CN1019799B - 用钯催化剂将不饱合烯烃化合物羰基化的方法 - Google Patents
用钯催化剂将不饱合烯烃化合物羰基化的方法Info
- Publication number
- CN1019799B CN1019799B CN87101635A CN87101635A CN1019799B CN 1019799 B CN1019799 B CN 1019799B CN 87101635 A CN87101635 A CN 87101635A CN 87101635 A CN87101635 A CN 87101635A CN 1019799 B CN1019799 B CN 1019799B
- Authority
- CN
- China
- Prior art keywords
- acid
- described method
- palladium
- mentioned arbitrary
- carboxylic acid
- 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
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 36
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 23
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 17
- 230000006315 carbonylation Effects 0.000 title claims abstract description 13
- -1 olefin compounds Chemical class 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 title description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 24
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 14
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
- 238000007172 homogeneous catalysis Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 229910000856 hastalloy Inorganic materials 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/04—Formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| GB8605034 | 1986-02-28 | ||
| GB868605034A GB8605034D0 (en) | 1986-02-28 | 1986-02-28 | Carbonylation of compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87101635A CN87101635A (zh) | 1988-01-20 |
| CN1019799B true CN1019799B (zh) | 1992-12-30 |
Family
ID=10593872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87101635A Expired CN1019799B (zh) | 1986-02-28 | 1987-02-26 | 用钯催化剂将不饱合烯烃化合物羰基化的方法 |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0235864B1 (enExample) |
| JP (1) | JP2614442B2 (enExample) |
| KR (1) | KR950008892B1 (enExample) |
| CN (1) | CN1019799B (enExample) |
| AR (1) | AR242772A1 (enExample) |
| AT (1) | ATE52759T1 (enExample) |
| AU (1) | AU591242B2 (enExample) |
| BR (1) | BR8700909A (enExample) |
| CA (1) | CA1303058C (enExample) |
| DE (1) | DE3762734D1 (enExample) |
| DK (1) | DK101187A (enExample) |
| ES (1) | ES2016102B3 (enExample) |
| FI (1) | FI86711C (enExample) |
| GB (1) | GB8605034D0 (enExample) |
| GR (1) | GR3000494T3 (enExample) |
| HU (1) | HU204248B (enExample) |
| IN (1) | IN167615B (enExample) |
| MX (1) | MX168032B (enExample) |
| NO (1) | NO165189C (enExample) |
| PL (1) | PL147076B1 (enExample) |
| SU (1) | SU1597095A3 (enExample) |
| ZA (1) | ZA871392B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8712455D0 (en) * | 1987-05-27 | 1987-07-01 | Shell Int Research | Preparation of cyclic carboxylic anhydrides |
| GB8729267D0 (en) * | 1987-12-15 | 1988-01-27 | Shell Int Research | Process for production of propionate esters |
| GB2226822A (en) * | 1988-12-29 | 1990-07-11 | Shell Int Research | Process for the carbonylation polymerization of functionalized olefinically unsaturated compounds |
| GB8917579D0 (en) * | 1989-08-01 | 1989-09-13 | Shell Int Research | Preparation of alkyl propionates |
| US5166411A (en) * | 1990-02-05 | 1992-11-24 | Shell Oil Company | Carbonylation catalyst system |
| GB9002521D0 (en) * | 1990-02-05 | 1990-04-04 | Shell Int Research | Carbonylation catalyst system |
| US5304674A (en) * | 1992-06-29 | 1994-04-19 | Shell Oil Company | Preparation of alkanedioic derivatives |
