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Preparation method of 3-trifluoromethyl phenylacetonitrile

A technology of trifluoromethyl phenylacetonitrile and trifluoromethylation, which is applied in the field of preparation of m-trifluoromethyl phenylacetonitrile, can solve unsafe, clean production, low reaction yield, a large amount of waste sulfuric acid, fluorine-containing side effects Products and other issues, to achieve the effect of high yield, high product content, and less three wastes

Active Publication Date: 2015-03-25
SHANGHAI HETENG FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method will produce a large amount of waste sulfuric acid and fluorine-containing by-products, and the reaction yield is low, which is not suitable for the current safe and clean production requirements

Method used

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  • Preparation method of 3-trifluoromethyl phenylacetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 33 grams (0.25 moles) of p-aminophenylacetonitrile, 45 grams (0.5 moles) of tert-butyl hydroperoxide and 78 grams (0.5 moles) of sodium trifluoromethanesulfinate were added to the reaction flask at room temperature and stirred for 4 hours. Add 500 milliliters of water and 200 milliliters of ethyl acetate to the reaction product, stir and separate layers, and the oil layer is the ethyl acetate solution of the intermediate 3-trifluoromethyl-4-aminophenylacetonitrile. After concentrating the ethyl acetate solution of 3-trifluoromethyl-4-aminophenylacetonitrile solvent, add 100 ml of water and 62.5 g (0.625 moles) of 98% concentrated sulfuric acid, cool to 0°C, keep warm at -2-5°C and drop Add 129.4 g (0.375 mol) of 20% sodium nitrite aqueous solution to carry out diazotization reaction, and stir for 30 minutes after the dropwise addition, and the prepared diazonium salt mixture is used for the next reaction.

[0021] Add 66 g (0.5 moles) of 50% hypophosphorous acid dropwis...

Embodiment 2

[0023] 33 grams (0.25 moles) of p-aminophenylacetonitrile, 112.5 grams (1.25 moles) of tert-butyl hydroperoxide and 195 grams (1.25 moles) of sodium trifluoromethanesulfinate were added to the reaction flask at room temperature and stirred for 2.5 hours, Add 1500 milliliters of water and 200 milliliters of ethyl acetate to the reaction product, stir and separate layers, and the oil layer is the ethyl acetate solution of the intermediate 3-trifluoromethyl-4-aminophenylacetonitrile. After concentrating the ethyl acetate solution of 3-trifluoromethyl-4-aminophenylacetonitrile solvent, add 200 ml of water and 125 g (1.25 moles) of 98% concentrated sulfuric acid, cool to 0°C, keep warm at -2-5°C and drop Add 172.5 g (0.5 moles) of 20% sodium nitrite aqueous solution to carry out diazotization reaction, and stir for 30 minutes after the dropwise addition, and the prepared diazonium salt mixture is used for the next reaction.

[0024] Add 165 g (1.25 moles) of 50% hypophosphorous aci...

Embodiment 3

[0026] Add 33 grams (0.25 moles) of p-aminophenylacetonitrile, 22.5 grams (0.25 moles) of tert-butyl hydroperoxide and 39 grams (0.25 moles) of sodium trifluoromethanesulfinate into the reaction flask and stir at 55-60°C for reaction After 2 hours, 400 milliliters of water and 200 milliliters of ethyl acetate were added to the reaction product, and the layers were stirred and separated. The oil layer was the ethyl acetate solution of the intermediate 3-trifluoromethyl-4-aminophenylacetonitrile. Concentrate the ethyl acetate solution of 3-trifluoromethyl-4-aminophenylacetonitrile solvent, add 100 ml of water and 50 g (0.5 moles) of 98% concentrated sulfuric acid, cool to 0°C, keep warm at 10-20°C and add dropwise 86.25 g (0.25 mole) of 20% sodium nitrite aqueous solution was subjected to diazotization reaction, and the dropwise addition was completed and stirred for 30 minutes, and the prepared diazonium salt mixture was used for the next reaction.

[0027] Add 33 grams (0.25 m...

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Abstract

The invention relates to a preparation method of 3-trifluoromethyl phenylacetonitrile. According to the preparation method, aminobenzyl cyanide is taken as a raw material and has a trifluoromethylation reaction, a diazotization reaction and a reduction reaction sequentially to prepare 3-trifluoromethyl phenylacetonitrile. The preparation method has a reasonable process, high yield and few side effects and is applicable to industrial production.

Description

technical field [0001] The invention relates to chemical products, in particular to a preparation method of m-trifluoromethyl benzyl nitrile. Background technique [0002] m-Trifluoromethyl benzyl nitrile is a kind of pesticide and pharmaceutical intermediate, and there are some reports in domestic and foreign open technologies. [0003] 1), US4144265 discloses a kind of preparation method of m-trifluoromethyl benzyl nitrile, is to take benzotrifluoride, chloromethyl methyl ether and chlorosulfonic acid as raw material to first synthesize m-trifluoromethyl chlorobenzyl, then m-trifluoromethyl The reaction between methyl chloride and sodium cyanide synthesizes m-trifluoromethyl benzyl acetonitrile. In this method, the raw material chloromethyl methyl ether is a strong carcinogen, chlorosulfonic acid is a highly corrosive dangerous product, and sodium cyanide is a highly toxic dangerous product, so it is not suitable for large-scale production. [0004] 2), DE3717434 disclos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/35
Inventor 施冠成孟海成秦爱忠
Owner SHANGHAI HETENG FINE CHEM
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