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Preparation methd of 2,2',3,4'-diphenyl thioether tetra acid dianhydride

A technology of diphenyl sulfide and tetraacid dianhydride, which is applied in 2 fields, can solve the problems of difficult complete dehydration of vulcanizing agents, low yield, and difficult separation, etc., and achieves improved yield, reduced production cost, and simple synthesis process Effect

Inactive Publication Date: 2006-01-25
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention aims to solve the problem that anhydrous sodium sulfide is difficult to completely dehydrate as a vulcanizing agent, or that after dehydration, it absorbs water or is oxidized by air to affect the reaction, and the product needs to be separated from the mixture of three isomers in the sodium sulfide method, sulfur and potassium carbonate method. , the difficulty of separation is large and the purity and yield are low

Method used

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  • Preparation methd of 2,2',3,4'-diphenyl thioether tetra acid dianhydride
  • Preparation methd of 2,2',3,4'-diphenyl thioether tetra acid dianhydride
  • Preparation methd of 2,2',3,4'-diphenyl thioether tetra acid dianhydride

Examples

Experimental program
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Embodiment 1

[0025] (1) In a dry 500 ml round bottom flask, add 39.12 grams (0.2mol) of N-methyl-4-chlorophthalimide, 14.63 grams (0.106mol) of anhydrous potassium carbonate, 17.46 grams The mass percentage content is 68-72% sodium hydrosulfide and 120 grams of dimethyl sulfoxide, feed nitrogen to remove the air in the bottle, stir mechanically, heat up to 130 ° C for 2 hours, cool to room temperature, and slowly Pour into 400 ml of 20% dilute hydrochloric acid, collect the solid, then dissolve the crude product in 650 ml of 5% potassium carbonate solution, filter to remove insoluble matter, acidify the filtrate to PH=1 with dilute hydrochloric acid, and precipitate white Precipitate, filter, wash the filter cake three times with distilled water, and dry under vacuum at 80°C to obtain 35.53 grams of N-methyl-4-mercapto substituted phthalimide, with a yield of 92% (based on N-methyl-4-chloro Phthalimide calculation), the melting point of 136-138 ° C.

[0026] (2) Add 19.31 (0.1mol) gram N-...

Embodiment 2

[0029] (1) Add 51.54 grams (0.2mol) of N-phenyl-4-chlorophthalimide, 14.63 grams (0.106mol) of anhydrous potassium carbonate, 17.46 grams in a dry 500 milliliter round bottom flask The mass percentage content is 68-72% sodium hydrosulfide and 170 grams of dimethyl sulfoxide, feed nitrogen to remove the air in the bottle, mechanically stir, heat up to 150 ° C for 2 hours, after cooling to room temperature, slowly Pour into 1000 ml of 20% dilute hydrochloric acid, collect the solid, then dissolve the crude product in 1000 ml of 3% potassium carbonate solution, filter to remove insoluble matter, acidify the filtrate to PH=2 with dilute hydrochloric acid, and precipitate white Precipitate, filter, wash the filter cake three times with distilled water, and dry under vacuum at 80°C to obtain 46.45 grams of N-phenyl-4-mercapto substituted phthalimide, with a yield of 91% (based on N-phenyl-4-chloro phthalimide calculation).

[0030] (2) Add 25.52 (0.1mol) gram N-phenyl-4-mercapto su...

Embodiment 3

[0033] (1) Add 39.12 grams (0.2mol) of N-methyl-3-chlorophthalimide 13.81 grams (0.10mol) of anhydrous potassium carbonate in a dry 500 milliliter round bottom flask, 17.46 grams of quality The percentage content is 68-72% sodium hydrosulfide and 250 grams of dimethylformamide, pass nitrogen gas to remove the air in the bottle, stir mechanically, heat up to 150 ° C for 0.5 hours, after cooling to room temperature, pour it slowly into 400 milliliters of 10% dilute hydrochloric acid, collect the solid, then dissolve the crude product in 500 milliliters of 20% potassium carbonate solution, filter to remove the insolubles, and acidify the filtrate to PH=3 with dilute hydrochloric acid, and precipitate a white precipitate , filtered, the filter cake was washed three times with distilled water, and vacuum-dried at 80°C to obtain 33.99 grams of N-methyl-3-mercapto substituted phthalimide, with a yield of 88% (using N-methyl-3-chloro-ortho phthalimide calculation).

[0034] (2) Add 1...

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Abstract

The invention belong to the art of preparation technique of 2, 3', 3, 4'-diphenyl sulfide tetra-acid dianhydride. It adopts sodium hydrosulfide as a sulfuration agent to react N- substituted- 4- or- 3- phthalimide chloride non-protonic polar solvent to generate intermediate product N- substituted- 4- or- 3- phthalimide sulfhydryl substituted; the latter reacting N- substituted- 3- or- 4- phthalimide chloride non-protonic polar solvent in faintly alkaline condition to generate asymmetric N, N'- double substituted- 2, 3', 3, 4'-diphenyl sulfide tetra imide, hydrolyzing, acidifying, by toluene and dimethylbenzene with water to prepare directly asymmetric2,3',3,4'- diphenyl sulfide tetra-acid dianhydride, which can be used to synthesize polyimide.

Description

technical field [0001] The invention belongs to the technical field of preparation of 2,3',3,4'-diphenylsulfide tetraacid dianhydride. Background technique [0002] Diphenyl sulfide tetraacid dianhydride is one of the raw materials for synthesizing polyimide. In addition to the characteristics of general polyimide, thioether dianhydride polyimide also has the characteristics of easy to obtain raw materials, no crystallization, and easy processing. At present, it can be used as matrix resin and engineering plastics of composite materials. There are three isomers of diphenyl sulfide tetra-acid dianhydride, namely symmetrical 3,3',4,4'-diphenyl sulfide tetra-acid dianhydride, 2,2',3,3'-diphenyl sulfide Tetraacid dianhydride and asymmetric 2,3′,3,4′-diphenylsulfide tetraacid dianhydride, there are many and mature methods for synthesizing symmetrical diphenylsulfide tetraacid dianhydride, Chinese Academy of Sciences Changchun Applied Chemistry Research Institute (Chemistry Bull...

Claims

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Application Information

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IPC IPC(8): C07D307/89C07D209/48
Inventor 张敏王震丁孟贤
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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