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WO2016200000A1 - Composé ligand, composé de chrome organique, système catalyseur pour l'oligomérisation d'oléfines, et procédé d'oligomérisation d'oléfines au moyen de ce dernier - Google Patents

Composé ligand, composé de chrome organique, système catalyseur pour l'oligomérisation d'oléfines, et procédé d'oligomérisation d'oléfines au moyen de ce dernier Download PDF

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Publication number
WO2016200000A1
WO2016200000A1 PCT/KR2015/014032 KR2015014032W WO2016200000A1 WO 2016200000 A1 WO2016200000 A1 WO 2016200000A1 KR 2015014032 W KR2015014032 W KR 2015014032W WO 2016200000 A1 WO2016200000 A1 WO 2016200000A1
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group
carbon atoms
formula
chromium
compound
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English (en)
Korean (ko)
Inventor
사석필
이용호
신은지
이기수
박진영
임슬기
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020150182257A external-priority patent/KR101757835B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to US15/566,120 priority Critical patent/US10392451B2/en
Priority to CN201580078751.8A priority patent/CN107438616B/zh
Priority to JP2017556205A priority patent/JP6507262B2/ja
Priority to EP15895068.3A priority patent/EP3260460B1/fr
Publication of WO2016200000A1 publication Critical patent/WO2016200000A1/fr
Anticipated expiration legal-status Critical
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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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • 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
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/90—Antimony 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/69—Chromium, molybdenum, tungsten or compounds thereof

