JPH06509343A - 接触水素化分解 - Google Patents
接触水素化分解Info
- Publication number
- JPH06509343A JPH06509343A JP5502987A JP50298793A JPH06509343A JP H06509343 A JPH06509343 A JP H06509343A JP 5502987 A JP5502987 A JP 5502987A JP 50298793 A JP50298793 A JP 50298793A JP H06509343 A JPH06509343 A JP H06509343A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- less
- ppm
- carbon
- method characterized
- 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
Links
- 238000004517 catalytic hydrocracking Methods 0.000 title claims description 11
- 239000003054 catalyst Substances 0.000 claims description 82
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 claims description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 238000010306 acid treatment Methods 0.000 claims description 5
- 125000002015 acyclic group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 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 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 238000002144 chemical decomposition reaction Methods 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000001307 helium Substances 0.000 description 26
- 229910052734 helium Inorganic materials 0.000 description 26
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000002245 particle Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- -1 unsaturated glycol diester Chemical class 0.000 description 3
- SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- AFTSHZRGGNMLHC-UHFFFAOYSA-N 1,1-dichloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)(Cl)Cl AFTSHZRGGNMLHC-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- JOHBOPZZWOWUHM-UHFFFAOYSA-N 4,5-dichloro-1,1,2,2,3,3-hexafluorocyclopentane Chemical compound FC1(F)C(Cl)C(Cl)C(F)(F)C1(F)F JOHBOPZZWOWUHM-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 102100040550 FXYD domain-containing ion transport regulator 4 Human genes 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001364889 Helius Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 101710182657 Reduced folate transporter Proteins 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001260 acyclic compounds Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 108010070092 corticosteroid hormone-induced factor Proteins 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- MSNOMDLPLDYDME-UHFFFAOYSA-N gold nickel Chemical compound [Ni].[Au] MSNOMDLPLDYDME-UHFFFAOYSA-N 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- RWRDJVNMSZYMDV-UHFFFAOYSA-L radium chloride Chemical compound [Cl-].[Cl-].[Ra+2] RWRDJVNMSZYMDV-UHFFFAOYSA-L 0.000 description 1
- 229910001630 radium chloride Inorganic materials 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式:CnHmFpXq 式中 nは1ないし6の整数であり、 mは0ないし12の整数であり、 pは1ないし13の整数であり、 qは1ないし13の整数であり、そして各Xは互いに独立にCIとBrから選ば れ、ここで m+p+qは、同化合物が飽和して非環状である場合は2n+2に等しく、 飽和して環状であるか、またはオレフィン系で非環状の場合は2nに等しく、そ してオレフィン系で環状の場合は2n−2に等しい、を有する環状または非環状 化合物を、炭素触媒用支持体上に担持された、レニウム、コバルト、ニッケル、 ルテニウム、ロジウム、パラジウム、オスミウム、イリジウムおよび白金からな る群れから選ばれる少なくとも一つの金属である触媒を使用して、接触的に水素 化分解する方法において、該炭素触媒用支持体の灰分含量が約0.1重量%以下 であることを特徴てする接触水素化分解法。 2.請求の範囲1記載の方法において、該炭素触媒用支持体が初めに弗化水素酸 以外の酸で処理され、次いで弗化水素酸で処理されることを特徴とする方法。 3.請求の範囲2記載の方法において、初めの酸処理で、リンおよび硫黄のどち らも含んでいない酸を使用することを特徴とする方法。 4.請求の範囲2記載の方法において、初めの酸処理で、HCIまたはHNO3 を使用することを特徴とする方法。 5.請求の範囲1記載の方法において各XがCIであることを特徴とする方法。 6.請求の範囲5記載の方法において、該触媒が200ppm以下のリンを含ん でいることを特徴とする方法。 7.請求の範囲5記載の方法において、該触媒が200ppm以下の硫黄を含ん でいることを特徴とする方法。 8.請求の範囲5記載の方法において、該触媒が100ppm以下のカリウムを 含んでいることを特徴とする方法。 9.請求の範囲8記載の方法において、該触媒が100ppm以下のナトリウム を含んでいることを特徴とする方法。 10.請求の範囲9記載の方法において、該触媒が100ppm以下の鉄を含ん でいることを特徴とする方法。 11.請求の範囲1記載の方法において、nが1ないし3であり、mが0ないし 6であり、pが1ないし7であり、そしてqが1ないし7であることを特徴とす る方法。 12.請求の範囲1記載の方法において、少なくとも1種の金属が、該触媒の約 0.1ないし10重量%を構成することを特徴とする方法。 13.請求の範囲1記載の方法において、水素化分解を約125℃ないし約35 0℃の温度で実施することを特徴とする方法。 14.請求の範囲1記載の方法において、2,2−ジクロロ−1,1,1,2− テトラフルオロエタンを2−クロロ−1,1,1,2−テトラフルオロエタンお よび1,1,1,2−テトラフルオロエタンに変換することを特徴とする方法。 15.請求の範囲1記載の方法において、2−クロロ−1,1,1,2−テトラ フルオロエタンを1,1,1,2−テトラフルオロエタンに変換することを特徴 とする方法。 16.請求の範囲1記載の方法において、該触媒が100ppm以下のカリウム を含んでいることを特徴とする方法。 17.請求の範囲1記載の方法において、該触媒が100ppm以下のナトリウ ムを含んでいることを特徴とする方法。 18.請求の範囲1記載の方法において、該触媒が100ppm以下の鉄を含ん でいることを特徴とする方法。 19.請求の範囲1記載の方法において、該触媒が200ppm以下のリンを含 んでいることを特徴とする方法。 20.請求の範囲1記載の方法において、該触媒が200ppm以下の硫黄を含 んでいることを特徴とする方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/734,407 US5136113A (en) | 1991-07-23 | 1991-07-23 | Catalytic hydrogenolysis |
