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Method for preparing diether type tetraacid dianhydride isomer

A technology of tetraacid dianhydride and isomer is applied in the field of preparation of bisether-type tetraacid dianhydride isomer, and can solve the problems of high cost of raw materials, difficult environmental protection and the like

Inactive Publication Date: 2006-10-25
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0003] In order to solve the problems of high raw material cost and difficult environmental protection problems in the existing method, the present invention adopts the N-substituted chlorinated phthalimide isomer prepared by the cheap and easy-to-obtain chlorinated phthalic anhydride isomer as initial Raw materials, one-pot preparation of intermediate N, N'-disubstituted bis-ether tetraimide isomers with bisphenol and anhydrous potassium carbonate in an aprotic polar solvent. The tetraimide is dehydrated by hydrolysis and acidification Obtain bis-ether tetraacid dianhydride isomers

Method used

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  • Method for preparing diether type tetraacid dianhydride isomer
  • Method for preparing diether type tetraacid dianhydride isomer
  • Method for preparing diether type tetraacid dianhydride isomer

Examples

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Embodiment 1

[0026] Add 0.1mol (11.0 grams) of hydroquinone, 0.216mol (42.25 grams) of N-methyl-4-chlorophthalimide, 0.22mol (30.36 g) anhydrous potassium carbonate and 250 milliliters of dry dimethyl sulfoxide, stir after nitrogen deoxygenation, heat to 90 ° C, and stir at this temperature for 5 hours, after the reactant is cooled to room temperature, pour it into The precipitate was filtered out in 500 ml of water, washed with hot water and hot ethanol respectively, and dried to obtain 40.7 g of the product 4,4'-hydroquinone tetraimide with a yield of 95%. 21.4 g of the obtained product was heated and refluxed in 140 ml of 10% aqueous sodium hydroxide solution for 5 hours, and the aqueous solution was acidified to PH=3 with hydrochloric acid, and a white solid was precipitated, filtered, washed with water, and dried to obtain tetraacid, which was dehydrated to obtain 19.3 gram of 4,4'-hydroquinone-type tetraacid dianhydride, and the yield was 96%.

Embodiment 2

[0028] Add 0.1mol (22.83 grams) bisphenol A, 0.22mol (43.03 grams) N-methyl-4-chlorophthalimide, 0.24mol (33.12 grams) anhydrous potassium carbonate in a 500 ml three-necked flask and 170 ml of dry dimethylformamide, stirred with nitrogen to remove oxygen, heated to 130 ° C, and stirred at this temperature for 10 hours, after the reactant was cooled to room temperature, it was poured into 400 ml of water, filtered out The precipitate was washed with hot water and hot ethanol respectively, and dried to obtain 50.8 g of the product 4,4'-bisphenol A tetraimide with a yield of 93%. The resulting 27.3 g product was heated to reflux in 80 ml of 20% sodium hydroxide aqueous solution for 5 hours, and the aqueous solution was acidified to PH=2 with hydrochloric acid. After boiling for 5 minutes, the white solid was cooled and precipitated, filtered, washed with water, and then dried to obtain the tetraacid. The tetraacid was dehydrated with acetic anhydride to obtain 23.7 g of 4,4'-bis...

Embodiment 3

[0030] Add 0.1mol (11.0 grams) of resorcinol, 0.18mol (46.38 grams) of N-phenyl-4-chlorophthalimide, 0.20mol (27.6 grams) of anhydrous Potassium carbonate and 140 ml of dry N-methylpyrrolidone, after nitrogen deoxygenation, stirred and heated to 180 ° C, and continued to react at this temperature for 3 hours, cooled and poured into 400 ml of water, a white precipitate was precipitated, and the solid was collected by filtration , washed the filter cake twice with hot water and hot ethanol respectively, and dried to obtain 51.4 grams of 4,4'-resorcinol-type tetraimide, with a yield of 94%. The obtained 27.6 g of tetraimide and 70 ml of 30% sodium hydroxide aqueous solution were heated and refluxed for 5 hours, the aqueous solution was acidified to PH=1 with hydrochloric acid, a white solid was precipitated, filtered, washed with water and then dried to obtain the tetra-acid, and the tetra-acid was washed with ethyl alcohol. The acid anhydride was dehydrated to obtain 18.1 g of 4...

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Abstract

This invention relates to bi aether style tetracid bi anhydride isomer prepeartion method. N-substitution-4-chlorine phthalic imidine or / and N-substitution-3- chlorine phthalic imidine, bisphenoland anhydrous potassium carbonate are used to generate N,N'-bi substitution bi aether style tetracid bi anhydride different isomer, then the quadric acid imide is hydrolyzed and acidified, and different bi aether style tetracid bi anhydride isomers are got after dewatering. Chlorine benzene anhydride isomer that cheap and easy get is used in this invention, initial material is N-substitution chlorine phthalic imidine made by the chlorine benzene anhydride isomer, so the environmental pollution brought by using materials of nitro substitution acid imide or nitro substitution benzene dinitrile is avoided, and problem of product deep color and low purity is also avoided. The reaction is happened in one tank, so its operation is simple and procedures are saved. Bi aether style tetracid bi anhydride isomer is synthesized first time, especially 3, 4'-bit isomer.

Description

technical field [0001] The invention belongs to the technical field of preparation of bis-ether tetraacid dianhydride isomers. Background technique [0002] Polyimide is widely used in aviation, aerospace, electronics, nuclear power and Widely used in the automotive industry. In addition to the above characteristics, bis-ether polyimide also has the advantages of easy processing. Diether tetraacid dianhydride is one of the important raw materials for the synthesis of polyimide. Diether tetraacid dianhydride has three isomers namely 4,4'-biether tetraacid dianhydride, 3,4'-biether tetraacid dianhydride and 3,3'-biether tetraacid dianhydride anhydride. U.S. Patent 3,879,428, 4,017,511 and 3,957,862 report that the phthalimide substituted by nitro, the alkali metal salt of bisphenol and sodium hydroxide or bisphenol react in polar aprotic solvent to prepare bis-imide, and then After hydrolysis, acidification and dehydration, the bis-ether tetraacid dianhydride can be obtai...

Claims

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Application Information

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IPC IPC(8): C07D307/89C07D307/885
Inventor 张敏王震丁孟贤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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