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A kind of synthetic method and application of sulfur ylide containing sulfonic acid group

A synthesis method and sulfonate technology, applied in organic chemistry, sulfide preparation, etc., can solve problems such as difficult separation, low economic value, and inability to recycle, and achieve solid-liquid separation, reduce industrial costs, and have little irritation Effect

Active Publication Date: 2022-04-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, p-propoxyanisole sulfide has the characteristics of high boiling point and close to epoxy compounds, it is difficult to separate and cannot be recycled, and has low economic value

Method used

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  • A kind of synthetic method and application of sulfur ylide containing sulfonic acid group
  • A kind of synthetic method and application of sulfur ylide containing sulfonic acid group
  • A kind of synthetic method and application of sulfur ylide containing sulfonic acid group

Examples

Experimental program
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Effect test

Embodiment 1

[0034] A kind of synthetic method of 4-(4-(methylthio)phenoxy)butane-1-sodium sulfonate, described method is: In a 500ml four-neck flask, add 12.6g (0.10mol) of anhydrous sodium sulfite, 28.0g (0.10mol) of 1-(4-bromobutoxy)-4-(methylthio)benzene, 120ml of distilled water, and 110ml of ethanol in sequence , 0.1g copper powder, magnetic stirring, oil bath heating to 80 ℃ reflux. After reflux for 12 h, the reaction solution was distilled off under reduced pressure to remove water until all white solids were precipitated. The resulting solid and 500ml of ethanol were added to a 1L flask, and heated to reflux for 1h. Then it was suction filtered while it was hot, and after the filtrate was cooled, it was placed overnight at 0°C. Finally, it was filtered and dried by suction to obtain sodium 4-(4-(methylthio)phenoxy)butane-1-sulfonate as a white powder crystal, with a yield of 25.1 g and a yield of 84.2%.

[0035] A kind of synthetic method of sulfur ylide containing sulfonic ac...

Embodiment 2

[0039] A kind of synthetic method of 4-(4-(methylthio)phenoxy)butane-1-sodium sulfonate, described method is: in 500ml four-necked flask, add 16.4g (0.13mol) anhydrous successively Sodium sulfite, 28.0g (0.10mol) 1-(4-bromobutoxy)-4-(methylthio)benzene, 120ml distilled water, 110ml ethanol, 0.1g copper powder, magnetic stirring, heating in an oil bath to 80°C and reflux . After 15 h of reflux, the reaction solution was distilled off under reduced pressure to remove water until all white solids were precipitated. The resulting solid and 500ml of ethanol were added to a 1L flask, and heated to reflux for 1h. Then it was suction filtered while it was hot, and after the filtrate was cooled, it was placed overnight at 0°C. Finally, it was filtered and dried by suction to obtain sodium 4-(4-(methylthio)phenoxy)butane-1-sulfonate as a white powder crystal, with a yield of 25.2 g and a yield of 84.6%.

[0040]A kind of synthetic method of sulfur ylide containing sulfonic acid group...

Embodiment 3

[0043] A kind of synthetic method of 4-(4-(methylthio)phenoxy)butane-1-sodium sulfonate, described method is: in 500ml four-necked flask, add 20.2g (0.16mol) anhydrous successively Sodium sulfite, 28.0g (0.1mol) 1-(4-bromobutoxy)-4-(methylthio)benzene, 120ml distilled water, 110ml ethanol, 0.1g copper powder, magnetic stirring, heating the oil bath to 60°C and reflux . After 15 h of reflux, the reaction solution was distilled off under reduced pressure to remove water until all white solids were precipitated. The resulting solid and 500ml of ethanol were added to a 1L flask, and heated to reflux for 1h. Then it was suction filtered while it was hot, and after the filtrate was cooled, it was placed overnight at 0°C. Finally, it was filtered and dried by suction to obtain sodium 4-(4-(methylthio)phenoxy)butane-1-sulfonate as a white powder crystal, with a yield of 25.0 g and a yield of 84.0%.

[0044] A kind of synthetic method of sulfur ylide containing sulfonic acid group, ...

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Abstract

A method for synthesizing sulfur ylides containing sulfonic acid groups. The sulfonate salt synthesized by formula (IV) is reacted with a methylating reagent at a reaction temperature of 220-260° C. and a reaction time of 1-6 hours, and the reaction ends Obtain the sulfur ylide shown in formula (Ⅲ); then carry out the carbonyl compound shown in formula (Ⅲ) and formula (II) in solvent, reaction temperature 40~60 ℃, reaction time 1~7h and alkaline substance In the epoxidation reaction, the reaction liquid is post-treated to obtain oxirane derivatives as shown in formula (I), and the original solid sulfonate generated is treated and recovered simultaneously. And the application of a kind of sulfur ylide containing sulfonic acid group. The invention has little irritation and is easily soluble in water. When applied to the epoxidation reaction, the raw material alkyl sulfonate can be recycled and reused, which reduces the industrial cost and improves the production efficiency.

Description

technical field [0001] The invention relates to a synthesis method and application of sulfur ylides containing sulfonic acid groups. Background technique [0002] With the rapid development of the economy and the gradual improvement of people's living standards, various sulfonate compounds have been widely used in industry and daily life, playing an increasingly important role. Organic sulfonates and their derivatives are a very important class of chemical products, which play an important role in medicine, industry, and chemical manufacturing. Some aliphatic and aromatic sulfonates are often used as anionic surfactants for detergents, and aliphatic and aromatic sulfonates with substituents are widely used in the pharmaceutical and dye industries. Other applications of acid salts have also received more and more attention from scientific researchers. Epoxy compounds are key intermediates in the synthesis of pesticides and medicines. Usually, carbonyl compounds react with s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/12C07C319/20C07C323/20C07D301/02C07D303/04
CPCC07C381/12C07C319/20C07D301/02C07D303/04C07C323/20
Inventor 杜晓华时亮
Owner ZHEJIANG UNIV OF TECH