JP2742091B2 - 触媒組成物、それらの調製方法及びこれらの組成物によるクロロフルオロアルケンの水素化方法 - Google Patents
触媒組成物、それらの調製方法及びこれらの組成物によるクロロフルオロアルケンの水素化方法Info
- Publication number
- JP2742091B2 JP2742091B2 JP1131262A JP13126289A JP2742091B2 JP 2742091 B2 JP2742091 B2 JP 2742091B2 JP 1131262 A JP1131262 A JP 1131262A JP 13126289 A JP13126289 A JP 13126289A JP 2742091 B2 JP2742091 B2 JP 2742091B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst composition
- metal
- alkaline earth
- metals
- catalyst
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000003054 catalyst Substances 0.000 title claims description 81
- 238000002360 preparation method Methods 0.000 title description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 17
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 230000000737 periodic effect Effects 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- 229910052792 caesium Inorganic materials 0.000 claims description 9
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 229910001626 barium chloride Inorganic materials 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- 150000004679 hydroxides Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 229910001632 barium fluoride Inorganic materials 0.000 claims 1
- 229910001863 barium hydroxide Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 16
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 10
- 239000011148 porous material Substances 0.000 description 9
- 239000001307 helium Substances 0.000 description 8
- 229910052734 helium Inorganic materials 0.000 description 8
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 8
- 238000005470 impregnation Methods 0.000 description 8
- 239000000395 magnesium oxide Substances 0.000 description 7
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 7
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 7
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- 239000003708 ampul Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 101150003085 Pdcl gene Proteins 0.000 description 3
- -1 alkaline earth metal salts Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007036 catalytic synthesis reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- FPBWSPZHCJXUBL-UHFFFAOYSA-N 1-chloro-1-fluoroethene Chemical group FC(Cl)=C FPBWSPZHCJXUBL-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- QGKQZUBNOZRZAH-UHFFFAOYSA-K magnesium;potassium;trifluoride Chemical class [F-].[F-].[F-].[Mg+2].[K+] QGKQZUBNOZRZAH-UHFFFAOYSA-K 0.000 description 1
- SOYXEODKJRNYFJ-UHFFFAOYSA-K magnesium;sodium;trifluoride Chemical class [F-].[F-].[F-].[Na+].[Mg+2] SOYXEODKJRNYFJ-UHFFFAOYSA-K 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229940102127 rubidium chloride Drugs 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007086 side reaction 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
- B01J23/38—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
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8806991 | 1988-05-24 | ||
| FR8806991A FR2631858A1 (fr) | 1988-05-24 | 1988-05-24 | Compositions catalytiques, procede pour leur obtention et procede d'hydrogenation de chlorofluoralcenes au moyen de ces compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0217944A JPH0217944A (ja) | 1990-01-22 |
| JP2742091B2 true JP2742091B2 (ja) | 1998-04-22 |
Family
ID=9366628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1131262A Expired - Lifetime JP2742091B2 (ja) | 1988-05-24 | 1989-05-24 | 触媒組成物、それらの調製方法及びこれらの組成物によるクロロフルオロアルケンの水素化方法 |
Country Status (8)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2635471A1 (fr) * | 1988-08-22 | 1990-02-23 | Solvay | Compositions catalytiques, procede pour leur obtention et procede d'hydrogenation de 1,1,2-trichloro-1,2,2-trifluorethane au moyen de ces compositions |
| US5057470A (en) * | 1990-05-22 | 1991-10-15 | E. I. Du Pont De Nemours And Company | Regeneration of noble metal catalysts used in hydrodehalogenation of halogen-substituted hydrocarbons containing fluorine and at least one other halogen |
| BE1007822A5 (fr) * | 1993-12-10 | 1995-10-31 | Solvay | Support pour un catalyseur d'hydrogenation, systeme catalytique comprenant ce support et procede d'hydrodechloration d'hydrocarbures chlorofluores. |
