DE3336500A1 - Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinen - Google Patents
Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinenInfo
- Publication number
- DE3336500A1 DE3336500A1 DE19833336500 DE3336500A DE3336500A1 DE 3336500 A1 DE3336500 A1 DE 3336500A1 DE 19833336500 DE19833336500 DE 19833336500 DE 3336500 A DE3336500 A DE 3336500A DE 3336500 A1 DE3336500 A1 DE 3336500A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- nickel
- alkyl
- aryl
- polymerization
- 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.)
- Withdrawn
Links
- 239000003054 catalyst Substances 0.000 title claims description 21
- 150000002816 nickel compounds Chemical class 0.000 title claims description 16
- 238000006116 polymerization reaction Methods 0.000 title claims description 14
- 150000001336 alkenes Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 31
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
- 229910052759 nickel Inorganic materials 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- -1 nickel (0) compound Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- 229940076442 9,10-anthraquinone Drugs 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- RGBIPJJZHWFFGE-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;triphenylphosphane Chemical compound O=C1C=CC(=O)C=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RGBIPJJZHWFFGE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004950 naphthalene Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011877 solvent mixture Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833336500 DE3336500A1 (de) | 1983-10-07 | 1983-10-07 | Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinen |
| DE8484111315T DE3471659D1 (en) | 1983-10-07 | 1984-09-22 | Organic nickel compounds, their preparation and use as catalysts in the polymerisation of olefins |
| EP84111315A EP0137389B1 (de) | 1983-10-07 | 1984-09-22 | Organische Nickel-Verbindungen, deren Herstellung und Verwendung als Katalysatoren bei der Polymerisation von Olefinen |
| US06/654,227 US4620021A (en) | 1983-10-07 | 1984-09-25 | Organic nickel compounds, production and use thereof as catalysts in the polymerization of olefins |
| JP59206502A JPS60123507A (ja) | 1983-10-07 | 1984-10-03 | 有機ニツケル化合物、その製造及びオレフイン重合触媒としての使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833336500 DE3336500A1 (de) | 1983-10-07 | 1983-10-07 | Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3336500A1 true DE3336500A1 (de) | 1985-04-25 |
Family
ID=6211235
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833336500 Withdrawn DE3336500A1 (de) | 1983-10-07 | 1983-10-07 | Organische nickel-verbindungen deren herstellung und verwendung als katalysatoren bei der polymerisation von olefinen |
| DE8484111315T Expired DE3471659D1 (en) | 1983-10-07 | 1984-09-22 | Organic nickel compounds, their preparation and use as catalysts in the polymerisation of olefins |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484111315T Expired DE3471659D1 (en) | 1983-10-07 | 1984-09-22 | Organic nickel compounds, their preparation and use as catalysts in the polymerisation of olefins |
Country Status (4)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3506835A1 (de) * | 1985-02-27 | 1986-08-28 | Bayer Ag, 5090 Leverkusen | Organische nickel-verbindungen, deren herstellung und verwendung als polymerisationskatalysatoren |
| DE3526234A1 (de) * | 1985-07-23 | 1987-01-29 | Bayer Ag | Verfahren zur polymerisation von acetylen in gegenwart von polymeren und polyacetylenhaltige polymerprodukte |
| GB8522833D0 (en) * | 1985-09-16 | 1985-10-23 | Exxon Chemical Patents Inc | Dithiophosphonates |
| DE4018068A1 (de) * | 1990-06-06 | 1991-12-19 | Bayer Ag | Verfahren zur herstellung von an der doppelbindung mit ethylen verlaengerten styrol-derivaten mit in der gebildeten verlaengerungskette verbleibender doppelbindung |
| US5198512A (en) * | 1991-12-16 | 1993-03-30 | Phillips Petroleum Company | Polymerization catalyst and process |
| US5338812A (en) * | 1991-12-24 | 1994-08-16 | Phillips Petroleum Company | Olefin polymerization |
| IT1254224B (it) * | 1992-02-26 | 1995-09-14 | Donegani Guido Ist | Catalizzatore al nichel attivo nella omo e copolimerizzazione di etilene |
| DE4242469A1 (de) * | 1992-12-16 | 1994-06-23 | Wacker Chemie Gmbh | Katalysatoren für Hydrosilylierungsreaktionen |
| DE19637019A1 (de) * | 1996-09-12 | 1998-03-19 | Bayer Ag | Nickel-Katalysatoren für die Polymerisation |
| DE19955454A1 (de) | 1999-11-17 | 2001-05-23 | Basf Ag | Substituierte Phosphinophenolat-Metall-Komplexe zur Polymerisation von Olefinen |
| MXPA02009497A (es) * | 2000-03-31 | 2004-05-14 | Polimeri Europa Spa | Catalizadores de polimerizacion complejos para la homopolimerizacion de etileno y para la copolimerizacion de etileno. |
| JP2004501877A (ja) * | 2000-06-26 | 2004-01-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ホスフィンオキシド化合物およびスルホキシド化合物を用いる触媒作用 |
| DE10234005A1 (de) * | 2002-07-25 | 2004-02-05 | Basf Ag | Verfahren zur Emulsionspolymerisation von Olefinen |
| DE10335990A1 (de) * | 2003-08-01 | 2005-02-24 | Basf Ag | Verfahren zur Emulsionspolymerisation von Olefinen |
| DE102004017026A1 (de) * | 2004-04-02 | 2005-10-20 | Merck Patent Gmbh | Ionische Flüssigkeiten mit Fluoralkyltrifluorborat-Anionen |
| JP7670805B2 (ja) * | 2020-08-12 | 2025-04-30 | エルジー・ケム・リミテッド | ０価ニッケル化合物の製造方法および重合体の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH630928A5 (de) * | 1976-03-25 | 1982-07-15 | Hoechst Ag | Verfahren zur herstellung von doppelylid-komplexen von metallen. |
| DE2701143C2 (de) * | 1977-01-13 | 1985-08-22 | Hoechst Ag, 6230 Frankfurt | Doppelylid-Komplexe von Metallen sowie Verfahren zu ihrer Herstellung und deren Verwendung |
| DE2923206A1 (de) * | 1979-06-08 | 1980-12-11 | Huels Chemische Werke Ag | Verfahren zur herstellung von polyethylenwachsen |
| US4529554A (en) * | 1980-08-18 | 1985-07-16 | Gulf Research & Development Company | Process for the preparation of nickel ylides containing ylide ligands with a sulfonated group V component |
| US4293502A (en) * | 1980-08-18 | 1981-10-06 | Gulf Research & Development Company | Nickel ylides |
| US4537982A (en) * | 1982-08-03 | 1985-08-27 | Bayer Aktiengesellschaft | Production of organic nickel compounds |
-
1983
- 1983-10-07 DE DE19833336500 patent/DE3336500A1/de not_active Withdrawn
-
1984
- 1984-09-22 DE DE8484111315T patent/DE3471659D1/de not_active Expired
- 1984-09-22 EP EP84111315A patent/EP0137389B1/de not_active Expired
- 1984-09-25 US US06/654,227 patent/US4620021A/en not_active Expired - Lifetime
- 1984-10-03 JP JP59206502A patent/JPS60123507A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0137389A2 (de) | 1985-04-17 |
| JPS60123507A (ja) | 1985-07-02 |
| JPH051796B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-11 |
| EP0137389B1 (de) | 1988-06-01 |
| DE3471659D1 (en) | 1988-07-07 |
| US4620021A (en) | 1986-10-28 |
| EP0137389A3 (en) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |