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Production of secondary-amine compound

A technology of ketone compounds and compounds, which is applied in the field of preparation of secondary amine compounds, can solve the problems of long reaction steps in preparation methods, different selectivity of preparation methods, product-mixture, etc., and achieve low production cost, broad application prospects, and excellent reaction process simple effect

Inactive Publication Date: 2007-04-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the prior art fully provides the method for preparing secondary amine compounds, there are still some deficiencies: the selectivity of some preparation methods is different, and the product is often a mixture; the reaction steps of some preparation methods are longer, and the yield is low, etc.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: catalyst preparation

[0027] Raney nickel (Raney Ni) catalyst preparation:

[0028] In a 1L three-necked flask equipped with stirring, add 500ml of 20% sodium hydroxide aqueous solution, heat to 90°C, and under stirring, add 40g of nickel-aluminum alloy (Ni:Al=50:50, Hangzhou Jia Lee Metal Co., Ltd.). The speed of addition should keep the temperature of the solution between 90 and 95°C, and the addition should be completed within about 30 minutes. Stirring was continued for 1 hour. Let stand to allow the nickel to settle, and pour off the supernatant. Wash 5 times by pouring method, each time with 200ml distilled water. Then wash 5 times with ethanol pouring method, 50ml each time. The prepared Raney Ni catalyst was stored in absolute ethanol for subsequent use.

[0029] Preparation of supported nickel (Ni) catalyst:

[0030]In a 150mL three-necked flask equipped with stirring, add 6.22g of nickel nitrate and 30mL of water, add 20g of silica gel af...

Embodiment 2

[0036] In a volume of 500 milliliters, in an autoclave equipped with stirrer, electric heater, gas guide pipe, pressure and temperature indicating instrument, 0.93 gram of glyoxal, 4.0 gram of nitrobenzene, 0.3 gram of embodiment 1 are loaded into Raney Ni catalyst and 100 ml ethanol. Then, the reaction system was successively replaced three times with nitrogen and hydrogen respectively, and the temperature was controlled at about 80°C. 2 Catalytic hydrogenation under pressure until hydrogen absorption is complete. After cooling, the material was discharged, filtered, and the solvent was evaporated under reduced pressure to obtain 4.8 grams of N,N'-diphenylethylenediamine product. The product contained 99% of N,N'-diphenylethylenediamine through high performance liquid chromatography analysis. The yield was 97%.

Embodiment 3

[0038] In a volume of 500 milliliters, in an autoclave equipped with stirrer, electric heater, air duct, pressure and temperature indicating instrument, charge 2.9 grams of 2,3-dichlorobenzaldehyde, 2.6 grams of nitrobenzene, 0.5 grams Raney Ni catalyst prepared in Example 1 and 100 milliliters of ethanol. Then, the reaction system was successively replaced three times with nitrogen and hydrogen respectively, and the temperature was controlled at about 80°C. 2 Catalytic hydrogenation under pressure until hydrogen absorption is complete. After cooling, the material is discharged, filtered, and the solvent is evaporated under reduced pressure to obtain 5.4 grams of N-(2,3-dichlorophenyl)aniline product. The product contains N-(2,3-dichlorophenyl) through high performance liquid chromatography analysis. Aniline 97.5%, the yield is 94.8%.

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Abstract

Production of secondary amine compound is carried out by taking nitro-compound, phenol or aldehyde compound as raw materials, catalytic hydrogenation reacting for 1-20hrs at 0.5-5.0MPa and 30-200 degree under the existence of solvent and catalyst, and separation purifying to obtain the final product. The solvent is fatty alcohol containing 1-4 atoms or its solution or water; the catalyst can be Raney Ni catalyst or nickel-carried catalyst or noble- metal-carried catalyst; the noble-metal-carried catalyst can be palladium-carried or platinum-carried or ruthenium-carried catalyst. It's simple and cheap, has higher conversion percent and better selectivity.

Description

(1) Technical field [0001] The invention relates to a method for preparing secondary amine compounds by using nitro compounds, aldehyde or ketone compounds and hydrogen as raw materials in the presence of a catalyst in one pot. (2) Background technology [0002] Secondary amine compounds are an important class of organic synthesis intermediates, widely used in the dye industry, pharmaceutical industry, food industry, pesticide industry and other fields. [0003] Methods for preparing organic amines are numerous and have been known for a long time. For example: the N-alkylation reaction of halogenated hydrocarbons with ammonia, primary amines, and secondary amines to prepare amine compounds. In this method, the structure of the reactants has a significant impact on the resulting products. When the activity of the halogenated hydrocarbon is high, the basicity of the primary amine is relatively high, and both have no steric hindrance, mixed amines are often obtained; when the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/26C07C211/34C07C211/03C07C211/43C07D333/20C07D333/36C07D213/74
Inventor 施介华陈克喜
Owner ZHEJIANG UNIV OF TECH
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