JPH0822912B2 - 触媒組成物 - Google Patents
触媒組成物Info
- Publication number
- JPH0822912B2 JPH0822912B2 JP62046951A JP4695187A JPH0822912B2 JP H0822912 B2 JPH0822912 B2 JP H0822912B2 JP 62046951 A JP62046951 A JP 62046951A JP 4695187 A JP4695187 A JP 4695187A JP H0822912 B2 JPH0822912 B2 JP H0822912B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- catalyst composition
- carbon monoxide
- bridge
- composition according
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002941 palladium compounds Chemical class 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 239000011574 phosphorus Substances 0.000 claims abstract description 7
- 229910052787 antimony Chemical group 0.000 claims abstract description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 26
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 229920001897 terpolymer Polymers 0.000 claims description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 150000002940 palladium Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 15
- 229910052763 palladium Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 229940005561 1,4-benzoquinone Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- AIACLXROWHONEE-UHFFFAOYSA-N 2,3-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C=CC1=O AIACLXROWHONEE-UHFFFAOYSA-N 0.000 description 2
- QFSYADJLNBHAKO-UHFFFAOYSA-N 2,5-dihydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C(O)=CC1=O QFSYADJLNBHAKO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VTWDKFNVVLAELH-UHFFFAOYSA-N methyl-p-benzoquinone Natural products CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KSFNQTZBTVALRV-UHFFFAOYSA-N 2,3,5-trichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C(Cl)=C(Cl)C1=O KSFNQTZBTVALRV-UHFFFAOYSA-N 0.000 description 1
- FDOKWKTVAJNFLT-UHFFFAOYSA-N 2,5-dihydroxy-3,6-dinitrocyclohexa-2,5-diene-1,4-dione Chemical compound OC1=C([N+]([O-])=O)C(=O)C(O)=C([N+]([O-])=O)C1=O FDOKWKTVAJNFLT-UHFFFAOYSA-N 0.000 description 1
- JCARTGJGWCGSSU-UHFFFAOYSA-N 2,6-dichlorobenzoquinone Chemical group ClC1=CC(=O)C=C(Cl)C1=O JCARTGJGWCGSSU-UHFFFAOYSA-N 0.000 description 1
- SENUUPBBLQWHMF-UHFFFAOYSA-N 2,6-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=C(C)C1=O SENUUPBBLQWHMF-UHFFFAOYSA-N 0.000 description 1
- VSHVAOIJUGIMJM-UHFFFAOYSA-N 2-nitrocyclohexa-2,5-diene-1,4-dione Chemical compound [O-][N+](=O)C1=CC(=O)C=CC1=O VSHVAOIJUGIMJM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- WBXHOXGVPNQEJP-UHFFFAOYSA-N bis(4-methoxyphenyl)phosphane;propane Chemical compound CCC.C1=CC(OC)=CC=C1PC1=CC=C(OC)C=C1 WBXHOXGVPNQEJP-UHFFFAOYSA-N 0.000 description 1
- YFXWBJYXAOVVDR-UHFFFAOYSA-N bis(4-methylphenyl)phosphane;propane Chemical compound CCC.C1=CC(C)=CC=C1PC1=CC=C(C)C=C1 YFXWBJYXAOVVDR-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0205—Oxygen-containing compounds comprising carbonyl groups or oxygen-containing derivatives, e.g. acetals, ketals, cyclic peroxides
- B01J31/0208—Ketones or ketals
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0209—Esters of carboxylic or carbonic acids
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1895—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing arsenic or antimony
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polyethers (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Paper (AREA)
