CN114835553A - 制备1,1,1,2,2-五氟丙烷的方法 - Google Patents
制备1,1,1,2,2-五氟丙烷的方法 Download PDFInfo
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- CN114835553A CN114835553A CN202210480789.XA CN202210480789A CN114835553A CN 114835553 A CN114835553 A CN 114835553A CN 202210480789 A CN202210480789 A CN 202210480789A CN 114835553 A CN114835553 A CN 114835553A
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- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 claims abstract description 176
- 230000008569 process Effects 0.000 claims abstract description 140
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 121
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 115
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 230000003197 catalytic effect Effects 0.000 claims abstract description 81
- 238000007033 dehydrochlorination reaction Methods 0.000 claims abstract description 57
- 239000007789 gas Substances 0.000 claims abstract description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 25
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 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 abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 141
- 238000003682 fluorination reaction Methods 0.000 claims description 56
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- 239000011701 zinc Substances 0.000 claims description 42
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052751 metal Inorganic materials 0.000 claims description 35
- 239000002184 metal Substances 0.000 claims description 35
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 34
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 34
- 239000012071 phase Substances 0.000 claims description 34
- 229910052725 zinc Inorganic materials 0.000 claims description 31
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 229910001507 metal halide Inorganic materials 0.000 claims description 11
- 150000002739 metals Chemical class 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- 238000005796 dehydrofluorination reaction Methods 0.000 claims description 10
- 229910052723 transition metal Inorganic materials 0.000 claims description 10
- 150000003624 transition metals Chemical class 0.000 claims description 10
- 150000005309 metal halides Chemical class 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical class 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 239000002274 desiccant Substances 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 229910052750 molybdenum Inorganic materials 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 229910052738 indium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000011651 chromium Substances 0.000 description 15
- 229910052804 chromium Inorganic materials 0.000 description 14
- -1 WO 2008/054781 Chemical compound 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 238000004939 coking Methods 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 150000003752 zinc compounds Chemical class 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000004820 halides Chemical class 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 239000000571 coke Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 3
- ZPIFKCVYZBVZIV-UHFFFAOYSA-N 3-chloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CCCl ZPIFKCVYZBVZIV-UHFFFAOYSA-N 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 230000000979 retarding effect Effects 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 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 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 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
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical class [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 229910001119 inconels 625 Inorganic materials 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- 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
-
- 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
