Method for implementing amine compound N-methylation by photocatalysis

An amine compound and methylation technology, applied in the field of photocatalytic synthesis, can solve the problems of high energy consumption, expensive catalyst, and high toxicity of raw materials, and achieve the effects of good selectivity, low cost, and low toxicity

Active Publication Date: 2017-07-28
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to improve the problems of expensive N-methylation reaction catalysts, large reaction energy consumption, and high toxicity of raw materials in the prior art, and to synthesize N-methylated amines greenly and economically.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add titanium dioxide to the transparent reaction bottle filled with methanol, seal it tightly, and adjust the stirring speed to about 20 rpm, then irradiate the transparent reaction bottle with a 100-watt mercury lamp. After 3 hours of irradiation, the solution turns milky white into a suspension The liquid turned into a blue suspension. Then add formic acid and aniline in a molar ratio of 100:1, wherein the molar ratio of titanium dioxide and aniline is 1:10. After continuing stirring under the same conditions and irradiating light for 3 hours, the reaction was stopped. The reaction product is mainly N,N-dimethylaniline, the selectivity of N,N-dimethylaniline is 77.2%, and the yield of N,N-dimethylaniline is 61%.

Embodiment 2

[0031] Add titanium dioxide to the transparent reaction bottle filled with methanol, seal it tightly, and adjust the stirring speed to about 20 rpm, then irradiate the transparent reaction bottle with a 100-watt mercury lamp. After 3 hours of irradiation, the solution turns milky white into a suspension The liquid turned into a blue suspension. Then add formic acid and benzylamine in a molar ratio of 100:1, wherein the molar ratio of titanium dioxide and benzylamine is 1:100. After continuing stirring under the same conditions and irradiating light for 3 hours, the reaction was stopped. The reaction product is mainly N,N-dimethylbenzylamine, the selectivity of N,N-dimethylbenzylamine is 65.1%, and the yield of N,N-dimethylbenzylamine is 51%.

Embodiment 3

[0033] Add titanium dioxide to the transparent reaction bottle filled with methanol, seal it tightly, and adjust the stirring speed to about 20 rpm, then irradiate the transparent reaction bottle with a 100-watt mercury lamp. After 3 hours of irradiation, the solution turns milky white into a suspension The liquid turned into a blue suspension. Then add formic acid and phenethylamine in a molar ratio of 100:1, wherein the molar ratio of titanium dioxide and phenethylamine is 1:50. After continuing stirring under the same conditions and irradiating light for 3 hours, the reaction was stopped. The reaction product is mainly N,N-dimethylphenethylamine, the selectivity of N,N-dimethylphenethylamine is 90.5%, and the yield of N,N-dimethylphenethylamine is 82%.

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Abstract

The invention belongs to the technical field of photocatalysis synthesis, and particularly relates to a method for implementing amine compound N-methylation by photocatalysis. The method includes the steps: 1) adding photocatalyst TiO2 and N-methylation carbon sources into a photocatalysis reactor to form a reaction system, and stirring the reaction system under ultraviolet irradiation; 2) adding reducing agents and amine compounds into the reaction system obtained in the step 1), and continually stirring mixture under ultraviolet irradiation to obtain N-methylation products. Compared with the prior art, the preparation method has the main advantages that selected raw materials are low in cost and toxicity, reaction conditions are mild, energy consumption is less, used catalysts are low in cost and easy to obtain, reaction operations are simple, and products are high in yield and good in selectivity.

Description

technical field [0001] The invention belongs to the technical field of photocatalytic synthesis, in particular to a method for realizing N-methylation of amine compounds by photocatalysis. Background technique [0002] N-methylated amine compounds widely exist in natural products, and they are also important intermediates in the synthesis of industrial drugs, dyes and other fine chemicals (such as agricultural chemicals, etc.). Due to the importance of this type of compound, the research on its synthesis method has also made continuous progress and breakthroughs. The traditional method in industry is through Eschweiler-Clarke Methylation reaction (Eschweiler-Clarke Methylation), using more toxic formaldehyde or paraformaldehyde as raw material, using carboxylic acid as reducing agent to realize N-methylation of amine. Under laboratory conditions, the main carbon sources for N-methylation of amines include formaldehyde, methyl iodide, methanol, dimethyl carbonate, dimethyl s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/48C07C209/18C07C211/27C07C209/16
CPCC07C209/16C07C209/18C07C211/48C07C211/27
Inventor 赵进才龚原正籍宏伟陈春城马万红
Owner INST OF CHEM CHINESE ACAD OF SCI
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