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Method for photocatalytic synthesis of azoxybenzene and azobenzene compounds

A technology for oxidizing azobenzene and compounds, applied in the direction of organic chemistry, etc., can solve the problems of unsuitable industrial catalysts, expensive gold, etc., and achieve the effects of high product yield, high selectivity and short reaction period

Active Publication Date: 2013-08-28
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This technology has the advantages of simple operation, energy-saving environment and good selectivity, but gold is expensive and not suitable for industrial catalyst applications

Method used

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  • Method for photocatalytic synthesis of azoxybenzene and azobenzene compounds
  • Method for photocatalytic synthesis of azoxybenzene and azobenzene compounds
  • Method for photocatalytic synthesis of azoxybenzene and azobenzene compounds

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Experimental program
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Effect test

Embodiment 1

[0031]

[0032] After mixing nitrobenzene, potassium hydroxide and ethanol solution uniformly according to the molar ratio of 1:0.12:200, add a copper / graphene catalyst with a copper content of 2wt% according to the mass ratio of 1:0.001, and disperse it by ultrasonic (electric power 60W) for 30 minutes , the dispersed suspension was heated to 40°C under the protection of xenon light and argon o C stirring and reacting for 6h can obtain azobenzene oxide, wherein the conversion rate of nitrobenzene is 90%, and the selectivity of azobenzene oxide is 94%; heating to 100 o C Stirring reaction 5h reaction can obtain azobenzene, wherein the conversion rate of nitrobenzene is 95%, and the selectivity of azobenzene is 98%.

Embodiment 2

[0034]

[0035] After mixing p-chloronitrobenzene, potassium tert-butoxide and 2-heptanol solution according to the molar ratio of 1:0.3:500, add a copper / graphene catalyst with a copper content of 7wt.% according to the mass ratio of 1:0.01, and ultrasonically (Electric power 80W) After dispersing for 90 minutes, heat the dispersed suspension to 80°C under the protection of xenon light and neon gas. o C stirred and reacted for 3h to obtain p-azobenzene oxychloride, wherein the conversion rate of p-chloronitrobenzene was 91%, and the selectivity of p-azobenzene oxychloride was 89%; heating to 100 o C Stirred and reacted for 3 hours to obtain p-chloroazobenzene, wherein the conversion rate of p-chloronitrobenzene was 94%, and the selectivity of p-chloroazobenzene was 85%.

Embodiment 3

[0037]

[0038] After p-methylnitrobenzene, sodium tert-butoxide and isopropanol solution are mixed uniformly according to the molar ratio 1:0.24:240, add the copper / graphene catalyst that copper content is 5wt% by mass ratio 1:0.04, ultrasonic ( Electric power 150W) After dispersing for 30min, the dispersed suspension was heated to 60°C under the protection of xenon light and nitrogen o C stirring reaction 5h can obtain p-methylazobenzene oxide, wherein p-methylnitrobenzene conversion rate is 91%, and p-methylazobenzene oxide selectivity is 90%; Heating to 110 o C Stirred reaction 5h reaction can obtain p-methylazobenzene, wherein the conversion rate of p-methylnitrobenzene is 95%, and the selectivity of p-methylazobenzene is 97%.

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Abstract

The invention relates to a method for photocatalytic synthesis of azoxybenzene and azobenzene compounds. The method comprises the following steps: uniformly mixing a nitrobenzene compound, alkali and alcohol by molar ratio of 1:(0.1-20):(40-1000) to form a liquor; adding a copper / graphene catalyst into the liquor for ultrasonic dispersion for 5-240 minutes by mass ratio of the nitrobenzene compound and the catalyst: 1:(0.001-2); irradiating the dispersed liquor protected by inert gas and stirred with intensity of 0.001-5W / cm<2>, and heating to 20-80 DEG C and reacting for 3-10 hours to obtain the azoxybenzene compound; and heating to over 80 DEG C but below 150 DEG C and reacting for 3-10 hours to obtain the azobenzene compound. The method provided by the invention has the advantages of environmental friendliness, low cost, mild operation condition and high yield.

Description

technical field [0001] The invention belongs to a method for synthesizing azobenzene compounds and azobenzene compounds, in particular to a photocatalytic method for synthesizing azobenzene compounds and azobenzene compounds. Background technique [0002] Azobenzene compounds and azobenzene compounds are important organic synthesis intermediates and fine chemical raw materials. They are widely used, including organic dyes, pharmaceutical intermediates, photosensitive materials, liquid crystal display and optical switch control materials, etc. At the same time, it also has important applications in the construction of natural compounds and functional materials. [0003] At present, the preparation of azobenzene compounds is mainly achieved by reducing nitrobenzene compounds, such as the reduction of nitrobenzene compounds by hydrogenation, the reduction of nitrobenzene compounds by glucose (concentrated alkali conditions), and the reduction of nitrobenzene compounds by fo...

Claims

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Application Information

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IPC IPC(8): C07C245/08C07C291/08
Inventor 郭向云郭晓宁靳国强
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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