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- 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
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/22—Halogenating
- B01J37/26—Fluorinating
-
- 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
-
- 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
- C07C17/093—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
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- 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
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00162—Controlling or regulating processes controlling the pressure
-
- 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
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/866—Nickel and chromium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1512557.8 | 2015-07-17 | ||
| GB1512557.8A GB2540421C (en) | 2015-07-17 | 2015-07-17 | Process for preparing 245cb from 243db |
| PCT/GB2016/052133 WO2017013403A1 (en) | 2015-07-17 | 2016-07-14 | Process for the preparation of 1,1,1,2,2-pentafluoropropane |
| CN201680037553.1A CN107801391B (zh) | 2015-07-17 | 2016-07-14 | 制备1,1,1,2,2-五氟丙烷的方法 |
Related Parent Applications (1)
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Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009125201A2 (en) * | 2008-04-09 | 2009-10-15 | Ineos Fluor Holdings Liimited | Process |
| WO2009158321A1 (en) * | 2008-06-26 | 2009-12-30 | Arkema Inc. | Catalytic gas phase fluorination of 1230xa to 1234yf |
| CN102099319A (zh) * | 2008-04-09 | 2011-06-15 | 墨西哥化学阿玛科股份有限公司 | 制备2，3，3，3-四氟丙烯方法 |
| CN102666452A (zh) * | 2009-12-23 | 2012-09-12 | 阿克马法国公司 | 243db到1234yf的催化气相氟化 |
| CN102686543A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1230xa到1234yf的催化气相氟化 |
| CN102686542A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1233xf到1234yf的催化气相氟化 |
| CN103180275A (zh) * | 2010-10-22 | 2013-06-26 | 阿克马法国公司 | 2,3,3,3-四氟丙烯的制备方法 |
| CN103328422A (zh) * | 2011-01-21 | 2013-09-25 | 阿克马法国公司 | 通过五氯丙烷的气相氟化制造2,3,3,3-四氟丙烯的方法 |
| CN103827066A (zh) * | 2011-09-27 | 2014-05-28 | 阿克马法国公司 | 制备2,3,3,3-四氟丙烯的方法 |
| CN103946192A (zh) * | 2011-11-16 | 2014-07-23 | 阿科玛股份有限公司 | 用于制造氢氟烯烃的方法 |
| CN103998405A (zh) * | 2011-12-14 | 2014-08-20 | 阿克马法国公司 | 2,3,3,3-四氟丙烯的制备方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931840A (en) | 1958-11-25 | 1960-04-05 | Du Pont | Process for preparing 2, 3, 3, 3-tetrafluoropropene |
| GB9104775D0 (en) | 1991-03-07 | 1991-04-17 | Ici Plc | Fluorination catalyst and process |
| FR2740994B1 (fr) | 1995-11-10 | 1997-12-05 | Atochem Elf Sa | Catalyseurs massiques a base d'oxyde de chrome, leur procede de preparation et leur application a la fluoration d'hydrocarbures halogenes |
| US6403524B2 (en) | 1996-09-10 | 2002-06-11 | Imperial Chemical Industries Plc | Fluorination catalyst and process |
| WO1998047841A1 (en) | 1997-04-23 | 1998-10-29 | Asahi Glass Company Ltd. | Process for producing halogenated hydrocarbons |
| US8058486B2 (en) | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| GB0507139D0 (en) | 2005-04-08 | 2005-05-18 | Ineos Fluor Holdings Ltd | Catalyst |
| CN103193584B (zh) * | 2006-01-03 | 2015-07-01 | 霍尼韦尔国际公司 | 制备氟化有机化合物的方法 |
| KR101397113B1 (ko) † | 2006-10-03 | 2014-05-19 | 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. | 탄소수 3-6의 (하이드로)플루오로알켄의 생성을 위한 탈수소할로겐화 방법 |
| CN103553871A (zh) | 2006-10-31 | 2014-02-05 | 纳幕尔杜邦公司 | 氟丙烷、卤代丙烯以及2-氯-3,3,3-三氟-1-丙烯与hf的共沸组合物和1,1,1,2,2-五氟丙烷与hf的共沸组合物的制备方法 |
| WO2009003084A1 (en) † | 2007-06-27 | 2008-12-31 | Arkema Inc. | Process for the manufacture of hydrofluoroolefins |
| US9035111B2 (en) | 2007-08-22 | 2015-05-19 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| CA3008510C (en) | 2008-05-07 | 2021-03-09 | E. I. Du Pont De Nemours And Company | Compositions comprising 2,3-dichloro-1,1,1-trifluoropropane, 2-chloro-1,1,1-trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane or 2,3,3,3-tetrafluoropropene |
| GB0906191D0 (en) | 2009-04-09 | 2009-05-20 | Ineos Fluor Holdings Ltd | Process |
