WO2005044444A1 - Catalyseur d'oligomerisation d'olefine - Google Patents

Catalyseur d'oligomerisation d'olefine Download PDF

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Publication number
WO2005044444A1
WO2005044444A1 PCT/JP2004/016622 JP2004016622W WO2005044444A1 WO 2005044444 A1 WO2005044444 A1 WO 2005044444A1 JP 2004016622 W JP2004016622 W JP 2004016622W WO 2005044444 A1 WO2005044444 A1 WO 2005044444A1
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Prior art keywords
tris
group
phosphine
arsine
olefin
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PCT/JP2004/016622
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English (en)
Japanese (ja)
Inventor
Seiji Oda
Takahiro Hino
Kazunori Iwakura
Masao Yanagawa
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Sumitomo Chemical Company, Limited
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Publication of WO2005044444A1 publication Critical patent/WO2005044444A1/fr

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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
    • B01J31/24—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
    • 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
    • B01J31/02—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
    • B01J31/146—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 boron
    • 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
    • C07C2/36—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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/20—Olefin oligomerisation or telomerisation
    • 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
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates

Definitions

  • the present invention relates to a catalyst for oligomerization of orefin and a method for oligomerization of orefin.
  • the oligomer refers to a polymer having a ⁇ gfi total, that is, a small number of s of repeating units and a molecular weight of approximately 100 or less.
  • a horned butterfly having good oligomerization activity is obtained.
  • the present invention provides a method for oligomerizing an olefin which comprises a coordinating compound, a palladium compound and an aluminoxane, and which oligomerizes the olefin in the presence of an catalyst. Is what you do. BEST MODE FOR CARRYING OUT THE INVENTION
  • the olefin oligomerization angle ⁇ of the present invention contains a coordinating compound, a palladium compound and an aluminoxane.
  • Preferred specific examples of the coordinating compound of the present invention include a compound represented by the following formula (1).
  • A represents a Group 15 element in the periodic table
  • B ls B 2 and B 3 each represent an aryl group that may contain a heteroatom having 6 to 20 carbon atoms.
  • C 1 C 2 and C 3 each independently represent an S group containing an element of group 14, 15, 15, 16 or 17 of the periodic table.
  • Nitrogen, phosphorus or arsenic, C 2 and C 3 which are fiber bases containing the fifteenth group of the periodic table.
  • the Group 15 element represented by ⁇ includes, for example, a nitrogen atom, a phosphorus atom, an arsenic atom, an antimony atom, a bismuth atom, and the like. An atom and an arsenic atom are preferred, and a phosphorus atom is more preferred.
  • Examples of the aryl group having 6 to 20 carbon atoms and the aryl group containing a heteroatom having 3 to 20 carbon atoms represented by B 2 and B 3 include, for example, phenyl, naphthyl, anthracenyl, and phenantreninolene.
  • a aryl group having 6 to 20 carbon atoms such as a phenyl group, a phenyl group, a furyl group, a vinyl group, an isobenzofuranyl group, a pyrrolinole group containing a hetero atom selected from a nitrogen atom, a sulfur atom, an oxygen atom, etc.
  • C1-20 haguchi alkyl groups such as trimethylsilyl group, triisopropyl silyl group C1-20 alkyl groups such as tert-butyldimethylsilyl group, triphenylsilyl group, etc. It is exemplified silyl group containing a silyl group substituted with Ariru group of C6- 20.
  • Examples of the substituent containing a Group 15 element in the periodic table represented by C x , C 2 and C 3 include, for example, a compound having a nitrogen atom or a phosphorus atom as the Group 15 element in the periodic table.
  • a compound having a nitrogen atom or a phosphorus atom as the Group 15 element in the periodic table.
  • n _butylphosphino group di sec-butylphosphino group, ditert-butylphosphino group, din-pentylphosphino group, dineopene
  • a phosphino group such as a thiophosphino group and a diphenylphosphino group, or a phosphino group formed by a phenyl group.
  • group elements represented by C 2 and C 3 for example, methoxyethanol, ethoxy, isopropoxy group, n- propoxy group, n- butoxy group, sec- butoxy
