Method for preparing polymer monomer 3,4-ethylenedioxythiophene

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...

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Problems solved by technology

[0003] The synthesis of 3,4-ethylenedioxythiophene (EDOT) has been reported in the literature as early as 1998 as a classic five-step synthesis method, but because the yield is only 25-30%, the process lacks innovation and is relatively backward

However, the market price of 2,3-dimethoxy-1,3-butadiene is expensive, which greatly increases the cost of the process and is not conducive to cost control, so this route is only used for laboratory methodological exploration, which is inconvenient for industrial production

Heterocycles, 82 (1), 449-460 in 2010; 2010 literature uses butynediol, benzyl bromide and bromoethanol as raw materials, and through eight steps, the final product 3,4-ethylenedioxythiophene (EDOT ), the method used in this document is only suitable for laboratory methodology. Lithium aluminum hydride and sodium hydrogen are relatively dangerous chemical raw materials, which are not suitable for industrial production. , resulting in higher cost and increased production cycle

Another patent in 2010, Jpn.Kokai Tokkyo Koho, 2010132571, 17 Jun 2010, reported a change in the classic five-step method, using methyl chloroacetate and sodium sulfide as raw materials to synthesize the final product 3,4-ethylene Dioxythiophene (EDOT), the total yield is 60%, but there are many temperature control links in this patent, and it is not suitable for process amplification

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