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

Method used

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

Examples

Experimental program
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Example Embodiment

[0022] Example 1

[0023] 1. Preparation of disodium ethylene glycol

[0024] Dissolve 31 g (0.5 mole) of ethylene glycol and 40 g (1.0 mole) of sodium hydroxide in 500 ml of toluene, and react under reflux for 1.5 hours. After the reaction, the toluene and water are distilled off, and then the toluene and water are further removed by vacuum , And then dried at 130°C for 0.5 hours to obtain disodium ethylene glycol.

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

[0026] The 53 g of disodium ethylene glycol obtained in step 1 was cooled to 50°C, and 500 ml of N,N-dimethylformamide, 109 g (0.45 mol) of 3,4-dibromothiophene, and bromine were sequentially added to the reaction vessel. 13 grams (0.09 mol) of cuprous oxide, the temperature was raised to 110°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 s...

Example Embodiment

[0027] Example 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 g of disodium ethylene glycol obtained in step 1 into the reaction vessel, add 500 ml of N-methylpyrrolidone, 109 g (0.45 mol) of 3,4-dibromothiophene, and 36 g (0.45 mol) of copper oxide. And 0.82 g (0.005 mol) of potassium iodide, heated to 50°C, and reacted 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 g of the product with a yield of 86%.

Example Embodiment

[0032] Example 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] The 53 g of disodium ethylene glycol obtained in step 1 was cooled to 50°C, and 500 ml of N-methylpyrrolidone, 109 g (0.45 mol) of 3,4-dibromothiophene, and 17.14 cuprous iodide were sequentially added to the reaction vessel. G (0.09 mol), heated to 150°C, 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 obtain 51 g 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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