WO2023124896A1 - Composé silane, composition de catalyseur, procédé de préparation correspondant et utilisation associée - Google Patents

Composé silane, composition de catalyseur, procédé de préparation correspondant et utilisation associée Download PDF

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Publication number
WO2023124896A1
WO2023124896A1 PCT/CN2022/137838 CN2022137838W WO2023124896A1 WO 2023124896 A1 WO2023124896 A1 WO 2023124896A1 CN 2022137838 W CN2022137838 W CN 2022137838W WO 2023124896 A1 WO2023124896 A1 WO 2023124896A1
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Prior art keywords
bis
amino
trifluoromethanesulfonyl
silane
compound
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PCT/CN2022/137838
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English (en)
Chinese (zh)
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李红明
义建军
窦彤彤
孟子逸
张明革
雷珺宇
朱百春
洪柳婷
高玉李
李荣波
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中国石油天然气股份有限公司
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Publication of WO2023124896A1 publication Critical patent/WO2023124896A1/fr

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    • 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
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon 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
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/04—Monomers containing three or four carbon atoms
    • C08F110/06—Propene
    • 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
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/646—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64
    • 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
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/647—Catalysts containing a specific non-metal or metal-free compound
    • 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
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/647—Catalysts containing a specific non-metal or metal-free compound
    • C08F4/649—Catalysts containing a specific non-metal or metal-free compound organic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T10/00—Road transport of goods or passengers
    • Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
    • Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction 

