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Method for synthesizing amine and imine

A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, condensation/addition reaction to prepare amino compounds, etc., can solve problems such as reaching 22.3%

Inactive Publication Date: 2013-04-24
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(As shown in Formula 1) There have been reported Ru homogeneous catalytic reaction systems (Org.Lett., 2010, 12, 4888) in which alcohols and nitrobenzene generate tertiary amines, while reports of heterogeneous reaction systems only found One example: the synthesis of nitrobenzene and linear alkanes with the participation of TiO2semiconductor photocatalyst, but the highest yield can only reach 22.3% (nitrobenzene and isoamyl alcohol to form imine system, Tetrahedron Lett., 2010, 15, 2730), the yield still needs further improvement

Method used

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  • Method for synthesizing amine and imine
  • Method for synthesizing amine and imine
  • Method for synthesizing amine and imine

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Weigh 0.0354gPdCl 2 , add 30 mL of deionized water to dissolve, add 2 mol / L hydrochloric acid to adjust the pH of the solution to 3, add 1 g of hydrotalcite HT to the above solution, stir at room temperature for 4 hours, and let stand for 10 hours. The mixture was evaporated to dryness at 45°C. The obtained powder was ground and dried at 120° C. for 10 hours to obtain a 2 wt % Pd / HT catalyst (Pd loading 0.2 mmol / g).

[0027] Catalyst performance evaluation was carried out in an atmospheric continuous reactor. Weigh 0.1g of 2wt% Pd / HT catalyst and add it into a 30mL reaction tube, add the reaction substrate benzyl alcohol 3mmol, nitrobenzene 1mmol, solvent toluene 2mL and internal standard n-dodecane 10μL under anaerobic conditions. The reaction temperature is controlled at 130 degrees Celsius by an oil bath. The above-mentioned reaction tube was placed in an oil bath with a stable temperature, and the reaction system was magnetically stirred at the same time, and the...

Embodiment 2

[0033] Weigh 0.0354gPdCl 2 , add 30 mL of deionized water to dissolve, add 2 mol / L hydrochloric acid to adjust the pH of the solution to 3, add 1 g of hydrotalcite HT to the above solution, stir at room temperature for 4 hours, and let stand for 10 hours. The mixture was evaporated to dryness at 45°C. The obtained powder was ground and dried at 120° C. for 10 hours to obtain a 2 wt % Pd / HT catalyst (Pd loading 0.2 mmol / g).

[0034] Catalyst performance evaluation was carried out in an atmospheric continuous reactor. Weigh 0.1g of 2wt% Pd / HT catalyst into a 30mL reaction tube, add 4mmol of benzyl alcohol, 1mmol of nitrobenzene, 2mL of solvent toluene and 10μL of internal standard n-dodecane under anaerobic conditions. The reaction temperature is controlled at 120 degrees centigrade by an oil bath. The above-mentioned reaction tube was placed in an oil bath with a stable temperature, and the reaction system was magnetically stirred at the same time, and the reaction timing st...

Embodiment 3

[0039] Weigh 0.0354gPdCl 2, add 30mL deionized water to dissolve, add 2mol / L hydrochloric acid to adjust the pH of the solution to 3, add 1g hydrotalcite HT to the above solution, stir at room temperature for 4 hours, and let stand for 10 hours. The mixture was evaporated to dryness at 45°C. The obtained powder was ground and dried at 120° C. for 10 hours to obtain a 2 wt % Pd / HT catalyst (Pd loading 0.2 mmol / g).

[0040] Catalyst performance evaluation was carried out in an atmospheric continuous reactor. Weigh 0.1g of 2wt% Pd / HT catalyst and add it into a 30mL reaction tube, add 15mmol of benzyl alcohol, 1mmol of nitrobenzene, solvent toluene and 10μL of internal standard n-dodecane under anaerobic conditions. The reaction temperature is controlled at 130 degrees Celsius by an oil bath. The above-mentioned reaction tube was placed in an oil bath with a stable temperature, and the reaction system was magnetically stirred at the same time, and the reaction timing started. ...

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Abstract

The invention provides a method for synthesizing N-benzalaniline and N-benzyl aniline, and relates to an efficient method for synthesizing N-benzalaniline and N-benzyl aniline through a continuous reaction on raw materials of aromatic alcohol and nitryl aromatic compound in the presence of a transition metal supported solid catalyst. The catalyst is loaded on hydrotalcite, hydroxyapatite and oxides by using palladium, gold or rhodium through an impregnation method or a precipitation method. The catalytic reaction is carried out in an inert atmosphere; conversion rate of nitrobenzene and total yield of N-benzalaniline and N-benzyl aniline can reach higher than 99% (imine yield of 93%, and amine yield of 7%). The catalyst can be used repeatedly. The method is applicable to a variety of substituted aromatic alcohols and substituted aromatic compounds, and can realize high conversion rate and high selectivity.

Description

Technical field [0001] The present invention involves a method of continuously reacting the Nitrocellous aromatherapy compound and aromatol continuous reaction under the participation of the transitional metal load solid catalyst under the participation of the transitional metal load. Background technique [0002] Nitrogen -containing compounds can be used as fuel, electrodes, extract agents, stabilizers, chemical agricultural products, and biological active species, and are an important type of chemicals.The selection of nitrotid compounds is the most direct organic synthesis method for generating nitrogen -containing compounds.Industrially uses excessive expensive and toxic reducing reagents. The use of environmentally friendly, high -efficiency, high -chemical tolerance and selectivity restoration system is currently the research direction that researchers are increasingly attached to.AU / TIO 2 The restoration of the nitrotic compound in the hydrogen atmosphere can reach 98.5 %...

Claims

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Application Information

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IPC IPC(8): C07B43/04C07C251/24C07C249/02C07C211/48C07C211/52C07C209/60C07C213/02C07C217/58C07C227/04C07C229/38C07C217/84C07C211/51C07C231/12C07C233/43C07D317/58C07D295/135B01J23/44B01J23/46B01J27/18
Inventor 陈静苏伟平黄世俊阚剑
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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