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Preparation and refining method of 4-Cl-(trifluoromethyl) benzene sulfonyl chloride

A technology of trifluoromethyl and benzenesulfonyl chloride is applied in the preparation of sulfonic acid, the preparation of organic compounds, chemical instruments and methods, etc., which can solve the problems of low reaction yield, air pollution, high price, etc., and improve the reaction yield. efficiency, reducing environmental pollution, and reducing production risks

Inactive Publication Date: 2012-02-01
天津均凯农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, the traditional preparation method of 4-chloro-3-(trifluoromethyl)benzenesulfonyl chloride usually adopts in China: (1) obtain by reacting o-chlorobenzotrifluoride and chlorosulfonic acid, but the reaction yield is low, chlorine Sulfonic acid Chlorosulfonic acid excess of 500% or more; (2) obtained by reacting 4-chloro-3-(trifluoromethyl)benzenesulfonic acid with thionyl chloride or phosphorus pentachloride or phosphorus oxychloride, 4-chloro -3-(trifluoromethyl)benzenesulfonic acid is not easy to obtain, and the price is expensive; (3) 4-chloro-3-(trifluoromethyl)thiophenol is obtained by reacting with chlorine gas and water in dichloromethane, but replacing The price of thiophenol is expensive, and the smell is very strong, and the air pollution is serious

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1.25 kg of o-chlorobenzotrifluoride, lower the temperature to below 10°C, add mixed acid dropwise, and raise the temperature to about 40°C to react after the dropwise addition. After the basic reaction of the raw materials is complete, let it stand, separate layers, take the organic phase, wash with water, and take the organic phase, which is 2-chloro-5-nitrobenzotrifluoride, which is directly used in the next step reaction.

[0026] Mixed acid configuration: Slowly add 0.43 kg of 95% nitric acid to 0.67 kg of 98% sulfuric acid at low temperature, stir evenly and cool down for later use

Embodiment 2

[0028] Add 1.25 kg of o-chlorobenzotrifluoride, 3.1 kg of acetic anhydride, and add 1.5 kg of copper nitrate in batches. After the addition, react at room temperature until the basic reaction of the raw materials is complete. Pour the reaction solution into 6 kg of crushed ice, stir, and layer , take the organic phase, and take the organic phase after washing with water, which is 2-chloro-5-nitrobenzotrifluoride, which is directly used in the next step reaction.

[0029] Preparation of the second part 4-chloro-3-(trifluoromethyl)aniline

Embodiment 3

[0031] Add 1.7 kg of iron powder, 3 kg of ethanol, and 1.4 kg of water into the reaction kettle, stir to raise the temperature to about 45°C, add 0.81 kg of concentrated hydrochloric acid, raise the temperature to 60°C to 70°C, and slowly add the above-mentioned 2-chloro-5-nitrotri Fluorotoluene solution, after the basic reaction of the raw materials is complete, adjust the reaction pH to 9 with sodium hydroxide, filter while it is hot, rinse the filter cake with a small amount of ethanol, leave the filtrate to separate layers, take the organic phase, and extract the water phase with toluene until it is free product so far,

[0032] After drying the product with anhydrous sodium sulfate, filter and distill off the toluene to obtain 0.66 kg of the product as light yellow liquid 4-chloro-3-(trifluoromethyl)aniline, the yield is 55%.

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PUM

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Abstract

The invention provides a preparation and refining method of 4-Cl-(trifluoromethyl) benzene sulfonyl chloride, which comprises the following steps of: reacting o-chloro benzo trifluoride and mixed acid to generate 2-Cl-5-nitro trifluoromethyl benzene, reducing to obtain 2-Cl-5-amino trifluoromethyl benzene, generating diazo salt with sodium nitride and hydrochloric acid in a polar solvent at a low temperature, reacting with sulfur dioxide and cuprous chloride in the polar solvent at a low temperature to generate rough 4-Cl-(trifluoromethyl) benzene sulfonyl chloride, distilling and recrystallizing to obtain a pure product. The invention has the characteristics that the reaction yield is improved, production danger is lowered, environment pollution is reduced, and the quality of the refined fine product is improved on the basis of improving the yield.

Description

technical field [0001] The invention belongs to the preparation method of 4-chloro-3-(trifluoromethyl)benzenesulfonyl chloride, which is an important intermediate for synthesizing fine chemicals such as pesticides, medicines and dyes. At the same time, it can also carry out hydrolysis, amination and other reactions, so as to regenerate a series of new compounds with biological activity and multiple uses. Background technique [0002] At present, the traditional preparation method of 4-chloro-3-(trifluoromethyl)benzenesulfonyl chloride usually adopts in China: (1) obtain by reacting o-chlorobenzotrifluoride and chlorosulfonic acid, but the reaction yield is low, chlorine Sulfonic acid Chlorosulfonic acid excess of 500% or more; (2) obtained by reacting 4-chloro-3-(trifluoromethyl)benzenesulfonic acid with thionyl chloride or phosphorus pentachloride or phosphorus oxychloride, 4-chloro -3-(trifluoromethyl)benzenesulfonic acid is not easy to obtain, and the price is expensive;...

Claims

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Application Information

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IPC IPC(8): C07C309/86C07C303/02C07C303/44
Inventor 尚振华栗晓东张慧丽
Owner 天津均凯农业科技有限公司
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