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A kind of method of synthesizing hydroxymethyl edot

A technology for synthesizing methylol and methylol, applied in the chemical industry, can solve the problems of long reaction route, complicated post-processing and high production cost, and achieve the effects of short reaction route, low price and low cost

Active Publication Date: 2020-09-01
BEILI CHEM ZHANGJIAGANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is: in order to solve the technical problems of low yield, long reaction route, high production cost and complex post-processing in the existing method for synthesizing hydroxymethyl EDOT, a method for synthesizing hydroxymethyl EDOT is provided. method

Method used

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  • A kind of method of synthesizing hydroxymethyl edot
  • A kind of method of synthesizing hydroxymethyl edot
  • A kind of method of synthesizing hydroxymethyl edot

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Experimental program
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Embodiment 1

[0030] This embodiment provides a method for synthesizing hydroxymethyl EDOT, comprising the following steps:

[0031] S1: Add 132.7g of dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate, 62.1g of glycerol and 233.2g of tributylphosphine into 265.4g of tetrahydrofuran in a nitrogen atmosphere and avoid light. Add 250.1g of diisopropyl azodicarboxylate dropwise, then raise the temperature to 50°C and stir the reaction for 20 hours, distill under reduced pressure to obtain the initial oil, add diethyl ether for slurry, filter to remove the solid, and concentrate the filtrate to obtain 147.0g of 2-hydroxymethyl- Methyl 2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylate, the content detected by gas chromatography was 97.4%, and the yield was 87.2%;

[0032] S2: Add sodium hydroxide to 2-hydroxymethyl-2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid methyl ester prepared in S1 The aqueous solution makes the pH of the reaction system between 12-14, heats to 60°C, st...

Embodiment 2

[0037] This embodiment provides a method for synthesizing hydroxymethyl EDOT, comprising the following steps:

[0038] S1: Add 132.5g dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate, 77.5g glycerol and 324.0g triphenylphosphine to 662.5g 1,4-bis 200.5 g of diethyl azodicarboxylate was injected into the oxyhexane at room temperature, then heated up to 80°C and stirred for 12 hours, distilled under reduced pressure to obtain initial oil, added ether for beating, filtered to remove solids, and the filtrate was concentrated to obtain 145.8 g 2-Hydroxymethyl-2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid methyl ester, the gas chromatography detection content is 97.6%, The yield is 86.8%;

[0039] S2: Add sodium hydroxide to 2-hydroxymethyl-2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid methyl ester prepared in S1 The aqueous solution makes the pH of the reaction system between 12-14, heats to 120 ° C, stirs and reacts for 2 hours, adjusts the pH to 2-3...

Embodiment 3

[0044] This embodiment provides a method for synthesizing hydroxymethyl EDOT, comprising the following steps:

[0045] S1: Add 133.1g of dimethyl 3,4-dihydroxythiophene-2,5-dicarboxylate, 67.2g of glycerol and 239.6g of tributylphosphine to 366.4g of toluene in a nitrogen atmosphere and avoid light. Add 239.4g of diisopropyl azodicarboxylate dropwise, then raise the temperature to 70°C and stir the reaction for 15 hours, distill under reduced pressure to obtain the initial oil, add diethyl ether for slurry, filter to remove the solid, and concentrate the filtrate to obtain 148.7g of 2-hydroxymethyl- Methyl 2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylate, the content detected by gas chromatography was 97.8%, and the yield was 88.3%;

[0046] S2: Add sodium hydroxide to 2-hydroxymethyl-2,3-dihydrothieno[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid methyl ester prepared in S1 The aqueous solution makes the pH of the reaction system between 12-14, heats to 80°C, stirs and re...

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Abstract

The invention relates to a method for synthesizing hydroxymethyl EDOT (Ethylenedioxythiophene). The method comprises the following steps: 3,4-dihydroxythiophene-2,5-dimethyl isophthalate, glycerol andcatalyst are heated to react in organic solvent to obtain 2-hydroxymethyl-2,3-dihydrothiophene[3,4-b]-[1,4]-dioxin-5,7-methyl diformate; the 2-hydroxymethyl-2,3-dihydrothiophene[3,4-b]-[1,4]-dioxin-5,7-2-methyl diformate is added into strong base aqueous solution to be subjected to heating reaction; then, strong acid aqueous solution is used for acidification to obtain 2-hydroxymethyl-2,3-dihydrothiophene[3,4-b]-[1,4]-dioxin-5,7-dicarboxylic acid; the 2-hydroxymethyl-2,3-dihydrothiophene[3,4-b]-[1,4]-dioxin-5,7-methyl diformate and catalyst are heated to react in organic solvent to obtain thehydroxymethyl EDOT. The method disclosed by the invention has the advantages of short reaction line, high product yield and low cost.

Description

technical field [0001] The invention relates to a method for synthesizing hydroxymethyl EDOT, which belongs to the technical field of chemical industry. Background technique [0002] The conductive polymer PEDOT is widely used in organic thin film solar cell materials, electrochromic display devices, organic light emitting diodes, supercapacitors, In the fields of antistatic coatings, corrosion inhibitors, printed circuit smart windows, microwave absorbing materials, chemical / biological sensors, etc., the synthesis of conductive polymers with more excellent properties is still a research hotspot in this field, especially those with active groups The EDOT derivative monomer provides a new idea for designing PEDOT derivatives with different properties. Among them, thieno[3,4-B]-1,4-dioxin-2-methanol (also known as hydroxymethyl EDOT), as one of the EDOT derivatives, can be used to synthesize poly(3,4-dioxo- Hydroxymethyl-ethylthiophene) (PEDTM), PEDTM introduces a hydroxymet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
CPCC07D495/04
Inventor 徐晓东杨巧梅程文峰张雯君
Owner BEILI CHEM ZHANGJIAGANG