Definitions

  • the invention relates to the field of catalytic polymerization of olefins, in particular to a silane compound, a catalyst composition and a preparation method and application thereof.
  • the solid catalyst based on magnesium, titanium, halogen and electron donor can be used for the polymerization of ethylene or propylene.
  • cocatalyst alkylaluminum compound and external electron donor component should be added at the same time. If no external electron donor is added, the isotacticity of the polymer obtained by most catalysts is low, generally lower than 90%, which is not conducive to industrial production and polymer application. Therefore, for most propylene polymerization catalysts, the addition of external electron donors plays a very important role.
  • CN111978346A uses arylamino-containing siloxane compound as an external electron donor, which improves the hydrogen tuning sensitivity of the catalyst and is used to prepare high-flow polypropylene materials, but the prepared polypropylene isotacticity is low;
  • CN1583805B discloses a Containing a new type of silicon ether compound, it is used as an external electron donor component in an olefin polymerization catalyst.
  • CN109535287A uses silicon Oxylkane, glycerol fatty acid esters containing polar groups, and polyglycerol fatty acid esters are used as external electron donor components to solve the problem of the activity of ethers on catalytic polymerization. It is suitable for various processes of propylene polymerization, but the The external electron donor contains three compounds, and the process technology is complicated and the cost is high.
  • the inventor unexpectedly found that when the propylene polymerization catalyst is used for propylene polymerization, a new type of silane compound is added as an external electron donor, the catalytic system has good hydrogen modulation sensitivity and polymerization activity, and can To obtain a polymer with higher isotacticity; based on the above findings, the purpose of the present invention is to provide a silane compound, a catalyst composition and a preparation method and application thereof.
  • the first aspect of the present invention provides a silane compound having a structure represented by the following general formula (I):
  • R 1 and R 2 are the same or different, and R 1 and R 2 are each independently selected from hydrogen atom, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl , substituted or unsubstituted aralkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted heteroatom-containing ring;
  • R 3 , R 4 , R 5 are each independently selected from C 1 -C 8 Straight chain or branched chain alkyl, C 1 -C 8 straight chain or branched chain alkoxy.
  • At least one of R 3 , R 4 , and R 5 is selected from C 1 -C 8 linear or branched alkoxy groups.
  • R1 and R2 are independently selected from fluorine atom, bromine atom, methyl group, ethyl group, benzenesulfonylmethyl group, difluoromethyl group, Dibromomethyl, trifluoromethyl, tribromomethyl.
  • R 3 , R 4 , and R 5 are each independently selected from methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy base, 3-propoxy.
  • At least one of R 3 , R 4 , and R 5 is selected from methoxy, ethoxy, and 3-propoxy.
  • R 1 and R 2 are each independently selected from difluoromethyl, dibromomethyl, trifluoromethyl, tribromomethyl;
  • R 3 , R 4 and R 5 are each independently selected from methyl, ethyl, methoxy, and ethoxy, and at least one of R 3 , R 4 , and R 5 is selected from methoxy or ethoxy.
  • R 3 , R 4 , and R 5 are not methyl at the same time.
  • the silane compound is selected from [bis(trifluoromethanesulfonyl)amino]trimethoxysilane, [bis(trifluoromethanesulfonyl)amino] Triethoxysilane, [bis(trifluoromethanesulfonyl)amino]tris(3-propoxy)silane, [bis(trifluoromethanesulfonyl)amino]methyldimethoxysilane, [bis(trifluoromethanesulfonyl)amino]methyldimethoxysilane, [bis(trifluoromethanesulfonyl)amino] Fluoromethylsulfonyl)amino]methyldiethoxysilane, [bis(trifluoromethanesulfonyl)amino]methylbis(3-propoxy)silane, [bis(trifluoromethanesulfonyl)amino]methylbis(3-prop
  • the present invention provides the structural formulas of five typical above-mentioned silane compounds (compounds A-E), specifically as follows:
  • the second aspect of the present invention provides a method for preparing the above-mentioned silane compounds, comprising the following steps:
  • n 0, 1 or 2
  • R and R' are each independently selected from C 1 -C 8 straight chain or branched chain alkyl groups.
  • R and R' are each independently selected from methyl, ethyl, n-propyl or isopropyl.
  • the molar ratio of the sulfonylimine compound to the alkyllithium is 1:(1-5).
  • the molar ratio of the sulfonylimine compound to (R) m SiCl 4-m is 1:(1-5).
  • the molar ratio of the intermediate to R'OH is 1:(1-100), more preferably 1:(2-40).
  • the sulfonylimine compound is reacted with alkyllithium for 1-48 hours; after adding the (R) m SiCl 4-m , the reaction is carried out for 1-48 hours.
  • the reaction time is 4-60 h.
  • the organic solvent is selected from one or more of toluene, benzene, diethyl ether, tetrahydrofuran, pentane, hexane, heptane or octane, more Preference is given to tetrahydrofuran or toluene.
  • the alkyllithium is butyllithium, more preferably n-butyllithium.
  • the protective gas is nitrogen, helium or argon.
  • the third aspect of the present invention provides a catalyst composition, comprising a titanium-containing solid catalyst, an aluminum alkyl, and the above-mentioned silane compound.
  • the titanium-containing solid catalyst comprises titanium, magnesium, halogen and an internal electron donor compound.
  • the internal electron donor compound is selected from polycarboxylic acid esters, acid anhydrides, ketones, ethers or sulfonyl compounds.
  • the preparation method of the titanium-containing solid catalyst comprises: reacting magnesium chloride alkoxide and titanium tetrachloride at a low temperature of -40°C to 0°C, Then, the temperature of the reaction system is raised to 40°C-140°C and the electron donor compound is added to carry out the reaction, the solid obtained in the reaction is filtered and reacted with titanium tetrachloride again, and the obtained solid product is washed and dried to obtain the titanium-containing solid catalyst.
  • the preparation method of the main catalyst adding spherical magnesium chloride alcoholate particles with the general formula MgCl 2 nROH into the titanium tetrachloride solution at low temperature, reacting for a period of time; gradually heating up to 40°C-140°C, add one or two internal electron donors, continue to react for a period of time; filter, add a certain amount of titanium tetrachloride, react for a period of time, repeat adding titanium tetrachloride and filtering steps 1-3 times; finally washed with an inert hydrocarbon solvent and dried to obtain a spherical solid catalyst.
  • the general formula of the aluminum alkyl is Al(R 6 ) n X 3-n , where R 6 is selected from a hydrogen atom or a C 1 - C20 hydrocarbon group, X is halogen, n is 2 or 3.
  • the alkylaluminum is selected from triethylaluminum, tripropylaluminum, tri-n-butylaluminum, triisobutylaluminum, tri-n-octylaluminum Aluminum, Triisobutylaluminum, Diethylaluminum monohydrogen, Diisobutylaluminum monohydrogen, Diethylaluminum monochloride, Diisobutylaluminum monochloride, Sesquiethylaluminum chloride, Ethyl dichloride Aluminum, preferably triethylaluminum, triisobutylaluminum.
  • the fourth aspect of the present invention provides an application of the above-mentioned silane compound or the above-mentioned catalyst composition in olefin polymerization.
  • the silane compound is used as an external electron donor compound in the catalyst composition.
  • the titanium-containing solid catalyst is used as a main catalyst, and the alkylaluminum is used as a co-catalyst.
  • the olefin polymerization reaction is homopolymerization or copolymerization of propylene.
  • the silane compound of the present invention can be applied to olefin polymerization, especially the homopolymerization or copolymerization of propylene.
  • the polymerization temperature is 0°C-150°C, more preferably 50°C-100°C.
  • the olefin polymerization method is an olefin polymerization reaction carried out in the presence of a main catalyst, a cocatalyst and an external electron donor, and the propylene polymerization and copolymerization of the present invention are carried out according to methods known in the art Carried out, in liquid phase bulk or bulk solution in an inert solvent, or in gas phase, or by combined polymerization processes in gas-liquid phase.
  • the polymerization temperature is generally 0°C-150°C, preferably 50°C-100°C; the polymerization reaction pressure is normal pressure or higher.
  • silane compound a silane compound, catalyst composition and preparation method and application thereof of the present invention have the following beneficial effects:
  • the silane compound of the present invention When used as the external electron donor of the catalyst composition in the olefin polymerization reaction, it can make the catalytic system have good hydrogen adjustment sensitivity, and can obtain olefin polymers with higher yield and higher isotacticity .
  • the evaluation and analysis methods adopted include:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • the NMR data are as follows: 1 H NMR ( ⁇ , ppm, TMS, CDCl 3 ): 0.24 (3H, s, CH 3 ), 1.22 (6H, t, OCH 2 CH 3 ), 3.83 (4H, q, OCH 2 ).
  • Compound D synthesized external electron donor compound
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • This embodiment provides a preparation method of silane compounds and an olefin polymerization method, specifically as follows:
  • Example 2 Using the same titanium-containing solid catalyst component and polymerization method as in Example 1, the only difference is that the external electron donor compound is replaced by cyclohexylmethyldimethoxysilane.
  • Example 6 Using the same titanium-containing solid catalyst component and polymerization method as in Example 6, the only difference is that the external electron donor compound is replaced by cyclohexylmethyldimethoxysilane.
  • the melt index of the polypropylene obtained by the propylene polymerization reaction is significantly higher than that of the comparative example, and as the amount of hydrogen added, the polymer The growth rate of the melt index is obviously faster than that of the comparative example, which shows that the novel silane compound of the present invention has good hydrogen tuning sensitivity as the propylene polymerization catalyst of the external electron donor; and the catalyst activity and the isotacticity of polypropylene are also relatively High, can be used to prepare polypropylene materials with high flow and high isotacticity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)

