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Preparation method of rubber anti-reversion agent 1,3-bis(citraconimidomethyl)benzene

A technology for twisting furfurimide methyl group and anti-reversion agent, applied in the field of rubber auxiliaries preparation, can solve the problems of less than 80% product conversion rate, high solvent toxicity and corrosiveness, and no treatment, etc. Excellent product quality, high selectivity, and low environmental pollution

Active Publication Date: 2019-07-12
山东斯递尔化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Chinese journal "Guangdong Chemical Industry" 2006, No. 4, Volume 33, titled the synthesis of anti-reversion agent 1,3-bis(citraconate imidomethyl)benzene, the synthesis method is mainly divided into two steps: first Synthesis of 2-methylmaleic anhydride (citraconic anhydride): use itaconic acid to be dehydrated by acetic anhydride, and then catalyzed by a catalyst to form citraconic anhydride, then citraconic anhydride and m-xylylenediamine react in the presence of a catalyst in a solvent Remove the water, add water in the later stage to make the product precipitate, and the obtained product 1,3-bis(furoimidomethyl) will produce a large amount of acetic acid in the first step of manufacturing citraconic anhydride, which will corrode the equipment and Environmental pollution is relatively large; the solvent used in the second step is highly toxic and corrosive and has not been treated, and the conversion rate of the final product is less than 80%, which is relatively low

Method used

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  • Preparation method of rubber anti-reversion agent 1,3-bis(citraconimidomethyl)benzene

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Embodiment 1

[0021] Take 60g of citraconic anhydride with a content of 98% and 150mL of solvent xylene into a four-necked flask with a condensation and water separation device, then add 6g of acetic acid, raise the temperature to about 120°C in a reflux state, and add 35.5g of m-xylylenediamine dropwise , the dropping time is controlled at about 0.5 hours, keep the temperature and continue to reflux for 2.5 hours, and continue to separate out the moisture brought out by xylene; after the reaction is completed, evaporate xylene under reduced pressure at 0.6atm, cool down to 60°C, and add 100g Ethanol, stirred evenly, filtered after cooling, the filter cake was dried, and the filtrate was collected and recycled; the finished product was tested: the appearance was white powder, the melting point was 78.2 ° C, the yield was 96.2%, and its content was determined by high performance liquid chromatography. 99.1%.

Embodiment 2

[0023] Take 60g of citraconic anhydride with a content of 98% and 150mL of solvent toluene into a four-necked flask (with condensation and water separation device), then add 10g of acetic acid, raise the temperature to about 110°C in a reflux state, and add 35.5g of m-xylylenediamine dropwise , the dropping time is controlled at about 0.6 hours, keep the temperature and continue to reflux for 2.5 hours, after the reaction is over, steam the toluene at normal pressure, lower the temperature to 60°C, add 100g of ethanol, stir evenly, filter after cooling, and dry the filter cake. The filtrate was collected and recycled; the finished product was tested: the appearance was white powder, the melting point was 79.0°C, the yield was 97.2%, and the content was 99.3% as determined by high performance liquid chromatography.

Embodiment 3

[0025] Take 60g of citraconic anhydride with a content of 98% and 150mL of solvent xylene into a four-necked flask (with condensation and water separation device), then add 6g of formic acid, raise the temperature to about 120°C in a reflux state, and add 35.5g of m-phthalylene dropwise Amine, the dropping time is controlled at about 0.6 hours, keep the temperature and continue to reflux for 2.5 hours, after the reaction is over, distill out the xylene under reduced pressure at 0.2atm, lower the temperature to 60°C, add 100g of methanol, stir evenly, and filter after cooling. The filter cake is dried, the filtrate is collected and recycled, and the finished product is tested: the appearance is white powder, the melting point is 77.1 ° C, the yield is 96.0%, and the content is 99.0% as determined by high performance liquid chromatography.

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Abstract

The invention relates to the technical field of preparation of rubber auxiliaries, in particular to a preparation method of a rubber anti-reversion agent 1,3-bis(citraconimidomethyl)benzene. The preparation method comprises the following steps: (1) mixing citraconic anhydride with a benzene-series solvent in a four-necked flask with a condensing water separator, adding an organic acid catalyst, and raising the temperature for reflux; (2) adding m-xylylenediamine dropwise to the system of the step (1) with an addition time of 0.3-1.0 h, keeping reflux for 1-5 h, and separating water which is brought out by the benzene-series solvent continuously; (3) distilling the benzene-series solvent out, reducing the temperature to 60 DEG C, adding an alcohol solvent, and performing even stirring; and(4) performing cooling, performing filtration, drying the filter cake, collecting the filtrate, and performing recycling. The preparation method has a high conversion rate of the reactants, few by-products and high selectivity of the reaction; and the solvents are all recoverable, less wastewater is generated, and pollution to the environment is small.

Description

technical field [0001] The invention relates to the technical field of preparation of rubber additives, in particular to a method for preparing a rubber anti-reversion agent 1,3-bis(furoimidomethyl)benzene. Background technique [0002] Anti-reversion agent is a new type of functional rubber additive. 1,3-bis(furfurimidemethyl)benzene is an anti-reversion agent. The carbon cross-links replace the sulfur cross-links that have been destroyed by reduction during compression or during product use, resulting in long-term thermal stability of the sulfur-cured compound. [0003] Chinese journal "Guangdong Chemical Industry" 2006, No. 4, Volume 33, titled the synthesis of anti-reversion agent 1,3-bis(citraconate imidomethyl)benzene, the synthesis method is mainly divided into two steps: first Synthesis of 2-methylmaleic anhydride (citraconic anhydride): use itaconic acid to be dehydrated by acetic anhydride, and then catalyzed by a catalyst to form citraconic anhydride, then citrac...

Claims

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Application Information

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IPC IPC(8): C07D207/448
CPCC07D207/448
Inventor 朱嘉震田旭赵新远刘书源
Owner 山东斯递尔化工科技有限公司