Definitions

  • the present invention relates to a ligand compound, an organic chromium compound, a catalyst system for urepin oligomerization comprising the ligand compound or an organic chromium compound, and a method for oligomerization of urepin using the same.
  • Linear alpha-olefins such as 1-nuxene and 1-octene, are used as detergents, lubricants, and plasticizers, and as comonomers for controlling the density of polymers in the production of high linear density polyethylene (LLDPE). It is used a lot.
  • LLDPE high linear density polyethylene
  • the present invention is to provide a novel ligand compound that enables the expression of high catalytic activity and selectivity in the reaction of oligomerization of olefins.
  • the present invention also provides a novel organic chromium compound which enables the expression of high catalytic activity and selectivity in the oligomerization reaction of olefins.
  • the present invention is to provide a catalyst system for olefin oligomerization comprising the ligand compound or an organic chromium compound.
  • the present invention is to provide a method for the oligomerization of urepin using the catalyst system.
  • the present invention provides a ligand compound comprising at least one group represented by the following formula (1) in the molecule.
  • A is boron (B), nitrogen (N), phosphorus (P) or antimony (Sb)
  • Each X is independently phosphorus (P), arsenic (As), or antimony (Sb),
  • R1 to R4 are each independently;
  • the present invention also provides an organic crumb compound comprising the ligand compound and chromium (Cr).
  • the present invention also provides a catalyst system for olefin oligomerization comprising the ligand compound, chromium source, and cocatalyst.
  • the present invention also provides a method for the oligomerization of olephine, which comprises the step of undergoing the oligomerization reaction of olephine in the presence of the above-described catalyst system to form alpha- olephine.
  • the olefin oligomerization catalyst system according to the invention exhibits high selectivity for 1-nuxene or 1-octene while having good catalytic activity, allowing the production of more efficient alpha-olefins. [Specific contents to carry out invention]
  • catalyst system means a three component comprising a chromium source, a ligand compound and a promoter, or alternatively, two components of an organic chromium compound and a promoter are added simultaneously or in any order. It means the state which can be obtained with an active catalyst composition. Three components of the catalyst system Or the two components may be added in the presence or absence of a solvent and a monomer, and may be used in a supported or unsupported state.
  • a ligand compound comprising at least one group represented by the formula (1) in the molecule.
  • A is boron (B), nitrogen (N), phosphorus (P) or antimony (Sb),
  • Each X is independently phosphorus (P), arsenic (As), or antimony (Sb),
  • R1 to R4 are each independently;
  • an aryl group having 6 to 20 carbon atoms optionally substituted at the meta or para position, with one or more substituents selected from the group consisting of alkyl groups, alkoxy, alkylsulfanyl groups, and alkylsilyl groups.
  • the ligand compound comprises a group represented by the formula (1) in the molecule (particularly, diphosphino aminyl moiety), at the end of the diphosphino aminyl moiety, a specific substituent It may have a form that can be connected to an aryl group having and serve as a strong electron donating group by itself.
  • the ligand compound can be applied to the lyremerization catalyst system of leupin to exhibit high lygomerization reaction activity.
  • it can exhibit high selectivity for 1-hexene, 1-octene and the like.
  • This can be considered to be due to the interaction between adjacent adjacent active points of activity, in particular in the diphosphino aminyl group, when an aryl is substituted or substituted by a specific substituent to the phosphorus (P) atom of the diphosphino aminyl group.
  • the electron density increases at the phosphorus (P) atom and the nitrogen (N) atom, and the electrical and steric properties of the entire ligand compound may change.
  • the bond between the ligand and the chromium atom may be changed, the structure of the catalyst may be more stable, and the energy of the transition state, that is, the activation energy of reaction reaction, may be changed, compared to the conventional metallacycloheptane or metallacyclononane form. It is possible to form alpha-olepin with high activity and selectivity, and to further reduce the amount of by-products such as high molecular weight solid alpha-olepin such as PE Wax.
  • a small amount in the oligomerization reaction can significantly reduce the amount of 1-nucleene isomers that have a great effect on the product, and concomitantly, separation may not be necessary due to an increase in 1-nucleene and a decrease in 1-nucenne isomers. It can also bring about energy savings.
  • X in Chemical Formula 1 may be each independently phosphorus (P), arsenic (As), or antimony (Sb).
  • the group represented by Formula 1 may be a diphosphino aminyl moiety in which each X is phosphorus (P).
  • An aryl group having 6 to 20 carbon atoms in which one or more substituents selected from the group consisting of an alkyl group, an alkoxy, an alkylsulfanyl group, and an alkylsilyl group is substituted or bonded.
  • each of R1 to R4 independently; 6 or more carbon atoms, in which one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylsulfanyl group having 1 to 10 carbon atoms, and an alkylsilyl group having 1 to 10 carbon atoms are substituted or bonded. It may be an aryl group of 20 to.
  • R1 to R4 are each independently in the form of a phenyl group having 6 to 20 carbon atoms in total; Only one of the meta positions relative to the X linking site is a group consisting of an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylsulfanyl group having 1 to 10 carbon atoms, and an alkylsilyl group having 1 to 10 carbon atoms It may be substituted or combined with one substituent selected from.