| TW272949B (enExample) * | 1994-07-22 | 1996-03-21 | Taishal Kagaku Kogyo Kk | |
| US5495041A (en) * | 1995-02-22 | 1996-02-27 | Dsm N.W. | Process for the preparation of a pentenoate ester |
| GB0218613D0 (en) | 2002-08-10 | 2002-09-18 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds |
| TWI301481B (en) | 2002-08-10 | 2008-10-01 | Lucite Int Uk Ltd | A catalyst system |
| JP2007516197A (ja) | 2003-07-03 | 2007-06-21 | ルーサイト インターナショナル ユーケー リミテッド | エチレン性不飽和化合物のヒドロホルミル化方法 |
| GB0403592D0 (en) | 2004-02-18 | 2004-03-24 | Lucite Int Uk Ltd | A catalyst system |
| GB0411951D0 (en) | 2004-05-28 | 2004-06-30 | Lucite Int Uk Ltd | Carbonylation of ester |
| GB0516556D0 (en) | 2005-08-12 | 2005-09-21 | Lucite Int Uk Ltd | Improved catalyst system |
| EA025600B1 (ru) | 2005-11-17 | 2017-01-30 | ЛУСАЙТ ИНТЕРНЕЙШНЛ Ю Кей ЛИМИТЕД | Способ карбонилирования этиленненасыщенных соединений, каталитическая система и бидентатный лиганд |
| GB0607494D0 (en) | 2006-04-13 | 2006-05-24 | Lucite Int Uk Ltd | Metal complexes |
| GB2437930A (en) | 2006-05-10 | 2007-11-14 | Lucite Int Uk Ltd | Mixing apparatus |
| CA2671409C (en) | 2006-12-02 | 2016-07-26 | Lucite International Uk Limited | Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds |
| DE102007014914B4 (de) * | 2007-03-26 | 2013-09-12 | Heraeus Precious Metals Gmbh & Co. Kg | Katalytisch hochwirksame Edelmetall-Carboxylat-Verbindungen von Ir, Ru, Rh, Pd, Pt und Au |
| GB0812297D0 (en) | 2008-07-04 | 2008-08-13 | Lucite Int Uk Ltd | Novel carbonylation ligand sand thier use of in the carbonylation of ethylenically unsaturated compounds |
| GB0921876D0 (en) | 2009-12-15 | 2010-01-27 | Lucite Int Uk Ltd | Improved carbonylation process |
| GB0921875D0 (en) | 2009-12-15 | 2010-01-27 | Lucite Int Uk Ltd | A continuous process for the carbonylation of ethylene |
| GB201000078D0 (en) | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
| GB201122054D0 (en) | 2011-12-21 | 2012-02-01 | Lucite Int Uk Ltd | A continuous process for the carbonylation of ethylene |
| WO2017209199A1 (ja) * | 2016-05-31 | 2017-12-07 | 宇部興産株式会社 | 脂環式テトラカルボン酸二無水物の製造方法 |
| ES2807544T3 (es) * | 2017-12-21 | 2021-02-23 | Evonik Operations Gmbh | Procedimiento para la hidroxicarbonilación de diisobuteno catalizada con Pd: proporción ácido sulfúrico/ligando |
| ES2807998T3 (es) * | 2017-12-21 | 2021-02-25 | Evonik Operations Gmbh | Procedimiento para la hidroxicarbonilación de diisobuteno catalizada con Pd: proporción ligando/Pd |
| CN115304505B (zh) * | 2021-05-08 | 2023-06-27 | 西北大学 | 烯烃羰基化合成酰胺的方法 |
| CN115403465B (zh) * | 2022-05-20 | 2023-08-18 | 湖南工程学院 | 一种二氧化碳和烯烃合成有机羧酸酯的制备方法 |
| CN115870002B (zh) * | 2022-12-12 | 2025-06-03 | 万华化学集团股份有限公司 | 一种不饱和烯烃甲氧羰基化的催化剂及方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1051627A (enExample) * | 1961-12-29 | |||
| DE1249867B (de) * | 1964-12-19 | 1967-09-14 | Badische Anilin- &. Soda-Fabnk Aktiengesellschaft, Ludwigshaf en/Rhem | Verfahren zur Herstellung von Carbonsauren oder Carbonsaureestern |
| EP0055875B1 (en) * | 1981-01-06 | 1986-08-20 | Shell Internationale Researchmaatschappij B.V. | Process for the carbonylation of olefins |
| JPS5910545A (ja) * | 1982-07-08 | 1984-01-20 | Mitsubishi Petrochem Co Ltd | カルボン酸もしくはそのエステルの製造法 |
