JP5791516B2 - ジヒドロフッ素化オレフィンを製造するための水素化脱塩素の方法 - Google Patents
ジヒドロフッ素化オレフィンを製造するための水素化脱塩素の方法 Download PDFInfo
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- JP5791516B2 JP5791516B2 JP2011542547A JP2011542547A JP5791516B2 JP 5791516 B2 JP5791516 B2 JP 5791516B2 JP 2011542547 A JP2011542547 A JP 2011542547A JP 2011542547 A JP2011542547 A JP 2011542547A JP 5791516 B2 JP5791516 B2 JP 5791516B2
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- 150000001336 alkenes Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title description 42
- 230000008569 process Effects 0.000 title description 14
- 239000003054 catalyst Substances 0.000 claims description 146
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 95
- 239000010949 copper Substances 0.000 claims description 56
- 239000011651 chromium Substances 0.000 claims description 38
- 229910052759 nickel Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 229910052802 copper Inorganic materials 0.000 claims description 25
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- 229910052700 potassium Inorganic materials 0.000 claims description 21
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 17
- 229910052804 chromium Inorganic materials 0.000 claims description 17
- 239000011591 potassium Substances 0.000 claims description 17
- 150000001345 alkine derivatives Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229910052792 caesium Inorganic materials 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 9
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- 229910052701 rubidium Inorganic materials 0.000 claims description 5
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000002002 slurry Substances 0.000 description 22
- 238000005984 hydrogenation reaction Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 229910052783 alkali metal Inorganic materials 0.000 description 16
- 150000001340 alkali metals Chemical class 0.000 description 16
- 239000010453 quartz Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 229910004261 CaF 2 Inorganic materials 0.000 description 12
- 229910018590 Ni(NO3)2-6H2O Inorganic materials 0.000 description 11
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 11
- 229910001634 calcium fluoride Inorganic materials 0.000 description 11
- 239000011698 potassium fluoride Substances 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 229910002804 graphite Inorganic materials 0.000 description 9
- 239000010439 graphite Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003570 air Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 description 4
- 229910001026 inconel Inorganic materials 0.000 description 4
- 229910001512 metal fluoride Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-UHFFFAOYSA-N 0.000 description 2
- XDIDQEGAKCWQQP-UHFFFAOYSA-N 2,3-dichloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical group FC(F)(F)C(Cl)=C(Cl)C(F)(F)F XDIDQEGAKCWQQP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- -1 CuF Chemical class 0.000 description 2
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 2
- 229910001632 barium fluoride Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 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
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 2
- 229910001637 strontium fluoride Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XDIDQEGAKCWQQP-OWOJBTEDSA-N (e)-2,3-dichloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical group FC(F)(F)C(\Cl)=C(/Cl)C(F)(F)F XDIDQEGAKCWQQP-OWOJBTEDSA-N 0.000 description 1
- NLOLSXYRJFEOTA-UPHRSURJSA-N (z)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C/C(F)(F)F NLOLSXYRJFEOTA-UPHRSURJSA-N 0.000 description 1
- JRENXZBKMHPULY-UPHRSURJSA-N (z)-2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C(/Cl)C(F)(F)F JRENXZBKMHPULY-UPHRSURJSA-N 0.000 description 1