  • R1 to R4 are each independently a phenyl group having 6 to 20 carbon atoms in total; At least two of the meta and para positions with respect to the X linking site may be an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylsulfanyl group having 1 to 10 carbon atoms, and a carbon group having 1 to 10 carbon atoms. It may be substituted or bonded with one or more substituents selected from the group consisting of alkylsilyl groups.
  • X in formula 1 is phosphorus (P), and the residues represented by (R 1 ) (R 2 ) X- and (R 3 ) (R 4 ) X- of formula 1 ( Moiety) may be represented by the following structural formula, respectively, but is not necessarily limited thereto.
  • two or more groups represented by Formula 1 may be included in one compound.
  • the linker connecting the two groups may be an aliphatic group having 2 to 20 carbon atoms, a heteroaliphatic group having 2 to 20 carbon atoms, and 2 to 20 carbon atoms.
  • the linker may be an aliphatic group having 2 to 20 carbon atoms (for example, an alkylene group, an alkenylene group, an alkynylene group, or Heteroaliphatic group containing a hetero atom in the aliphatic group, alicyclic group having 2 to 20 carbon atoms (for example, cycloalkylene group , A cycloalkyl alkenylene group, cyclo alkynylene group, or wherein the alicyclic group contains a hetero atom ⁇ heterocyclic aliphatic group), or the aliphatic (or heterocyclic aliphatic) group and the alicyclic (or by interrogating alicyclic) groups combined It may be in the form.
  • the compound which has a structure as follows is mentioned.
  • the group represented by Formula 1 is represented by [A], [ ⁇ ′] or [ ⁇ ′′] for convenience, and [ ⁇ ], [ ⁇ ′] and [ ⁇ ′′] may be the same or different.
  • Ligand compounds according to the present invention can be implemented in various combinations in the range satisfying the above conditions in addition to the above examples.
  • the ligand compound may be synthesized by applying known reactions, and a more detailed synthesis method is described in the Examples section.
  • an organic cream compound including the above-described ligand compound and chromium (Cr).
  • the organic cream compound may be a compound in which the ligand compound is coordinated with a ligand, and a chromium atom as a center metal, and may include, for example, a group represented by the following Chemical Formula 1-1. .
  • ⁇ is each independently phosphorus (p), arsenic (As), or antimony (Sb),
  • R1 to R4 are each independently;
  • Cr is chromium
  • Y 1 to Y 3 are each independently halogen, hydrogen, hydrocarbyl having 1 to 10 carbon atoms, or heterohydrocarbyl having 1 to 10 carbon atoms.
  • the organic chromium compound may be a chromium complex compound of the above-described ligand compound, and may have a form in which chromium of a creme source forms a coordinative bond to the X portion of the group represented by Formula 1.
  • These organic kink compounds can be applied to the catalyst system for the oligomerization reaction mixture of olefins to exhibit good catalytic activity and high selectivity for 1-nuxene or 1-octene.
  • Formula 1-1 descriptions and specific examples of X and R1 to R4 are the same as those described for the ligand compound of Formula 1.
  • A is boron (B), nitrogen (N), phosphorus (P) or antimony (Sb),
  • Each X is independently phosphorus (P), arsenic (As), or antimony (Sb)
  • R1 to R4 are each independently;
  • Cr is chromium
  • Y1 to Y3 are each independently halogen, hydrogen, hydrocarbyl having 1 to 10 carbon atoms, or heterohydrocarbyl having 1 to 10 carbon atoms.
  • the catalyst system for olefin oligomerization comprises: i) a three-component catalyst system comprising a chromium source, a ligand compound, and a promoter as described above, or ii) a two-component catalyst comprising an organic crum compound and a promoter as described above. It may be a component catalyst system.
  • the chromium source is an organic or inorganic crescent compound in which the oxidation state of the crack is 0 to 6, for example chromium metal, or a compound in which any organic or inorganic radical is bonded to the crack.
  • the organic radical may be an alkyl, alkoxy, ester, ketone, amido, carboxylate radical, etc. having 1 to 20 carbon atoms per radical
  • the inorganic radical may be a halide, sulfate, oxide, or the like.
  • the chromium source is a compound that may exhibit high activity in oligomerization of olepin and is easy to use and obtain, such as chromium (III) acetylacetonate, chromium chloride, tetrahydrofuran, chromium ( III) 2-Ethylnucleoate chromium (III) acetate, chromium (III) butyrate, chromium (III) pentanoate, chromium ( ⁇ ) laurate, chromium ( ⁇ ) Tris (2,2,6) , 6-tetramethyl-3.5-heptanedionate), and chromium (III) stearate.
  • chromium (III) acetylacetonate such as chromium (III) acetylacetonate, chromium chloride, tetrahydrofuran, chromium ( III) 2-Ethylnucleoate chromium (III) acetate,
  • the promoter is an organic metal comprising a Group 13 metal
  • the compound as long as it can be used when polymerizing the olefin under the catalyst of the transition metal compound, it can be applied without particular limitation.
  • the promoter may be at least one compound selected from the group consisting of compounds represented by Formulas 4 to 6 below:
  • Rx is the same or different from each other, and each independently a halogen radical, a hydrocarbyl radical of 1 to 20 carbon atoms, or a hydro of 1 to 20 carbon atoms substituted with halogen A carbyl radical, c is an integer of 2 or more, and [Formula 5]
  • D is aluminum or boron
  • Ry is 1 to carbon atoms
  • L is a neutral Lewis base
  • [LH] + is Bronsted acid
  • Q is boron or aluminum in the +3 type oxidation state
  • each E is independently at least one hydrogen atom is halogen, a hydrocarbyl having 1 to 20 carbon atoms, An aryl group having 6 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with an alkoxy functional group or a phenoxy functional group.
  • the compound represented by Formula 4 may be alkyl aluminoxane, such as methyl aluminoxane, ethyl aluminoxane, isobutyl aluminoxane, butyl aluminoxane.