  • Examples thereof include a C16 alkoxy group such as a tert-butoxy group, an n-pentyloxy group, a neopentyloxy group and a phenoxy group, and a C6-10 aryloxy group, and further include a methinorethio group, an ethinorethio group, and an isopropylthio group.
  • C16 alkylthio and C6 such as n-propylthio, n-butylthio, sec-butynolethio, tert-butylthio, n-pentylthio, neopentylthio, n-hexylthio, phenylthio, etc. — 10 arylthio groups S exemplified.
  • Examples of elements containing Group 17 elements of the periodic table represented by CC 2 and C 3 include fluorine, chlorine, bromine, and iodine.
  • the coordinating compound represented by the formula (1) include, for example, tris-1 (0-dimethinorea minofeninole) phosphine, tris-1 (0-getinoleaminopheninole) phosphine, tris-1 (0-diisopropinoleaminophenyl) phosphine, tris- (0-di-n-propynoleaminophenyl) phosphine, tris- (0-diisobutynoleaminophenyl) phosphine, tris- (o-n-butynole) Aminopheninolephosphine, tris- (o-di-tert-butynoleaminophenyl) phosphine, trisone (o-dimethinoleaminophenyl) amine, tris-one (o-decinoleaminophenyl) amine, tris-one o-diisoprop
  • the compound having the rooster identity represented by the formula (1) can be produced, for example, according to the method described in the Journal of Chemical Society (1965) 5210, by using a halide of an element in Group 15 of the periodic table.
  • a halogenated aryl having a substituent containing a Group 14, 15, 16 or 17 element of the periodic table can be produced by the action of ⁇ such as n-butyllithium.
  • Preferred specific compounds include tris- (0-dimethylaminophenyl) phosphine.
  • Preferred specific examples of the palladium compound of the present invention include those represented by the following formula (2). '
  • examples of the cationic ligand of D include sodium, potassium, and ammonium.
  • examples of the anionic ligand of E include, for example, hexafluoroacetylaminoacetate. Na, acetyl acetonate, trifluoroacetate, acetate, cyano group, utop group, tetrafluoroborate, thiosulfuric acid, nitric acid, chlorine, bromine, etc.
  • ligand for example, triphenylphosphine, acetonitrile, benzonitrile, bicyclo [2.2.1] hepta-1,2,5-gen, 2,2′-biviridyl, 1,2-bis (diphenylinolephosphino) ethane , (R) — (+) -2,2_bis (diphenylphosphorino) 1,1,1-binaphtinole, ammoyua, 1,5-cyclooctadiene, ethylenediamine, N, N, ⁇ ', ⁇ '-tetramethy Len 1,1,10—phenanthroline, 2- [1- (dimethylamino) ethyl] phenyl C, N, 2- (dimethylamino) ethyl, 2-[(dimethylamino) methyl] phenyl C, N, Examples include dimethinolepheninolephosphine, methinolesphenin
  • the palladium compound represented by the formula (2) include, for example, ammonium palladium paradate (II), trans-benzinole (black mouth) bis (tripheninolephosphine) palladium (II), ( Bicyclo [2.2.1] hepta-1,2,5-diene) dichloropalladium (II), (2,2,1-biviridyl) dichloropalladium (II), bis (acetate) bis (triphenolephosphine) palladium ( II), bis (acetonitrinole) chloronitropalladium (II), bis (benzonitrinole) dichlorono ⁇ .
  • a palladium compound having a halogen and a palladium compound having a ⁇ -diketonate group are preferably used from the viewpoint of ease of handling and stability. More preferred are palladium (II) acetyl acetate, palladium (II) hexafluoroacetylacetonate, sodium palladium (II) chloride, and potassium palladium (II) chloride.
  • the above-mentioned palladium compounds can be used not only in insects, but also in a mixture of two or more.
  • the catalyst of the present invention may contain an aluminoxane or an organic aluminum compound and a boron compound in addition to the coordinating compound and the palladium compound.
  • aluminoxane include a cyclic aluminoxane having the following formula (3) and a linear aluminoxane having an ffit represented by the following formula (4).
  • G1 to G7 are the same or different and are a hydrocarbon group having 1 to 8 carbon atoms, a is a number from 0 to 1, b is an integer of 2 or more, c is 1 or more Represents an integer.
  • the carbon atoms of G1 to G7 are, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, normal pentyl, neopentyl * Is an alkyl group. More preferably, G 1 to G 7 include a methyl group and an isobutyl group.
  • an aluminoxane having the following formula (5) is also preferable.
  • d represents a number greater than 0 and less than 1
  • e represents an integer of 1 or more.
  • aluminoxanes are made by various methods. There is no particular limitation on the method, provided that it is made according to a known method. For example: 1. Dissolve real quinole aluminum (for example, trimethinoreanore aluminum) in an appropriate amount of IJ (such as benzene, and Yuzuki male charcoal), and use the water as a water source. Make insects. Another example is a method of making a trial quinole aluminum (eg, trimethylaluminum) by throwing it onto a metal salt containing crystal water (eg, sulfuric acid hydrate). As the organoaluminum compound, an aluminum compound having an ffit represented by the following formula (6) is preferable.
