Synthesis process of tolylsulfonyl chloride

A technology of toluenesulfonyl chloride and a new method, applied in the field of toluenesulfonyl chloride synthesis, can solve the problems of large amount of chlorosulfonic acid, large amount of thionyl chloride, low yield, etc., and achieve the effects of high product yield and low amount

Inactive Publication Date: 2003-08-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In above method (3) method thionyl chloride consumption is big, uneconomical; Other methods then yield is not high, and the consumption of chlorosulfonic acid is big, produces a large amount of acid waste water after excessive chlorosulfonic acid hydrolysis, becomes the pollution source of atmosphere, needs control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0007] The new preparation method of toluenesulfonyl chloride: take 1.0 mole of toluene as raw material, react under the action of sulfonating agent chlorosulfonic acid 1.0-2.0 mole, phosphorus oxychloride 0.3-0.8 mole, sulfonation auxiliary agent 0.03-0.2 mole, react The pressure is normal pressure, the reaction temperature is 10-110° C., and the reaction time is 2.0-7.0 hours. After the reaction is over, the reaction solution is cooled, hydrolyzed at low temperature, extracted with solvent oil, washed with water, and the water phase is separated. The oil phase is crystallized at 0-5°C, filtered, and the solid is dried to obtain p-toluenesulfonyl chloride; the filtrate is decompressed After distillation, the solvent oil is evaporated, and the sulfonated oil based on o-toluenesulfonyl chloride can be obtained.

[0008] The sulfonation aid is one of ammonium chloride, ammonium sulfate, sulfamic acid or their mixture, and its dosage is 0.01-0.2 moles.

Embodiment 1

[0010] Add 163.2 parts of chlorosulfonic acid in the 500ml four-neck flask with agitator, thermometer, waste gas outlet and feeding port, add sulfonation aid (a kind of in ammonium chloride, ammonium sulfate, sulfamic acid) under stirring Or their mixture, hereinafter the same) 10 parts, add dropwise 92 parts of toluene, after the addition, the temperature is raised to 75°C, 100 parts of phosphorus oxychloride is added dropwise, the temperature is raised to 110°C, and the reaction is carried out at constant temperature for 6 hours. After the reaction, the reaction solution was cooled to 20°C, hydrolyzed at low temperature, extracted with solvent oil, washed with water, and the water layer was separated. The oil layer was crystallized and filtered at 0-5°C, and the solid was dried to obtain 163.39 g of p-toluenesulfonyl chloride, with a purity of 99.61%. 26.2g, the purity of toluenesulfonyl chloride is 95.39%. The overall yield was 98.8% (P / O=88 / 12).

Embodiment 2

[0012] Add 152.0 parts of chlorosulfonic acid in the 500ml four-necked flask that has agitator, thermometer, waste gas outlet and feeding port, add sulfonation auxiliary agent (a kind of in ammonium chloride, ammonium sulfate, sulfamic acid) under stirring Or their mixture, hereinafter the same) 12 parts, add dropwise 92 parts of toluene, after the addition, the temperature is raised to 75°C, 92 parts of phosphorus oxychloride is added dropwise, the temperature is raised to 110°C, and the reaction is carried out at constant temperature for 6 hours. After the reaction, the reaction solution was cooled to 20°C, hydrolyzed at low temperature, extracted with solvent oil, washed with water, and the water layer was separated. The oil layer was crystallized and filtered at 0-5°C, and the solid was dried to obtain 127.2 g of p-toluenesulfonyl chloride with a purity of 99.17%. 48.8g, the purity of tosyl chloride is 92.42%. The overall yield was 92.07% (P / O=80 / 20).

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Abstract

The present invention is the new synthesis process of tolylsulfonyl chloride with toluene as material, chlorosulfonic acid and phosphorus oxychlorides as sulfonating agent and inorganic ammonium slat as sulfonating assistant. Under the action of sulfonating agent chlorosulfonic acid and phosphorus oxychloride and sulfonating assistant, the material toluene is sulfochlorinated to produce the reacted liquid; and the reacted liquid is made to pass through low temperature hydrolysis, solvent extraction, water washing, eliminating water layer, crystallization of the oil phase at temperature lower than 5 deg.c, filtering and drying to obtain solid tolylsulfonyl chloride. The filtrate is decompression distilled to eliminate solvent to obtain sulfonated oil with o-tolylsulfonyl chloride as main component with total yield as high as 98.8%.

Description

technical field [0001] The invention relates to a new method for synthesizing toluenesulfonyl chloride. Background technique [0002] The p-toluenesulfonyl chloride and o-toluenesulfonyl chloride produced by the chlorosulfonation reaction of toluene are important fine chemical products, important intermediates in the pharmaceutical, dye, pigment, and plastic additive industries, and have a wide range of uses. [0003] Toluenesulfonyl chloride is generally obtained by chlorosulfonation of toluene and chlorosulfonic acid, but the amount of chlorosulfonic acid is large and the yield is low. In order to improve the above shortcomings, a lot of research has been carried out at home and abroad such as: 1) US 3.686.300 and CN.1163264, the method of adding sulfonation auxiliary inorganic salt with toluene and chlorosulfonic acid; The method of concentrated sulfuric acid and phosphorus oxychloride; 3) EP 04039422 uses the method of toluene, chlorosulfonic acid to add thionyl chlorid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/02C07C309/86
Inventor 陈钟秀丁同富
Owner ZHEJIANG UNIV
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