US734,407 | 1991-07-23 | ||
PCT/US1992/006002 WO1993002029A1 (en) | 1991-07-23 | 1992-07-23 | Catalytic hydrogenolysis |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH06509343A true JPH06509343A (ja) | 1994-10-20 |
JP3130042B2 JP3130042B2 (ja) | 2001-01-31 |
Family
ID=24951577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP05502987A Expired - Lifetime JP3130042B2 (ja) | 1991-07-23 | 1992-07-23 | 接触水素化分解 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5136113A (ja) |
EP (1) | EP0596007B1 (ja) |
JP (1) | JP3130042B2 (ja) |
CN (1) | CN1068810A (ja) |
AU (1) | AU2398292A (ja) |
DE (1) | DE69211347T2 (ja) |
ES (1) | ES2088587T3 (ja) |
MX (1) | MX9201146A (ja) |
WO (1) | WO1993002029A1 (ja) |
ZA (1) | ZA921883B (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07112944A (ja) * | 1993-08-27 | 1995-05-02 | Daikin Ind Ltd | ヘキサフルオロシクロブテンの製造方法及びヘキサフルオロシクロブタンの製造方法 |
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Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103691430A (zh) * | 2012-09-28 | 2014-04-02 | 中化蓝天集团有限公司 | 一种用于四氟二氯乙烷加氢脱氯的催化剂及其制备方法 |
EP3331846B1 (en) | 2015-08-07 | 2020-10-28 | The Chemours Company FC, LLC | Catalytic isomerization of z-1,1,1,4,4,4-hexafluoro-2-butene |
MX2021014764A (es) | 2019-06-04 | 2022-01-18 | Chemours Co Fc Llc | Composiciones de 2-cloro-3,3,3-trifluoropropeno (1233xf) y metodos para fabricar y usar las composiciones. |
EP4326697A1 (en) | 2021-04-19 | 2024-02-28 | The Chemours Company FC, LLC | Compositions containing 3,3,3-trifluoropropene (1243zf) and methods for making and using the compositions |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA593529A (en) * | 1960-03-01 | B. Miller Charles | Hydrogenation of fluorochloro olefins | |
US2942036A (en) * | 1957-12-13 | 1960-06-21 | Allied Chem | Manufacture of halopropane |
US3439052A (en) * | 1967-10-23 | 1969-04-15 | Phillips Petroleum Co | Fluoroform production |
GB1578933A (en) * | 1977-05-24 | 1980-11-12 | Ici Ltd | Manufacture of halogenated hydrocarbons |
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 |
JP2531205B2 (ja) * | 1987-11-13 | 1996-09-04 | 旭硝子株式会社 | 1,1,1,2−テトラフルオロエタンの製造法 |
EP0347830B1 (en) * | 1988-06-21 | 1994-01-26 | Asahi Glass Company Ltd. | Process for producing 1,1,1,2-tetrafluoroethane |
FR2641780B1 (fr) * | 1989-01-19 | 1991-04-19 | Atochem | Hydrogenolyse selective de derives perhalogenes de l'ethane |
FR2655982B1 (fr) * | 1989-12-15 | 1992-03-27 | Atochem | Fabrication de chlorofluoroethanes par hydrogenolyse selective de derives perhalogenes de l'ethane. |
-
1991
- 1991-07-23 US US07/734,407 patent/US5136113A/en not_active Expired - Lifetime
-
1992
- 1992-03-13 ZA ZA921883A patent/ZA921883B/xx unknown
- 1992-03-16 MX MX9201146A patent/MX9201146A/es unknown
- 1992-03-30 CN CN92102179A patent/CN1068810A/zh active Pending
- 1992-07-23 AU AU23982/92A patent/AU2398292A/en not_active Abandoned
- 1992-07-23 EP EP92916702A patent/EP0596007B1/en not_active Expired - Lifetime
- 1992-07-23 DE DE69211347T patent/DE69211347T2/de not_active Expired - Fee Related
- 1992-07-23 ES ES92916702T patent/ES2088587T3/es not_active Expired - Lifetime
- 1992-07-23 JP JP05502987A patent/JP3130042B2/ja not_active Expired - Lifetime
- 1992-07-23 WO PCT/US1992/006002 patent/WO1993002029A1/en active IP Right Grant
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07112944A (ja) * | 1993-08-27 | 1995-05-02 | Daikin Ind Ltd | ヘキサフルオロシクロブテンの製造方法及びヘキサフルオロシクロブタンの製造方法 |
WO2011162339A1 (ja) * | 2010-06-23 | 2011-12-29 | 旭硝子株式会社 | 2,3,3,3-テトラフルオロプロペンの製造方法 |
US8530710B2 (en) | 2010-06-23 | 2013-09-10 | Asahi Glass Company, Limited | Process for producing 2,3,3,3-tetrafluoropropene |
JP5786858B2 (ja) * | 2010-06-23 | 2015-09-30 | 旭硝子株式会社 | 2,3,3,3−テトラフルオロプロペンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
AU2398292A (en) | 1993-02-23 |
US5136113A (en) | 1992-08-04 |
ZA921883B (en) | 1993-09-13 |
MX9201146A (es) | 1993-01-01 |
JP3130042B2 (ja) | 2001-01-31 |
WO1993002029A1 (en) | 1993-02-04 |
DE69211347T2 (de) | 1996-12-05 |
ES2088587T3 (es) | 1996-08-16 |
CN1068810A (zh) | 1993-02-10 |
DE69211347D1 (de) | 1996-07-11 |
EP0596007B1 (en) | 1996-06-05 |
EP0596007A1 (en) | 1994-05-11 |
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