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Novel synthetic method for 1,3-bis((3-methyl-2,5-dioxopyrrol-1-yl)methyl)benzol

The technology of a citraconic imide methyl group and a new method is applied in the field of a new process for synthesizing an anti-reversion agent 1,3-bisphenyl, which can solve the problems of large solvent pollution, high cost, low environmental pollution and the like, and achieves the The effect of less environmental pollution, less equipment corrosion, and reliable production practicability

Inactive Publication Date: 2016-11-09
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention overcomes some defects such as large solvent pollution and high cost existing in the existing production technology of producing 1,3-bis(citraconimidemethyl)benzene, and provides a kind of low environmental pollution, high yield, A new synthesis method of 1,3-bis(citraconimidemethyl)benzene with high purity, low cost and little corrosion to equipment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0016] Example 1: Add 112 g (1 mol) of 2-methylmaleic anhydride, 224 g of acetic acid as a solvent, and 68 g (0.5 mol) of m-xylylenediamine to a 500ml three-necked flask in sequence, heat the oil bath to 110°C, and keep the temperature for reaction After 6 hours, the reaction was completed, and the solvent was evaporated by distillation under reduced pressure, and the temperature was lowered to 70° C., and 300 grams of a mixed solvent of ethanol and toluene was added to the reaction system, and the off-white crystals were produced after stirring and cooling to room temperature, and filtered to obtain a white filter cake. After washing with a large amount of water and drying, the target product 1,3-bis(citraconimidemethyl)benzene can be obtained. The purity can reach 99.5% by gas phase detection, and the yield is 91%.

example 2

[0017] Example 2: Add 112 g (1 mol) of 2-methylmaleic anhydride, 224 g of acetic acid as a solvent, and 68 g (0.5 mol) of m-xylylenediamine in a 500 ml three-necked flask, and heat the oil bath to 120° C. for insulation reaction After 3 hours, the reaction was finished, and the solvent was evaporated by decompression distillation, and the temperature was lowered to 70 degrees. In the reaction system, 300 grams of mixed solvents of methanol and toluene were added, stirred and cooled to room temperature to produce off-white crystals, and filtered to obtain a white filter cake. After washing with a large amount of water and drying, the target product 1,3-bis(citraconimidemethyl)benzene can be obtained. The purity can reach 98% by gas phase detection, and the yield is 89.3%.

example 3

[0018] Example 3: Add 112 g (1 mol) of 2-methylmaleic anhydride, 224 g of acetic acid as a solvent, and 68 g (0.5 mol) of m-xylylenediamine in a 500ml three-necked flask. Heat the oil bath to 110°C and keep it warm After reacting for 4 hours, the reaction was completed, and the solvent was distilled off under reduced pressure, and the temperature was lowered to 70 degrees, and 300 grams of ethyl acetate and petroleum ether mixed solvent were added to the reaction system, and the off-white crystals were formed after stirring and cooling to room temperature, and off-white crystals were obtained by filtration. The filter cake is washed with a large amount of water and dried to obtain the target product 1,3-bis(citraconimidemethyl)benzene. The purity can reach 99.5% by gas phase detection, and the yield is 92%.

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PUM

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Abstract

The invention relates to a novel synthetic method for 1,3-bis((3-methyl-2,5-dioxopyrrol-1-yl)methyl)benzol. The novel synthetic method comprises the following steps: citraconic anhydride, m-xylylenediamine and a solvent are mixed in proportion and subjected to thermal reaction for multiple hours, the solvent is removed through reduced pressure distillation after the reaction, a mixed solvent is added for recrystallization, and a product is obtained after cooling, filtering and drying. The novel synthetic method is simple to operate, stable, reliable, high in reaction yield and applicable to industrial production, the requirement for equipment is low, the purity can reach 98%, and the production cost is reduced greatly through recycling of the solvent.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a new synthesis process of an anti-reversion agent 1,3-bis(citraconimidemethyl)benzene. Background technique [0002] Anti-reversion agent is the latest type of rubber additives at home and abroad. It can keep the vulcanized network stable, and the rubber properties of the vulcanized rubber will not decline under heat or dynamic conditions. 1,3-bis(citraconimidemethyl)benzene is an ideal anti-reversion agent, which can generate thermally stable carbon-carbon crosslinks to compensate for broken polysulfide bonds, so that The crosslink density and physical properties of the vulcanizate remain unchanged. It can not only improve the anti-reversion performance of the rubber compound, but also improve the elasticity of the rubber compound after vulcanization, reduce heat generation, improve tear strength and wear resistance, which is important for the fatig...

Claims

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Application Information

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IPC IPC(8): C07D207/448
CPCC07D207/448
Inventor 谭成侠江哲龙谢旭峰
Owner ZHEJIANG UNIV OF TECH
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