- NIJFGUAYRFPTBD-UHFFFAOYSA-N 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluorooct-4-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C=CC(F)(F)C(F)(F)C(F)(F)F NIJFGUAYRFPTBD-UHFFFAOYSA-N 0.000 description 1
- NVSXSBBVEDNGPY-UHFFFAOYSA-N 1,1,1,2,2-pentafluorobutane Chemical compound CCC(F)(F)C(F)(F)F NVSXSBBVEDNGPY-UHFFFAOYSA-N 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
- CVMVAHSMKGITAV-UHFFFAOYSA-N 1,1,1,4,4,5,5,5-octafluoropent-2-ene Chemical compound FC(F)(F)C=CC(F)(F)C(F)(F)F CVMVAHSMKGITAV-UHFFFAOYSA-N 0.000 description 1
- DXPCVBMFVUHPOU-UHFFFAOYSA-N 1,3,3,4,4,4-hexafluorobut-1-yne Chemical compound FC#CC(F)(F)C(F)(F)F DXPCVBMFVUHPOU-UHFFFAOYSA-N 0.000 description 1
- YDYCBRDUVSCRAV-UHFFFAOYSA-N 2,3-dichloro-1,1,1,4,4,5,5,5-octafluoropent-2-ene Chemical group FC(F)(F)C(Cl)=C(Cl)C(F)(F)C(F)(F)F YDYCBRDUVSCRAV-UHFFFAOYSA-N 0.000 description 1
- PREWBNUKNNTMHC-UHFFFAOYSA-N 2-chloro-1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CC(Cl)C(F)(F)F PREWBNUKNNTMHC-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910021593 Copper(I) fluoride Inorganic materials 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 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
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- XHFVDZNDZCNTLT-UHFFFAOYSA-H chromium(3+);tricarbonate Chemical compound [Cr+3].[Cr+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O XHFVDZNDZCNTLT-UHFFFAOYSA-H 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- PBNUPTVXUMHAIW-UHFFFAOYSA-N copper fluoro hypofluorite Chemical compound [Cu].FOF PBNUPTVXUMHAIW-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- 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
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- 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
- B01J23/78—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 alkali- or alkaline earth metals
-
- 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
- B01J23/83—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 rare earths or actinides
-
- 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
-
- 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
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| US9000241B2 (en) * | 2010-11-02 | 2015-04-07 | E. I. Du Pont De Nemours And Company | Use of copper-nickel catalysts for dehlogenation of chlorofluorocompounds |
| TW201226368A (en) * | 2010-12-10 | 2012-07-01 | Du Pont | Purification of cis-1,1,1,4,4,4-hexafluoro-2-butene via extractive distillation |
| MX340092B (es) * | 2012-01-09 | 2016-06-27 | Du Pont | Proceso para pasivacion de reactores. |
| CN102989496B (zh) * | 2012-12-17 | 2014-10-08 | 南京信息工程大学 | 用于制备1,1,1,2,3,3,3-七氟丙烷的催化剂及其制备方法和应用 |
| KR20230031374A (ko) * | 2014-02-07 | 2023-03-07 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | Z-1,1,1,4,4,4-헥사플루오로-2-부텐의 생산을 위한 통합 공정 |
| EP3253844B1 (en) | 2015-02-06 | 2022-06-22 | The Chemours Company FC, LLC | Compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof |
| ES2886899T3 (es) | 2015-02-06 | 2021-12-21 | Chemours Co Fc Llc | Composiciones que comprenden E-1,1,1,4,4,4-hexafluoro-2-buteno y usos del mismo |
| EP3663274B1 (en) | 2015-08-07 | 2025-02-19 | The Chemours Company FC, LLC | Catalytic isomerization of z-1,1,1,4,4,4-hexafluoro-2-butene to e-1,1,1,4,4,4-hexafluoro-2-butene |
| CN107262092B (zh) * | 2017-06-16 | 2021-03-09 | 巨化集团技术中心 | 一种合成顺式1,1,1,4,4,4-六氟-2-丁烯的催化剂及其制备方法和用途 |
| JP6860032B2 (ja) * | 2019-04-04 | 2021-04-14 | ダイキン工業株式会社 | パーフルオロアルキン化合物の製造方法 |
| JP7553758B2 (ja) * | 2019-07-10 | 2024-09-19 | ダイキン工業株式会社 | ビニル化合物の製造方法 |
| CN110563547A (zh) * | 2019-09-24 | 2019-12-13 | 浙江三美化工股份有限公司 | 一种1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
