Method for preparing polymer monomer 3,4-ethylenedioxythiophene

A technology of ethylenedioxythiophene and polymer materials, applied in organic chemistry and other directions, can solve problems such as being unsuitable for industrial production, unfavorable cost control, unsuitable for process amplification, etc., to achieve large-scale production, low synthesis cost, Simple and convenient post-processing methods

A technology of ethylenedioxythiophene and polymer materials, applied in organic chemistry and other directions, can solve problems such as being unsuitable for industrial production, unfavorable cost control, unsuitable for process amplification, etc., to achieve large-scale production, low synthesis cost, Simple and convenient post-processing methods

CN102775423AActive Publication Date: 2012-11-14TAISHAN MEDICAL UNIV
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  • Method for preparing polymer monomer 3,4-ethylenedioxythiophene
  • Method for preparing polymer monomer 3,4-ethylenedioxythiophene

Examples

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Embodiment 1

[0045] (1) Synthesis of diethyl thiodiacetate

[0046] Ethyl chloroacetate (245.2g, 2.0mol) was added dropwise to sodium sulfide (78g, 1.0mol) in acetone solution (2L), and stirred at room temperature for 2 hours to generate diethyl thiodiacetate; after monitoring the reaction, Direct filtration, evaporation of solvent to obtain 323 grams of crude product, directly used in the next step without further purification;

[0047] (2) Synthesis of sodium 2,5-dicarboxylate-3,4-thiophenediol

[0048] The raw material (323g) of the previous step was dissolved in ethanol (2L), sodium ethoxide (136g, 2mol) was added in batches at room temperature, diethyl oxalate (146g, 1mol) was slowly added, and the temperature was raised to reflux for 4 hours. After monitoring the completion of the reaction, we obtained The ethanol solution of the intermediate 2,5-dicarboxylate-3,4-thiophenediol sodium, which can be directly used in the next reaction without any purification;

[0049] (3) Synthesis ...

Embodiment 2

[0054] (1) Synthesis of diethyl thiodiacetate

[0055] Ethyl chloroacetate (245.2g, 2.0mol) was added dropwise to sodium sulfide (78g, 1.0mol) in acetone solution (2L), and stirred at room temperature for 4 hours to generate diethyl thiodiacetate; after monitoring the reaction, Direct filtration, evaporation of solvent to obtain 324 grams of crude product, directly used in the next step without further purification;

[0056] (2) Synthesis of sodium 2,5-dicarboxylate-3,4-thiophenediol

[0057] The raw material (324g) of the previous step was dissolved in ethanol (2L), sodium ethoxide (150g, 2.2mol) was added in batches at room temperature, diethyl oxalate (146g, 1mol) was slowly added, and the temperature was raised to reflux for 4 hours. After the reaction was completed, Obtain an ethanol solution of the intermediate sodium 2,5-dicarboxylate-3,4-thiophenediol, which can be directly used in the next reaction without any purification;

[0058] (3) Synthesis of ethyl 3,4-ethyle...

Embodiment 3

[0063] (1) Synthesis of diethyl thiodiacetate

[0064] Ethyl chloroacetate (245.2g, 2.0mol) was added dropwise to sodium sulfide (78g, 1.0mol) in acetone solution (2L), and stirred at room temperature for 6 hours to generate diethyl thiodiacetate; after monitoring the reaction, Direct filtration, evaporation of solvent to obtain 324 grams of crude product, directly used in the next step without further purification;

[0065] (2) Synthesis of sodium 2,5-dicarboxylate-3,4-thiophenediol

[0066] The raw material (324g) of the previous step was dissolved in ethanol (2L), sodium ethoxide (150g, 2.2mol) was added in batches at room temperature, diethyl oxalate (146g, 1mol) was slowly added, and the temperature was raised to reflux for 4 hours. After the reaction was completed, Obtain an ethanol solution of the intermediate sodium 2,5-dicarboxylate-3,4-thiophenediol, which can be directly used in the next reaction without any purification;

[0067] (3) Synthesis of ethyl 3,4-ethyle...

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Abstract

The invention relates to a method for preparing polymer monomer 3,4-ethylenedioxythiophene. The method includes firstly dissolving ethyl chloroacetate and sodium sulphide in acetone to react to obtain diethyl thioglycolate; secondly, dissolving the diethyl thioglycolate to ethanol, adding sodium ethoxide and diethyl oxalate into the ethanol, heating and reflowing to obtain ethanol solution of 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium; thirdly, adding dichloroethane and tetrabutylammonium bromide into the ethanol solution of the 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium, heating and reflowing to obtain 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene; fourthly, dissolving the 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene in mixed solvent, adding sodium chloride, heating and reacting, and finally reducing pressure and rectifying. The method for preparing polymer monomer 3,4-ethylenedioxythiophene is few in procedures, low in cost, safe and reliable in technique, simple and fast in post-treatment method, and products are high in yield and purity.

Description

technical field [0001] The invention belongs to the field of preparation of heterocyclic compounds, in particular to a preparation method of polymer material monomer 3,4-ethylenedioxythiophene. Background technique [0002] EDOT was first discovered as a pharmaceutical intermediate, and later its polymer PEODT was discovered as an excellent polymer conductive material, thus creating the era of polymer conductive materials, and its discoverer was awarded the 2000 Nobel Prize in Chemistry. PEDOT has many advantages such as high conductivity, good transparency, high stability, and easy processing, and is used in organic thin film solar cell materials, solid capacitors, conductive inks, OLED materials, electrochromic materials, antistatic materials, new electromagnetic shielding Materials and other fields, and because of its excellent characteristics, PEODT will be used in research in a wider range of fields, and the market demand for this material monomer is increasing. [000...

Claims

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Application Information

Patent Timeline
14 Nov 2012
Publication
CN102775423A
IPC
C07D495/04
Inventors
张艳