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Synthesis method of high-purity benzene sulfonyl chloride

A technology of benzenesulfonyl chloride and a synthesis method is applied in the field of synthesis of high-purity benzenesulfonyl chloride, and can solve the problems of low product purity, inability to provide high-purity benzenesulfonyl chloride in a production process, and not being ideal.

Inactive Publication Date: 2019-03-08
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using this production process, the yield of benzenesulfonyl chloride is around 80%, which is not very ideal. A large amount of benzenesulfonic acid is dissolved in the by-product sulfuric acid, resulting in a low conversion rate, and the COD in the by-product sulfuric acid and washing wastewater is too high defects; and in the production process, impurities such as diphenyl sulfone, chlorobenzene, and chlorobenzenesulfonyl chloride will also be produced. These impurities will inevitably be brought into the finished product, resulting in low purity of the product, which cannot meet the requirements of pharmaceutical and electronic chemistry. production needs
[0003] Since the existing production process cannot provide high-purity benzenesulfonyl chloride, it is very meaningful to find a novel synthetic method to obtain high-purity benzenesulfonyl chloride, and the key is to suppress the generation of impurities and fully remove impurities, and finally obtain high-purity benzenesulfonyl chloride product

Method used

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  • Synthesis method of high-purity benzene sulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 800 milliliters of water to 500 grams of benzenesulfonic acid, add dropwise 32% liquid caustic soda to pH~7.5, add 5 grams of activated carbon, heat and reflux for 30 minutes, and suction filter while it is hot; Clear, cool naturally to 15°C to crystallize, filter with suction, and dry in an oven at 125°C to constant weight.

[0026] Add 1 liter of toluene to the solid, add 800 grams of phosphorus pentachloride in batches under stirring, heat and reflux for 5 hours; cool, slowly pour the reaction solution onto crushed ice to extract the reaction, separate the liquids, and wash the organic phase once with water , dried over anhydrous sodium sulfate, concentrated to remove toluene, and distilled under reduced pressure to obtain 380 g of benzenesulfonyl chloride with a purity of 99.6%.

Embodiment 2

[0028] Add 500 grams of benzenesulfonic acid, 80 grams of magnesium oxide and 800 milliliters of water into the reaction flask, heat and reflux for 2 hours; cool to 90 ° C, add 5 grams of activated carbon, heat and reflux for 30 minutes, and suction filter while it is hot; concentrate the filtrate and add 600 Milliliter of ethanol, then heated to dissolve the liquid, cooled naturally to 15°C to crystallize, filtered with suction, and dried in an oven at 125°C to constant weight.

[0029] Cool 1 liter of N,N-dimethylformamide to -5°C, slowly add 560 g of thionyl chloride dropwise, stir for 30 minutes, then add the above dry solid in batches within 1 hour; raise the temperature to 25°C, Stir the reaction for 24 hours, slowly pour the reaction solution onto crushed ice to extract the reaction, extract with chloroform, combine the organic phases and wash with water, dry over anhydrous sodium sulfate, concentrate to remove toluene, and distill under reduced pressure to obtain 482 gr...

Embodiment 3

[0031] Add 500 grams of benzenesulfonic acid, 85 grams of lithium hydroxide and 800 milliliters of isopropanol into the reaction flask, heat and reflux for 2 hours; cool to 50°C, add 5 grams of activated carbon, heat and reflux for 30 minutes, and suction filter while hot; the filtrate is naturally Cool to 10°C to crystallize, filter with suction, and dry in an oven at 125°C to constant weight.

[0032] Add 1 liter of acetonitrile and 20 ml of N,N-dimethylformamide to the solid, add 650 g of phosphorus oxychloride dropwise under reflux, and continue heating to reflux for 5 hours; distill off the acetonitrile, add 1 liter of dichloromethane, Cool with ice water to control the temperature below 20°C, add 600 g of ice water dropwise to extract the reaction, separate the liquid, wash the organic phase once with water, dry with anhydrous sodium sulfate, concentrate to remove toluene, and distill under reduced pressure to obtain 260 g of benzenesulfonyl chloride with a purity of 99.5...

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Abstract

The invention discloses a synthesis method of high-purity benzene sulfonyl chloride. The synthesis method comprises the following steps: firstly, taking benzenesulfonic acid as a raw material and reacting to prepare benzene sulfonate; secondly, purifying the benzene sulfonate synthesized in the first step by using a recrystallization method and removing impurities to obtain the benzene sulfonate;thirdly, enabling the benzene sulfonate purified in the second step to react with a chloride agent in a solvent to obtain the benzene sulfonyl chloride. By adopting the mode, a high-purity benzene sulfonyl chloride product can be prepared by the synthesis method disclosed by the invention; the purity of the benzene sulfonyl chloride product can be up to 99.9 percent and the benzene sulfonyl chloride product can meet the production requirements of pharmaceutical and electronic chemicals.

Description

technical field [0001] The invention relates to the technical field of chemical production, in particular to a method for synthesizing high-purity benzenesulfonyl chloride. Background technique [0002] Sulfonyl chloride products are a class of extremely important organic chemical intermediates, widely used in the production of medicines, pesticides, and dyes, and aromatic sulfonyl chlorides are mostly important intermediates for the production of sulfonamide drugs, dyes, and insecticides. The most in demand is benzenesulfonyl chloride. At present, the production process of benzenesulfonyl chloride is as follows: under the condition of stirring, control the reaction temperature at about 20°C, add benzene dropwise to chlorosulfonic acid, the reaction is complete, cool and drop cold water for hydrolysis, separate the sulfuric acid layer, and wash the organic layer with water; The crude sulfonyl chloride was dehydrated under reduced pressure, and the finished product was obtai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/86C07C303/42
CPCC07C303/02C07C303/42C07C309/86
Inventor 刘明荣陆军刘辉吴志民许佳
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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