| JP3335000B2 (ja) * | 1994-03-31 | 2002-10-15 | 株式会社トクヤマ | 有機塩素化物の水素還元反応触媒の再生方法 |
| US5892135A (en) * | 1996-08-23 | 1999-04-06 | E. I. Du Pont De Nemours And Company | Process for the production of trifluoroethylene |
| JP2008510831A (ja) * | 2004-08-26 | 2008-04-10 | グレート・レイクス・ケミカル・コーポレイション | 化合物生成方法及び化合物生成システム |
| US8158549B2 (en) * | 2009-09-04 | 2012-04-17 | Honeywell International Inc. | Catalysts for fluoroolefins hydrogenation |
| JP5056963B2 (ja) | 2010-03-31 | 2012-10-24 | ダイキン工業株式会社 | 含フッ素アルカンの製造方法 |
| JP5964823B2 (ja) * | 2010-07-01 | 2016-08-03 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | トリフルオロエチレンの合成のための方法 |
| US9101914B2 (en) | 2011-03-31 | 2015-08-11 | Nissan Motor Co., Ltd. | Exhaust gas purifying catalyst, exhaust gas purifying monolith catalyst, and method for manufacturing exhaust gas purifying catalyst |
| US9352301B2 (en) | 2012-09-10 | 2016-05-31 | Nissan Motor Co., Ltd. | Exhaust gas purification catalyst, exhaust gas purification monolith catalyst, and method for producing exhaust gas purification catalyst |
| US9180433B2 (en) * | 2013-03-14 | 2015-11-10 | Honeywell International, Inc. | Catalysts for 2-chloro-1,1,1,2-tetrafluoropropane dehydrochlorination |
| CN105457651B (zh) * | 2014-09-05 | 2018-12-11 | 浙江蓝天环保高科技股份有限公司 | 一种加氢脱氯催化剂及其在三氟氯乙烯制备中的应用 |
| CN105944734B (zh) * | 2016-05-17 | 2019-08-06 | 常熟三爱富氟化工有限责任公司 | 一种用于三氟三氯乙烷催化加氢脱氯制备三氟氯乙烯的催化剂及其制备方法 |
| WO2018019724A1 (en) | 2016-07-26 | 2018-02-01 | Solvay Specialty Polymers Italy S.P.A. | Method for the manufacture of perfluorovinylethers |
| JP6886290B2 (ja) * | 2016-12-26 | 2021-06-16 | 太陽化学株式会社 | 低温酸化触媒の製造方法 |
| JP6837828B2 (ja) * | 2016-12-26 | 2021-03-03 | 太陽化学株式会社 | 低温酸化触媒 |
| FR3115786B1 (fr) * | 2020-11-03 | 2022-11-04 | Arkema France | Procédé de production du trifluoroéthylène |
| CN113649030B (zh) * | 2021-09-22 | 2024-01-26 | 上海华谊（集团）公司 | 加氢脱卤催化剂和三氟氯乙烯与三氟乙烯的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2207868A (en) * | 1938-01-25 | 1940-07-16 | Hercules Powder Co Ltd | Hydrogenation catalyst and method of preparing the same |
| BE469585A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1945-12-22 | 1900-01-01 | ||
| US3505417A (en) * | 1966-10-05 | 1970-04-07 | Phillips Petroleum Co | Dehalogenation of fluorohalocarbons |
| US3846281A (en) * | 1972-04-03 | 1974-11-05 | Exxon Research Engineering Co | Platinum-magnesium reforming catalyst |
| US3876557A (en) * | 1973-06-29 | 1975-04-08 | Jackie Lou Bland | Metallic catalyst |
| US4289710A (en) * | 1979-12-19 | 1981-09-15 | Union Carbide Corporation | Process for producing methanol from synthesis gas with palladium-calcium catalysts |
| DE3170139D1 (en) * | 1980-12-09 | 1985-05-30 | Allied Corp | Preparation of chlorotrifluoroethylene and trifluoroethylene |
| US4621149A (en) * | 1981-12-25 | 1986-11-04 | Asahi Kasei Kogyo Kabushiki Kaisha | Production of urethane compounds |
| JPS6056703B2 (ja) * | 1982-03-26 | 1985-12-11 | 旭化成株式会社 | ウレタンの製造方法 |
| 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 |
| US4740642A (en) * | 1986-08-21 | 1988-04-26 | The Bf Goodrich Company | Catalyst and process for the fluid-bed oxychlorination of ethylene to EDC |
-
1988
- 1988-05-24 FR FR8806991A patent/FR2631858A1/fr active Pending
-
1989
- 1989-05-05 US US07/347,926 patent/US5089454A/en not_active Expired - Lifetime
- 1989-05-12 ES ES198989201198T patent/ES2034586T3/es not_active Expired - Lifetime
- 1989-05-12 EP EP89201198A patent/EP0343707B1/fr not_active Expired - Lifetime
- 1989-05-12 DE DE8989201198T patent/DE68902509T2/de not_active Expired - Lifetime
- 1989-05-12 AT AT89201198T patent/ATE79566T1/de not_active IP Right Cessation
- 1989-05-24 JP JP1131262A patent/JP2742091B2/ja not_active Expired - Lifetime
-
1992
- 1992-09-07 GR GR920401962T patent/GR3005632T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5089454A (en) | 1992-02-18 |
| DE68902509T2 (de) | 1993-02-11 |
| EP0343707A1 (fr) | 1989-11-29 |
| EP0343707B1 (fr) | 1992-08-19 |
| DE68902509D1 (de) | 1992-09-24 |
| ES2034586T3 (es) | 1993-04-01 |
| JPH0217944A (ja) | 1990-01-22 |
| FR2631858A1 (fr) | 1989-12-01 |
| GR3005632T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-06-07 |
| ATE79566T1 (de) | 1992-09-15 |
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