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Method for synthesizing chloro-aniline by chloronitrobenzene selective hydrogenation in alcohol-water system

A kind of technology of chlorinated nitrobenzene and chlorinated aniline

Inactive Publication Date: 2008-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the hydrogenation of such substances makes it difficult to separate the reaction products, which adds certain difficulties to industrial production and application.

Method used

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  • Method for synthesizing chloro-aniline by chloronitrobenzene selective hydrogenation in alcohol-water system
  • Method for synthesizing chloro-aniline by chloronitrobenzene selective hydrogenation in alcohol-water system
  • Method for synthesizing chloro-aniline by chloronitrobenzene selective hydrogenation in alcohol-water system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The reaction was carried out in a 500ml stainless steel autoclave, and 0.4g of Ru / SiO prepared by impregnation method 2 After the catalyst is reduced with potassium borohydride solution, it is used after washing and centrifuging with water and ethanol. Add 1.5g of p-chloronitrobenzene, 105ml of absolute ethanol and 45ml of water to the reactor, close the reactor, and replace it 3 times to get rid of air. It was heated to 100°C under stirring to start the reaction. The reaction was completed within 25min, and the content of each component of the reaction solution was analyzed by gas chromatography. The conversion rate was 99.9%, the yield was 98.6%, and the TOF was 3.20×10 -2 S -1 .

Embodiment 2

[0020] The reaction was carried out in a 500ml stainless steel autoclave, 0.4g Ru / SiO 2 After the catalyst is reduced with potassium borohydride solution, it is used after washing and centrifuging with water and ethanol. Add 1.5g of p-chloronitrobenzene and 150ml of methanol to the reaction kettle, close the reactor, and replace it 3 times to exclude air. Heated to 100°C to start the reaction. After reacting for 120 minutes, the content of each component of the reaction solution was analyzed by gas chromatography. The reaction results are shown in Table 1.

Embodiment 3

[0022] Except using 150ml butanol as solvent, other steps are the same as in Example 3, and the reaction results are shown in Table 1.

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Abstract

Provided is a method for synthesizing chlorophenylamine, which adopts chloronitrobenzene as raw material to react under the temperature of 40-140 DEG C and the pressure of 0.2-4 Mpa and the existence of composite solution of alcohol and water and catalyst, wherein the chloronitrobenzene is selectively hydrogenated to produce chlorophenylamine. The method uses alcohol water as solvent and is directly applied in the chloronitrobenzene which is selectively hydrogenated to produce chlorophenylamine, thereby the method has the advantages of high catalyst activity, milder reaction condition and high the yield.

Description

technical field [0001] The invention relates to a method for synthesizing chloroaniline by selective hydrogenation of chloronitrobenzene. Specifically, it relates to a method for selectively reducing chloronitrobenzene to synthesize chloroaniline using an alcohol-water system. Background technique [0002] Chloroaniline is an important organic intermediate, widely used in synthetic rubber, photosensitive materials, dyes, medicines, pesticides, etc. For example, p-chloroaniline (p-CAN) is an intermediate for azo dyes and naphthol AS-LB, as well as an intermediate for Moxie drugs (Limining, phenacetin), and can also be used as an intermediate for the production of color film Color coupler; m-chloroaniline (m-CAN) can be used as the chromogen of ice-dyed dyes, can make chlorpromazine, promazine phosphate, chloroquine phosphate, etc. in medicine, and can also be used as the preparation of insecticides [CN 1660774 ][CN 1762588]. Halogenated anilines are generally generated by ...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/36
Inventor 徐杰宁剑波
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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