  • the compound represented by Chemical Formula 5 is trimethylaluminum, triethylaluminum, triisobutylaluminum, tripropylaluminum, tributylaluminum, dimethylchloroaluminum, dimethylisobutylaluminum, dimethylethylaluminum, di Ethylchloroaluminum , triisopropylaluminum , tri-S-butylaluminum , tricyclopentylaluminum, Tripentyl aluminum, triisopentyl aluminum, trinuclear sil aluminum, ethyl dimethyl aluminum, methyl diethyl aluminum triphenyl aluminum, tri-P- ryl aluminum, dimethyl aluminum hydroxide, dimethyl aluminum ethoxide, trimethyl boron, triethyl boron, Triisobutyl boron, tripropyl boron, tributyl boron and the like.
  • the compound represented by Formula 6 is triethylammonium tetraphenylboron, tributylammonium tetraphenylboron, trimethylammonium tetraphenylboron, tripropylammonium tetraphenylboron, trimethylammonium Tetra (P-Lyl) boron, tripropyl ammonium tetra (P-lryl) boron ⁇ triethyl ammonium tetra ( ⁇ , ⁇ -dimethylphenyl) boron, trimethyl ammonium tetra ( ⁇ , ⁇ -dimethylphenyl) boron, tri Butyl ammonium tetra ( ⁇ -trifluoromethylphenyl) boron, trimethyl ammonium tetra ( ⁇ -trifluoro methylphenyl) boron,
  • the promoter may be an organoaluminum compound, an organoboron compound, an organomagnesium compound, an organozinc compound, an organolithium compound, or a combination thereof.
  • the promoter is preferably an organoaluminum compound, more preferably trimethyl aluminum, triethyl aluminum, triisopropyl aluminum, triisobutyl aluminum (triisobutyl aluminum), ethylaluminum sesquichloride, diethylaluminum chloride, ethyl aluminum dichloride, methylaluminoxane, and modified methylaluminoxane It may be one or more compounds selected from the group consisting of
  • the content ratio of the components constituting the catalyst system may be determined in consideration of the catalytic activity and the selectivity to the linear alpha-lefin.
  • the molar ratio of diphosphino aminyl residue: chromium source: cocatalyst of the ligand compound is about 1: 1: 1 to 10: 1: 10,000, or about 1: 1: 1 It is advantageous to adjust from: 100 to 5: 1: 3,000.
  • the molar ratio of diphosphino aminyl moiety: cocatalyst of the organic kneading compound is 1: 1 to 1: 10,000, or 1: 1 to 1: 5,000, or 1: 1 to 1: 1. It is advantageous to adjust to 3,000.
  • suitable solvents include heptane, toluene, cyclonucleic acid, methylcyclonucleic acid, 1-nuxene 1-octene, diethyl ether, tetrahydrofuran, acetonitrile, dichloromethane, chloroform, chlorobenzene, methanol, acetone, and the like. Can be.
  • the catalyst system may further comprise a carrier. That is, the ligand compound of Formula 1 may be applied to ethylene oligomerization in a form supported on a carrier.
  • the carrier may be a metal, a metal salt, a metal oxide, or the like applied to a conventional supported catalyst.
  • the carrier may be silica, silica-alumina, silica-magnesia, and the like, Oxides, carbonates, sulfates, nitrates of metals such as Na 2 O, K 2 CO 3, BaS0 4 , Mg (N0 3 ) 2, and the like.
  • Such a catalyst system can preferably be used for the quaternization reaction of ethylene, allowing the production of 1-octene with high selectivity as described above.
  • proceeding the oligomerization reaction of the olepin, to form the alpha- olepin; comprising; This is provided.
  • the oligomerization reaction of the olefin may be a quaternization reaction of ethylene, and may form 1-octene as a reaction product.
  • the method for the ligomerization of leupine can be carried out by applying the above-described catalyst system with conventional elepine (for example, ethylene) as a raw material and conventional apparatus and contacting techniques.
  • the ligomerization reaction of leulevine may be a homogeneous liquid reaction in the presence or absence of an inert solvent, or a slurry reaction in which the catalyst system is partially or completely undissolved, or a product of alpha-olefin. It may be carried out as a bulk reaction, or as a gas reaction, acting as the main medium.
  • the oligomerization reaction of the olepin can be performed under an inert solvent.
  • the inert solvent may be benzene, toluene, xylene, cumene, chlorobenzene, dichlorobenzene, heptane, cyclonucleic acid, methylcyclonucleic acid, methylcyclopentane, n-nucleic acid, 1-nuxene, 1-octene, etc. have.
  • the oligomerization reaction of the olefin can be carried out at a temperature of about 0 to about 200 ° C, or about 0 to about 150 ° C, or about 30 to about 100 ° C, or about 50 to about 100 ° C. have.
  • the reaction may be performed under a pressure of about 15 to about 3000 psig, or about 15 to about 1500 psig, or about 15 to about 1000 psig.
  • chromium (III) acetylacetonate (17.5 mg, 0.05 mmol) and a ligand compound (0.025 mmol) according to the above synthesis and comparative synthesis examples were put in a flask, and 10 ml of cyclonucleic acid was added thereto. By stirring, 5 mM (based on Cr) of the catalyst solution was prepared.
  • the reactor was cooled to 0 ° C using a dry ice / acetone bath, slowly unvented ethylene was vented, and 0.5 ml of nonane (GC internal standard) was added thereto. After stirring for 10 seconds, 2 ml of the liquid portion of the reaction mixture was quenched with water, and the obtained organic portion was filtered with a PTFE syringe filter to make a GC-FID sample. And the distribution of the liquid product was analyzed by GC. In addition, 400 ml of ethanol / HCI (10 vol% of aqueous 12M HCI solution) was added to the remaining reaction solution, followed by stirring and filtering to analyze the amount of solids. The obtained polymer was dried overnight in a 65 ° C vacuum oven.
  • the results of the Examples and Comparative Examples are summarized in the table below.
  • the diphosphine group of the ligand compound having a specific structure includes an aryl group substituted with a separate substituent, alpha-olefins (1-nuxene and 1-octene) in the ligomerization reaction are included. It can be seen that the selectivity can be improved, and the amount of PE Wax, which is alpha-olepin and solid alpha-olefin in the form of undesirable isomers, can be reduced.

