WO2012133935A1 - Procédé de production d'un complexe métal de transition, catalyseur de trimérisation, procédé de production de 1-hexène, procédé de production d'un composé de cyclopentadiène substitué (3) - Google Patents

Procédé de production d'un complexe métal de transition, catalyseur de trimérisation, procédé de production de 1-hexène, procédé de production d'un composé de cyclopentadiène substitué (3) Download PDF

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Publication number
WO2012133935A1
WO2012133935A1 PCT/JP2012/059294 JP2012059294W WO2012133935A1 WO 2012133935 A1 WO2012133935 A1 WO 2012133935A1 JP 2012059294 W JP2012059294 W JP 2012059294W WO 2012133935 A1 WO2012133935 A1 WO 2012133935A1
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Prior art keywords
silyl
carbon atoms
tris
halogen atom
group
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PCT/JP2012/059294
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English (en)
Inventor
Taichi Senda
Masaya Tanimoto
Hidenori Hanaoka
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Sumitomo Chemical Company, Limited
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Publication date
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Publication of WO2012133935A1 publication Critical patent/WO2012133935A1/fr

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    • 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
    • C07F17/00—Metallocenes
    • 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
    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • C07C2/34—Metal-hydrocarbon complexes
    • 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
    • B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
    • B01J2531/002—Materials
    • B01J2531/007—Promoter-type Additives
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • 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
    • 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

Definitions

  • Examples of the substituted cyclopentadiene compound (4) include the following cyclopentadiene, methylcyclopentadiene, 1,2-dimethylcyclopentadiene, 1,3- dimethylcyclopentadiene, 1,4-dimethylcyclopentadiene, 2,3-dimethylcyclopentadiene, 1,2,3- trimethylcyclopentadiene, 1,2,4-trimethylcyclopentadiene, 1,2,3,4-tetramethylcyclopentadiene, ethylcyclopentadiene, 1,2-diethylcyclopentadiene, 1,3-diethylcyclopentadiene, 1,4- diethylcyclopentadiene, 2,3-diethylcyclopentadiene, 1,2,3-triethylcyclopentadiene, 1,2,4- triethylcyclopentadiene, 1,2,3,4-tetraethylcyclopentadiene, n-propylcyclopent
  • the substituted cyclopentadiene compounds (4) exemplified above may have isomers differing in the double bond position of each cyclopentadiene ring. A mixture of these isomers may be used.
  • secondary amines such as N-methylaniline, N-ethylaniline, diphenylamine, N- methylchloroaniline, N-methylbromoaniline, N-methylfluoroaniline, N-methylanisidine, N- methylmethylaniline, N-methylethylaniline, N-methyl-n-propylaniline, N- methylisopropylaniline, diethylamine, dipropylamine, diisopropylamine, dipentylamine, dihexylamine, dicyclohexylamine, diheptylamine, dioctylamine, morpholine, piperidine, 2,2,6,6- tetramethylpiperidine, pyrrolidine, 2-methylaminopyridine, 3-methylaminopyridine and 4- methylaminopyridine; and
  • alkylaluminum dichloride examples include methylaluminum dichloride, ethylaluminum dichloride, propylaluminum dichloride, isobutylaluminum dichloride and hexylaluminum dichloride.
  • dialkylaluminum hydride examples include dimethylaluminum hydride, diethylaluminum hydride, dipropylaluminum hydride, diisobutylaluminum hydride and dihexylaluminum hydride.
  • borate compound (B3) represented by formula (L- H) + (BQ 8 Q 9 Q l0 Q 11 ) " include triethyl ammonium tetrakis(pentafluorophenyl)borate,
  • the catalyst for trimerization of the present invention is a catalyst for trimerization obtained by bringing the transition metal complex (1) into contact with an activating co-catalyst component and is a catalyst capable of producing 1-hexene by ethylene trimerization.
  • Each of the transition metal complex (1) and the activating co-catalyst component is also referred to as a catalytic component.
  • Measurement parameter Probe (5 mm in diameter), OBNUC 13 C, PULPROG zgpg30, accumulated number 256 times or more

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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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

