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Synthetic method of 2-chloro-3-phenoxyl-6-nitroaniline

The technology of a nitroaniline and a synthesis method is applied in the field of synthesis of 2-chloro-3-phenoxy-6-nitroaniline, and can solve the problems of difficult types of solvents, many impurities in products, inconvenient industrialized production and operation, and the like, To achieve the effect of simplifying the production process, high yield and reducing varieties

Inactive Publication Date: 2013-08-14
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to obtain a synthetic method with high product purity and yield, solve the problems in the prior art that there are many impurities in the product, and the industrial production operation is inconvenient, and there are many types of solvents that are difficult to recycle. A kind of 2-chloro-3 -The synthetic method of phenoxy group-6-nitroaniline

Method used

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Examples

Experimental program
Comparison scheme
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preparation example Construction

[0011] The invention provides a synthetic method of 2-chloro-3-phenoxy-6-nitroaniline, which comprises: (1) under the conditions of ammonolysis reaction, 2,3,4-trichloronitrobenzene contacting with an aminating agent in the presence of an organic solvent; (2) under etherification reaction conditions, purifying or not purifying the ammonolysis reaction product in the mixture obtained in step (1) and contacting with phenol in the presence of a basic compound, and The mixture obtained by contacting is separated into solid and liquid to obtain 2-chloro-3-phenoxy-6-nitroaniline; the basic compound is potassium carbonate and / or sodium carbonate.

[0012] According to the present invention, the amount of the aminating agent used in the ammonolysis reaction, as long as the ammonolysis reaction to 2,3,4-trichloronitrobenzene can be completed to obtain the target product of the ammonolysis reaction, but for The yield of the target product in which the chlorine at the 2-position on the b...

Embodiment 1

[0042] This example is used to illustrate the synthesis method of 2-chloro-3-phenoxy-6-nitroaniline.

[0043] (1) Ammonolysis reaction: Add 77.0g (0.34mol) of 2,3,4-trichloronitrobenzene and 770g of dimethyl sulfoxide into the autoclave in sequence and stir evenly; heat up to 50 °C; 29.0 g (1.7 mol) of ammonia gas was introduced, the pressure of the autoclave was 0.3 MPa, and the reaction was carried out for 26 hours. The autoclave was cooled to 30°C, and the materials therein were removed to obtain the ammonolysis reaction product;

[0044] (2) Etherification reaction: 30.8g (0.32mol) of phenol and 58.8g (0.42mol) of potassium carbonate were added to the ammonolysis reaction product, and the temperature was raised to 70°C for 20 hours of reaction. The temperature was lowered to 25°C, and the filter cake of the etherification reaction product was obtained by filtration; the filter cake was rinsed with a small amount of dimethyl sulfoxide, recrystallized by adding 120 g of met...

Embodiment 2

[0048] This example is used to illustrate the synthesis method of 2-chloro-3-phenoxy-6-nitroaniline.

[0049] (1) Ammonolysis reaction: Add 79.3g (0.35mol) of 2,3,4-trichloronitrobenzene and 555g of N-methylpyrrolidone (NMP) into the autoclave in sequence and stir evenly; heat up to The temperature is 70°C; 17.9g (1.05mol) of liquid ammonia is introduced, the pressure of the autoclave is 0.5MPa, and the reaction is carried out for 20 hours. The temperature of the autoclave was lowered to 30° C., and the materials therein were removed to obtain the ammonolysis reaction product.

[0050] (2) Etherification reaction: Add 64.0 g (0.67 mol) of phenol and 121.0 g (0.87 mol) of potassium carbonate to the ammonolysis reaction product, raise the temperature to 90° C., and react for 15 hours. The temperature was lowered to 25°C, and the filter cake of the etherification reaction product was obtained by filtration; the filter cake was rinsed with a small amount of NMP, recrystallized by...

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Abstract

The invention discloses a synthetic method of 2-chloro-3-phenoxyl-6-nitroaniline. The method comprises the following steps of: (1) under an ammonolysis reaction condition, contacting 2, 3, 4-trichloronitrobenzene with an aminating agent in the presence of an organic solvent; and (2) under an etherification reaction condition, contacting the purified or non-purified products of ammonolysis reaction in the mixture obtained by the step (1) with phenol in the presence of an alkali compound, and performing solid-liquid separation for the mixture obtained by contact to obtain 2-chloro-3-phenoxyl-6-nitroaniline, wherein the alkali compound is potassium carbonate and / or sodium carbonate. According to the method provided by the invention, the yield of the synthesized 2-chloro-3-phenoxyl-6-nitroaniline is high and the purity is good, the method is simplified in industrialized production and operation, and the solvent can be recycled.

Description

technical field [0001] The invention relates to a synthesis method of 2-chloro-3-phenoxy-6-nitroaniline. Background technique [0002] 2-Chloro-3-phenoxy-6-nitroaniline is a diphenyl ether herbicide and a protoporphyrinogen oxidase inhibitor. It is mainly used for pre-emergence control of grass weeds and broad-leaved weeds in potato, sunflower and winter wheat fields. Its mechanism of action is as follows: after application, a layer of medicinal film is deposited on the soil surface. When grass weeds and broad-leaved weeds penetrate the soil surface, the herbicide is absorbed by the young shoots, hypocotyls and coleoptiles of the seedlings respectively. After a few days of inhalation, the seedlings turn yellow, their growth is stunted, and they eventually die. 2-Chloro-3-phenoxy-6-nitroaniline is less dependent on soil moisture than most herbicides. [0003] At present, there are various methods for producing 2-chloro-3-phenoxy-6-nitroaniline, but when these methods are u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/00
Inventor 赵建民霍世勇王文军金文涛路凤奇吴国林张艳芳金辰
Owner NUTRICHEM LAB CO LTD