| CN110950735B (zh) * | 2019-10-22 | 2022-08-30 | 浙江巨化技术中心有限公司 | 一种气相法制备1,1,1,4,4,4-六氟-2-丁炔的方法 |
| US12440826B2 (en) | 2019-11-29 | 2025-10-14 | Zhejiang Lantian Environmental Protection Hi-Tech Co., Ltd. | Nitrogen-phosphorus-modified granular carbon-supported bimetallic catalyst, preparation method therefor and use thereof |
| JP7719333B2 (ja) * | 2020-10-21 | 2025-08-06 | Agc株式会社 | 1-クロロ-2,3,3,3-テトラフルオロプロペンの製造方法 |
| EP4235702A4 (en) | 2020-10-22 | 2024-07-24 | Agc Inc. | ELECTRICAL EQUIPMENT |
| FR3115786B1 (fr) * | 2020-11-03 | 2022-11-04 | Arkema France | Procédé de production du trifluoroéthylène |
| CN112495394A (zh) * | 2020-12-10 | 2021-03-16 | 中化蓝天集团有限公司 | 一种加氢脱氯催化剂及三氟氯乙烯的制备方法 |
| WO2022131226A1 (ja) | 2020-12-16 | 2022-06-23 | Agc株式会社 | 電気設備、充填設備、および貯蔵設備 |
| CN114713250B (zh) * | 2022-04-06 | 2023-05-23 | 中南大学 | 一种氯化氢催化氧化制氯气的催化剂及其制备方法和应用 |
Family Cites Families (19)
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| US2774799A (en) * | 1954-04-01 | 1956-12-18 | Kellogg M W Co | Selective dehydrohalogenation of fluorohaloalkanes using a copper catalyst |
| US2802887A (en) * | 1955-08-08 | 1957-08-13 | Allied Chem & Dye Corp | Hydrogenation of chlorotrifluoroethylene |
| US2900423A (en) * | 1957-12-13 | 1959-08-18 | Allied Chem | Manufacture of perfluoropropene |
| ES289529A1 (es) | 1962-07-03 | 1963-11-01 | Allied Chem | Procedimiento de obtencion de alcohol hexafluoroisopropilico |
| DE3170139D1 (en) | 1980-12-09 | 1985-05-30 | Allied Corp | Preparation of chlorotrifluoroethylene and trifluoroethylene |
| IT1186307B (it) * | 1985-06-10 | 1987-11-26 | Montefluos Spa | Procedimento per la preparazione di 1,2-difluoroetilene e 1-cloro-1,2-difluoro-etilene |
| US5243103A (en) * | 1988-05-24 | 1993-09-07 | Solvay S.A. | Process for obtaining catalytic compositions and process for hydrogenation of chlorofluoroalkenes by means of these compositions |
| JP2746478B2 (ja) | 1989-02-03 | 1998-05-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 改良された水添分解/脱ハロゲン化水素方法 |
| US5068472A (en) * | 1989-12-19 | 1991-11-26 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| US5057634A (en) * | 1989-12-19 | 1991-10-15 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| JP3275338B2 (ja) | 1992-01-13 | 2002-04-15 | ダイキン工業株式会社 | 1,1,1,4,4,4−ヘキサフルオロブタンの製造方法 |
| JPH05213793A (ja) * | 1992-02-06 | 1993-08-24 | Daikin Ind Ltd | 1,1,1,4,4,4−ヘキサフルオロブタンの製造方法 |
| JPH05215793A (ja) | 1992-02-07 | 1993-08-24 | Fujitsu Ltd | 消費電流積算方式 |
| DE4305163A1 (de) | 1993-02-19 | 1994-08-25 | Bayer Ag | Verfahren zur Herstellung von Hexafluorbuten |
| AU7559194A (en) | 1993-08-16 | 1995-03-14 | Allied-Signal Inc. | Process for combining chlorine-containing molecules to synthesize fluorine-containing products |
| US5892135A (en) * | 1996-08-23 | 1999-04-06 | E. I. Du Pont De Nemours And Company | Process for the production of trifluoroethylene |
| US20050038302A1 (en) * | 2003-08-13 | 2005-02-17 | Hedrick Vicki E. | Systems and methods for producing fluorocarbons |
| JP4867474B2 (ja) * | 2006-05-31 | 2012-02-01 | 日本ゼオン株式会社 | パーフルオロアルキン化合物の製造方法 |
| US7795482B2 (en) * | 2007-07-03 | 2010-09-14 | E. I. Du Pont De Nemours And Company | Method of hydrodechlorination to produce dihydrofluorinated olefins |
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| BRPI0916488A2 (pt) | 2016-08-02 |
| KR20110114595A (ko) | 2011-10-19 |
| WO2010075284A1 (en) | 2010-07-01 |
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| JP2012513405A (ja) | 2012-06-14 |
| ES2414854T3 (es) | 2013-07-23 |
| CN102264674A (zh) | 2011-11-30 |
| US20100160696A1 (en) | 2010-06-24 |
| TW201035008A (en) | 2010-10-01 |
| CN102264674B (zh) | 2015-05-20 |
| EP2373600A1 (en) | 2011-10-12 |
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