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Method used for preparing 2, 4, 6-trichloroaniline

A technology of trichloroaniline and chlorine, which is applied in the preparation of amino compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high risk and low yield, etc., and achieves simple post-processing operation, mild reaction conditions, and ease of use. The effect of industrialization

Active Publication Date: 2014-12-24
INSIGHT HIGH TECH JIANGSU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation method is carried out in the organic solvent acetic acid, the risk is relatively high, and the yield is not high due to the production of a large number of by-products

Method used

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  • Method used for preparing 2, 4, 6-trichloroaniline
  • Method used for preparing 2, 4, 6-trichloroaniline

Examples

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Embodiment 1

[0021] Add 137.1g (1.0mol) anthranilic acid and 1000.0g of 20% hydrochloric acid to a 2000ml reaction flask, react with chlorine gas at 25°C, and react with chlorine gas for 15h. After the reaction is over, stop the chlorine gas; add 10% hydroxide while stirring The sodium solution adjusted the pH of the reaction solution to 7, and filtered to obtain 2,4,6-trichloroaniline, namely compound II, 157.2g (0.80mol), HPLC content 99.1%, yield 80.0%.

Embodiment 2

[0023] In a 2000ml reaction flask, add 137.1g (1.0mol) anthranilic acid, 10% hydrochloric acid 1371.0g, react with chlorine at -5°C, react with chlorine for 30h, after the reaction is over, stop the introduction of chlorine; add 30% hydrogen with stirring The pH of the reaction solution was adjusted to 7 with sodium oxide solution, and 2,4,6-trichloroaniline was filtered to obtain compound II, 176.8g (0.90mol), HPLC content 98.6%, yield 90.0%.

Embodiment 3

[0025] Add 137.1g (1.0mol) anthranilic acid, 685.5g of 30% hydrochloric acid to a 1000ml reaction flask, react with chlorine gas at 30℃, and react with chlorine gas for 10 hours. After the reaction is complete, stop the introduction of chlorine gas; add 20% hydroxide while stirring The sodium solution adjusted the pH of the reaction solution to 7, and filtered to obtain 2,4,6-trichloroaniline, namely compound II, 167.0g (0.85mol), HPLC content 98.5%, yield 85.0%.

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Abstract

The invention discloses a preparation method of 2, 4, 6-trichloroaniline which can be used as raw material of azo dyes, pesticides, bactericides, herbicides, basic fuchsin coupling agent used for photographing, and the like. According to the preparation method, anthranilic acid is taken as a raw material, one-step chlorination process is adopted, and a reaction solvent and chlorine are added so as to obtain the target product. The preparation method is capable of realizing direct substitution of carboxyl by chlorine, and reaction in hydrochloric acid system; reaction conditions are mild; operation is simple; and the preparation method is safer than a preparation method, in which the target product is prepared via chlorination of 4-aminobenzoic acid in acetate system, and possesses higher industrial amplification value.

Description

Technical field [0001] The invention relates to a method for preparing chemical intermediate 2,4,6-trichloroaniline. Background technique [0002] 2,4,6-Trichloroaniline is an important organic synthesis intermediate, which can be used as a raw material for azo dyes, insecticides, fungicides, herbicides, and basic fuchsin coupling agents for photography. [0003] Regarding the synthesis of 2,4,6-trichloroaniline, the literature Recueil des Travaux Chimiques des Pays-Bas; vol. 44; (1925); p. 1108; reported that p-aminobenzoic acid was used as a raw material, at 20 ℃ in acetic acid Chlorine reaction in the system, the reaction process is shown in the following formula: [0004] [0005] Ⅰp-aminobenzoic acid Ⅱ2,4,6-triaminoaniline [0006] In this method, p-aminobenzoic acid (formula I) and chlorine undergo a substitution reaction in an acetic acid solvent system to obtain 2,4,6-triaminoaniline (formula II), which is a byproduct of 3,5-dichloro-4- Aminobenzoic acid. After treatment an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/52C07C209/74
Inventor 吴国平孙贤袁忠华范明黄玲胡圣祥罗必奎
Owner INSIGHT HIGH TECH JIANGSU CO LTD