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Pyrrole imine vanadium olefin polymerization catalyst, preparation method and applications thereof

A pyrroleimide vanadium catalyst and a technology for olefin polymerization are applied to the pyrroleimide vanadium olefin polymerization catalyst, preparation method and application field, and can solve the problems of low molecular weight of copolymer, low copolymerization activity, poor copolymerization activity and the like

Active Publication Date: 2009-10-14
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when using Group 4 transition metal catalysts to catalyze the copolymerization of ethylene and functional monomers, due to the strong oxophilicity of Group 4 metals, the copolymerization activity is low and the insertion rate of polar monomers is also very low.
Although Ni, Pd and other Group 10 transition metal catalysts can obtain copolymers with higher intercalation rates, the resulting copolymerization activity is poor and the molecular weight of the copolymers is low.

Method used

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  • Pyrrole imine vanadium olefin polymerization catalyst, preparation method and applications thereof
  • Pyrrole imine vanadium olefin polymerization catalyst, preparation method and applications thereof
  • Pyrrole imine vanadium olefin polymerization catalyst, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Add 30 mg (1.25 mmol) of sodium hydride to 0.18 g (1 mmol) of Schiff base ligand and 20 ml of tetrahydrofuran at room temperature under a nitrogen atmosphere, and stir at room temperature for 4 hours. Add this anion solution dropwise to 0.37 g (1 mmol) of tetrahydrofuran complex VCl3·3THF of vanadium trichloride in 10 ml of tetrahydrofuran at room temperature, and continue to stir the reaction at room temperature for 12 h. The solvent was removed in vacuo to obtain a crude product, which was dissolved by adding 20ml of toluene and stirred for 10min. After vacuum filtration, the filtrate was concentrated to 10ml, and 20ml of n-hexane was added to precipitate a brown crystalline compound to obtain the pyrrolimide vanadium olefin polymerization catalyst 1a-1 (0.33 g, yield 75%). According to mass spectrometry, the molecular ion peak m / e is 440. Elemental analysis found values: C, 51.58%; H, 7.04%; N, 6.38%; theoretical values: C, 51.71%; H, 7.08%; N, 6.35%.

[...

Embodiment 2

[0031] Example 2 uses R as phenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, p-methylphenyl, p-methoxyphenyl, p-trifluoromethylphenyl Or the Schiff base ligand of pentafluorophenyl respectively replaces the Schiff base ligand in which R is cycloethyl in Example 1, and the other preparation methods are the same as catalyst 1a-1 or 1a-2 in Example 1. Correspondingly, following pyrrole imide vanadium olefin polymerization catalyst 2a-1 (75%); 2a-2 (67%); 3a-1 (87%); 3a-2 (58%); 4a-1 (73%) 4a-2 (65%); 5a-1 (76%); 5a-2 (67%); 6a-1 (77%); 6a-2 (82%); 7a-1 (65%); 7a -2 (81%); 8a-1 (79%); or 8a-2 (80%). Analysis data such as "analysis data table".

[0032] The structural formula of the pyrrole imide vanadium olefin polymerization catalyst that embodiment 1-2 obtains is as follows:

[0033]

[0034] Analysis data table:

[0035]

[0036]

Embodiment 3

[0037] Example 3 Under an ethylene atmosphere, add anhydrous toluene 50ml, 2M toluene solution of diethyl aluminum chloride 0.4ml, 0.5M toluene solution 0.12ml in a 150ml polymerization bottle successively, at 25 After stirring at -70°C for 5 minutes, add 0.2 ml of pyrrolimide vanadium olefin polymerization catalysts 1a-1 to 8a-1 and 1a-2 to 8a-2 respectively, the concentration of which is 1 μmol / ml, and polymerize under stirring for 10 minutes. Pour the reactants into 200ml of 0.5% (mass fraction) hydrochloric acid ethanol solution, filter, wash with 0.5% (mass fraction) hydrochloric acid ethanol solution, then wash with ethanol, and vacuum dry to obtain polyethylene products respectively. Ethylene homopolymerization results are shown in the table below.

[0038]

[0039]

[0040]

[0041] Note: Cat is catalyst; T is polymerization reaction temperature; W is polyethylene weight; Activity is activity; M W is the weight average molecular weight; M w / M n is the mole...

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Abstract

The invention relates to a pyrrole imine vanadium olefin polymerization catalyst, a preparation method and applications of the catalyst in the catalization of ethylene polymerization, copolymerization of ethylene and undecylenic alcohol, copolymerization of ethylene and olefin butyl alcohol and copolymerization of ethylene and methyl undecylenate. The condensation reaction is carried out on 2-formylpyrrole and amine compounds in methanol solution under the catalysis of methanoic acid to obtain Schiff base; the deprotonation of hydrogen is carried out on the Schiff base, then the coordination reaction is carried out on the Schiff base and vanadium trichloride under anhydrous and oxygen-free condition, so as to obtain the pyrrole imine vanadium olefin polymerization catalyst. The catalyst can catalyze the ethylene polymerization, the copolymerization of ethylene and undecylenic alcohol, the copolymerization of ethylene and olefin butyl alcohol and the copolymerization of ethylene and methyl undecylenate under the action of diethylaluminum chloride. The catalyst has the advantages of convenient preparation, high catalytic activity, good thermal stability, strong copolymerization ability and the like.

Description

technical field [0001] The invention relates to a pyrrole imide vanadium olefin polymerization catalyst, a preparation method and an application. Background technique [0002] Since Ziegler and Natta discovered that transition metal complexes can catalyze olefin polymerization under mild conditions in the 1950s, polyolefin products have been widely used in industry, agriculture, national defense, transportation and people's daily life. It has brought about revolutionary changes in human society. In the following fifty years, a large number of transition metal catalytic systems with high activity and high control over product structure have emerged. Especially since the 1990s, the advent of a series of "non-metallocene" transition metal catalysts has greatly promoted the development of olefin polymerization catalysts. Therefore, effective molecular structure design of organic ligands to improve catalyst performance occupies a core position in the field of catalyst research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F4/76C08F4/68C08F10/02
Inventor 刘靖宇徐宝昌李悦生李彦国刘三荣
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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