HU204292B - Process for dimerizing lower alpha-olephines - Google Patents
Process for dimerizing lower alpha-olephines Download PDFInfo
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- HU204292B HU204292B HU8723A HU2387A HU204292B HU 204292 B HU204292 B HU 204292B HU 8723 A HU8723 A HU 8723A HU 2387 A HU2387 A HU 2387A HU 204292 B HU204292 B HU 204292B
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- Prior art keywords
- catalyst
- alkyl
- formula
- nickel
- component
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
-
- 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
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J31/0231—Halogen-containing 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0264—Phosphorus acid amides
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- 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
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- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
-
- 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
- B01J2231/20—Olefin oligomerisation or telomerisation
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
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- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/20—Non-coordinating groups comprising halogens
- B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
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- 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
- B01J31/1845—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 phosphorus
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (4)
- SZABADALMIIGÉNYPONTOK1. Eljárás rövidszénláncú α-olefinek dimerizálására olyan katalizátor-rendszer jelenlétében, amely a következő komponenseket tartalmazza:(A) egy szervessav-nikkelsót vagy nikkel-komplexet, (B) valamely trialkil-alumíníumot, (C) legalább egy háromértékű foszforvegyületet az (I), (Π) vagy (ΠΙ) általános képletű vegyületekközülPr2r2r3(i)P(NR12)3(II) ρ<οκΜ“>55 e képletekben R1, R2 és R3 egymástól függetlenül 1-8 szénatomos alkilcsoport, 3-7 szénatomos cikloalkilcsoport, fenilcsoport, 1, 2 vagy 3 1-3 szénatomos alkilcsoporttal vagy 1-3 szénatomos alkoxicsoporttal helyettesített fenilcsoport, vagy benzil- vagy fenetil60 csoport ésHü 204292 Β (D) egyfluorozott alkanolt, mimellett akatalizátor komponensekegymáshozviszonyított mólaránya a kővetkező: (B):(A)« 5-50, (C):(A)« 0,5:5 és (D):(B)- 0,5:10, azzal jellemezve, hogy 5¢)) fluorozott alkanolkomponensként egy (IV) általános képletű izopropanoltOH alkalmazunk, amelyben m és n mindegyike olyan szám,amelykielégítia4 < m+n < 6képletet,és adott esetben a katalizátor-rendszerhez a (B) komponens mólnyi mennyiségére számítva legfeljebb 0,9 mól (E) és 0,05-0,8 mól (F) komponenst is adunk, amely (E) legalább egy olyan katalizátor koaktivátor, amely az (V) és (VI) általános képletű halogénezett vegyületekközül keriilki, fenil-CH3.nX[1 . (V) ésR4R5R6CX (VI), amely képletekbenX jelentése halogénatom, R4,R5 és R6 mindegyike 1-4 szénatomos alkilcsoport és n értéke 1,2vagy 3. (ELSŐbbsége: 1986.01.06.)
- 2. Eljárás rövidszénláncú α-olefinek dimerizálására olyan katalizátor-rendszer, jelenlétében, amely a következőkomponenseket tartalmazza:(A) egy szervessav-nikkelsótvagy nikkel-komplexet, (B) valamelytrialkil-alummiumot, (C) legalább egy háromértékű foszforvegyületet az (Ί), (Π) vagy (E) általános képletű vegyűletekközülPr2r%3(!)P(OR1)3(m) e képletekben R1, R2 és R3 egymástól függetlenül 1-8 szénatomos alkilcsoport, 3-7 szénatomos cikloalkilcsoport, fenilcsoport, 1, 2 vagy 3 1-3 szénatomos alkilcsoporttal vagy 1-3 szénatomos alkoxicsoporttal helyettesített fenilcsoport, vagy benzil- vagy fenetücsoport,és (D) egyfluorozott alkanolt, mimellett a katalizátor komponensek egymáshoz viszonyított mólaránya a következő: (B):(A)« 5-50, (Q:(A)- 0,55 és (D):(B)« 0,5:10, azzal jellemezve, hogy (D) fluorozott alkanol komponensként egy (TV) általános képletű izopropanolt ^mH3-m'^H'Cín.H3-ii QW OH alkalmazunk, amelyben m és n mindegyike olyan szám,amelykielégítia4 £ m+n á 6 képletet, és kívánt esetben a katalizátor-rendszerhez a (B) komponens mólnyi mennyiségére számítva legfeljebb 0,9 mól (E) és 0,05-0,8 mól (F) komponenst is adunk, amely (E) legalább egy olyan katalizátor koaktivátor, amely az (V) és (VI) általános képletű halogénezett vegyűletekközül kerül ki, fenil-CH3.nXn(V) ésR4R5R6CX(VI), amely képletekbenX jelentése halogénatom, R4, R5 és R6 mindegyike 1-4 szénatomos alkilcsoport és n értéke 1,2 vagy 3, és (F) egy 10-20 szénatomos alifás alkohol vagy karbonsavvagy az alifás karbonsav 1-6 szénatomos alkilcsoporttal képzett észtere, (ELSŐbbsége: 1986.03.22.)
- 3. Az 1. igénypont szerinti eljárás, azzal jeliemezve, hogyakatalizátor-rendszera (D) és a (B) komponenseket 0,5-5, az(E) ésa ©komponenseket 0-0,5 mólarányokban tartalmazza. (ELSŐbbsége: 1986.01.06.)
