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Synthesis method of 3,4-ethylenedioxythiophene (EDOT) as novel conductive high polymer monomer

An ethylenedioxythiophene and conductive polymer technology, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions, poor color, and low product yield, and achieve the effects of mild reaction conditions, simple process flow, and low raw material cost.

Inactive Publication Date: 2012-10-17
BEILI CHEM ZHANGJIAGANG
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AI Technical Summary

Problems solved by technology

[0003] Existing domestic and foreign at present many papers report the synthetic method of EDOT and its intermediate, starting material is mainly based on thiodiglycolic acid, but its esterification yield is generally on the low side (Polymer such as Qibing Pei, 1994, Vol.35 , No.7, 1374-1351), and the cost of raw materials is high. In addition, this step also requires vacuum distillation to purify thiodiglycolic acid ester, otherwise impurities will affect the quality of EDOT products, the color is poor, and it is difficult to purify as high Pure grade for the increasingly demanding electronics industry
In addition, there are many reaction steps (CN101591345B, CN101429205B) and the frequent transfer of reaction materials affects the yield, and increases the cost and unnecessary labor and energy consumption for industrialization
[0004] Keegstra M A et al. proposed to use 3,4-dibromothiophene as a starting material to react 3,4-ethylenedioxythiophene (see Tetrahedron, 1992,48(17):3633-3652). This method is expensive and the reaction conditions Harsh, the product yield is low, only suitable for the laboratory

Method used

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  • Synthesis method of 3,4-ethylenedioxythiophene (EDOT) as novel conductive high polymer monomer
  • Synthesis method of 3,4-ethylenedioxythiophene (EDOT) as novel conductive high polymer monomer
  • Synthesis method of 3,4-ethylenedioxythiophene (EDOT) as novel conductive high polymer monomer

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Experimental program
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Effect test

Embodiment 1

[0035] Synthesis reaction of thiodiglycolic acid ester

[0036] Under the protection of nitrogen, put 80g (1.025mol) of sodium sulfide, 500ml of absolute ethanol, and 0.5g of crown ether (15-crown-5) in a four-necked bottle, and add 122.5g (1mol) of ethyl chloroacetate dropwise at room temperature After the dropwise addition, raise the temperature to 45-55°C, keep it warm for 1 hour, take a sample for GC tracking, and if the content of ethyl chloroacetate is ≤2%, the reaction is complete. After filtering, the filter cake was washed twice with 30 ml of absolute ethanol and the combined filtrate was obtained to obtain 705 g, with a GC content of 27.1%, equivalent to 191.4 g of diethyl thiodiglycolate, and a molar yield of 92.9%.

Embodiment 2－8

[0038] Synthesis reaction of thiodiglycolic acid ester

[0039]

[0040]

Embodiment 9

[0042] Synthesis of 2,5-dicarboxylic acid-3,4-ethylenedioxythiophene (Ⅴ)

[0043] Under the protection of nitrogen, add 350g of the diethyl thiodiglycolate filtrate into a four-neck flask, add 150g of a mixture of diethyl oxalate and sodium ethylate dropwise at a temperature of 40-50°C, and after the addition is complete, heat up to 65-50°C Incubate at 70°C for 5 hours. HPLC tracking diethyl thiodiglycolate (Ⅱ) content ≤ 1.5%. Cool down and add 140g of 1,2-dichloroethane, raise the temperature to 75°C, keep warm for 12h under the action of the crown ether remaining in the vulcanization reaction, and track 2,5-dicarboxylic acid diester-3,4-dihydroxy sodium thiophene by HPLC (Ⅲ) content ≤ 1%, recover the dry solvent, add 300g of 10% caustic soda solution, heat up and reflux for 3 hours, and track the content of 2,5-dicarboxylate-3,4-ethylenedioxythiophene (Ⅳ) by HPLC ≤ 1%, add pre-prepared 50% dilute sulfuric acid to analyze to pH 3, stir for 30 minutes, filter to obtain 106.8...

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Abstract

The invention discloses a synthesis method of 3,4-ethylenedioxythiophene (EDOT) as a novel conductive high polymer monomer. The synthesis method comprises the following steps of: taking chloracetate as a starting material; carrying out a vulcanization reaction to obtain sulfo-diglycolic acid ester, and then carrying out a one-pot reaction of condensation, etherification, saponification and acidification to prepare 3,4-ethylenedioxythiophene-2,5-dicarboxylic acid; and then carrying out a decarboxylic reaction to obtain the 3,4-ethylenedioxythiophene. The synthesis method has the advantages of low price of raw materials, moderate reaction conditions, simplicity and convenience in operations, short production period and high product quality.

Description

technical field [0001] The invention relates to a method for synthesizing a new conductive polymer monomer 3,4-ethylenedioxythiophene (EDOT). Background technique [0002] Polyethylene dioxythiophene is a new type of organic conductive luminescent material. It has the advantages of high conductivity, good environmental thermal stability, easy film production and good transparency. It is widely used in antistatic packaging materials, solar cells, supercapacitor plastics, etc. Electronic equipment such as antistatic coatings, sensors, etc. Due to its unique electrical and optical properties and a wide range of applications, the development of high-quality EDOT that is reasonable, efficient and suitable for industrial production has increasingly become the direction of efforts of various companies. [0003] Existing domestic and foreign at present many papers report the synthetic method of EDOT and its intermediate, starting material is mainly based on thiodiglycolic acid, but...

Claims

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Application Information

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IPC IPC(8): C07D495/04
Inventor 杨巧梅徐晓东张雯君程文峰陆伟
Owner BEILI CHEM ZHANGJIAGANG
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