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Three-tooth salicylaldehyde imine vanadium olefin polymerizing catalyst, preparation and uses thereof

A technology for tridentate salicylaldimine vanadium olefin and salicylaldimine vanadium olefin, which is applied to the tridentate salicylaldimine vanadium olefin polymerization catalyst and the fields of preparation and application, and can solve the problem of poor high temperature resistance, low catalytic activity, easy deactivation, etc. question

Inactive Publication Date: 2010-10-27
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the shortcomings of low catalytic activity, easy deactivation, poor high temperature resistance and weak copolymerization ability, one of the purposes of the present invention is to provide a tridentate salicylaldimine vanadium olefin polymerization catalyst

Method used

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  • Three-tooth salicylaldehyde imine vanadium olefin polymerizing catalyst, preparation and uses thereof
  • Three-tooth salicylaldehyde imine vanadium olefin polymerizing catalyst, preparation and uses thereof
  • Three-tooth salicylaldehyde imine vanadium olefin polymerizing catalyst, preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 9.77g of salicylaldehyde equivalent to 80mmol, 6.00g of 2-methoxyethylamine equivalent to 80mmol, 60ml of methanol, and 2ml of formic acid into the dry reactor, and react at 25°C for 12h. The solvent methanol was evaporated with a rotary evaporator, and 1000ml of a solution with a volume ratio of ethyl acetate and petroleum ether of 1:100 was used as an eluent, and the residue was subjected to column chromatography to obtain 16.5 g of yellow solid Schiff's base. 92%. 1 HNMR (300MHz, CDCl3 ): δ3.36(s, 3H, CH 3 ), 3.65(t, 2H, CH 2 N), 3.77(t, 2H, CH 2 O), 6.85-7.31 (m, 4H, Ar-H), 8.37 (s, 1H, CH=N), 13.41 (s, 1H, OH). According to mass spectrometry, the molecular ion peak m / e is 179. Elemental analysis measured value: C, 67.11%; H, 7.33%; N, 7.79%; theoretical value (C 10 h 13 NO 2 ): C, 67.02%; H, 7.31%; N, 7.82%.

[0029] Under a nitrogen atmosphere, add 0.27 g of the above-obtained Schiffer’s base equivalent to 1.5 mmol and 20 ml of anhydrous tetrahydrofura...

Embodiment 2

[0036] Salicylaldehyde 4.89g is equivalent to 40mmol, and N, N-dimethylethylenediamine 3.53g is equivalent to 40mmol to replace 2-methoxyethylamine in Example 1, methanol 30ml, formic acid 1ml, and react at 25°C for 6h. The experimental operation was the same as in Example 1, and 7.15 g of yellow solid Schiff's base was obtained, with a yield of 93%. 1 H MR (300MHz, CDCl 3 ): δ2.30(s, 6H, CH 3 ), 2.63(t, 2H, CH 2 N), 3.73(t, 2H, CH 2 N), 6.84-7.32 (m, 4H, Ar-H), 8.37 (s, 1H, CH=N), 13.47 (s, 1H, OH). According to mass spectrometry, the molecular ion peak m / e is 192. Elemental analysis measured value: C, 68.70%; H, 8.40%; N, 14.58%; Theoretical value (C 11 h 16 N 2 O): C, 68.72%; H, 8.39%; N, 14.57%.

[0037] Under a nitrogen atmosphere, add 0.19 g of the above-obtained Schiffer’s base equivalent to 1.0 mmol and 10 ml of anhydrous tetrahydrofuran to a dry reactor, stir at room temperature for 10 min to dissolve the solid, add 26.4 mg of sodium hydride equivalent to 1.1 ...

Embodiment 3

[0044] 7.33g of salicylaldehyde is equivalent to 60mmol, and 6.49g of 2-aminomethylpyridine is equivalent to 60mmol instead of 2-methoxyethylamine, 30ml of methanol, 1ml of formic acid in Example 1, and reacted at 25°C for 48h. The experimental operation is the same as the implementation Example 1, 10.19 g of yellow liquid Schiffer's base was obtained, and the yield was 80%. 1 H NMR (300MHz, CDCl 3 ): δ4.95(s, 2H, CH 2), 6.77-7.72 (m, 7H, Ar-H and pyridine-H), 8.55 (s, 1H, CH=N), 8.48 (d, 1H, pyridine-H), 13.28 (s, 1H, OH). According to mass spectrometry, the molecular ion peak m / e is 212. Elemental analysis measured value: C, 73.69%; H, 5.72%; N, 13.24%; Theoretical value (C 13 h 12 N 2 O): C, 73.56%; H, 5.70%; N, 13.20%.

[0045] Under a nitrogen atmosphere, add 0.21 g of the above-obtained Schiffer’s base equivalent to 1.0 mmol and 10 ml of anhydrous tetrahydrofuran to a dry reactor, stir at room temperature for 10 minutes to dissolve the solid, add 36 mg of sodium hy...

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Abstract

The invention relates to a polymerization catalyst of tridentate salicylaldehyde imine vanadium alkene, a preparation method thereof and an application thereof. By the catalysis of formic acid, condensation reaction is carried out between the derivatives salicylaldehyde or salicylaldehyde, and amine compounds in methanol solution to obtain Schiff base; under the condition of no water and no oxygen, the Schiff base strips hydrogen protons and complexation reaction is carried out with vanadium trichloride to obtain the polymerization catalyst of tridentate salicylaldehyde imine vanadium alkene;by the action of aluminium diethyl monochloride, the polymerization catalyst is applied to catalyzing ethylene for polymerization; and by the action of aluminium diethyl monochloride, the polymerization catalyst is applied to the copolymerization of ethylene and 1-hexylene at 25 DEG C and used for catalyzing the copolymerization of ethylene and norbornene at the temperature of 50 DEG C. The polymerization catalyst has the advantages of convenient preparation, high catalytic activity, good heat stability, strong copolymerization capacity, etc.

Description

technical field [0001] The invention relates to a tridentate salicylaldimine vanadium olefin polymerization catalyst, a preparation method and an application. Background technique [0002] In the 1950s, Ziegler and Natta each discovered that transition metal complexes could catalyze the polymerization of olefins under mild conditions. In the following fifty years, a large amount of research has emerged to develop high activity and high control over the product structure. active transition metal catalyst system. At the same time, the continuous renewal of polyolefin products has brought revolutionary changes to people's lives, and they are increasingly widely used in industry, agriculture, national defense, transportation and people's daily life. Therefore, the effective molecular structure design of organic ligands and the improvement of catalyst performance occupy a core position in the field of catalyst research and development. In the 1950s, Carrick reported using trans...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F4/68C08F10/00C08F10/02C08F210/16C08F210/02
Inventor 刘靖宇李悦生吴集钱
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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