  • IJ such as benzene, and Yuzuki male charcoal
  • G 8 is the same or different, and the number of carbon atoms:! To 8 is an elementary group, Y is the same or different, represents a hydrogen atom or a halogen atom, and f is 1, 2 or 3 Represents.
  • organic aluminum compound represented by the above formula (6) include, for example, trialkyl quinone aluminum such as trimethyl aluminum, triethynole aluminum, tripropyl aluminum, triisobutyl aluminum, and trihexyl aluminum.
  • Dialkylaluminum such as dimethyla / leminium chloride, getylaluminum chloride, dipropyl 77-leminium chloride, diisobutinole aluminum halide, dihexylaluminum chloride Chloride; alkylaluminum dichloride such as methylaluminum dichloride, ethynoleanoleminium dichloride, propylaluminum dichloride, isoptinolenoleminium dichloride, hexylaluminum dichloride; dimethylaluminum hydride, getinolealuminum hydride And dialkylaluminum hydrides such as dipropylaluminum hydride, diisobutylalum
  • Preferred specific examples of the boron compound include at least a compound selected from the following compounds (B1) to (B3).
  • B is a trivalent in-situ boron atom
  • Q 1 to Q 3 are nitrogen atoms, and 1 to 20 carbon atoms.
  • Preferred Q 1 to Q 3 are a halogen atom, a hydrocarbon group having from! To 20 carbon atoms, and a hydrogen atom group having from 1 to 20 carbon atoms.
  • boron compound (B1) examples include tris (pentafluorophenyl) borane, tris (2,3,5,6-tetrafluorophenyl) borane, and tris (2,3,4,5-tetrafluorophenyl) Borane, Tris (3,4,5-trifluorophenyl) Poran, Tris (2, Examples thereof include 3,4-trifluorophenyl) porane and pheninolebis (pentafluorophenyl) borane, and more preferably, tris (pentafluorophenyl) borane.
  • Z + is an inorganic or organic cation
  • B is a boron atom in a trivalent valence state
  • Q 1 to Q 4 are the same ones listed et al and Q 1 to Q 3 in the above (B1)
  • Z + which is a cation of fiber, includes phenocenium cation, anolequino-converted ferrosenium cation, and silver cation.
  • the Z ⁇ is an organic cation, such as Torifuwe two / Les methyl cations like et be.
  • L is a medium-rein ass
  • (L-H) + is a Prensted acid.
  • B is a boron atom in a trivalent valence state
  • Q 1 to Q 4 are the same as Q 1 to Q 3 in (B1) above.
  • the (L ⁇ ) + which is a Brönsted acid includes trianolecyl fi3 ⁇ 4ammonium, N, N—Jia Examples include ruquinoleanium, dianolequinoleammonium, and triarylphosphonium.
  • One example of (BQ 1 Q 2 Q 3 Q 4 ) is S.
  • the olefin oligomerization catalyst of the present invention can be prepared by inverting fftt self-coordinating compound, palladium compound and aluminoxane in a solvent.
  • the pseudo-obstruction method is not particularly limited. For example, a method of initiating the oligomerization reaction at the same time as removing the coordinating compound, palladium compound and aluminoxane below the olefin of the oligomerization reaction raw material, or , A palladium compound and an aluminoxane are removed in advance to prepare a catalyst, and then oligomerization reaction is carried out with fiber and olefin.
  • the mixed jl drunk of these raw doughs is not particularly limited, but a method using a reaction of a coordinating compound and a palladium compound is more preferable.
  • the oligomerization method of the olefin according to the present invention is to oligomerize the olefin under the oligomerization angle of the olebuin according to the present invention described above.
  • the method of oligomerization is not particularly limited, but it is possible to carry out oligomerization by contacting a coordinating compound as a catalyst, a palladium compound, and aluminoxane with orefin, which is a source of oligomerization, as desired.
  • a solvent is used in preparing the oligomerization II of the present invention and in the oligomerization reaction.
  • Specific examples used herein include, for example, butane, pentane, hexane, heptane, octane, isooctane, cyclopentane, methinolecyclopentane, cyclohexane, methyl cyclohexane, cyclooctane, decalin, etc.
  • Aromatic hydrocarbons such as hydrogen peroxide, benzene, toluene, xylene, cumene, ethylbenzene, monochlorobenzene, dichlorobenzene, etc .; halogenated carbons such as dichloromethane, chloroform, dichloroethane, etc.b ⁇ etc. are listed.