Abstract

Un objet de la présente invention est de pourvoir à un complexe métal de transition Cp-Ar à pont silicium qui sert de composant catalytique capable de produire de manière efficace et très sélective du 1-hexène par la réaction de trimérisation de l'éthylène. Le complexe métal de transition selon l'invention est représenté par la formule générale (1) suivante, etc. : où M1 représente un atome de métal de transition du Groupe 4 de la Classification périodique des éléments; X1, X2, X3, R1, R2, R3 et R4 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un groupe alkyle ayant 1 à 20 atomes de carbone pouvant contenir un atome d'halogène, un groupe alcoxy ayant 1 à 20 atomes de carbone pouvant contenir un atome d'halogène, un groupe aryle ayant 6 à 20 atomes de carbone pouvant contenir un atome d'halogène, un groupe aryloxy ayant 6 à 20 atomes de carbone pouvant contenir un atome d'halogène, un groupe aralkyle ayant 7 à 20 atomes de carbone pouvant contenir un atome d'halogène, un groupe aralkyloxy ayant 7 à 20 atomes de carbone pouvant contenir un atome d'halogène, ou autre.
PCT/JP2012/059294 2011-03-29 2012-03-29 Procédé de production d'un complexe métal de transition, catalyseur de trimérisation, procédé de production de 1-hexène, procédé de production d'un composé de cyclopentadiène substitué (3) WO2012133935A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-071903 2011-03-29
JP2011071903 2011-03-29

Publications (1)

Publication Number Publication Date
WO2012133935A1 true WO2012133935A1 (fr) 2012-10-04

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JP (1) JP2012214459A (fr)
WO (1) WO2012133935A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003992A1 (fr) * 1995-07-14 1997-02-06 Sumitomo Chemical Company, Limited Complexe a base de metal de transition, procede de preparation dudit complexe, catalyseur de polymerisation pour des olefines le contenant et procede de production de polymeres d'olefines
JP2004524959A (ja) * 2001-02-22 2004-08-19 ステフティング ダッチ ポリマー インスティテュート オレフィンの三量化のための触媒系
JP2006347899A (ja) * 2005-06-13 2006-12-28 Mitsui Chemicals Inc 遷移金属化合物、該遷移金属化合物の製造方法、該遷移金属化合物からなるオレフィン重合用触媒成分、該オレフィン重合用触媒成分を用いたオレフィンの重合方法
WO2011040555A1 (fr) * 2009-09-30 2011-04-07 住友化学株式会社 Complexe de métaux de transition, procédé de préparation desdits complexes de métaux de transition, catalyseur de trimérisation, procédé de préparation de 1-hexène, procédé de préparation d'un polymère d'éthylène, composé de cyclopentadiène substitué, et procédé de préparation dudit composé de cyclopentadiène substitué

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003992A1 (fr) * 1995-07-14 1997-02-06 Sumitomo Chemical Company, Limited Complexe a base de metal de transition, procede de preparation dudit complexe, catalyseur de polymerisation pour des olefines le contenant et procede de production de polymeres d'olefines
JP2004524959A (ja) * 2001-02-22 2004-08-19 ステフティング ダッチ ポリマー インスティテュート オレフィンの三量化のための触媒系
JP2006347899A (ja) * 2005-06-13 2006-12-28 Mitsui Chemicals Inc 遷移金属化合物、該遷移金属化合物の製造方法、該遷移金属化合物からなるオレフィン重合用触媒成分、該オレフィン重合用触媒成分を用いたオレフィンの重合方法
WO2011040555A1 (fr) * 2009-09-30 2011-04-07 住友化学株式会社 Complexe de métaux de transition, procédé de préparation desdits complexes de métaux de transition, catalyseur de trimérisation, procédé de préparation de 1-hexène, procédé de préparation d'un polymère d'éthylène, composé de cyclopentadiène substitué, et procédé de préparation dudit composé de cyclopentadiène substitué

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JORG SABMANNSHAUSEN ET AL.: "Half-sandwich complexes of titanium and zirconium with pendant phenyl substituents. The influence of ansa-aryl coordination on the polymerisation activity of half-sandwich catalysts", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 592, 2002, pages 84 - 94, XP001033815, DOI: doi:10.1016/S0022-328X(99)00488-X *
PATRICK J. W. DECKERS ET AL.: "Catalytic Trimerization of Ethene with Highly Active Cyclopentadienyl-Arene Titanium Catalysts", ORGANOMETALLICS, vol. 21, no. 23, 2002, pages 5122 - 5135, XP001132361, DOI: doi:10.1021/om020765a *

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