JP2010532760A - 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方法 Download PDFInfo
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- copper
- catalyst
- nickel
- carbon
- calcium fluoride
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- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 84
- 239000010949 copper Substances 0.000 claims abstract description 62
- 229910052802 copper Inorganic materials 0.000 claims abstract description 45
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011737 fluorine Substances 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 85
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 229910052759 nickel Inorganic materials 0.000 claims description 32
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 28
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 28
- 229910052763 palladium Inorganic materials 0.000 claims description 21
- 239000011651 chromium Substances 0.000 claims description 19
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 13
- 229910021563 chromium fluoride Inorganic materials 0.000 claims description 7
- 229910000990 Ni alloy Inorganic materials 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 5
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 5
- 229910001626 barium chloride Inorganic materials 0.000 claims description 5
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011981 lindlar catalyst Substances 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000047 product Substances 0.000 description 18
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 14
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 14
- 229910000856 hastalloy Inorganic materials 0.000 description 13
- 230000008901 benefit Effects 0.000 description 7
- 229910004261 CaF 2 Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910001026 inconel Inorganic materials 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming 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
- MWGAPWWJNYJGMF-UHFFFAOYSA-N 4,5-dichloro-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(Cl)=C(Cl)C(F)(F)C(F)(F)C(F)(F)F MWGAPWWJNYJGMF-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (e)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 description 1
- 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
- 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
- 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
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 239000004604 Blowing Agent Substances 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
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 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
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 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
- 238000001556 precipitation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000004876 x-ray fluorescence Methods 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
- 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
- B01J23/72—Copper
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead
-
- 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
- B01J23/74—Iron group metals
- B01J23/755—Nickel
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- 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
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- 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
- B01J23/868—Chromium copper and chromium
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
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- 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
