トリフルオロプロペンであり、且つ、ハイドロフルオロアルカンが、3−クロロ−1,1,1,3−テトラフルオロプロパンである請求項1に記載の方法。
- オレフィンが、1−クロロ−2,3,3,3−トリフルオロプロペンであり、且つ、ハイドロフルオロアルカンが、1,1,1,2,2−ペンタフルオロ−3−クロロプロパンおよび1,1,1,2,3−ペンタフルオロ−3−クロロプロパンである請求項1に記載の方法。
- オレフィンが、2,3,3,3−テトラフルオロプロペンであり、且つ、ハイドロフルオロアルカンが、1,1,1,2,2−ペンタフルオロプロパンである請求項1に記載の方法。
- オレフィンが、1,3,3,3−テトラフルオロプロペンであり、且つ、ハイドロフルオロアルカンが、1,1,1,3,3−ペンタフルオロプロパンである請求項1に記載の方法。
- 温度が、約−10℃〜約40℃である請求項1に記載の方法。
- 温度が、約0℃〜約30℃である請求項19に記載の方法。
- 温度が、約5℃〜約25℃である請求項20に記載の方法。
- オレフィン対ハイドロフルオロアルカンのフィード材料比率が、1モル%よりも大きい請求項1に記載の方法。
- 2−クロロ−1,1,1,2−テトラフルオロプロパンを調製する方法であって、
液相中、SbF5の存在下、約−30℃〜約65℃の範囲の温度で、2−クロロ−1,1,1−トリフルオロプロペンとHFを反応させる工程を含むことを特徴とする方法。 - 2−クロロ−1,1,1,2−テトラフルオロプロパンが、脱塩化水素されて、2,3,3,3−テトラフルオロ−1−プロペンを形成する請求項16に記載の方法。
- 2,3,3,3−テトラフルオロ−1−プロペンを調製する方法であって、
65℃よりも高い反応温度で、フッ化水素処理触媒を充填した液相反応器中で、2−クロロ−1,1,1−トリフルオロプロペンとHFを反応させて、2−クロロ−1,1,1−トリフルオロプロペンと、2−クロロ−1,1,1,2−テトラフルオロプロパンの混合物を生成する工程、
HFと、前記混合物を、SbF5の存在下の液相中で、約−30℃〜約65℃の範囲の温度で反応させて、未変換の2−クロロ−1,1,1−トリフルオロプロペンを、さらに反応させて、追加の2−クロロ−1,1,1,2−テトラフルオロプロパンを形成させる工程、及び、
2−クロロ−1,1,1,2−テトラフルオロプロパンを、触媒の存在下又は不存在下で蒸気相容器中で脱ハロゲン化水素させ、2,3,3,3−テトラフルオロ−1−プロペンを形成する工程、を含むことを特徴とする方法。
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MX2017014398A (es) | 2018-03-23 |
EP3297980A4 (en) | 2018-12-26 |
MX2022010851A (es) | 2022-09-27 |
EP3984986A1 (en) | 2022-04-20 |
US11008267B2 (en) | 2021-05-18 |
US20210221756A1 (en) | 2021-07-22 |
JP6962822B2 (ja) | 2021-11-05 |
US20190284117A1 (en) | 2019-09-19 |
US20230075222A1 (en) | 2023-03-09 |
US20200239391A1 (en) | 2020-07-30 |
CN113527036A (zh) | 2021-10-22 |
US20220213009A1 (en) | 2022-07-07 |
US10988422B2 (en) | 2021-04-27 |
US11572326B2 (en) | 2023-02-07 |
US10301236B2 (en) | 2019-05-28 |
WO2016187507A1 (en) | 2016-11-24 |
EP3297980A1 (en) | 2018-03-28 |
KR20180000720A (ko) | 2018-01-03 |
US20180127338A1 (en) | 2018-05-10 |
CN107635955A (zh) | 2018-01-26 |
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