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Process for preparing o-trifluoromethyl aniline

A technology of trifluoromethylaniline and trifluoromethylbenzene, which is applied in the field of hydrogenolysis dechlorination technology and the preparation of o-trifluoromethylaniline, can solve the problems of unavailable raw materials, long synthetic route, poor process technology, etc., and achieve the best results Good, short synthetic route, advanced technology

Active Publication Date: 2005-09-14
ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention solves the technical problems in the prior art that the synthetic route is long, the raw materials are not easy to obtain, and the process technology is not good enough, etc., and provides a convenient, economical and industrialized preparation method for o-trifluoromethylaniline

Method used

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  • Process for preparing o-trifluoromethyl aniline
  • Process for preparing o-trifluoromethyl aniline
  • Process for preparing o-trifluoromethyl aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: In a 1000 ml flask, put 400 g of trifluorotoluene and 10 g of ferric chloride into the flask, keep the reaction temperature at 10-15° C., feed chlorine gas for 9 hours under stirring, and after the reaction is complete, use compressed air to drive out the reaction flask. Residual chlorine and hydrogen chloride gas, filter to remove the catalyst, the filtrate is analyzed by gas chromatography, the content of each component is: 4.8% benzotrifluoride, 72.8% m-chlorobenzotrifluoride, 4.2% o-chlorobenzotrifluoride, 6.2% p-chloro Trifluorotoluene, 12% as polychlorides. The reaction liquid is rectified, and the 120-130°C / 0.04Mpa (vacuum degree) fraction is collected, which is a mixture of ortho, meta and para isomers with m-chlorobenzotrifluoride as the main content.

Embodiment 2-5

[0019] Embodiment 2-5 is the same as embodiment 1.

[0020] Table 1 Quantitative data table of the influence of main reaction conditions on the reaction in the ring chlorination reaction

[0021]

[0022] Nitration of a mixture of m-chlorobenzotrifluoride and its isomers:

[0023] Embodiment 1: In a 1000ml flask, drop into 210g of concentrated sulfuric acid, under cold water cooling, dropwise add 104.4g of fuming nitric acid, and keep the reaction temperature at 10-15°C, add dropwise 270.7g of m-chlorotrifluorotoluene and its iso The mixture of conformers was added dropwise for about 1 hour. After the dropwise addition, react at 45-50°C for 2 hours. After the reaction, the waste acid in the lower layer is separated, and the nitrated product in the upper layer is washed with water and neutralized. The main content of the mixture of various isomers, the content is 79.6%.

[0024] Embodiment 2-5 is the same as embodiment 1.

[0025] Table 2 Quantitative data table ...

Embodiment 2-9

[0029] Embodiment 2-9 is the same as embodiment 1.

[0030] Table 3 Quantitative data table of the influence of main reaction conditions on the reaction in catalytic hydrogenation-hydrogenolysis dechlorination reaction

[0031]

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PUM

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Abstract

This invention is a preparation method of near trifluoromethyl aniline, the material is benzotrifluoride, and it is generated into compound of between chlorine benzotrifluoride and its isomer through circle chlorination reaction. Then the got compound is generated into compound of 2-nitryl-5-chlorine benzotrifluoride and its isomer through nitration. Finally the compound after nitration is proceeded by catalytic hydrogenation-hydrogenolysis dechlorination reaction to generate three isomers compound which is mainly near trifluoromethyl aniline, then pure near trifluoromethyl aniline is got after rectification. The synthesis line is short, technique is advanced, and result is good and easy to be industrial generated.

Description

technical field [0001] The invention relates to a preparation method of a product, in particular to a preparation method of o-trifluoromethylaniline and a hydrogenolysis and dechlorination technology of chlorine atoms on an aromatic ring. Background technique [0002] O-trifluoromethylaniline is an important intermediate in organic synthesis, mainly used in the synthesis of dyes and pesticides. For example, o-trifluoromethylaniline can be used to synthesize acyl dihydroxyphenyl azo dyes, which are used in the dyeing of polyolefins, especially polypropylene fabrics, and can produce strong bright hues, and the color is firm and does not fade. Another example is that o-trifluoromethylaniline can be used to synthesize N-alkyldiphenylamine compounds, which can be used to make genusicides and insecticides. [0003] Regarding the preparation of o-trifluoromethylaniline, Forbes et al. used m-trifluoromethylaniline as a raw material to prepare o-nitrotrifluoromethylaniline through a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/36C07C211/52
Inventor 王千杰
Owner ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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