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Preparation method of maleimide

A technology of maleimide and maleic anhydride, applied in organic chemistry and other directions, can solve the problems of many by-products, low yield, troublesome post-processing, etc., and achieves short experimental route, strong experimental operability, and safe raw materials. high sex effect

Pending Publication Date: 2022-03-22
SUZHOU HIGHFINE BIOTECH
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  • Abstract
  • Description
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Problems solved by technology

[0003] At present, the commonly used synthetic method is to utilize potassium dichromate to oxidize pyrrole in sulfuric acid to prepare maleimide. However, the raw materials used in this synthetic method are highly toxic and explosive, which greatly reduces the safety of the experiment and will produce A large amount of waste acid water containing heavy metal chromium has a high cost of treating waste water. In addition, this method has many by-products, troublesome post-treatment, and low yield

Method used

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  • Preparation method of maleimide
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  • Preparation method of maleimide

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preparation example Construction

[0029] According to the preparation method of the maleimide of the embodiment of the present invention, comprising:

[0030] Step S1, reacting maleic anhydride with p-methoxybenzylamine to generate 3-(4-methoxybenzylcarbamoyl)acrylic acid.

[0031] That is to say, firstly, intermediate 1, namely 3-(4-methoxybenzylcarbamoyl)acrylic acid was synthesized by using maleic anhydride and p-methoxybenzylamine as raw materials.

[0032] Its reaction formula is shown in following formula (1):

[0033]

[0034] Specifically, for example, the maleic anhydride can be added to the DMF solution to fully dissolve, and the p-methoxybenzylamine is added dropwise therein to generate the 3-(4-methoxybenzylaminomethyl acyl) acrylic acid.

[0035] That is, the above synthetic reaction was carried out in DMF medium to generate Intermediate 1.

[0036] Wherein, the molar ratio of maleic anhydride to p-methoxybenzylamine is 1:0.8-1.2, for example, the above-mentioned synthesis reaction can occur...

Embodiment 1

[0062](1) Preparation of compound 3-(4-methoxybenzylcarbamoyl)acrylic acid

[0063] Take a 1L reaction bottle, add maleic anhydride (30g, 0.31mol, 1.0eq) into DMF (120mL, 4P), and add p-methoxybenzylamine (42.5g, 0.31mol, 1.0eq ), stirred for 6 hours and the reaction ended. Pour the reaction solution into an appropriate amount of ice water to precipitate solids, filter them with suction, wash them once with water, and dry the solids to obtain 67g of 3-(4-methoxybenzylcarbamoyl)acrylic acid with a yield of 92%.

[0064] (2) Preparation of compound 1-(4-methoxybenzyl)maleimide

[0065] Take a 1L reaction bottle and add 3-(4-methoxybenzylcarbamoyl)acrylic acid (67.0g, 0.28mol, 1.0eq) and sodium acetate (13.8g, 0.168mol, 0.6eq) into the acetic anhydride solution (85.7 g, 0.84mol, 3.0eq), the temperature of the oil bath was controlled at 90-100°C for 2 hours. After the reaction is complete, add ice water dropwise to the reaction solution to quench acetic anhydride, continue to s...

Embodiment 2

[0071] (1) Preparation of compound 3-(4-methoxybenzylcarbamoyl)acrylic acid

[0072] Take a 1L reaction bottle and add maleic anhydride (98g, 1mol, 1.0eq) into DMF (400mL, 4P), and add p-methoxybenzylamine (137.1g, 1mol, 1.0eq) dropwise at a temperature of 20-25°C, After stirring for 7 hours, the reaction was completed. Pour the reaction solution into an appropriate amount of ice water to precipitate solids, filter them with suction, wash them with water once, and dry the solids to obtain 221 g of 3-(4-methoxybenzylcarbamoyl)acrylic acid with a yield of 94%.

[0073] (2) Preparation of compound 1-(4-methoxybenzyl)maleimide

[0074] Take a 1L reaction bottle and add 3-(4-methoxybenzylcarbamoyl)acrylic acid (221.0g, 0.94mol, 1.0eq) and sodium acetate (46.2g, 0.56mol, 0.6eq) into the acetic anhydride solution (287.7 g, 2.82mol, 3.0eq), the temperature of the oil bath was controlled at 90-100°C for 3 hours. After the reaction was complete, add ice water dropwise to the reaction...

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Abstract

The invention provides a preparation method of maleimide, which comprises the following steps: S1, reacting maleic anhydride with p-methoxybenzylamine to generate 3-(4-methoxybenzylamino) acrylic acid; step S2, enabling the 3-(4-methoxybenzyl carbamoyl) acrylic acid to react with acetic anhydride, so as to generate 1-(4-methoxybenzyl) maleimide; and S3, removing the 1-(4-methoxybenzyl) group from the 1-(4-methoxybenzyl) maleimide under the action of an oxidizing agent, so as to generate the maleimide. The preparation method provided by the embodiment of the invention has the advantages of short experimental route, high raw material safety, strong experimental operability and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of maleimide. Background technique [0002] Maleimide is a heterobifunctional protein cross-linking agent, which has special effects in enzyme-antibody cross-linking and targeted drugs. Maleimide resin is also used as a thermosetting polyimide, which is widely used in laminates, copper clad laminates and other fields, and has excellent heat resistance, radiation resistance, dimensional stability and other advantages. [0003] At present, the commonly used synthetic method is to utilize potassium dichromate to oxidize pyrrole in sulfuric acid to prepare maleimide. However, the raw materials used in this synthetic method are highly toxic and explosive, which greatly reduces the safety of the experiment and will produce A large amount of waste acid water containing heavy metal chromium has a high cost of treating waste water. In addition, this method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/448
CPCC07D207/448
Inventor 骆浩王桂春刘炼吕敏杰
Owner SUZHOU HIGHFINE BIOTECH
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