| CA1231346A (en) * | 1982-09-30 | 1988-01-12 | Eit Drent | Process for the carbonylation of olefinically unsaturated compounds with a palladium catalyst |
| GB8432376D0 (en) * | 1984-12-21 | 1985-02-06 | Shell Int Research | Carbonylation of acetylenically unsaturated compounds |
| GB8501919D0 (en) * | 1985-01-25 | 1985-02-27 | Shell Int Research | Carbonylation of allenically unsaturated compounds |
| GB8509641D0 (en) * | 1985-04-15 | 1985-05-22 | Shell Int Research | Carboxylic di-esters/acids |
-
1986
- 1986-02-28 GB GB868605034A patent/GB8605034D0/en active Pending
-
1987
- 1987-02-04 CA CA000528952A patent/CA1303058C/en not_active Expired - Fee Related
- 1987-02-25 AT AT87200329T patent/ATE52759T1/de not_active IP Right Cessation
- 1987-02-25 DE DE8787200329T patent/DE3762734D1/de not_active Expired - Lifetime
- 1987-02-25 EP EP87200329A patent/EP0235864B1/en not_active Expired - Lifetime
- 1987-02-25 ES ES87200329T patent/ES2016102B3/es not_active Expired - Lifetime
- 1987-02-26 JP JP62041608A patent/JP2614442B2/ja not_active Expired - Lifetime
- 1987-02-26 ZA ZA871392A patent/ZA871392B/xx unknown
- 1987-02-26 SU SU874202046A patent/SU1597095A3/ru active
- 1987-02-26 BR BR8700909A patent/BR8700909A/pt not_active IP Right Cessation
- 1987-02-26 NO NO870804A patent/NO165189C/no unknown
- 1987-02-26 PL PL1987264319A patent/PL147076B1/pl unknown
- 1987-02-26 AU AU69295/87A patent/AU591242B2/en not_active Ceased
- 1987-02-26 KR KR1019870001657A patent/KR950008892B1/ko not_active Expired - Fee Related
- 1987-02-26 HU HU87758A patent/HU204248B/hu not_active IP Right Cessation
- 1987-02-26 IN IN170/DEL/87A patent/IN167615B/en unknown
- 1987-02-26 AR AR87306847A patent/AR242772A1/es active
- 1987-02-26 DK DK101187A patent/DK101187A/da not_active Application Discontinuation
- 1987-02-26 FI FI870841A patent/FI86711C/fi not_active IP Right Cessation
- 1987-02-26 CN CN87101635A patent/CN1019799B/zh not_active Expired
- 1987-02-27 MX MX005389A patent/MX168032B/es unknown
-
1990
- 1990-05-21 GR GR90400315T patent/GR3000494T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL264319A1 (en) | 1988-03-31 |
| DK101187D0 (da) | 1987-02-26 |
| NO165189C (no) | 1991-01-09 |
| JPS62221652A (ja) | 1987-09-29 |
| FI86711B (fi) | 1992-06-30 |
| SU1597095A3 (ru) | 1990-09-30 |
| EP0235864A1 (en) | 1987-09-09 |
| GB8605034D0 (en) | 1986-04-09 |
| FI870841A0 (fi) | 1987-02-26 |
| ATE52759T1 (de) | 1990-06-15 |
| HUT45728A (en) | 1988-08-29 |
| AU6929587A (en) | 1987-09-03 |
| CA1303058C (en) | 1992-06-09 |
| FI870841L (fi) | 1987-08-29 |
| ZA871392B (en) | 1987-09-30 |
| PL147076B1 (en) | 1989-04-29 |
| AR242772A1 (es) | 1993-05-31 |
| EP0235864B1 (en) | 1990-05-16 |
| MX168032B (es) | 1993-04-29 |
| CN87101635A (zh) | 1988-01-20 |
| AU591242B2 (en) | 1989-11-30 |
| DE3762734D1 (de) | 1990-06-21 |
| IN167615B (enExample) | 1990-11-24 |
| GR3000494T3 (en) | 1991-06-28 |
| BR8700909A (pt) | 1987-12-15 |
| KR950008892B1 (ko) | 1995-08-09 |
| NO870804D0 (no) | 1987-02-26 |
| ES2016102B3 (es) | 1990-10-16 |
| FI86711C (fi) | 1992-10-12 |
| HU204248B (en) | 1991-12-30 |
| NO165189B (no) | 1990-10-01 |
| DK101187A (da) | 1987-08-29 |
| JP2614442B2 (ja) | 1997-05-28 |
| NO870804L (no) | 1987-08-31 |
| KR870007872A (ko) | 1987-09-22 |
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