  • the reaction itself of the oligomerization reaction source itself may be a reaction medium, for example, a reaction medium such as 1-butene, hexene, otaten or the like. These storage media may be reduced by warworms or a mixture of two or more.
  • the concentration of the coordinating compound in preparing the oligomerization catalyst of the present invention is not particularly limited, but is usually 0.001 micromol to 100 millimol, preferably 1 milliliter, per liter of the solvent. The range is from 0.01 micromol to 10 mmol.
  • the concentration of the palladium compound in preparing the oligomerized angle butterfly of the present invention is not particularly limited, but is usually 0.001 micromol to 100 millimol, preferably 0.01 micromol, per liter of the solvent. Moles to 10 mmol.
  • the amount of aluminoxane used in preparing the oligomerized angle butterfly of the present invention is not particularly limited, but is usually 0.1 to: L 0, 000 equivalents, preferably 1 equivalent of the noradium compound. It is in the range of 3 to 3 000 equivalents, more preferably 10 to 2 000 equivalents.
  • the amount of the aluminum fiber compound used in preparing the oligomerized angle butterfly of the present invention is not particularly limited, but is usually 0.1 to 0.1 equivalent per 1 palladium compound. It is preferably in the range of 3 to 3,000 equivalents, more preferably in the range of 10 to 2,000 equivalents. If the concentration of the phenol compound is too low, the productivity S decreases, while if the concentration of the organic aluminum compound is too high, the operability deteriorates.
  • the amount of the boron compound used in preparing the oligomerization angle ⁇ of the present invention is not particularly limited, but is usually 0.1 to 1,000,000 equivalents, preferably 0.1 equivalent, per 1 mol of the palladium compound. 5 to 100 equivalents, more preferably :! ⁇ 30 equivalents.
  • the temperature for preparing the oligomerized pentagon of the present invention is usually 100 to 250 ° C, preferably 0 to 200 ° C. Tactile tongue force M lowers if the degree of transposition is too low or too high.
  • the oligomerization of olefins is accelerated.
  • the conversion of the angle of the present invention is not particularly limited, it is usually in the range of 0.01 micromol to 100 millimol, preferably 0.01 micromol to 10 millimol, per liter of the solvent. is there.
  • olefin to be converted as a source for example, ethylene, propylene,
  • Branched olefins such as 1-butene, 4-methyl-11-pentene, 2-ethyl-11-hexene and the like, and geoolefins such as 1,3-butadiene, isoprene, 1,4-pentadiene, 1,5-hexadiene, etc. No.
  • ⁇ -olefin that is useful as a # comonomer of LLDPE can be efficiently and selectively produced.
  • the temperature of the oligomerization reaction of the present invention is usually from 100 to 250 ° C, preferably from 0 to 20 ° C.
  • the reaction pressure is usually 0 to 30 OMPa, preferably 0:! To 30 MPa.
  • Raw #olefin may be supplied continuously to maintain the pressure, or may be sealed at the start with tiflS pressure and reacted. Alternatively, an olefin treated with nitrogen, argon, helium, or the like may be used.
  • This reaction may be performed batchwise, semi-; After the completion of the reaction, the reaction solution is stopped by using a deactivator such as water, alcohol, supplement, sodium hydroxide water pool, etc. After the reaction is stopped, the deactivated catalyst is removed by a known decalcification method such as extraction with water or an aqueous alkali solution, and then the desired olefin can be separated by a known operation such as distillation or extraction. ⁇
  • a deactivator such as water, alcohol, supplement, sodium hydroxide water pool, etc.
  • the deactivated catalyst is removed by a known decalcification method such as extraction with water or an aqueous alkali solution, and then the desired olefin can be separated by a known operation such as distillation or extraction.
  • the reaction vessel was heated to room temperature and then returned to normal pressure in the next step.
  • the reaction solution was analyzed by gas chromatography. Still, the solid content contained in the reaction solution was separated by filtration using a filter paper, and after that, it was dried under water and its weight was measured.
  • the oligomer activity of this catalyst system was 258.6 m 01 / m 01 (cat.) / H. The results are shown in Table 1. Ratio 1
  • Example 1 uses tris- (0-dimethylaminophenyl) phosphine, which is an amphoteric compound, and Example 1 has a high oligomeric activity, while tris- (o-dimethyl), a coordinating compound, is used. (Aminophenyl) The activity was low in Comparative Example 1 in which phosphine was not used.
  • a product having good oligomerization activity can be obtained.