Abstract

La présente invention concerne un composé silane, une composition de catalyseur, un procédé de préparation correspondant et une utilisation associée. Le composé silane a une structure telle que représentée dans la formule générale suivante (I), dans laquelle R1 et R2 sont identiques ou différents ; R1 et R2 sont chacun indépendamment choisis parmi des atomes d'hydrogène, halogène, alkyle substitué ou non substitué, cycloalkyle, aryle, aralkyle, alkylaryle, et un cycle contenant un hétéroatome ; et R3, R4 et R5 sont chacun indépendamment choisis parmi un alkyle linéaire ou ramifié en C1-C8 et un alcoxy linéaire ou ramifié en C1-C8. Le composé silane selon la présente invention peut être utilisé dans une réaction de polymérisation d'oléfines en tant que donneur d'électrons externe de la composition de catalyseur, ce qui permet à un système catalytique d'avoir une bonne sensibilité de régulation d'hydrogène, et d'obtenir un polymère d'oléfine ayant un haut rendement et une isotacticité élevée.
PCT/CN2022/137838 2021-12-30 2022-12-09 Composé silane, composition de catalyseur, procédé de préparation correspondant et utilisation associée WO2023124896A1 (fr)

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CN202111656551.XA CN116410355A (zh) 2021-12-30 2021-12-30 硅烷类化合物、催化剂组合物及其制备方法和应用

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