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Synthetic process of 3, 4-ethylenedjoxythiophene

A technology of ethylenedioxythiophene and synthesis process, applied in 3 fields, can solve the problems of unstable product, influence product yield and quality, long reaction route, etc., and achieve the effect of simplifying synthesis route

Active Publication Date: 2009-11-04
CHONGQING KOOPPER CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The first route has a long reaction route, and the yield of the decarboxylation reaction in the last step is low; the second and third routes both undergo ether exchange reaction between 3,4-dimethoxythiophene and ethylene glycol to obtain the final product
This one-step reaction is carried out under acidic conditions, and the product is unstable under acidic conditions, thus greatly affecting the yield and quality of the product

Method used

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  • Synthetic process of 3, 4-ethylenedjoxythiophene
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  • Synthetic process of 3, 4-ethylenedjoxythiophene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1. Preparation of disodium ethylene glycol

[0024] 31 grams (0.5 moles) of ethylene glycol and 40 grams (1.0 moles) of sodium hydroxide were dissolved in 500 milliliters of toluene, and refluxed for 1.5 hours. After the reaction, the toluene and water were distilled off, and the toluene and water were further removed by vacuuming. , and then dried at 130°C for 0.5 hours to obtain disodium ethylene glycol.

[0025] 2. Preparation of 3,4-ethylenedioxythiophene

[0026] Cool 53 grams of disodium ethylene glycol obtained in Step 1 to 50° C., and add 500 milliliters of N,N-dimethylformamide, 109 grams (0.45 moles) of 3,4-dibromothiophene, and bromine 13 g (0.09 mol) of cuprous chloride was heated up to 110° C., and reacted at this temperature for 5 hours. After the reaction, the reaction solution was poured into 2 liters of water, and the product was extracted with toluene; after the extraction, the toluene solution was distilled to dryness to obtain 50 g of 3,4-ethylened...

Embodiment 2

[0028] 1. Preparation of disodium ethylene glycol

[0029] Using ethylene glycol and sodium as raw materials, it is prepared according to the existing technology.

[0030] 2. Preparation of 3,4-ethylenedioxythiophene

[0031] Put 53 grams of disodium ethylene glycol obtained in step 1 into a reaction vessel, add 500 milliliters of N-methylpyrrolidone, 109 grams (0.45 moles) of 3,4-dibromothiophene, and 36 grams (0.45 moles) of copper oxide and potassium iodide 0.82 g (0.005 mol), the temperature was raised to 50° C., and the reaction was carried out at this temperature for 24 hours. After the reaction, the reaction solution was poured into 2 liters of water, and the product was extracted with toluene; after the extraction, the toluene solution was distilled to obtain 55 grams of the product, with a yield of 86%.

Embodiment 3

[0033] 1. Preparation of disodium ethylene glycol

[0034] The preparation method is the same as in Example 1.

[0035] 2. Preparation of 3,4-ethylenedioxythiophene

[0036] Cool 53 grams of disodium ethylene glycol obtained in step 1 to 50°C, and add 500 milliliters of N-methylpyrrolidone, 109 grams (0.45 moles) of 3,4-dibromothiophene, and 17.14 cuprous iodide to the reaction vessel. g (0.09 moles), the temperature was raised to 150° C., and the reaction was carried out at this temperature for 5 hours. After the reaction, the reaction solution was poured into 2 liters of water, and the product was extracted with toluene; after the extraction, the toluene solution was distilled to obtain 51 grams of the product, with a yield of 80%.

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Abstract

The invention discloses a synthetic process of 3, 4-ethylenedjoxythiophene. 3, 4-dibromothiophene and disodium ethylene glycol are taken as raw materials to synthesize 3, 4-ethylenedjoxythiophene in the presence of catalyst, the reaction conditions are as follows: the temperature is 50-150 DEG C, the reaction time is 5-24 hours; the catalyst is halogenated kupfer, or compound of cupric oxide and halogenated potassium. Compared with the prior art, the invention has the superiorities of short line and high yield.

Description

technical field [0001] The invention relates to a process for chemically synthesizing medicines, in particular to a process for synthesizing 3,4-ethylenedioxythiophene. Background technique [0002] 3,4-Ethylenedioxythiophene, English name: 3,4-ethylene dioxythiophene (EDOT), EDOT monomer is obtained through chemical polymerization or electrochemical polymerization to obtain polyethylenedioxythiophene (PEDOT), PEDOT is developed by Bayer company in Germany A new type of organic conductive luminescent material, which has the advantages of high electrical conductivity, high luminous efficiency, good environmental stability, easy film production and good transparency, etc. It is used to prepare polymer solid capacitors, organic light-emitting diodes (OLEDs), and solar cells. , anti-static coating, printed circuit boards and other electronic equipment. At present, the synthesis techniques of 3,4-ethylenedioxythiophene mainly include the following types: [0003] 1. Using ethyl...

Claims

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Application Information

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IPC IPC(8): C07D495/04
Inventor 王宇丁东升李朝亮
Owner CHONGQING KOOPPER CHEM IND
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