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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)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un catalyseur d'oligomérisation d'oléfines qui contient un composé de coordination, un composé palladium et un aluminoxane
PCT/JP2004/016622 2003-11-06 2004-11-02 Catalyseur d'oligomerisation d'olefine WO2005044444A1 (fr)

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JP2003376588A JP2005139111A (ja) 2003-11-06 2003-11-06 オレフィンのオリゴマー化触媒及びオレフィンのオリゴマー化方法
JP2003-376588 2003-11-06

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JP5568976B2 (ja) * 2009-12-16 2014-08-13 東ソー株式会社 多置換ホスフィン化合物及び該ホスフィン化合物を含む触媒

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JPS6471828A (en) * 1987-08-28 1989-03-16 Shell Int Research Manufacture of butene
JPH01500733A (ja) * 1986-08-15 1989-03-16 シェブロン　リサーチ　カンパニー オレフインのオリゴマー化方法及び触媒
JPH0827037A (ja) * 1994-07-11 1996-01-30 Kyowa Hakko Kogyo Co Ltd 低級オレフィンの二量化法
JPH11506981A (ja) * 1996-04-04 1999-06-22 ビーピー ケミカルズ リミテッド 新規な触媒組成物
WO2001019513A1 (fr) * 1999-09-16 2001-03-22 Idemitsu Petrochemical Co., Ltd. CATALYSEURS DE METAUX DE TRANSITION ET PROCESSUS DE PRODUCTION DE POLYMERES COMPOSES D'α-OLEFINES ET DE VINYLE
JP2001096164A (ja) * 1999-09-30 2001-04-10 Tosoh Corp エチレンの三量化触媒及びこの触媒を用いるエチレンの三量化方法
JP2003301011A (ja) * 2002-04-09 2003-10-21 Sumitomo Chem Co Ltd オレフィン重合用触媒およびオレフィン重合体の製造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01500733A (ja) * 1986-08-15 1989-03-16 シェブロン　リサーチ　カンパニー オレフインのオリゴマー化方法及び触媒
JPS6471828A (en) * 1987-08-28 1989-03-16 Shell Int Research Manufacture of butene
JPH0827037A (ja) * 1994-07-11 1996-01-30 Kyowa Hakko Kogyo Co Ltd 低級オレフィンの二量化法
JPH11506981A (ja) * 1996-04-04 1999-06-22 ビーピー ケミカルズ リミテッド 新規な触媒組成物
WO2001019513A1 (fr) * 1999-09-16 2001-03-22 Idemitsu Petrochemical Co., Ltd. CATALYSEURS DE METAUX DE TRANSITION ET PROCESSUS DE PRODUCTION DE POLYMERES COMPOSES D'α-OLEFINES ET DE VINYLE
JP2001096164A (ja) * 1999-09-30 2001-04-10 Tosoh Corp エチレンの三量化触媒及びこの触媒を用いるエチレンの三量化方法
JP2003301011A (ja) * 2002-04-09 2003-10-21 Sumitomo Chem Co Ltd オレフィン重合用触媒およびオレフィン重合体の製造方法

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