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Synthesis process of 4, 4'-dichlorodiphenyl sulfone

A technique for the synthesis of dichlorodiphenyl sulfone, which is applied in the field of synthesis of 4,4'-dichlorodiphenyl sulfone, can solve the problems of low cost of sulfuric acid process, low melting point of products, high production cost, and easy post-processing , low cost, less impurities

Active Publication Date: 2015-03-11
SHANDONG KAISHENG NEW MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sulfuric acid method has low cost and simple raw materials, but the conversion rate is low, the reaction time is long, the melting point of the product is low, and the quality is not good
The chlorosulfonic acid process is relatively mature, and the product quality is good, but the production cost is high and the three wastes are serious
The preparation of DDS by sulfur trioxide method is an improved method. It is reported that UCC Company of the United States adopts this method. It uses sulfur trioxide sulfonation and thionyl chloride acyl chloride route, and the process is relatively complicated.

Method used

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  • Synthesis process of 4, 4'-dichlorodiphenyl sulfone
  • Synthesis process of 4, 4'-dichlorodiphenyl sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] First add 112.5 g of chlorobenzene into the four-neck flask, then add 26.7 g of anhydrous aluminum trichloride, stir well, then add 23.8 g of thionyl chloride dropwise, the reaction is exothermic, and the temperature is controlled at 30°C. After adding the thionyl chloride dropwise, keep stirring for 1 hour. After the reaction, the temperature is lowered to 15°C for hydrolysis, and the heat is released by hydrolysis. The temperature is controlled at 45°C. After 0.5h, the hydrolysis was completed, the temperature was raised to 100°C, and the temperature was kept at reflux for 0.5h, then the temperature was lowered and cooled to 15°C, and the solid was filtered to obtain 51.2g of 4,4'-dichlorodiphenylsulfoxide. Heat to dissolve with glacial acetic acid, add hydrogen peroxide dropwise to oxidize at 60°C, keep warm and oxidize for 2 hours, cool down and filter to obtain 51.9g of 4,4'-dichlorodiphenylsulfone, the chromatographic content is 99.2%, and the yield is 90.4%.

Embodiment 2

[0024] First add 150 g of chlorobenzene into the four-neck flask, then add 26.7 g of anhydrous aluminum trichloride, stir well, then add 25 g of thionyl chloride dropwise, the reaction is exothermic, and the temperature is controlled at 27°C. After adding the thionyl chloride dropwise, keep stirring for 2 hours. After the reaction, the temperature is lowered to 15°C for hydrolysis, and the heat is released from the hydrolysis. The temperature is controlled at 30°C. After 1 hour, the hydrolysis was completed, the temperature was raised to 110°C, and the temperature was kept at reflux for 1 hour, then the temperature was lowered and cooled to 20°C, and 52.3 g of 4,4'-dichlorodiphenylsulfoxide was obtained by filtration. Heat to dissolve with glacial acetic acid, add hydrogen peroxide dropwise to oxidize at 80°C, keep warm and oxidize for 1 hour, cool down and filter to obtain 52.4g of 4,4'-dichlorodiphenylsulfone, the chromatographic content is 99.4%, and the yield is 91.0%.

Embodiment 3

[0026] First add 198g of chlorobenzene into the four-neck flask, then add 26.7g of anhydrous aluminum trichloride, stir well, then add 26.2g of thionyl chloride dropwise, the reaction exotherms, and the temperature is controlled at 23°C. After adding the thionyl chloride dropwise, keep stirring for 1.5 hours. After the reaction, the temperature is lowered to 15°C for hydrolysis, and the heat is released from the hydrolysis. The temperature is controlled at 20°C. After 1.5 hours, the hydrolysis was completed, the temperature was raised to 120°C, and the temperature was kept at reflux for 1 hour, then the temperature was lowered and cooled to 25°C, and 51.9 g of 4,4'-dichlorodiphenylsulfoxide was obtained by filtration. Heat to dissolve with glacial acetic acid, add hydrogen peroxide dropwise to oxidize at 70°C, keep warm and oxidize for 1 hour, cool down and filter to obtain 51.8g of 4,4'-dichlorodiphenylsulfone, the chromatographic content is 99.7%, and the yield is 90.2%.

[...

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Abstract

The invention belongs to the field of organic synthesis, and in particular relates to a synthesis process of 4, 4'-dichlorodiphenyl sulfone. The synthesis process comprises the following steps: firstly, performing a Friedel-Crafts reaction on sulfoxide chloride and chlorobenzene under the action of a catalyst; cooling and hydrolyzing -after the reaction; heating and dissolving ; cooling, separating out crystals and filtering so as to obtain 4, 4'-dichlorodiphenyl sulfoxide; dissolving 4, 4'-dichlorodiphenyl sulfoxide in glacial acetic acid, adding hydrogen peroxide for an oxidizing reaction; lowering the temperature and cooling after the reaction is completed, and filtering so as to obtain 4, 4'-dichlorodiphenyl sulfone. Chlorobenzene is used both as a reaction material and a solvent, and other solvent impurities are not mixed in chlorobenzene, so that after-treatment is easier when the cost is saved, and the product is high in purity. The synthesis process has the advantages of simple process, low cost and few impurities. The obtained product has high purity and has the content of above 99.2% and the yield of above 90%, so that the product is good in economic benefit and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis process of 4,4'-dichlorodiphenyl sulfone. Background technique [0002] 4,4'-Dichlorodiphenylsulfone (DDS) is an important organic synthesis product, the main raw material for the preparation of engineering plastics such as polysulfone and polyethersulfone, and an intermediate for medicine, dyes and pesticides. It can be used to prepare a variety of polymer products, such as resins such as bisphenol A polysulfone, polyphenylene ether sulfone, and polyamide sulfone, and can also be used to prepare 4,4'-diaminodiphenylsulfone, an intermediate of leprosy medicine. With the wide application of polymer materials, the demand for DDS is also increasing. [0003] There are many ways to produce DDS in industry, mainly including sulfuric acid method, chlorosulfonic acid method, sulfur trioxide method and sulfoxide oxidation method. The sulfuric acid method has low...

Claims

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Application Information

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IPC IPC(8): C07C317/14C07C315/02
Inventor 杨德耀宋国城张泰铭毕义霞张善民薛居强张聪聪谢圣斌
Owner SHANDONG KAISHENG NEW MATERIALS
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