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Synthesizing method of conductive high polymer monomer

A technology of conductive polymer and synthesis method, applied in the field of synthesis of conductive polymer monomers, can solve the problems of consumption, inability to meet the regulations on toxic substance content, and multiple energy sources.

Active Publication Date: 2011-11-23
TAIWAN FLUORO TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the preparation process of the No. 6,528,662 invention patent, it is necessary to use a dihaloalkyl group (such as dichloroethane) to prepare an intermediate product (3,4-alkenyldioxythiophene-2,5-dicarboxylate ), so that its final product (3,4-alkenyldioxythiophene-2,5-dicarboxylic acid) or its successor (dialkylthiophene) may contain residual halogen reactants, which cannot meet the increasingly stringent Toxic substance content regulations of environmental regulations
Furthermore, the above-mentioned step of using a dihaloalkyl group to prepare an intermediate product must be reacted at a temperature of 80 to 125° C., which consumes more energy.

Method used

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  • Synthesizing method of conductive high polymer monomer
  • Synthesizing method of conductive high polymer monomer
  • Synthesizing method of conductive high polymer monomer

Examples

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preparation example Construction

[0023] In the synthesis method of the conductive polymer monomer of the present invention, it uses thiodiglycolic acid (thiodiglycolic acid) as the starting material, and carries out esterification reaction (esterification), cyclization reaction (cyclization), ring closure reaction ( ring closure reaction), acidization reaction (acidization) and decarboxylation reaction (decarboxylation), to obtain 3,4-ethylenedioxythiophene (3,4-ethylenedioxythiophene, EDT) conductive polymer monomer product. More specifically, in a preferred embodiment of the present invention, the synthesis method of the conductive polymer monomer comprises the following steps:

[0024] Step 1: Using thiodiglycolic acid (formula I) as a starting material, carry out esterification reaction (esterification) with alcohols to obtain thiodiglycolic acid ester (formula II);

[0025]

[0026]

[0027] Step 2: Cyclization of thiodiglycolic acid ester (formula II) and esters to obtain dialkyl-3,4-dihydroxythio...

no. 1 example

[0044] Step 1: Synthetic reaction of thiodiglycolate (formula II)

[0045] Under a nitrogen system, put 75 grams of thiodiglycolic acid (formula I), 82.5 grams of butanol (BuOH) and 60 mL of toluene into a three-necked flask, set up a condenser, an oil-water separator and a temperature The controller was connected to the three-necked bottle and started to stir. Heated to 120°C and refluxed for 18 hours to remove the generated water. Then, the temperature was lowered to 100° C., and the solvent was separated by distillation under reduced pressure until the solvent was completely evaporated. Dry after filtration to obtain 133 g of thiodiglycolic acid ester (formula II).

no. 2 example

[0047] Step 2: Synthetic reaction of dialkyl-3,4-dihydroxythiophene-2,5-dicarboxylate (formula III)

[0048] Under a nitrogen system, 483 mL of methanol (CH 3 OH) into a three-necked flask, cooled to 10° C., poured 44 g of sodium metal, and stirred at room temperature for 1 hour. Set up condensing tube, thermostat and feeding tube to three-necked bottle, with 200 grams of thiodiglycolic acid ester (formula II) and 123 grams of diethyl oxalate (EtO 2 C-CO 2 Et) placed in the feed tube, slowly added to the three-necked bottle. Heated to 80°C and refluxed for 4 hours. Cool down to 35°C, add 1.5L deionized water, and stir for 30 minutes. Continue to lower the temperature of the three-necked flask to 10°C. Next, 158 mL of 37% hydrochloric acid (HCl) was added into the feeding tube, and slowly dropped into the three-necked flask. Stir for 10 minutes, and then measure whether the pH value is acidic with pH test paper. Next, filter to obtain a solid product, which is added to 5...

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Abstract

The invention relates to a synthesizing method of a conductive high polymer monomer. The conductive high polymer monomer of 3, 4-ethylenedioxythiophene (EDT) with high purity is obtained by using thiodiglycolic acid as initiator sequentially according to esterification, cyclization, ring closure reaction, acidization and decarboxylation, wherein the ring closure reaction does not use halogen reacting substances.

Description

technical field [0001] The invention relates to a synthesis method of a conductive polymer monomer, in particular to a synthesis method of a conductive polymer monomer for preparing high-purity 3,4-ethylenedioxythiophene (EDT). Background technique [0002] In 1958, Natta used organic matter containing aluminum and titanium as a catalyst, the so-called Ziegler-Natta catalyst, to polymerize acetylene gas into polyacetylene (PA). At that time, he had discovered that the conjugated polymer was conductive, but did not continue to study it further. In the early 1970s, Korean students of Japanese chemist Dr. Hideki Shirakawa who taught at Tokyo Institute of Technology mistakenly increased the amount of catalyst by 1000 times to obtain a silver-white cis-PA film. When the film is heated in vacuum or inert gas, the cis-polyacetylene will be transformed into golden-yellow trans-polyacetylene (trans-PA). He did not know at the time that the membrane could be used as an electrical co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04
Inventor 佘怡璇陈尹晨许光美
Owner TAIWAN FLUORO TECH