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Method for preparing 4,4'-dichloro sulfobenzide

A technology of dichlorodiphenyl sulfone and dichlorodiphenyl sulfoxide, which is applied in the field of preparing 4,4'-dichlorodiphenyl sulfone, can solve the problems of complex process, harm to production equipment, serious equipment corrosion and the like

Active Publication Date: 2017-01-25
江西金海新能源科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The sulfuric acid method has simple raw materials, low production cost, and can be continuous, but the reaction temperature is high, the reaction time is long, the equipment is severely corroded, the product quality is unstable, and the yield is low
[0008] The preparation of DCDPS by the sulfur trioxide method is an improved method. It is reported that the UCC company of the United States adopts this method. It uses sulfur trioxide sulfonation and thionyl chloride acyl chloride route. The process is relatively complicated and involves strong corrosion, strong acid and harmful gases. It is a potential huge hazard to both production equipment and human body
Among them, the oxidation of 4,4'-dichlorodiphenyl sulfoxide to 4,4'-dichlorodiphenyl sulfone generally uses glacial acetic acid and hydrogen peroxide for the oxidation reaction, but the existing technology still has the final product separation and purification and catalytic Difficulties in technical operation such as system reuse, low oxidation efficiency, and a large amount of waste liquid will be produced to pollute the environment

Method used

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  • Method for preparing 4,4'-dichloro sulfobenzide
  • Method for preparing 4,4'-dichloro sulfobenzide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Take 27.12 g (0.1 mol) of 4,4'-dichlorodiphenyl sulfoxide and dissolve it in 30 mL of dichloropropane and 5 mL of glacial acetic acid, add dropwise 4.0 g of catalyst sulfuric acid with a mass fraction of 50%, and heat at 70 °C Add 15 mL of 30% hydrogen peroxide dropwise, stir and react for 90 minutes, then let it stand to cool to room temperature, filter and separate the solid, wash the solid with a small amount of water, separate the filtrate, take the lower organic layer and concentrate, recover the solvent, crystallize and separate, and combine The solid was dried to obtain 26.8 g of 4,4'-dichlorodiphenyl sulfone, the product yield was 93.2%, the melting point was 147-149°C, and the chromatographic content was 99.3%. The upper layer is an aqueous solution of sulfuric acid and glacial acetic acid, which is recovered for next use.

Embodiment 2

[0022] Take 27.12 g (0.1 mol) of 4,4'-dichlorodiphenyl sulfoxide and dissolve it in 30 mL of dichloropropane and 5 mL of glacial acetic acid, add 6.0 g of catalyst sulfuric acid with a mass fraction of 50% dropwise, and heat at 80 °C Add 10 mL of 40% hydrogen peroxide dropwise, stir and react for 100 minutes, then let stand to cool to room temperature, filter and separate the solid, wash the solid with a small amount of water, separate the filtrate, take the lower organic layer and concentrate, recover the solvent, crystallize and separate, combine The solid was dried to obtain 27.8 g of 4,4'-dichlorodiphenyl sulfone, the product yield was 96.8%, the melting point was 147-149°C, and the chromatographic content was 99.8%. The upper layer is an aqueous solution of sulfuric acid and glacial acetic acid, which is recovered for next use.

Embodiment 3

[0024] Take 271.2 g (1.0 mol) of 4,4'-dichlorodiphenylsulfoxide and dissolve it in 250 mL of dichloropropane and 50 mL of glacial acetic acid, add 60 g of catalyst sulfuric acid with a mass fraction of 50%, and drop it at 80 °C Add 150 mL of 30% hydrogen peroxide, stir and react for 120 minutes, then let it stand to cool to room temperature, filter and separate the solid, wash the solid with a small amount of water, separate the filtrate, take the lower organic layer and concentrate, recover the solvent, crystallize and separate, and combine the solid And dried to obtain 277.1 g of 4,4'-dichlorodiphenyl sulfone, the product yield was 96.5%, the melting point was 147-149°C, and the chromatographic content was 99.7%. The lower layer of the solution is an aqueous solution of sulfuric acid and glacial acetic acid, which is recovered for next use.

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Abstract

The invention discloses a method for preparing 4,4'-dichloro sulfobenzide. 4,4'-dichloro diphenyl sulfoxide is taken as a raw material, sulfuric acid is taken as a catalyst and propylene dichloride and glacial acetic acid are taken as solvents. Under the reaction temperature at 60-90 DEG C, hydrogen peroxide is taken as an oxidizing agent and is used for oxidizing 4,4'-dichloro diphenyl sulfoxide and preparing 4,4'-dichloro sulfobenzide, wherein the concentration of hydrogen peroxide is 30%-50% and the dosage of the catalyst sulfuric acid is 6%-12% of the quantity of 4,4'-dichloro diphenyl sulfoxide, the dosage of the dissolvent propylene dichloride is 80%-120% of the quantity of 4,4'-dichloro diphenyl sulfoxide, the dosage of the glacial acetic acid is 15%-20% of the quantity of 4,4'-dichloro diphenyl sulfoxide and the reaction time is 90-120 minutes. The method provided by the invention has the advantages of mild reaction condition, high reaction yield, high catalytic efficiency and recoverable catalytic system and reaction solvent.

Description

[0001] Technical field: [0002] The invention relates to the field of organic chemical synthesis, in particular to a method for preparing 4,4'-dichlorodiphenyl sulfone. [0003] Background technique: [0004] 4,4'-dichlorodiphenyl sulfone (DCDPS), is an important organic chemical synthesis product, white crystal, sublimable, easily soluble in benzene, chlorobenzene, dimethylformamide and other organic solvents, slightly soluble in ethanol , Methanol, insoluble in water, its flash point is 233°C, and its boiling point is 397°C. 4,4'-dichlorodiphenyl sulfone is an important organic synthesis product. It is the main raw material for the preparation of engineering plastics such as polysulfone and polyethersulfone. It is also an intermediate for medicine, fuel and pesticides. It can be used for the preparation of leprosy drugs Intermediates such as 4,4'-diaminodiphenylsulfone are widely used in the fields of engineering plastics and fine chemicals. With the wide application of su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/02C07C317/14
CPCY02P20/584C07C315/02C07C317/14
Inventor 刘万云霍平李太菲熊知行陈辉丁玉堂陈建平万少华
Owner 江西金海新能源科技有限公司
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