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Method for preparing N-benzylidenebutylamine through efficient photocatalytic oxidation of benzylamine

A technology for photocatalytic oxidation and benzalkonium butylamine, which is applied in the field of photocatalytic oxidation, can solve the problems of difficult control of nucleophilic addition reaction, high price, environmental pollution, etc., and achieves the method of simple and easy operation, low cost and environmental friendliness. Effect

Active Publication Date: 2021-11-02
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally, Schiff base compounds are obtained by dehydration condensation reaction between amine compounds and carbonyl compounds, but this method has the disadvantage that the nucleophilic addition reaction between the two substances is not easy to control.
In addition, there are many ways to synthesize Schiff base compounds under the catalysis of catalysts, such as the condensation of hydroxyl compounds and amino compounds, the coupling of primary amines and the dehydrogenation of secondary amines. However, the currently reported Because the catalysts used in this method are generally expensive noble metal catalysts, the cost of synthesis is relatively high, and the use of noble metal catalysts will also pollute the environment.

Method used

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  • Method for preparing N-benzylidenebutylamine through efficient photocatalytic oxidation of benzylamine
  • Method for preparing N-benzylidenebutylamine through efficient photocatalytic oxidation of benzylamine
  • Method for preparing N-benzylidenebutylamine through efficient photocatalytic oxidation of benzylamine

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Effect test

Embodiment 1

[0021] The invention provides a method for preparing N-benzylbutylamine by photocatalytic oxidation of benzylamine with a flavin photosensitizer, namely:

[0022] (1) Add 3ml organic solvent in 10ml reaction vial, then add 0.2mmol benzylamine and 0.001mmol flavin photosensitizer;

[0023] (2) Under normal pressure air atmosphere, the light intensity is 1240W / m 2 1. The mixed solution is irradiated by an LED lamp with a wavelength of 451nm, and the illumination time is 1 to 9 hours, and circulating water is introduced to ensure that the reaction conditions are carried out at room temperature;

[0024] (3) Use thin-layer chromatography to monitor the reaction process, and stop the light when the substrate reaction is complete or no longer changes.

[0025] Adopt gas chromatography-mass spectrometry instrument, liquid chromatography-mass spectrometry instrument to carry out qualitative analysis to product, adopt gas chromatography (GC2012, hydrogen flame ionization detector, Ame...

Embodiment 2

[0027] In the case of keeping other experimental conditions consistent in implementation 1, the organic solvent used is acetonitrile, the substrate is benzylamine, and the flavin photosensitizer is self-synthesized 10-octylbenzo[g]pteridine-2,4( 3H,10H)-Diketones This flavin has the molecular formula C 18 h 22 N 4 o 2 , to discuss the influence of different light reaction times on the yield of reactants, and the labels of the obtained products were sample-1, sample-2, sample-3, sample-4, and sample-5.

[0028] The specific preparation method is:

[0029] (1) Add 3ml of acetonitrile in a 10ml reaction flask, then add 0.2mmol of benzylamine and 0.001mmol of 10-octylbenzo[g]pteridine-2,4(3H,10H)-dione;

[0030] (2) Under normal pressure air atmosphere, the light intensity is 1240W / m 2 1. An LED lamp with a wavelength of 451nm irradiates the mixed solution, and the illumination time is 1h, 3h, 5h, 7h, 9h respectively, and circulating water is introduced to ensure that the rea...

Embodiment 3

[0037] In the case of keeping other experimental conditions consistent in implementation 1, the substrate used is benzylamine, and the flavin photosensitizer is 10-octylbenzo[g]pteridine-2,4(3H,10H)-dione ( Molecular formula is C 18 h 22 N 4 o 2 ), the fixed reaction time was 9h, and the influence of different organic solvents on the yield of reactants was discussed. The labels of the prepared samples were sample-5, sample-6, and sample-7, respectively.

[0038] The specific preparation method is:

[0039] (1) 3ml of organic solvent was added to a 10ml reaction flask, followed by 0.2mmol of benzylamine and 0.001mmol of 10-octylbenzo[g]pteridine-2,4(3H,10H)-dione;

[0040] (2) Under normal pressure air atmosphere, the light intensity is 1240W / m 2 1. The mixed solution was irradiated by an LED lamp with a wavelength of 451nm for 9 hours, and circulating water was introduced to ensure that the reaction conditions were carried out at room temperature;

[0041] (3) Use thin-l...

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Abstract

The invention belongs to the technical field of photocatalytic oxidation, and particularly relates to a method for preparing N-benzylidenebutylamine through efficient photocatalytic oxidation of benzylamine. A flavin photosensitizer is used as a catalyst, and N-benzylidenebutylamine is prepared by a one-step method under the action of illumination. The preparation method specifically comprises the following steps: (1) dissolving the flavin photosensitizer and benzylamine in an organic solvent; and (2) introducing air into the mixed solution obtained in the step (1) at room temperature and normal pressure, and performing illumination to obtain the N-benzylidenebutylamine. The preparation process is simple, the preparation conditions are mild, no heavy metal is used in the preparation process, the preparation method is environment-friendly, and the cost is low; according to the method provided by the invention, N-benzylidenebutylamine can be prepared under the conditions of normal temperature and normal pressure, the energy consumption is low, the method is simple and easy to operate, and the method can be used for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of photocatalytic oxidation, and in particular relates to a method for preparing N-benzylbutylamine by highly efficient photocatalytic oxidation of benzylamine. Background technique [0002] Since Schiff base compounds can be used as intermediates in the synthesis of fine chemicals and drug molecules, it is very valuable to study the synthesis of Schiff bases. In recent years, with the continuous development of science and technology, there are more and more methods for preparing Schiff base compounds. Generally, Schiff base compounds are obtained from amine compounds and carbonyl compounds through dehydration condensation reaction, but this method has the disadvantage that the nucleophilic addition reaction between the two substances is not easy to control. In addition, there are many ways to synthesize Schiff base compounds under the catalysis of catalysts, such as the condensation of hydroxyl compounds a...

Claims

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Application Information

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IPC IPC(8): C07C249/02C07C251/24
CPCC07C249/02C07C251/24Y02P20/584
Inventor 郭慧敏邱阳雷志文张翔宇刘新
Owner DALIAN UNIV OF TECH
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