- Endoscopes (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8600563 | 1986-03-05 | ||
| NL8600563 | 1986-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62212432A JPS62212432A (ja) | 1987-09-18 |
| JPH0822912B2 true JPH0822912B2 (ja) | 1996-03-06 |
Family
ID=19847664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62046951A Expired - Lifetime JPH0822912B2 (ja) | 1986-03-05 | 1987-03-03 | 触媒組成物 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4831113A (en, 2012) |
| EP (1) | EP0239145B1 (en, 2012) |
| JP (1) | JPH0822912B2 (en, 2012) |
| KR (1) | KR960009687B1 (en, 2012) |
| CN (1) | CN1010026B (en, 2012) |
| AT (1) | ATE68798T1 (en, 2012) |
| AU (1) | AU591759B2 (en, 2012) |
| BR (1) | BR8700950A (en, 2012) |
| DE (1) | DE3773967D1 (en, 2012) |
| DK (1) | DK165225C (en, 2012) |
| ES (1) | ES2025628T3 (en, 2012) |
| FI (1) | FI870927A7 (en, 2012) |
| GR (1) | GR3003195T3 (en, 2012) |
| HU (1) | HU205958B (en, 2012) |
| IL (1) | IL81971A0 (en, 2012) |
| IN (1) | IN168306B (en, 2012) |
| NO (1) | NO167464C (en, 2012) |
| PL (1) | PL151375B1 (en, 2012) |
| ZA (1) | ZA871518B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE60363B1 (en) * | 1986-05-27 | 1994-07-13 | Shell Int Research | Process for the preparation of polymers |
| CA1305695C (en) * | 1986-08-22 | 1992-07-28 | Eit Drent | Catalyst compositions and process for olefin/co copolymerization |
| IN171627B (en, 2012) * | 1986-08-26 | 1992-11-28 | Shell Int Research | |
| US5194631A (en) * | 1987-03-14 | 1993-03-16 | Nihon Nohyaku Co., Ltd. | Process for producing carboxylic acids |
| JP3000220B2 (ja) * | 1987-03-14 | 2000-01-17 | 日本農薬株式会社 | カルボン酸の製造法 |
| JP2587856B2 (ja) * | 1987-03-27 | 1997-03-05 | シエル・インターナシヨナル，リサーチ・マートスハツペイ・ベー・ヴエー | オレフィン／ｃｏコポリマーからの触媒残留物の除去 |
| KR0128998B1 (ko) * | 1987-07-23 | 1998-04-07 | 오노 알버어스 | 신규 촉매 조성물 및 이를 이용하여 중합체를 제조하는 방법 |
| US4889914A (en) * | 1987-08-25 | 1989-12-26 | Shell Oil Company | Preparation of carbon monoxide/olefin copolymer with removal of s/Fe from carbon monoxide monomer |
| NL8702317A (nl) * | 1987-09-29 | 1989-04-17 | Shell Int Research | Katalysatorcomposities. |
| EP0319083A3 (en) * | 1987-11-30 | 1990-11-07 | Shell Internationale Researchmaatschappij B.V. | Polyketone polymer preparation |
| US4916208A (en) * | 1987-12-18 | 1990-04-10 | Shell Oil Company | Novel polymers |
| US4965341A (en) * | 1988-06-08 | 1990-10-23 | Shell Oil Company | Polymerization of co/olefin with catalyst comprising sulfur bidentate ligand |
| US5010171A (en) * | 1988-09-22 | 1991-04-23 | Shell Oil Company | Carbon monoxide/olefin polymerization with catalyst comprising p. bidentate ligand having non-hydrocarbyl substituent |
| GB2226821A (en) * | 1988-12-29 | 1990-07-11 | Shell Int Research | Process for the carbonylation polymerization of dienes in the presence of dicarboxylic acids or diols as coreactants |
| EP0380162B1 (en) * | 1989-01-26 | 1995-04-12 | Shell Internationale Researchmaatschappij B.V. | Catalyst compositions |
| US5057599A (en) * | 1989-07-14 | 1991-10-15 | Shell Oil Company | Polymerization of carbon monoxide/olefin with aromatic tetradentate phosphorus ligand |
| JPH05140300A (ja) * | 1991-05-08 | 1993-06-08 | Shell Internatl Res Maatschappij Bv | 一酸化炭素と１種以上のオレフインとの線状交互ポリマーの製造法 |
