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Preparation method of 4-phenylmercaptothiophenol

A technology of thiophenylthiophenol and vulcanization reaction, which is applied in the field of preparation of 4-thiophenylthiophenol, can solve the problems of many 3-bromine rearrangement by-products, high substitution reaction temperature, cumbersome preparation process of vulcanization reagents, etc., to achieve The effects of avoiding bromine rearrangement by-products, low reaction temperature, and less production of three wastes

Active Publication Date: 2020-06-19
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of the vulcanization reagent in this route is cumbersome, the substitution reaction temperature is high, and there are still many drawbacks of the above-mentioned synthetic route 3 bromine rearrangement by-products

Method used

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  • Preparation method of 4-phenylmercaptothiophenol
  • Preparation method of 4-phenylmercaptothiophenol
  • Preparation method of 4-phenylmercaptothiophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: Preparation of 4-bromodiphenyl sulfide (Ⅲ)

[0057] In the 1000 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser and dropping funnel, add 350 grams of dichloromethane, 37.2 grams (0.2 moles) of diphenyl sulfide, 41.0 grams (0.2 moles) of 40wt% hydrogen bromide Acid aqueous solution, keep internal temperature between 20-25°C, add dropwise 25.0 g (0.22 moles) of 30wt% hydrogen peroxide, dropwise complete in 1 hour, stir and react at 25-30°C for 2 hours. Stand to separate the layers, extract the water layer twice with dichloromethane, 20 grams each time, combine the dichloromethane layers, distill and recover the solvent dichloromethane, and distill under reduced pressure (110-125°C / 2-3mmHg) to obtain 51.6 grams 4-Bromodiphenylsulfide (Ⅲ), the yield is 97.4%, and the gas phase purity is 99.8%.

Embodiment 2

[0058] Embodiment 2: Preparation of 4-bromodiphenylsulfide (Ⅲ)

[0059] In the 1000 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser and dropping funnel, add 350 gram methylene dichloride, 37.2 gram (0.2 mole) diphenyl sulfide, 20.6 gram (0.2 mole) sodium bromide, 60.0 grams (0.12 moles) of 20wt% sulfuric acid aqueous solution, keep the internal temperature between 20-25 °C, add dropwise 27.5 grams (0.24 moles) of 30wt% hydrogen peroxide, add dropwise in 1 hour, drop it, and stir the reaction between 25-30 °C 2 hours. Stand to separate the layers, extract the water layer twice with dichloromethane, 20 grams each time, combine the dichloromethane layers, distill and recover the solvent dichloromethane, and distill under reduced pressure (110-125°C / 2-3mmHg) to obtain 51.2 grams 4-Bromodiphenylsulfide (Ⅲ), the yield is 96.6%, and the gas phase purity is 99.7%.

Embodiment 3

[0060] Embodiment 3: the preparation of 4-phenylmercaptothiophenol (Ⅰ)

[0061] Under nitrogen protection, 150 grams of tetrahydrofuran, 2.7 grams (0.11 moles) of magnesium powder, 0.5 grams of 1,2-dibromoethane, 1.5 grams of 4 prepared in Example 1 were added to a 500 milliliter four-necked flask equipped with a stirring and thermometer. -Bromodiphenyl sulfide (Ⅲ), 0.02 g of iodine, 40-45 ° C, 0.3 hours after initiation, drop 25.0 g (a total of 0.1 moles) of 4-bromodiphenyl prepared in Example 1 between 40-45 ° C The mixed solution of thioether (Ⅲ) and 100 g of tetrahydrofuran was dropped in 2 hours, and then stirred and reacted at 45-50° C. for 2 hours. Cool to 20-25°C, add 3.9 grams (0.12 moles) of sulfur, stir and react at 30-35°C for 3 hours, recover the solvent by distillation under reduced pressure, add 50 grams of water, 150 grams of dichloromethane to the residue, and use 20wt% sulfuric acid The pH value of the acidification system is 2.0-3.0, and the layers are sepa...

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Abstract

The invention provides a preparation method of 4-phenylthiolthiophenol. The preparation method comprises the following steps: performing a bromination reaction on diphenyl sulfide and a bromination reagent to prepare 4-bromodiphenyl sulfide, performing a Grignard reaction on the obtained 4-bromodiphenyl sulfide to obtain a corresponding Grignard reagent, reacting the Grignard reagent with sulfur,and acidifying to prepare the 4-phenylthiolthiophenol. The method has the advantages of cheap and accessible raw materials, simple operation technique and low cost, can easily implement the reaction conditions, and is low in wastewater generation, safe, environment-friendly, high in atom economy, few in byproducts, high in yield and purity and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 4-phenylmercaptothiophenol, belonging to the technical fields of organic chemical synthesis and polymer materials. Background technique [0002] 4-Phenylmercaptothiophenol (I) is a high-performance end-capping agent for engineering plastics polyphenylene sulfide (PPS). Polyphenylene sulfide (PPS) is an important polymer material widely used in electronic appliances and automobile industries, and is usually prepared by condensation of p-dichlorobenzene or p-dibromobenzene and sodium sulfide. PPS obtained by conventional preparation methods will have terminal halogens. With the emphasis on environmental protection, halogen regulations in various countries are becoming more and more stringent. Europe requires that the halogen residues in PPS materials used in the electronics industry be less than 900ppm, resulting in conventional PPS products that cannot meet the requirements of current halogen regulations....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/09C07C319/20C07C321/30C07C319/28
CPCC07C319/20C07C319/28C07C323/09C07C321/30
Inventor 吕强三戚聿新周立山
Owner XINFA PHARMA
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