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Abstract

La présente invention concerne un composé ligand, un système catalyseur pour l'oligomérisation d'oléfines, et un procédé d'oligomérisation d'oléfines au moyen de ce dernier. Le système catalyseur pour l'oligomérisation d'oléfines selon la présente invention présente une sélectivité élevée pour le 1-hexène ou le 1-octène tout en ayant une excellente activité catalytique, ce qui permet de préparer une alpha-oléfine de manière plus efficace.
PCT/KR2015/014032 2015-06-12 2015-12-21 Composé ligand, composé de chrome organique, système catalyseur pour l'oligomérisation d'oléfines, et procédé d'oligomérisation d'oléfines au moyen de ce dernier Ceased WO2016200000A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US15/566,120 US10392451B2 (en) 2015-06-12 2015-12-21 Ligand compound, organic chromium compound, catalyst system for olefin oligomerization, and method for oligomerizing olefins using the same thereof
CN201580078751.8A CN107438616B (zh) 2015-06-12 2015-12-21 配体化合物，有机铬化合物，用于烯烃低聚的催化剂体系和使用其低聚烯烃的方法
JP2017556205A JP6507262B2 (ja) 2015-06-12 2015-12-21 リガンド化合物、有機クロム化合物、オレフィンのオリゴマー化用触媒システム、およびこれを用いたオレフィンのオリゴマー化方法
EP15895068.3A EP3260460B1 (fr) 2015-06-12 2015-12-21 Composé ligand, composé de chrome organique, système catalyseur pour l'oligomérisation d'oléfines, et procédé d'oligomérisation d'oléfines au moyen de ce dernier

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2015-0083650 2015-06-12
KR20150083650 2015-06-12
KR10-2015-0182257 2015-12-18
KR1020150182257A KR101757835B1 (ko) 2015-06-12 2015-12-18 리간드 화합물, 유기 크롬 화합물, 올레핀 올리고머화용 촉매 시스템, 및 이를 이용한 올레핀의 올리고머화 방법

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3190118A4 (fr) * 2015-05-26 2018-02-21 LG Chem, Ltd. Composé ligand, composé de chrome organique, système catalyseur pour l'oligomérisation d'oléfines, et procédé d'oligomérisation d'oléfines au moyen de ce dernier
JP2021526540A (ja) * 2018-06-07 2021-10-07 アジュ ユニバーシティー インダストリー−アカデミック コーオペレイション ファウンデーションＡｊｏｕ Ｕｎｉｖｅｒｓｉｔｙ Ｉｎｄｕｓｔｒｙ−Ａｃａｄｅｍｉｃ Ｃｏｏｐｅｒａｔｉｏｎ Ｆｏｕｎｄａｔｉｏｎ ビスホスフィンリガンド化合物、クロム化合物、エチレンオリゴマー化触媒システム、及びエチレンオリゴマーの製造方法
CN113861317A (zh) * 2020-06-30 2021-12-31 中国石油化工股份有限公司 一种抗静电聚乙烯催化剂的制备方法
CN116917040A (zh) * 2021-03-12 2023-10-20 沙特阿拉伯石油公司 催化剂体系

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WO2008004986A1 (fr) * 2006-07-05 2008-01-10 National University Of Singapore Système catalytique pour l'oligomérisation des oléfines
US20120310025A1 (en) * 2009-12-29 2012-12-06 Petrochina Company Limited Catalyst for Synthesizing 1-Hexene from Ethylene Trimerization and Application Thereof
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US10688473B2 (en) 2014-12-11 2020-06-23 Lg Chem, Ltd. Ligand compound, organic chromium compound, catalyst system for oligomerization of olefins, and method for oligomerizing olefins using the same
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JP7299593B2 (ja) 2018-06-07 2023-06-28 アジュ ユニバーシティー インダストリー－アカデミック コーオペレイション ファウンデーション ビスホスフィンリガンド化合物、クロム化合物、エチレンオリゴマー化触媒システム、及びエチレンオリゴマーの製造方法
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