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Method for synthesizing 3,4-dimethoxythiophene

A technology of dimethoxythiophene and methoxythiophene, which is applied in the field of synthesizing 3,4-dimethoxythiophene, can solve the problems of environmental pollution, low product yield, high production cost, etc., and achieve reduction of environmental pollution, reaction The effect of low temperature and high utilization rate

Active Publication Date: 2018-04-24
贝利科技(重庆)有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The technical problem to be solved by the present invention is: in order to solve the technical problems of high production cost of 3,4-dimethoxythiophene in the prior art, low product yield and easy environmental pollution, a method for synthesizing 3,4-dimethoxythiophene is provided. Dimethoxythiophene method

Method used

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  • Method for synthesizing 3,4-dimethoxythiophene
  • Method for synthesizing 3,4-dimethoxythiophene
  • Method for synthesizing 3,4-dimethoxythiophene

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Add 293.2g of ethylene glycol dimethyl ether to 146.6g of 3,4-dihydroxythiophene-2,5-dicarboxylate dimethyl disodium salt, add 80.3g of dimethyl sulfate dropwise when heated to 70°C, and In the process of adding dimethyl sulfate dropwise, sodium hydroxide is added to make the pH value of the reaction system at 8-10. After adding dimethyl sulfate, the temperature is raised to 85°C, and the reaction is kept for 5 hours. After the reaction, ethylene glycol dimethyl ether is recovered. Add water to make a slurry, and filter to obtain 120.4g of dimethyl 3,4-methoxythiophene-2,5-dicarboxylate, detected by gas chromatography, with a yield of 87.2%;

[0029] Add 280mL of dodecylbenzene to the 3,4-dimethoxythiophene-2,5-dicarboxylic acid dimethyl ester obtained in the above reaction, and then add a 50 wt% sodium hydroxide aqueous solution to make the reaction system When the pH is 12-14, heat to 200° C., stir and react for 3 hours. After the reaction is completed, acidify to a p...

Embodiment 2

[0035] Add 713.5g N,N-dimethylformamide to 146.3g 3,4-dihydroxythiophene-2,5-dicarboxylate dimethyl disodium salt, add 200.4g dimethyl sulfate dropwise when heated to 120°C In the process of adding dimethyl sulfate dropwise, sodium carbonate is added to make the pH value of the reaction system at 8.5. After adding dimethyl sulfate, the temperature is raised to 150°C, and the reaction is kept for 2 hours; after the reaction, N,N-dimethylformaldehyde is recovered Amide, beating with water, and filtering to obtain 122.4 g of dimethyl 3,4-methoxythiophene-2,5-dicarboxylate. The yield was 88.8% as detected by gas chromatography.

[0036]Add 711.6mL of diamylbenzene to the 3,4-dimethoxythiophene-2,5-dicarboxylic acid dimethyl ester obtained in the above reaction, and then add an aqueous potassium hydroxide solution with a mass fraction of 50wt% to make the reaction system pH at 12-14, heated to 180°C, stirred and reacted for 5 hours, after the reaction, acidified with 50 wt% nitric ...

Embodiment 3

[0042] Add 550g xylene to 150.3g 3,4-dihydroxythiophene-2,5-dicarboxylate dimethyl disodium salt, add 117.3g dimethyl sulfate dropwise when heated to 50°C, add dimethyl sulfate dropwise Add sodium carbonate during the esterification process to make the pH value of the reaction system at 8-10. After adding dimethyl sulfate, raise the temperature to 120°C and keep it warm for 2 hours. After the reaction, recover xylene, add water to make a slurry, and filter to obtain the product 3,4- 124.0 g of dimethyl methoxythiophene-2,5-dicarboxylate, detected by gas chromatography, the yield was 87.6%.

[0043] Add 433 mL of n-pentylbenzene to the 3,4-dimethoxythiophene-2,5-dicarboxylic acid dimethyl ester obtained in the above reaction, and then add an aqueous sodium hydroxide solution with a mass fraction of 50 wt % to make the pH of the reaction system at 12-14, heated to 150°C, stirred and reacted for 8 hours, after the reaction was completed, acidified with a sulfuric acid aqueous sol...

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Abstract

The invention relates to a method for synthesizing 3,4-dimethoxythiophene. The method comprises steps as follows: S1, 2,5-dimethyl dicarboxylate-3,4-sodium thiophene diol and dimethyl sulfate are subjected to a heating reaction in an organic solvent, and 3,4-dimethoxythiophene-2,5-dimethyl dicarboxylate is obtained; S2, 3,4-dimethoxythiophene-2,5-dimethyl dicarboxylate is subjected to the heatingreaction with strong base in an alkylbenzene organic solvent with the boiling point not lower than 200 DEG C, then strong acid is added for acidification, and 3,4-dimethoxythiophene-2-formic acid is obtained; S3, 3,4-dimethoxythiophene-2-formic acid is subjected to a reduced-pressure heating reaction in a long-chain amine organic solvent with the boiling point not lower than 300 DEG C, and 3,4-dimethoxythiophene is obtained. The method is low in production cost, low in energy consumption and high in product yield, the organic solvents can be recycled, particularly, no catalyst is used in the step of decarboxylation, so that the cost is greatly reduced, and environmental pollution is reduced.

Description

Technical field [0001] The invention relates to a method for synthesizing 3,4-dimethoxythiophene and belongs to the technical field of chemical industry. Background technique [0002] As a good conductive polymer monomer, 3,4-dimethoxythiophene is expensive and has attracted much attention in recent years. The current industrial production methods mainly include: (1) using 3,4-dibromothiophene and sodium methoxide as raw materials to synthesize 3,4-dimethoxythiophene under catalyst conditions, but the raw material synthesized by this route is 3,4- Dibromothiophene is more expensive and has higher production costs; (2) react with diacetyl, trimethyl orthoformate and concentrated sulfuric acid to generate 2,3-dimethoxy-1,2-butadiene, and then add sodium acetate It reacts with sulfur dichloride to form a ring-forming product, but this route still has the disadvantages of relatively expensive raw materials and high production costs, and the treatment of the waste sulfuric acid ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/32
CPCY02P20/584C07D333/32
Inventor 徐晓东杨巧梅张雯君
Owner 贝利科技(重庆)有限公司
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