Method for synthesizing hydrogenated azo compounds

A technology for hydrogenating azo and compounds, which is applied in organic chemistry, hydrazine preparation, etc., can solve the problems of high cost and the reduction of azo oxide groups that have not been seen yet, and achieve the effects of low cost, easy subsequent separation, and high yield

Inactive Publication Date: 2006-03-22
LIAONING UNIVERSITY
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The preparation of hydroazo compounds mainly uses azobenzene compounds and azobenzene compounds as raw materials. Now the methods of reducing oxidized azo aromatic compounds to prepare hydroazo aromatic compounds mainly include: metal reduction method, catalytic hydrazine reduction method and Alkali sulfide reduction method, although the process of the above-mentioned method is relatively mature, the reaction by-products are all products that pollute the environment, which belongs to the method of elimination in the reduction process method, and its cost is relatively high for the catalytic hydrazine reduction method. The reduction of nitro groups has been reported, but there is no report on the reduction of azo oxide groups

Method used

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  • Method for synthesizing hydrogenated azo compounds
  • Method for synthesizing hydrogenated azo compounds

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Experimental program
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Effect test

Embodiment 1

[0021] Add azobenzene oxide 9.8g (50mmol), Se 0.08 (1mmol), H 2 O 9g (0.5mol), triethylamine 0.5g (5mmol) and solvent DMF 200mL, continue to pass through carbon monoxide, and heat to 88 ° C and stir for 0.5 hours, cool to room temperature, switch carbon monoxide to oxygen or air and stir for 0.5-1 hour Finally, filter out the selenium powder. The solvent was evaporated by distillation under reduced pressure (below 5kPa), washed with water, and filtered. The yield was 95%.

Embodiment 2

[0023] temperature(℃)

Embodiment 3

[0025] solvent

[0026] Alcohol

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Abstract

The present invention is the synthesis process of hydrogenating aromatic azo compound into hydrogenated azo compounds at normal pressure inside organic solvent in the presence of CO and water as well as Se as catalyst with or without organic or inorganic alkali as co-catalyst. Where, the aromatic azo compound may have substituted radical, and the reaction has molar ratio between aromatic azo compound and water of 1 to 1-20, molar ratio between aromatic azo compound and CO of 1 to 1.1-3, molar amount of Se in 0.1-8 % of aromatic azo compound, reaction time of 0.5-3 hr, and reaction time of 30-100 deg c. The synthesis process is simple and safe, and has easy to obtain material, no pollution, high selectivity, no influence on the sensitive radicals on the aromatic ring, high yield and reusability of the catalyst.

Description

technical field [0001] The invention relates to a synthesis method of azobenzene compounds, in particular to a method for synthesizing hydrogenated azobenzene compounds by catalytic reduction of carbon monoxide. Background technique [0002] As a large class of important organic synthesis intermediates and raw materials, hydroazobenzene is used in the fields of medicine and pesticides. The preparation of hydroazo compounds mainly uses azobenzene compounds and azobenzene compounds as raw materials. Now the methods of reducing oxidized azo aromatic compounds to prepare hydroazo aromatic compounds mainly include: metal reduction method, catalytic hydrazine reduction method and Alkali sulfide reduction method, although the process of the above-mentioned method is relatively mature, the reaction by-products are all products that pollute the environment, which belongs to the method of elimination in the reduction process method, and its cost is relatively high for the catalytic hy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/22C07C241/02
Inventor 刘晓智张欣李宏颖孙丹
Owner LIAONING UNIVERSITY
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