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Decarboxylation method of 3,4-ethylenedioxy thiophene

A technology for decarboxylation of ethylenedioxythiophene, applied in organic chemistry, chemical recovery, etc., can solve the problems of high cost of decarboxylation, unfriendly environment, high operation requirements, etc., and achieve the effect of low cost, environmental friendliness and high purity

Inactive Publication Date: 2011-11-16
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a synthetic method of 3,4-ethylenedioxythiophene to solve the problem of high decarboxylation cost and unfriendly environment of 2,5-dicarboxylic acid-3,4-ethylenedioxythiophene in the prior art , high operating requirements and low yield

Method used

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  • Decarboxylation method of 3,4-ethylenedioxy thiophene

Examples

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Embodiment 1

[0021] Such as figure 1 As indicated, weigh 23g 2,5-dicarboxylic acid-3,4-ethylenedioxythiophene and 0.2 g copper phthalocyanine ( figure 2 As shown, R=H, M=Cu), add it to a 250mL reaction bottle, add 100mL water, install an oil-water separator, heat to reflux, and an oily substance will separate out during the reaction. The separated oil was dried and distilled under reduced pressure to obtain 13.0 g of 3,4-ethylenedioxythiophene (92% yield). Product characterization results such as Figure 2-4 As shown, GC-MS: m / z =142, 127, 116, 95, 69, 58, 45; 1 H NMR (CDCl 3 ) δ (ppm): 6.320 (s, 2H, ArH), 4.193 (s, 4H, OCH 2 ); -1 .

Embodiment 2

[0023] Similar to Example 1, using different metal phthalocyanines as catalysts, the results are shown in the table below.

[0024]

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PUM

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Abstract

The invention discloses a decarboxylation method of 3,4-ethylenedioxy thiophene. The method comprises the following step of: decarboxylating 2,5-dicarboxylic acid-3,4-ethylenedioxy thiophene by taking metal phthalocyanine with the structure shown as a general formula (I) as a catalyst to obtain 3,4-ethylenedioxy thiophene, wherein M refers to Mg, Mn, Fe, Co, Ni, Cu, Ag or Zn; and R is independently selected from -H, -Et, -OH, -OCH3, -COOH, -COOEt, -NH2, -NO2, -CN, -F, -Cl, -Br, -I and -Ph. The yield of the 3,4-ethylenedioxy thiophene is high, a solvent used in a reaction is environmentally-friendly and low-cost water, and the catalyst is reusable. The method has the advantages of simple process, low cost, high yield and environmental friendliness, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing 3,4-ethylenedioxythiophene by a decarboxylation method, belonging to the technical field of organic synthesis. Background technique [0002] 3,4-Ethylenedioxythiophene (EDOT), English name is 3,4-ethylene dioxythiophene, the appearance is colorless or light yellow transparent liquid, CAS: 126213-50-1, melting point 10.5°C, boiling point 225°C. It was first discovered as a pharmaceutical intermediate in the second half of the 1980s. After that, the German Bayer company successfully developed poly(3,4-ethylenedioxythiophene), namely PEDOT. Subsequently, a water-soluble polymer electrolyte polystyrene sulfonic acid (PSS for short) was used to solve the processing problem of PEDOT. The obtained PSS / PEDOT film has high electrical conductivity, high mechanical strength, high visible light transmittance and superior The stability of antistatic coatings, solid electrolyte capacitors, through-hole circuit board p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCY02P20/584
Inventor 赵军龙李媛苟小锋花成文李小安宋扬扬
Owner NORTHWEST UNIV(CN)
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