- 4. Az 1. igénypontszerinti eljárás, azzal jellemezve, hogy a dimerizációs reakcióban a katalizátor-rendszert az (A) nikkel-komponensre számítya ÍO’MO'1 mólŰ koncentrációban alkalmazzuk. (ELSŐbbsége: 1986.01.06.)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61001168A JPH0662450B2 (ja) | 1986-01-06 | 1986-01-06 | 低級α−オレフインの二量化方法 |
JP61064531A JPH0698309B2 (ja) | 1986-03-22 | 1986-03-22 | 触媒の析出防止方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
HUT43095A HUT43095A (en) | 1987-09-28 |
HU204292B true HU204292B (en) | 1991-12-30 |
Family
ID=26334342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU8723A HU204292B (en) | 1986-01-06 | 1987-01-05 | Process for dimerizing lower alpha-olephines |
Country Status (6)
Country | Link |
---|---|
US (1) | US4709112A (hu) |
EP (1) | EP0231748B1 (hu) |
DE (1) | DE3760384D1 (hu) |
DK (1) | DK167317B1 (hu) |
HU (1) | HU204292B (hu) |
SU (1) | SU1690542A3 (hu) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT8629545V0 (it) * | 1986-06-12 | 1986-06-12 | Fina Ernesto | Set cateteri ureterali coassiali a palloncino per estrazione di calcoli ureterali |
JP2550641B2 (ja) * | 1988-02-29 | 1996-11-06 | 住友化学工業株式会社 | 低級α−オレフィンの二量化方法 |
US4973788A (en) * | 1989-05-05 | 1990-11-27 | Ethyl Corporation | Vinylidene dimer process |
FR2650760B1 (fr) * | 1989-08-08 | 1991-10-31 | Inst Francais Du Petrole | Nouvelle composition catalytique et sa mise en oeuvre pour l'oligomerisation des monoolefines |
US5245097A (en) * | 1991-12-18 | 1993-09-14 | Phillips Petroleum Company | Ethylene oligomerization |
US5221775A (en) * | 1992-03-19 | 1993-06-22 | Phillips Petroleum Company | Ethylene dimerization |
CA2095270C (en) * | 1992-05-08 | 2004-02-17 | Kotohiro Nomura | Dimerization of lower .alpha.-olefins |
DE59308118D1 (de) * | 1992-12-01 | 1998-03-12 | Merck Patent Gmbh | Koordinations-katalysatorsysteme |
JP2988207B2 (ja) * | 1993-03-04 | 1999-12-13 | 住友化学工業株式会社 | 2,3−ジメチル−2−ブテンの製造方法 |
EP0758563A4 (en) * | 1995-03-06 | 2000-06-28 | Nippon Mitsubishi Oil Corp | OLEFIN OLIGOMERIZATION CATALYST AND PROCESS FOR PREPARING THE OLEFIN OLIGOMER USING THE SAME |
US5663469A (en) * | 1996-02-05 | 1997-09-02 | Amoco Corporation | Production of vinylidene olefins |
US5659100A (en) * | 1996-02-05 | 1997-08-19 | Amoco Corporation | Production of vinylidene olefins |
US5625105A (en) * | 1996-02-05 | 1997-04-29 | Amoco Corporation | Production of vinylidene olefins |
FR2781792B1 (fr) * | 1998-07-28 | 2000-09-22 | Inst Francais Du Petrole | Procede pour la codimerisation de dienes de corps gras et d'olefines catalysee par des complexes au nickel |
FR2794038B1 (fr) * | 1999-05-27 | 2001-06-29 | Inst Francais Du Petrole | Composition catalytique amelioree et son application a l'oligomerisation des olefines |
US6388160B1 (en) | 1999-05-28 | 2002-05-14 | Sumitomo Chemical Company, Limited | Method for producing of 2,3-dimethylbutene-1 and 2,3-dimethylbutene-2 |
US7696123B2 (en) * | 2006-10-04 | 2010-04-13 | Conocophillips Company | Dimerization catalyst systems, their preparation, and use |
FR3074065B1 (fr) * | 2017-11-30 | 2019-12-13 | IFP Energies Nouvelles | Nouvelle composition catalytique a base de nickel, d’un phosphonium et son utilisation pour l’oligomerisation des olefines |
GB2582364A (en) * | 2019-03-21 | 2020-09-23 | Mexichem Fluor Sa De Cv | Methods |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5198242A (en) * | 1975-02-17 | 1976-08-30 | Isopurentorimaano seizoho | |
US4155946A (en) * | 1977-06-29 | 1979-05-22 | Sumitomo Chemical Company, Limited | Process for dimerizing lower alpha-olefins |
US4482640A (en) * | 1983-05-02 | 1984-11-13 | Phillips Petroleum Company | Ethylene oligomerization |
-
1986
- 1986-12-30 US US06/947,873 patent/US4709112A/en not_active Expired - Lifetime
-
1987
- 1987-01-05 SU SU874028774A patent/SU1690542A3/ru active
- 1987-01-05 HU HU8723A patent/HU204292B/hu not_active IP Right Cessation
- 1987-01-05 DK DK003787A patent/DK167317B1/da not_active IP Right Cessation
- 1987-01-05 EP EP87100066A patent/EP0231748B1/en not_active Expired
- 1987-01-05 DE DE8787100066T patent/DE3760384D1/de not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK3787D0 (da) | 1987-01-05 |
DK3787A (da) | 1987-07-07 |
US4709112A (en) | 1987-11-24 |
EP0231748B1 (en) | 1989-08-02 |
SU1690542A3 (ru) | 1991-11-07 |
DK167317B1 (da) | 1993-10-11 |
EP0231748A1 (en) | 1987-08-12 |
DE3760384D1 (en) | 1989-09-07 |
HUT43095A (en) | 1987-09-28 |
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HMM4 | Cancellation of final prot. due to non-payment of fee |