- B01J27/12—Fluorides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract
Description
本出願は、2007年7月3日出願の米国仮特許出願第60/958,190号明細書、および2007年11月27日出願の米国仮特許出願第61/004,518号明細書の優先権を主張するものである。
CT=接触時間
t−1336=E−1336mzz=E−CF3CH=CHCF3
c−1336=Z−1336mzz=Z−CF3CH=CHCF3
356mff=CF3CH2CH2CF3
1345=C4H3F5
346mdf=CF3CHClCH2CF3
1326=E−および/またはZ−CF3CH=CClCF3
t−1326mxz=Z−1326mxz=Z−CF3CH=CClCF3
c−1326mxz=E−1326mxz=E−CF3CH=CClCF3
1316mxx=E/Z−CF3CCl=CClCF3
t−1316mxx=E−1316mxx=E−CF3CCl=CClCF3
c−1316mxx=Z−1316mxx=Z−CF3CCl=CClCF3
171−14mccxx=E/Z−CF3CF2CF2CCl=CClCF2CF2CF3
173−14mcczz=E/Z−CF3CF2CF2CH=CHCF2CF2CF3
t−172−14=E−CF3CF2CF2CCl=CHCF2CF2CF3
c−172−14=Z−CF3CF2CF2CCl=CHCF2CF2CF3
HFB=CF3C≡CCF3
実施例1は、Cu/炭素触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例2は、Pd/BaCl2/Al2O3触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例3は、Pd/BaSO4触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例4は、Lindlar触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例5は、銅/炭素触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例6は、Cu/フッ化カルシウム触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例7は、Cu/Ni/炭素触媒上でのCFC−1316mxxのHFC−1336への転化を実証する。
実施例8は、Ni/炭素触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例9は、Ni/フッ化カルシウム触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
気のある固体に乾燥させた。次に触媒を、25℃で30分間500sccm(8.3×10−6m3/秒)N2で、次に15分間100sccmの各HeおよびH2でパージされる石英管に入れた。次に触媒をHe/H2中0.5℃/分で350℃に12時間加熱した。He/H2中で冷却した後、サンプルを室温で30分間2%O2・N2中で不動態化した。22.72gの触媒を製造した。
実施例10は、Cu/Ni/Cr/フッ化カルシウム触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例11は、Cu/Ni/Cr/フッ化カルシウム触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例12は、非担持銅/ニッケル触媒の調製を実証する。
た。46gの黒色粉末が製造された。粉末をプレスし、12〜20メッシュサイズへペレット化した。
実施例13は、実施例12の触媒上でのCFC−1316mxxのHFC−1336mzzへの転化を実証する。
実施例14は、Cu:Ni:Cr(0.5:0.48:0.02)触媒上での4,5−ジクロロパーフルオロ−4−オクテン(CFC−171−14mccx)の4,5−ジヒドロパーフルオロ−4−オクテン(173−14mccz)への転化を実証する。
400mlテフロンビーカーで、100mlの10%HCl/H2O中の3.33gのPdCl2(60%Pd)の溶液を作った。98gのCaF2をビーカーに加えた。スラリーを時折撹拌しながら室温で1時間放置し、次に時折撹拌しながら110℃で乾燥させた。乾燥固体を粉末に破砕し、粉末をHe−H2流れ中300℃で8時間還元した。還元のための初期ガス組成は10%H2であり、4時間にわたって100%に上げる。次に2.45gの酢酸鉛を100mlの水に溶解させた。酢酸鉛溶液入りビーカーに99.3gの2%Pd/CaF2を加えた。スラリーを50℃で2時間撹拌した。固体を濾紙上に集め、110℃で16時間乾燥させた。触媒をプレスし、12〜20メッシュサイズにペレット化した。
Hastelloy反応器15インチL×1インチ外径×0.074インチ壁に、5ccの実施例15の触媒を充填した。触媒を250℃で50sccm(8.3×10−7m3/秒)水素流れで順化させた。1316mxxの水素化脱塩素を200〜300℃の温度範囲にわたって調べ、生成物を下の表14に示した。接触時間は2.5〜30秒であった。水素対1316mxxの比は、示されるように2:1〜6.3:1であった。反応の生成物をGCMSによって分析すると表14にリストされるようなモル濃度を示した。
Claims (20)
- フッ素含有オレフィンを製造するためにクロロフルオロアルケンの塩素置換基の水素での置換を引き起こすのに十分な温度で触媒の存在下にクロロフルオロアルケンを水素と接触させる工程を含むフッ素含有オレフィンの製造方法。
- 触媒が、銅/炭素、銅/フッ化カルシウム、パラジウム/硫酸バリウム、パラジウム/塩化バリウム/アルミナ、リンドラー触媒(鉛で被毒されたパラジウム/CaCO3)、鉛で被毒されたパラジウム/フッ化カルシウム、銅およびニッケル/炭素、ニッケル/炭素、ニッケル/フッ化カルシウム、銅/ニッケル/クロム/フッ化カルシウム、ならびに銅とニッケルとの非担持合金からなる群から選択される請求項1に記載の方法。
- 触媒が銅/炭素、銅/フッ化カルシウム、銅およびニッケル/炭素、ニッケル/炭素、銅/ニッケル/クロム/フッ化カルシウム、ならびに銅とニッケルとの非担持合金からなる群から選択される請求項1に記載の方法。
- クロロフルオロアルケンが式RfCCl=CClRf(式中、各Rfは、CF3、C2F5、n−C3F7、i−C3F7、n−C4F9、i−C4F9およびt−C4F9からなる群から独立して選択されるパーフルオロアルキル基であり、そして式中Rf基の1つはFであってもよい)を有する請求項1に記載の方法。
- 各RfがCF3である請求項4に記載の方法。
- 各Rfがn−C3F7である請求項4に記載の方法。
- フッ素含有オレフィンが式E−またはZ−R1CH=CHR2(式中、R1およびR2のそれぞれは、CF3、C2F5、n−C3F7、i−C3F7、n−C4F9、i−C4F9およびt−C4F9からなる群から独立して選択されるパーフルオロアルキル基であり、そして式中R2はFであってもよい)を有する請求項1に記載の方法。
- R1およびR2のそれぞれがCF3である請求項7に記載の方法。
- R1およびR2のそれぞれがn−C3F7である請求項7に記載の方法。
- 約200℃〜約450℃の温度で行われる請求項1に記載の方法。
- 水素対クロロフルオロアルケンの比が約1:1〜約10:1である請求項1に記載の方法。
- 水素対クロロフルオロアルケンの比が約1:1〜約7.5:1である請求項1に記載の方法。
- 銅/ニッケル/クロム/フッ化カルシウム触媒中の銅:ニッケル:クロムのモル比が約0〜約1銅:約0.5〜約3.0ニッケル、および約0〜約2クロムである請求項3に記載の方法。
- 炭素またはフッ化カルシウム上の銅の量が約1質量%〜約25質量%である請求項3に記載の方法。
- 炭素またはフッ化カルシウム上の銅の量が約5質量%〜約25質量%である請求項3に記載の方法。
- 担体上に沈着された銅金属を含むクロロフルオロアルケンの水素化脱塩素のための触媒組成物。
- 担体が酸洗炭素またはフッ化カルシウムである請求項16に記載の触媒組成物。
- 銅金属が触媒組成物の約5質量%〜約25質量%を構成する請求項16に記載の触媒組成物。
- 鉛で被毒された、フッ化カルシウム上に沈着されたパラジウムを含むクロロフルオロアルケンの水素化脱塩素のための触媒組成物。
- パラジウムが触媒組成物の約0.02質量%〜約5質量%を構成する請求項19に記載の触媒組成物。
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- 2008-06-27 US US12/147,644 patent/US7795482B2/en active Active
- 2008-06-30 EP EP08781141.0A patent/EP2173693B1/en not_active Not-in-force
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- 2008-06-30 CN CN2008800230985A patent/CN101687736B/zh active Active
- 2008-06-30 JP JP2010515208A patent/JP5660891B2/ja active Active
- 2008-06-30 KR KR1020107001164A patent/KR20100046147A/ko not_active Application Discontinuation
- 2008-06-30 ES ES08781141.0T patent/ES2443024T3/es active Active
- 2008-06-30 CA CA002686603A patent/CA2686603A1/en not_active Abandoned
- 2008-06-30 WO PCT/US2008/068695 patent/WO2009006358A1/en active Application Filing
- 2008-06-30 CN CN201310429220.1A patent/CN103524297B/zh active Active
- 2008-07-02 TW TW097124919A patent/TW200922906A/zh unknown
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2009
- 2009-06-03 US US12/477,366 patent/US7795481B2/en active Active
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- 2012-09-07 US US13/606,233 patent/USRE45076E1/en active Active
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Cited By (11)
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JP2012513405A (ja) * | 2008-12-22 | 2012-06-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 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 |
JP2014503484A (ja) * | 2010-11-02 | 2014-02-13 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | クロロフルオロ化合物の脱ハロゲン化のための銅−ニッケル触媒の使用 |
JP2013180964A (ja) * | 2012-03-01 | 2013-09-12 | Asahi Glass Co Ltd | 2,3,3,3−テトラフルオロプロペンの製造方法 |
JP2017515789A (ja) * | 2014-02-07 | 2017-06-15 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンを生成するための統合方法 |
JP2019206569A (ja) * | 2014-02-07 | 2019-12-05 | ザ ケマーズ カンパニー エフシーリミテッド ライアビリティ カンパニー | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンを生成するための統合方法 |
JP2020094069A (ja) * | 2014-04-16 | 2020-06-18 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | より望ましいフルオロプロパン及びフルオロプロペンへのクロロフルオロプロパン及びクロロフルオロプロペンの変換 |
WO2016031777A1 (ja) * | 2014-08-25 | 2016-03-03 | 旭硝子株式会社 | ハイドロフルオロオレフィンの製造方法 |
JPWO2016031777A1 (ja) * | 2014-08-25 | 2017-06-08 | 旭硝子株式会社 | ハイドロフルオロオレフィンの製造方法 |
US9988327B2 (en) | 2014-08-25 | 2018-06-05 | Asahi Glass Company, Limited | Process for producing hydrofluoroolefin |
JP2019196411A (ja) * | 2014-08-25 | 2019-11-14 | Agc株式会社 | ハイドロフルオロオレフィンの製造方法 |
US10781151B2 (en) | 2014-08-25 | 2020-09-22 | AGC Inc. | Process for producing hydrofluoroolefin |
Also Published As
Publication number | Publication date |
---|---|
EP2173693B1 (en) | 2013-12-18 |
CN103524297A (zh) | 2014-01-22 |
EP2173693A1 (en) | 2010-04-14 |
JP2015061861A (ja) | 2015-04-02 |
US20090012335A1 (en) | 2009-01-08 |
WO2009006358A1 (en) | 2009-01-08 |
CN103524297B (zh) | 2016-08-17 |
JP2017075162A (ja) | 2017-04-20 |
CA2686603A1 (en) | 2009-01-08 |
KR20100046147A (ko) | 2010-05-06 |
JP5660891B2 (ja) | 2015-01-28 |
BRPI0810961A2 (pt) | 2016-06-07 |
USRE45076E1 (en) | 2014-08-12 |
TW200922906A (en) | 2009-06-01 |
US7795481B2 (en) | 2010-09-14 |
RU2476414C2 (ru) | 2013-02-27 |
US20090240089A1 (en) | 2009-09-24 |
US7795482B2 (en) | 2010-09-14 |
CN101687736B (zh) | 2013-10-30 |
ES2443024T3 (es) | 2014-02-17 |
CN101687736A (zh) | 2010-03-31 |
RU2010103460A (ru) | 2011-08-10 |
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