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Beta-hydroxy propyleneimine vanadium olefinic polymerization catalyst and its preparation method and uses

A technology of hydroxypropene imine vanadium olefin and polymerization catalyst is applied in the field of β-hydroxypropene imine vanadium olefin polymerization catalyst and preparation, and can solve the problems of low catalytic activity, poor high temperature resistance, easy deactivation and the like

Inactive Publication Date: 2006-12-20
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the shortcomings of low catalytic activity, easy deactivation, and poor high temperature resistance, one of the purposes of the present invention is to provide a β-hydroxypropyleneimine vanadium olefin polymerization catalyst

Method used

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  • Beta-hydroxy propyleneimine vanadium olefinic polymerization catalyst and its preparation method and uses
  • Beta-hydroxy propyleneimine vanadium olefinic polymerization catalyst and its preparation method and uses
  • Beta-hydroxy propyleneimine vanadium olefinic polymerization catalyst and its preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 11.85 g of 2-phenyl-3-hydroxy-acrolein (equivalent to 80 mmol), 3.73 g of aniline (equivalent to 40 mmol), 30 mL of methanol, and 2 mL of formic acid were added to a dry reactor, and heated to reflux for 24 hours. The solvent methanol was distilled off with a rotary evaporator, and petroleum ether containing 1% ethyl acetate was used as an eluent, and the residue was subjected to column chromatography to obtain 4.55 g of yellow solid Schiff's base, with a yield of 51%. 1H NMR (300MHz, DMSO): δ7.01-7.51 (m, 10H, Ar-H) 7.89-7.94 (d, 1H, CH=N) 9.30-9.35 (d, 1H, C=CHOH) 12.02-12.06 ( b, 1H, OH). According to mass spectrometry, the molecular ion peak m / e is 223. Elemental analysis measured value: C, 80.54%; H, 5.93%; N, 6.16%; Theoretical value (C 15 h 13 NO): C, 80.69%; H, 5.87%; N, 6.27%.

[0033] Under a nitrogen atmosphere, add 0.45 g of the above-obtained Schiffer’s base (equivalent to 2.0 mmol) and 20 mL of anhydrous tetrahydrofuran into a dry reactor, stir at room...

Embodiment 2

[0035] Use 2-phenyl-3-hydroxy-acrolein 5.93g equivalent to 40mmol, use 2-fluoroaniline 2.22g equivalent to 20mmol to replace the aniline, methanol 15mL, and formic acid 1mL in Example 1, heat and reflux for 36h, and the experimental operation is the same In Example 1, 2.36 g of yellow solid Schiff's base was obtained, with a yield of 49%. 1 H NMR (300MHz, CDCl 3 ): δ7.16-7.66 (m, 10H, Ar-H+CH=N) 9.76-9.77 (d, 1H, C=CHOH) 12.13-12.16 (b, 1H, OH). According to mass spectrometry, the molecular ion peak m / e is 241. Elemental analysis measured value: C, 74.51%; H, 5.13%; N, 5.92%; Theoretical value (C 15 h 12 FNO): C, 74.67%; H, 5.01%; N, 5.81%.

[0036] Using 0.48 g of the Schiffs base prepared in Example 2 is equivalent to 2 mmol to replace the Schiffs base obtained in Example 1, and the experimental operation was the same as in Example 1 to obtain 0.45 g of the brown complex with a yield of 45%. According to mass spectrometry, the molecular ion peak m / e is 505. Elemental a...

Embodiment 3

[0038] Replace the aniline in Example 1 with 8.89g of 2-phenyl-3-hydroxy-propenal equivalent to 60mmol, 4.83g of 3-trifluoromethylaniline equivalent to 30mmol, methanol 20mL, formic acid 1.5mL, heat and reflux for 48h , the experimental operation was the same as in Example 1, and 4.72 g of yellow solid Schiff's base was obtained, with a yield of 54%. According to mass spectrometry, the molecular ion peak m / e is 291. 1 H NMR (300MHz, CDCl 3 ): δ7.29-7.60 (m, 9H, Ar-H) 7.60-7.65 (m, 1H, CH=N) 9.73-9.74 (d, 1H, C=CHOH) 12.15-12.19 (b, 1H, OH) . Elemental analysis measured value: C, 65.83%; H, 4.09%; N, 4.73%; Theoretical value (C 16 h 12 f 3 NO): C, 65.98%; H, 4.15%; N, 4.81%.

[0039] Using 0.58 g of Schiffer's base prepared in Example 3, equivalent to 2 mmol, to replace the Schiffer's base obtained in Example 1, the experimental operation was the same as in Example 1, and 0.48 g of the brown complex was obtained, with a yield of 43%. According to mass spectrometry, the m...

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Abstract

This invention relates to a beta-hydroxy-propyleneimine-vanadium-alkene polymerization catalyst, method for making same, and the application of this catalyst in catalyzing ethylene polymerization, ethylene and norbornene polymerization, ethylene and alpha-alkene polymerization. Under the catalysis of formic acid, 2-phenyl-3-hydroxy-propenal performs condensation reaction with phenylamine or phenylamine derivant in methanol solution to produce Schiff's base; under the anhydrous and anaerobic condition, the above Schiff's base reacts with n-butyl-lithium to produce negative ion ligand; under the anhydrous and anaerobic condition, the negative ion ligand reacts with the coordinate position of vanadium trichloride to produce this invented beta-hydroxy-propyleneimine-vanadium-alkene polymerization catalyst. Under the action of diethyl-aluminium chloride, this invented catalyst can catalyze ethylene polymerization, ethylene and norbornene or alpha-alkene polymerization.This invention is characterized of convenient producing, high catalyzing activity, good thermal stability and strong polymerization.

Description

technical field [0001] The invention relates to a β-hydroxypropyleneimine vanadium olefin polymerization catalyst and a preparation method. [0002] The present invention also relates to the application of the above-mentioned β-hydroxypropyleneimine vanadium olefin polymerization catalyst in catalyzing ethylene polymerization, ethylene and norbornene copolymerization, ethylene and α-olefin copolymerization. Background technique [0003] 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 p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F10/02C08F4/76
Inventor 李悦生薄应建李彦国刘靖宇张所波
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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