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Method for preparing imine compound through primary amine oxidative coupling

A technology of oxidative coupling and oxidative coupling reaction, which is applied in the preparation of imino compounds, chemical instruments and methods, chemical/physical processes, etc., can solve the problems of high toxicity, difficult recycling, small specific surface area of ​​catalysts, etc. Effects of increased surface area, simple equipment, and well-characterized structures

Inactive Publication Date: 2018-08-21
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It solves the problems of small specific surface area, high toxicity and difficult recycling of existing catalysts

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of preparation method of SBA-15 loaded Anderson type heteropolyacid catalyst, comprises the steps:

[0026] (1) A step for preparing SBA-15, adding 1.33g of P123 and 1.467g of potassium chloride into a three-necked flask, adding 40ml of 2M dilute hydrochloric acid and stirring evenly. After mixing evenly, add 3ml of ethyl orthosilicate, and put it in an oil bath at 38°C. After stirring for 24 hours, it was taken out and transferred to a hydrothermal kettle at 100°C for reaction, and the pre-product was obtained after 24 hours. After washing several times with secondary water, dry in a vacuum oven at a drying temperature of 60°C. To obtain a sample, add 0.5 g and 0.6 g of ammonium acetate to 10 ml of ethanol to extract and remove the template agent P123, repeat the above steps once, and centrifuge to obtain a sample. Finally, it was washed several times with secondary water, dried and placed in a nitrogen-protected tube furnace for calcination.

[0027] Specifi...

Embodiment 2

[0031] A kind of preparation method of SBA-15 loaded Anderson type heteropolyacid catalyst, comprises the steps:

[0032] (1) A step for preparing SBA-15, adding 1.33g of P123 and 1.467g of potassium chloride into a three-necked flask, adding 40ml of 2M dilute hydrochloric acid and stirring evenly. After mixing evenly, add 3ml of ethyl orthosilicate, and put it in an oil bath at 38°C. After stirring for 24 hours, it was taken out and transferred to a hydrothermal kettle at 100°C for reaction, and the pre-product was obtained after 24 hours. After washing several times with secondary water, dry in a vacuum oven at a drying temperature of 60°C. To obtain a sample, add 0.5 g and 0.6 g of ammonium acetate to 10 ml of ethanol to extract and remove the template agent P123, repeat the above steps once, and centrifuge to obtain a sample. Finally, it was washed several times with secondary water, dried and placed in a nitrogen-protected tube furnace for calcination.

[0033] Specifi...

Embodiment 3

[0037] A kind of preparation method of SBA-15 loaded Anderson type heteropolyacid catalyst, comprises the steps:

[0038] (1) A step for preparing SBA-15, adding 1.33g of P123 and 1.467g of potassium chloride into a three-necked flask, adding 40ml of 2M dilute hydrochloric acid and stirring evenly. After mixing evenly, add 3ml of ethyl orthosilicate, and put it in an oil bath at 38°C. After stirring for 24 hours, it was taken out and transferred to a hydrothermal kettle at 100°C for reaction, and the pre-product was obtained after 24 hours. After washing several times with secondary water, dry in a vacuum oven at a drying temperature of 60°C. To obtain a sample, add 0.5 g and 0.6 g of ammonium acetate to 10 ml of ethanol to extract and remove the template agent P123, repeat the above steps once, and centrifuge to obtain a sample. Finally, it was washed several times with secondary water, dried and placed in a nitrogen-protected tube furnace for calcination.

[0039] Specifi...

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Abstract

The invention discloses a method for preparing imine compound through primary amine oxidative coupling. According to the method, the imine compound is prepared by performing oxidative coupling reaction on a primary amine compound in a solvent and under the action of a catalyst and an oxidizing agent, wherein the catalyst is SBA-15 loaded Anderson type heteropolyacid. The preparation process and the needed equipment are simple and the reaction time is short; and the reaction temperature is obviously reduced and large-scale production is easy to realize.

Description

technical field [0001] The invention relates to the technical field of catalytic oxidation synthesis, and relates to a method for preparing imine compounds through oxidative coupling of primary amines. Background technique [0002] Imines, also known as Schiff bases, are widely used as intermediates in drug synthesis and organic transformation. The C=N bond in imines is also widely used in organic transformations, such as reduction, addition, cyclization, and aziridine reactions. However, traditional imine synthesis involves unstable aldehydes and in many cases requires dehydrating agents as well as Lewis acid catalysts. We found three new methods by consulting the data, namely the cross-coupling of alcohols and amines, the self-coupling of primary amines and the oxidative dehydrogenation of secondary amines. The only by-product of the cross-coupling of alcohols with amines is water, and different symmetrical and unsymmetrical imines can be easily synthesized, choosing dif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02C07C251/16B01J29/03B01J27/188B01J35/10
CPCC07C249/02B01J27/188B01J29/0341B01J2229/18B01J35/61C07C251/16
Inventor 卢德力刘玥冉翟永彦韩生余焓任济夫
Owner SHANGHAI INST OF TECH