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Method for preparing p-chloroaniline through catalytic hydrogenation of p-chloronitrobenzene

A technology of p-chloronitrobenzene and p-chloroaniline, which is applied in the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of unstable reaction and low yield of chloroaniline, and achieve cost reduction, The effect of less environmental pollution and easy industrialization

Inactive Publication Date: 2012-02-15
CHINA PETROCHEMICAL CORP +1
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AI Technical Summary

Problems solved by technology

This method is simple and easy, but the yield of p-chloroaniline is low, only about 80%, and the reaction is unstable

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 50 g of p-chloronitrobenzene, 200 mL of absolute ethanol, and 3 g of catalyst. Put it into a high-pressure reactor, replace it with nitrogen for 5 times and replace it with hydrogen for 5 times, and keep the partial pressure of hydrogen at 2.5 MPa. The reaction was stirred at 70°C for 3h, and the yield of p-chloroaniline was 93.9%. .

Embodiment 2

[0021] 50 g of p-chloronitrobenzene, 200 mL of absolute ethanol, and 1 g of catalyst. Put it into a high-pressure reactor, replace it with nitrogen for 5 times, then replace it with hydrogen for 5 times, and keep the partial pressure of hydrogen at 1.5 MPa. The reaction was stirred at 80°C for 3h, and the yield of p-chloroaniline was 92.2%.

Embodiment 3

[0023] 50 g of p-chloronitrobenzene, 200 mL of absolute ethanol, and 2 g of catalyst. Put it into a high-pressure reactor, replace it with nitrogen for 5 times, then replace it with hydrogen for 5 times, and keep the partial pressure of hydrogen at 2.0 MPa. The reaction was stirred at 80°C for 2h, and the yield of p-chloroaniline was 96.9%.

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Abstract

The invention belongs to the technical field of organic synthesis and provides a method for performing catalytic hydrogenation on p-chloronitrobenzene with a modified Raney nickel catalyst and preparing p-chloroaniline. The method comprises the following steps: adding p-chloronitrobenzene, the modified Raney nickel catalyst with an additional metal material and a solvent in a high-pressure reaction kettle, wherein the weight ratio of p-chloronitrobenzene to the solvent is 1:2-1:5 and the weight ratio of p-chloronitrobenzene to the catalyst is 1:(0.02-0.06); performing nitrogen replacement, then performing hydrogen replacement, wherein the pressure of hydrogen is 1.0-3.5MPa and the reaction temperature is 60-100 DEG C; and stirring to react for 1-4 hours to obtain the product p-chloroaniline. The method has simple technology, low demand on equipment and low environmental pollution and is easy to realize industrialization; and the reaction conversion rate is 99.9%, the selectivity is not less than 98% and the yield is not less than 95%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and proposes a method for preparing p-chloroaniline by catalyzing the hydrogenation of p-chloronitrobenzene with a modified skeleton nickel catalyst. Background technique [0002] p-Chloroaniline is the main raw material and intermediate of synthetic rubber, chemical reagents, dyes, pigments and other chemical products, as well as medicine, pesticide, photography, medicine, etc., and has a wide range of uses. [0003] The processes for synthesizing p-chloroaniline mainly include: metal powder reduction method, sodium sulfide reduction method, electrochemical reduction method, CO reduction method, hydrazine hydrate reduction method, photocatalytic reduction method, borohydride reduction method, and catalytic hydrogenation reduction method. Among them, the metal powder reduction method causes serious corrosion and wear to the equipment, and the operation and maintenance costs are high; th...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/36
Inventor 孙盛凯徐冬梅黄伟李玉杰
Owner CHINA PETROCHEMICAL CORP
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