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Method for preparing paratoluensulfonyl chloride

A technology of p-toluenesulfonyl chloride and ammonium p-toluenesulfonate, which is applied in the field of preparation of p-toluenesulfonyl chloride, can solve problems such as complicated separation steps, unsafe use, and impact on product quality, and achieves convenient and easy-to-obtain raw materials and mild reaction conditions , The effect of simple purification method

Active Publication Date: 2012-04-11
SINOCHEM LANTIAN +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of these methods is: (1) thionyl chloride method can produce the sulfur dioxide by-product of polluting environment and the raw material cost of thionyl chloride is higher; Safety; (3) by-product phosphorous acid or phosphoric acid generated by phosphorus oxychloride method or phosphorus oxychloride method is difficult to remove, affecting product quality
The separation steps are more complex

Method used

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  • Method for preparing paratoluensulfonyl chloride
  • Method for preparing paratoluensulfonyl chloride
  • Method for preparing paratoluensulfonyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The reactor is a three-necked flask with a volume of 250ml, equipped with a thermometer, mechanical stirring, reflux condenser and drying tube. 18.9 g of ammonium p-toluenesulfonate (100 mmol), 0.73 g of N,N-dimethylformamide (10 mmol) and 50 g of dichloroethane were added to the flask at one time. Stirring was started, and at room temperature, the dichloroethane solution (which contained 10 g triphosgene (34 mmol), 50 g of dichloroethane) dissolved with triphosgene was slowly and uniformly added dropwise to the reaction flask, and the dropping time was 30 min. After adding, keep warm for 30min. After heat preservation, the temperature was raised until obvious reflux phenomenon appeared in the system, and the reaction was maintained under reflux conditions for three hours. After the reaction liquid is cooled, the filter cake ammonium chloride is removed by filtration, and the obtained filtrate is subjected to vacuum distillation operation. After recovering 92g of dichl...

Embodiment 2～7

[0031] The type and amount of the organic base catalyst were changed, and other reaction conditions and raw material dosage were the same as in Example 1. The experimental results are shown in Table 1 below:

[0032] Table 1

[0033]

[0034]

[0035]As can be seen from the results in Table 1, the use of different types of organic amines as catalysts can obtain better experimental results, and if the amount of catalyst is large, the yield of p-toluenesulfonyl chloride is slightly higher, but there is no great impact on product purity.

Embodiment 8～13

[0037] Using N,N-diethylacetamide as the organic amine, changing the type and amount of solvent used in the reaction, distilling the filtrate after the reaction to recover 92% of the organic solvent, and then proceeding to the crystallization operation. Other reaction conditions and raw material charging amount are identical with embodiment 1. The experimental results are shown in Table 2 below:

[0038] Table 2

[0039]

[0040] As can be seen from the results in Table 2, the use of different types of inert organic solvents can obtain better experimental results, but when using chloroform as a solvent, the p-toluenesulfonyl chloride crystalline purity obtained is slightly lower, and is obtained in ethyl acetate and The product in petroleum ether has good crystallization performance and the obtained product has high purity.

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Abstract

The invention discloses a method for preparing paratoluensulfonyl chloride, which comprises the following step of: reacting paratoluenesulfonic acid ammonium salt with bis(trichloromethyl) carbonate (commonly called triphosgene) in an inert organic solvent under the condition that organic alkali is used as a catalyst to synthesize the paratoluensulfonyl chloride. The preparation method has the advantages that: raw materials are conveniently and readily available, the process is simple and suitable for scale-up production, reaction conditions are mild, and a product is easy to purify. The prepared paratoluensulfonyl chloride is an important fine chemical product and can be used for preparing a dye intermediate, synthesizing intermediates of more than ten kinds of antibacterial medicines and anti-inflammatory medicines such as betamethasone, sulfamylon and the like and synthesizing plastic plasticizers, resin, coatings, pesticides and light-sensitive materials.

Description

technical field [0001] The invention relates to a preparation method of p-toluenesulfonyl chloride. Background technique [0002] p-toluenesulfonyl chloride, that is, 4-methylsulfonyl chloride, the English name is 4-toluene sulfonyl chloride, the CAS number is 98-59-9, and the molecular formula is C 7 h 7 ClO 2 S, the molecular weight is 190.65, the melting point is 69-71°C, and the boiling point is 145°C / 2.0kPa. P-toluenesulfonyl chloride is an important fine chemical product, which is widely used in the dye and pharmaceutical industries. It can be used as a basic raw material for the preparation of ice dyes, disperse dyes and intermediates of organic pigments. It is an important organic synthetic drug raw material, mainly used in the synthesis of chloramphenicol, chloramine-T, thiamphenicol and other drugs. In the pharmaceutical industry, it is used as an intermediate for the synthesis of more than ten kinds of antibacterial and anti-inflammatory drugs such as betamet...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02
Inventor 李华徐卫国杨箭
Owner SINOCHEM LANTIAN
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