| US5247065A (en) * | 1991-08-30 | 1993-09-21 | Shell Oil Company | Polymerization of CO/olefin with bidentate ligand having 2-hydroxy-2-alkyl-1,3-propylene bridging group |
| US5352767A (en) * | 1992-01-08 | 1994-10-04 | University Of Massachusetts - Amherst | Alpha-olefin/carbon monoxide attenuating copolymers and improved catalyst and method for copolymerizing the same |
| CA2091412A1 (en) * | 1992-03-11 | 1993-09-12 | Anna Sommazzi | Catalytic system and process for copolymerizing carbon monoxide with one or more olefins |
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-
1987
- 1987-02-16 IN IN131/DEL/87A patent/IN168306B/en unknown
- 1987-02-25 DE DE8787200333T patent/DE3773967D1/de not_active Expired - Lifetime
- 1987-02-25 AT AT87200333T patent/ATE68798T1/de not_active IP Right Cessation
- 1987-02-25 ES ES198787200333T patent/ES2025628T3/es not_active Expired - Lifetime
- 1987-02-25 EP EP87200333A patent/EP0239145B1/en not_active Expired - Lifetime
- 1987-02-27 BR BR8700950A patent/BR8700950A/pt not_active IP Right Cessation
- 1987-03-03 CN CN87101642A patent/CN1010026B/zh not_active Expired
- 1987-03-03 HU HU87862A patent/HU205958B/hu not_active IP Right Cessation
- 1987-03-03 DK DK109687A patent/DK165225C/da not_active IP Right Cessation
- 1987-03-03 KR KR1019870001857A patent/KR960009687B1/ko not_active Expired - Fee Related
- 1987-03-03 PL PL1987264408A patent/PL151375B1/pl unknown
- 1987-03-03 JP JP62046951A patent/JPH0822912B2/ja not_active Expired - Lifetime
- 1987-03-03 ZA ZA871518A patent/ZA871518B/xx unknown
- 1987-03-03 AU AU69645/87A patent/AU591759B2/en not_active Ceased
- 1987-03-03 NO NO870875A patent/NO167464C/no unknown
- 1987-03-03 FI FI870927A patent/FI870927A7/fi not_active Application Discontinuation
- 1987-03-05 US US07/021,946 patent/US4831113A/en not_active Expired - Lifetime
- 1987-03-23 IL IL81971A patent/IL81971A0/xx not_active IP Right Cessation
-
1988
- 1988-04-25 US US07/185,724 patent/US4851379A/en not_active Expired - Lifetime
-
1991
- 1991-11-25 GR GR91401814T patent/GR3003195T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU205958B (en) | 1992-07-28 |
| FI870927A7 (fi) | 1987-09-06 |
| KR870008615A (ko) | 1987-10-19 |
| DK165225C (da) | 1993-03-22 |
| NO870875D0 (no) | 1987-03-03 |
| EP0239145B1 (en) | 1991-10-23 |
| HUT48650A (en) | 1989-06-28 |
| ES2025628T3 (es) | 1992-04-01 |
| PL264408A1 (en) | 1988-07-21 |
| IL81971A0 (en) | 1987-10-20 |
| CN1010026B (zh) | 1990-10-17 |
| DE3773967D1 (de) | 1991-11-28 |
| US4851379A (en) | 1989-07-25 |
| GR3003195T3 (en) | 1993-02-17 |
| KR960009687B1 (ko) | 1996-07-23 |
| US4831113A (en) | 1989-05-16 |
| IN168306B (en, 2012) | 1991-03-09 |
| ATE68798T1 (de) | 1991-11-15 |
| NO167464C (no) | 1991-11-06 |
| DK109687A (da) | 1987-09-06 |
| AU6964587A (en) | 1987-09-10 |
| NO870875L (no) | 1987-09-07 |
| DK165225B (da) | 1992-10-26 |
| DK109687D0 (da) | 1987-03-03 |
| EP0239145A2 (en) | 1987-09-30 |
| FI870927A0 (fi) | 1987-03-03 |
| CN87101642A (zh) | 1987-09-30 |
| JPS62212432A (ja) | 1987-09-18 |
| NO167464B (no) | 1991-07-29 |
| BR8700950A (pt) | 1987-12-29 |
| ZA871518B (en) | 1987-08-24 |
| AU591759B2 (en) | 1989-12-14 |
| EP0239145A3 (en) | 1988-01-27 |
| PL151375B1 (en) | 1990-08-31 |
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