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Method for preparing arylamine by reducing aromatic nitro compound under radiation of visible light

A technology of aromatic nitro compounds, applied in the field of preparation of aromatic amines, can solve the problems of not being able to make full use of sunlight, and achieve the effects of small scale, high yield, and high added value

Inactive Publication Date: 2010-05-12
DALIAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the catalytic reduction of aromatic nitro compounds under light has attracted people's attention, but these photocatalytic reduction reactions all use ultraviolet light as the light source, mostly TiO 2 As a catalyst, this has made a certain breakthrough in energy utilization, but the ultraviolet light in the solar energy is less than 5%, so the sunlight cannot be fully utilized.

Method used

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  • Method for preparing arylamine by reducing aromatic nitro compound under radiation of visible light
  • Method for preparing arylamine by reducing aromatic nitro compound under radiation of visible light
  • Method for preparing arylamine by reducing aromatic nitro compound under radiation of visible light

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Effect test

Embodiment 1

[0019] Will contain 20mmol / L nitrobenzene, 10mmol / LCuCl 2 Add 4mL of isopropanol solution of 5mmol / L n-decane into an ordinary glass test tube, put the glass test tube close to the lamp tube of U23W warm white energy-saving lamp, turn on the light source to irradiate the reaction solution for 16h, and analyze the product by GC and GC-MS , the yield of aniline was 11%, and the selectivity was 92%.

Embodiment 2

[0023] Will contain 10mmol / L nitrobenzene, 10mmol / LCuCl 2 , 4mL of isopropanol solution of 60mmol / LPhCOPh and 5mmol / L n-decane was added to an ordinary glass test tube, and the glass test tube was placed close to the lamp tube of U23W warm white energy-saving lamp, and the light source was turned on to irradiate the reaction solution for 16h. GC-MS analysis shows that the yield of aniline is 30% and the selectivity is 30%; if the concentration of nitrobenzene is 200mmol / L, the reaction is carried out under the same conditions, the yield of aniline is 4% and the selectivity is 93%.

Embodiment 3

[0025] Will contain 20mmol / L p-nitrotoluene, 10mmol / LCuCl 2 , 4mL of isopropanol solution of 60mmol / LPhCOPh and 5mmol / L n-decane was added to an ordinary glass test tube, and the glass test tube was placed close to the lamp tube of U23W warm white energy-saving lamp, and the light source was turned on to irradiate the reaction solution for 16h. GC-MS analysis showed that the yield of p-toluidine was 63%, and the selectivity was 94%.

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Abstract

The invention relates to preparation of arylamine, in particular to a new method for preparing arylamine by catalyzing and reducing aromatic nitro compound with non-noble metal salt as catalyst under radiation of visible light. The method takes aromatic nitro compound as substrate, isopropanol as hydrogen donor, CuCl2 as catalyst and PhCOPh as photosensitizer to realize reduction of aromatic nitro compound under radiation of visible light to obtain reduzate arylamine. The reaction equation is as the following: G=-H, -CH3, -Cl, -COCH3, wherein the aromatic nitro compound is nitrobenzene, paranitrotoluene, parachloronitrobenzene or nitroacetophenone. The synthesis method of the invention can be carried out under radiation of visible light, has large application potential on fully utilizing sun light, and features simple and convenient operation, high safety, and no pollution; non-noble metal salt CuCl2 is used as catalyst, which is simple and available and convenient to store and use; photosensitizer PhCOPh can not be consumed in the reaction process and can be recycled; the selectivity of the sum yield is high, thus the invention is suitable for synthesis of fine chemicals with small scale and high added value.

Description

technical field [0001] The invention relates to the preparation of aromatic amines, in particular to a new method for preparing aromatic amines by catalytically reducing aromatic nitro compounds with non-noble metal salts as catalysts under visible light irradiation. Background technique [0002] Aromatic amines are important organic chemical raw materials and intermediates in the synthesis of many fine chemicals, and are widely used in dyes, medicines, pesticides and other industries. Reduction of aromatic nitro compounds is currently the main method for preparing aromatic amines. The current reduction methods mainly include catalytic hydrogenation and stoichiometric reduction (such as alkali sulfide, iron powder, etc.). Catalytic hydrogenation is widely used, but with hydrogen as the hydrogen source, the reaction requires high temperature and high pressure, and the risk factor is high; the stoichiometric reduction method is seriously polluting, so its application has been ...

Claims

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Application Information

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IPC IPC(8): C07C211/46C07C211/47C07C209/36
Inventor 尹静梅张瑞贾颖萍崔颖娜周广运高大彬
Owner DALIAN UNIVERSITY