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Clean production process of hydrogenated azobenzene

A hydrogenated azobenzene, clean production technology, applied in the direction of organic chemistry, hydrazine preparation, etc., can solve the problems of incomplete reaction, large amount of waste water, large safety risk, etc., and achieve the effect of saving alkali consumption

Active Publication Date: 2020-11-03
郑州科旷生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Hydroazobenzene is an important intermediate of the drug phenylbutazone. Its industrial synthesis method is the metal reduction method, which is not only costly, but also pollutes a lot. Hydrogen uses high pressure, which not only has great safety risks, but also has high investment in equipment, expensive catalysts, incomplete reaction, and difficult post-processing.

Method used

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  • Clean production process of hydrogenated azobenzene
  • Clean production process of hydrogenated azobenzene
  • Clean production process of hydrogenated azobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A clean production process of hydroazobenzene, comprising the steps of:

[0033] 1) In a 50ml four-necked reaction flask equipped with a stirrer, condenser and heater, add 16.00g of 25% sodium hydroxide solution, 2000.13g of polyethylene glycol, 0.03g of 1,4-naphthoquinone, and nitrobenzene 6.40g (0.052mol), slowly heat up to 65°C with stirring, add 1.91g (0.039mol) of hydrazine hydrate dropwise, dropwise for 1 hour, then raise the temperature to 70°C for 5 hours, and the peak of nitrobenzene disappears as detected by liquid chromatography , cooled to 18°C, kept warm for 4 hours, suction filtered, washed with water, and the filter cake was azobenzene oxide;

[0034] 2) Weigh 6.00g of azobenzene oxide, 7.80g of 5% sodium hydroxide solution, 2000.30g of polyethylene glycol, and 2.40g of hydrazine hydrate into a 25ml four-necked reaction flask equipped with a stirrer, condenser tube and heater After raising the temperature to 65°C, add 0.03g of Raney nickel, react for 4 h...

Embodiment 2

[0037] A clean production process of hydroazobenzene, comprising the steps of:

[0038] 1) Add 22.40 g of 20% sodium hydroxide solution, 15000.32 g of polyethylene glycol, 0.13 g of 1,4-naphthoquinone, and nitrobenzene 6.40g (0.052mol), slowly heat up to 40°C with stirring, add 2.55g (0.052mol) of hydrazine hydrate dropwise, dropwise for 1.5h, then heat up to 45°C and react for 10 hours, the peak of nitrobenzene is detected by liquid chromatography disappear, lower the temperature to 18°C, keep warm for 4 hours, filter with suction, wash with water, and the filter cake is azobenzene oxide;

[0039] 2) Weigh 6.00g of azobenzene oxide, 8.00g of 3% sodium hydroxide solution, 15000.48g of polyethylene glycol, and 3.00g of hydrazine hydrate into a 25ml four-necked reaction flask equipped with a stirrer, condenser tube and heater After raising the temperature to 55°C, add 0.12g of Raney nickel, react for 6 hours, drop to 20°C, filter with suction, wash with water, and dry in vacuum...

Embodiment 3

[0042] A clean production process of hydroazobenzene, comprising the steps of:

[0043] 1) In a 50ml four-necked reaction flask equipped with a stirrer, condenser and heater, add 32.00g of 15% sodium hydroxide solution, 8000.64g of polyethylene glycol, 0.32g of 1,4-naphthoquinone, and nitrobenzene 6.40g (0.052mol), slowly heat up to 85°C with stirring, add 3.04g (0.062mol) of hydrazine hydrate dropwise, dropwise for 2 hours, then heat up to 90°C for 3 hours, and the peak of nitrobenzene disappears as detected by liquid chromatography , cooled to 18°C, kept warm for 4 hours, suction filtered, washed with water, and the filter cake was azobenzene oxide;

[0044] 2) Weigh 6.00g of azobenzene oxide, 10.80g of 1% sodium hydroxide solution, 8000.60g of polyethylene glycol, and 3.60g of hydrazine hydrate into a 25ml four-necked reaction flask equipped with a stirrer, condenser tube and heater After raising the temperature to 85°C, add 0.30g of Raney nickel, react for 3 hours, lower ...

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Abstract

The invention discloses a clean production process of hydrogenated azobenzene, which comprises the following steps: 1) reducing nitrobenzene with hydrazine hydrate in an alkaline solution in the presence of polyethylene glycol by using a quinone compound as a catalyst to obtain azoxybenzene; and 2) reducing the azoxybenzene obtained in the step 1) with hydrazine hydrate in an alkaline solution inthe presence of polyethylene glycol by using Raney nickel as a catalyst to obtain the hydrogenated azoxybenzene. The clean production process of the hydrogenated azobenzene disclosed by the inventionis free of solid waste pollution, the alkali liquor can be repeatedly used, the alkali consumption can be greatly saved, and potential risks such as high temperature, high pressure, flammability, explosiveness and the like are avoided.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, in particular to a clean production process of hydroazobenzene. Background technique [0002] Hydroazobenzene is an important intermediate of the drug phenylbutazone. Its industrial synthesis method is the metal reduction method, which is not only costly, but also pollutes a lot. Hydrogen uses high pressure, which not only has great safety risks, but also has high investment in equipment, expensive catalysts, incomplete reaction, and difficult post-processing. Contents of the invention [0003] The purpose of the present invention is to provide a clean production process of hydroazobenzene in order to overcome the deficiencies of the prior art. [0004] The object of the present invention is achieved in that a kind of clean production technique of hydroazobenzene comprises the steps: [0005] 1) Nitrobenzene is in an alkaline solution, in the presence of polyethylene glycol, using a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C241/02C07C243/22
CPCC07C241/02C07C291/08C07C243/22
Inventor 牛国峰
Owner 郑州科旷生物科技有限公司
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