| EP3581631B1 (en) | 2009-12-22 | 2024-11-06 | The Chemours Company FC, LLC | Compositions comprising 2,3,3,3-tetrafluoropropene |
| US20110245548A1 (en) * | 2010-03-31 | 2011-10-06 | Honeywell International Inc. | Catalyst life improvement in the vapor phase fluorination of chlorocarbons |
| RU2541541C1 (ru) † | 2011-01-21 | 2015-02-20 | Аркема Франс | Каталитическое газофазное фторирование |
| CN103313960B (zh) † | 2011-01-21 | 2016-06-08 | 阿克马法国公司 | 催化气相氟化 |
| US9724684B2 (en) | 2011-02-21 | 2017-08-08 | The Chemours Company Fc, Llc | Selective catalytical dehydrochlorination of hydrochlorofluorocarbons |
| IN2014DN02914A (enExample) * | 2011-10-14 | 2015-05-15 | Honeywell Int Inc | |
| EP2773606B1 (en) | 2011-11-04 | 2019-08-07 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN104105681B (zh) | 2012-01-25 | 2016-11-09 | 大金工业株式会社 | 用于制造含氟烯烃的方法 |
| IN2014KN01700A (enExample) † | 2012-03-22 | 2015-10-23 | Daikin Ind Ltd | |
| US8728434B2 (en) | 2012-06-28 | 2014-05-20 | Evident Technologies, Inc. | Preparation of nanocrystals for thermoelectric and solar cell applications using sulfide-based nanocrystal precursors in colloidal systems |
| US9708234B2 (en) | 2012-07-10 | 2017-07-18 | Daikin Industries, Ltd. | Process for producing fluorine-containing olefin |
| US9422211B2 (en) † | 2012-08-08 | 2016-08-23 | Daikin Industries, Ltd. | Process for producing 2,3,3,3-tetrafluoropropene |
| CN104918700B (zh) | 2013-01-29 | 2021-05-25 | 阿科玛股份有限公司 | 氟化催化剂的活化和再生 |
| US9180433B2 (en) | 2013-03-14 | 2015-11-10 | Honeywell International, Inc. | Catalysts for 2-chloro-1,1,1,2-tetrafluoropropane dehydrochlorination |
| US20140275651A1 (en) | 2013-03-15 | 2014-09-18 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| FR3010996B1 (fr) | 2013-09-24 | 2015-09-25 | Arkema France | Procede de fluoration en phase gaz |
| CN104151131B (zh) † | 2014-08-08 | 2015-11-18 | 浙江衢化氟化学有限公司 | 一种2,3,3,3-四氟丙烯的制备方法 |
-
2015
- 2015-07-17 GB GB1802240.0A patent/GB2559056B/en active Active
- 2015-07-17 GB GB1512557.8A patent/GB2540421C/en active Active
-
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- 2016-07-14 ES ES19182618T patent/ES2941729T3/es active Active
- 2016-07-14 EP EP16751323.3A patent/EP3325434B2/en active Active
- 2016-07-14 WO PCT/GB2016/052133 patent/WO2017013403A1/en not_active Ceased
- 2016-07-14 CN CN202210479905.6A patent/CN114835552A/zh active Pending
- 2016-07-14 EP EP23157595.2A patent/EP4223734A1/en active Pending
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- 2016-07-14 US US15/745,529 patent/US10669219B2/en active Active
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- 2016-07-14 KR KR1020187004718A patent/KR102026251B1/ko active Active
-
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- 2020-04-22 US US16/855,500 patent/US11155506B2/en active Active
- 2020-07-29 JP JP2020128642A patent/JP7143372B2/ja active Active
-
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- 2021-10-08 US US17/497,071 patent/US11572327B2/en active Active
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009125201A2 (en) * | 2008-04-09 | 2009-10-15 | Ineos Fluor Holdings Liimited | Process |
| CN102099319A (zh) * | 2008-04-09 | 2011-06-15 | 墨西哥化学阿玛科股份有限公司 | 制备2，3，3，3-四氟丙烯方法 |
| WO2009158321A1 (en) * | 2008-06-26 | 2009-12-30 | Arkema Inc. | Catalytic gas phase fluorination of 1230xa to 1234yf |
| CN102666452A (zh) * | 2009-12-23 | 2012-09-12 | 阿克马法国公司 | 243db到1234yf的催化气相氟化 |
| CN102686543A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1230xa到1234yf的催化气相氟化 |
| CN102686542A (zh) * | 2009-12-23 | 2012-09-19 | 阿克马法国公司 | 1233xf到1234yf的催化气相氟化 |
| CN103180275A (zh) * | 2010-10-22 | 2013-06-26 | 阿克马法国公司 | 2,3,3,3-四氟丙烯的制备方法 |
| CN103328422A (zh) * | 2011-01-21 | 2013-09-25 | 阿克马法国公司 | 通过五氯丙烷的气相氟化制造2,3,3,3-四氟丙烯的方法 |
| CN103827066A (zh) * | 2011-09-27 | 2014-05-28 | 阿克马法国公司 | 制备2,3,3,3-四氟丙烯的方法 |
| CN103946192A (zh) * | 2011-11-16 | 2014-07-23 | 阿科玛股份有限公司 | 用于制造氢氟烯烃的方法 |
| CN103998405A (zh) * | 2011-12-14 | 2014-08-20 | 阿克马法国公司 | 2,3,3,3-四氟丙烯的制备方法 |
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