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Process for preparing N-phenyl maleimide

A maleimide and synthetic method technology, applied in the direction of organic chemistry, can solve the problems of environmental pollution, high water solubility of DMF, and high cost, and achieve the effects of reducing environmental pollution, reducing production costs, and simplifying the production process

Inactive Publication Date: 2007-05-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the main shortcoming of this method is that must use a large amount of poisonous solvent DMF, and DMF water solubility is big, and reclaiming is more difficult, will wash product with a large amount of water at the end of reaction, remove DMF, have brought serious environmental pollution
Method two is to make solvent with low toxicity, cheap acetone, take acetic anhydride as dehydrating agent, take sodium acetate as catalyst, also add a kind of stabilizer tertiary amine in addition, but there is cost height and environmental pollution problem; And in order to separate reaction The acid also needs to wash the reaction product with a large amount of water

Method used

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  • Process for preparing N-phenyl maleimide
  • Process for preparing N-phenyl maleimide

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Embodiment 1

[0014] Embodiment 1: a kind of synthetic method of N-phenylmaleimide, take maleic anhydride and aniline as main starting raw material, make through following steps successively:

[0015] (1) Acylation, the preparation of N-phenyl maleamic acid:

[0016] In the flask equipped with stirring, dropping funnel and thermometer, add maleic anhydride (25.0g, 0.26mol), toluene (120mL), add aniline (23.0mL, 0.26mol) in the dropping funnel, heat, 60°C Aniline was added dropwise, and the dropwise addition was completed within 1 hour to obtain a white milky solid.

[0017] 2) Dehydration to form a ring, preparation of N-phenylmaleimide crude product:

[0018] Add p-toluenesulfonic acid (2g, 0.01mol), hydroquinone (1g, 0.01mol) and N-ethylpyrrolidone (0.8mL, 0.80g), heat, and start dehydration when the temperature reaches 90°C, and when it reaches 110°C, Steady water flow. After 8 hours of reaction, anhydrous was formed, and the reaction was completed, and a reddish-brown transparent sol...

Embodiment 2

[0021] Embodiment 2: a kind of synthetic method of N-phenylmaleimide, take maleic anhydride and aniline as main starting raw material, make through following steps successively:

[0022] (1) Acylation, the preparation of N-phenylmaleic acid:

[0023] In the flask equipped with stirring, dropping funnel and thermometer, add maleic anhydride (17.8g, 0.18mol), toluene (120mL), add aniline (11.5mL, 0.13mol) in the dropping funnel, heat, 40°C Aniline was added dropwise, and the dropwise addition was completed within 5 hours to obtain a white milky solid.

[0024] 2) dehydration, preparation of N-phenylmaleimide:

[0025] Add p-toluenesulfonic acid (1g, 0.005mol), hydroquinone (0.5g, 0.005mol) and N-ethylpyrrolidone (0.7mL), heat, dehydration starts at 90°C, and stabilizes at 110°C. After 2 hours of reaction, anhydrous was formed, and the reaction was completed, and a reddish-brown transparent solution was obtained. The toluene was removed on a rotary evaporator to obtain 30 g of...

Embodiment 3

[0028] Embodiment 3: a kind of synthetic method of N-phenylmaleimide, take maleic anhydride and aniline as main starting raw material, make through following steps successively:

[0029] (1) Acylation, the preparation of N-phenyl maleamic acid:

[0030] In the flask equipped with stirring, dropping funnel and thermometer, add maleic anhydride (30.0g, 0.31mol), xylene (190mL), add aniline (23.0mL, 0.26mol) in the dropping funnel, heat, 20 The aniline was added dropwise at ℃, and the dropwise addition was completed within 2 hours to obtain a white milky solid.

[0031] 2) dehydration, preparation of N-phenylmaleimide:

[0032] Add p-toluenesulfonic acid (2g, 0.01mol), hydroquinone (1g, 0.01mol) and N-ethylpyrrolidone (1.2mL), heat, dehydration starts at 90°C, and stabilizes at 138°C. After 4 hours of reaction, anhydrous was formed, and the reaction was completed, and a reddish-brown transparent solution was obtained. The toluene was removed on a rotary evaporator to obtain 53...

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Abstract

The invention discloses a synthesizing method of N-phenyl maleimide, which comprises the following steps: 1) acylating the maleic anhydride and aniline in the solvent; 2) reacting N-phenyl maleamic acid with hydroquinone as inhibitor and p-toluenesulfonic acid and N-ethyl pyrrolidone as double catalyst; decompressing the liquid to remove solvent; obtaining the rought product; 3) recrystallizing to obtain the product.

Description

technical field [0001] The present invention relates to a kind of synthetic method of organic compound, especially a kind of synthetic method of N-phenylmaleimide. Background technique [0002] [0003] N-phenylmaleimide, whose molecular formula is shown in S-1, is a heat-resistant organic monomer developed in recent years. Because it has a five-membered ring structure, it can be embedded in a polymer chain, which can To enhance the internal rotation resistance of the chain, it is now widely used as an additive for ABS and other resins to improve its heat resistance. [0004] The synthetic method of this material mainly divides following several: method one, document (Tianjin Chemical Industry, 2003, 17 (4), 17-20) reports in organic solvent benzene, toluene or xylene, with maleic anhydride and aniline as raw material, DMF (N, N-dimethylformamide) was added as a co-solvent, and the target product was synthesized under the action of a catalyst. But the main shortcoming o...

Claims

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Application Information

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IPC IPC(8): C07D207/448
Inventor 陈新志张海江钱超
Owner ZHEJIANG UNIV
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