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A New Process for the Preparation of p-Toluenesulfonyl Chloride

A technology of methylbenzenesulfonyl chloride and a new process is applied in the field of pesticides to achieve the effects of improving reaction speed and improving safety

Inactive Publication Date: 2011-12-28
ANHUI FENGLE AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far there is no bibliographical report that the crude product sodium p-toluenesulfonate and sulfur oxychloride extracted from industrial waste water are in the toluene solvent that catalyst exists, carry out the process method of chlorination reaction to prepare p-toluenesulfonyl chloride

Method used

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  • A New Process for the Preparation of p-Toluenesulfonyl Chloride

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Embodiment 1

[0006] Embodiment one: a new preparation process of p-toluenesulfonyl chloride, the process uses crude product sodium p-toluenesulfonate as the main raw material to prepare p-toluenesulfonyl chloride through chlorination reaction, and the reaction formula is as follows:

[0007]

[0008] In a 500 ml four-necked flask equipped with a constant pressure funnel, a stirrer and a condenser, add 19.5 grams (100 percent) of crude product sodium p-toluenesulfonate, add 300 ml of toluene, add 1 ml of pyridine, and stir well Afterwards, the temperature was raised to reflux, and 18 grams of thionyl chloride began to be added dropwise from the liquid surface. After dropping, the reflux reaction was continued, and stirring was continued for 1 hour after the reaction solution became clear. After the end of the reaction, change it to a vacuum distillation device, and steam out toluene and pyridine under reduced pressure from the reaction solution (the solvent that is steamed out is directly...

Embodiment 2

[0009] Embodiment two: in the 500 milliliters of four-neck flasks that constant pressure funnel, agitator and condensing pipe are equipped with, add the crude product sodium p-toluenesulfonate of 19.5 grams (100 percent), add solvent 300 milliliters (embodiment one recovery), after stirring evenly, the temperature was raised to reflux, and 17 grams of thionyl chloride began to be added dropwise from the liquid surface. After dropping, the reflux reaction was continued, and the reaction solution continued to stir for 1 hour after the reaction solution became clear. After the reaction is over, change it to a vacuum distillation device, and steam out toluene and pyridine under reduced pressure from the reaction solution (the solvent that is steamed out is directly applied mechanically next time), wash with ice water, and dry to obtain 17.8 grams of product. Sodium acid calculated yield was 93.4%.

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Abstract

The invention provides a new process for the preparation of p-toluenesulfonyl chloride. The process uses crude sodium p-toluenesulfonate extracted from industrial waste water as a raw material, and uses thionyl chloride in a toluene solvent with catalyst pyridine. As a chlorination agent, p-toluenesulfonyl chloride is prepared, which is characterized in that toluene is used as a solvent and pyridine as a catalyst. The process reduces the consumption of thionyl chloride, greatly improves the safety of the reaction operation, accelerates the reaction speed, and the product yield reaches more than 93%.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a new preparation process of p-toluenesulfonyl chloride. Background technique [0002] As a fine chemical product, p-toluenesulfonyl chloride is widely used in the dyestuff, medicine, and pesticide industries. The commonly used synthesis methods are mainly tosylation and sodium toluenesulfonate chlorination. So far, there is no literature report on the process of preparing p-toluenesulfonyl chloride by chlorination of crude product sodium p-toluenesulfonate and thionyl chloride extracted from industrial waste water in toluene solvent in the presence of a catalyst. P-toluenesulfonyl chloride is one of the key raw materials for the synthesis of the herbicide quizalofop and quizalofop-p-ethyl at present, and sodium p-toluenesulfonate is formed after a series of reactions of p-toluenesulfonyl chloride One of the main by-products exists in wastewater, so the COD value ...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02
CPCY02P20/584
Inventor 周康伦赵国平金劲松胡志国凌朵朵陈克付
Owner ANHUI FENGLE AGROCHEM
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