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Method for green synthesis of N-benzylidenebutyramide by highly-selective oxidation of benzylamine

A technology of benzylamine oxide and synthesis method, which is applied in chemical instruments and methods, imino compound preparation, metal/metal oxide/metal hydroxide catalyst, etc., and can solve high reaction temperature, low photocatalytic activity, and long reaction Time and other issues, to achieve the effect of low energy consumption

Active Publication Date: 2017-07-14
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some defects in the existing oxidation method: higher reaction temperature, longer reaction time, a large amount of organic solvent used in the reaction or post-treatment
However, these photocatalysts have disadvantages such as low photocatalytic activity and weak response to visible light.

Method used

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  • Method for green synthesis of N-benzylidenebutyramide by highly-selective oxidation of benzylamine
  • Method for green synthesis of N-benzylidenebutyramide by highly-selective oxidation of benzylamine
  • Method for green synthesis of N-benzylidenebutyramide by highly-selective oxidation of benzylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The present invention prepares the photocatalyst with the different molar ratios of chromium tungstate and bismuth tungstate in the cadmium tungstate-bismuth tungstate composite photocatalyst:

[0027] Preparation of cadmium tungstate: Dissolve 1.234g cadmium nitrate in 40ml deionized water and mix with 0.240g ethylenediamine solution, stir well to form solution A; dissolve sodium tungstate in 40ml water to obtain solution B; mix and stir AB for 10min , to obtain solution C; then the obtained solution C was crystallized at 180° C. for 20 hours. The crystallization solution is separated by cooling and filtration, washed three times with deionized water and once with absolute ethanol, and dried at 80°C for 6 hours to obtain cadmium tungstate;

[0028] Preparation of composite material: Dissolve 0.041g of sodium tungstate in 10ml of ethylene glycol solution, stir well to form solution D; dissolve 0.121g of bismuth nitrate in 10ml of ethylene glycol solution, stir well to f...

Embodiment 2～5

[0032] For cadmium tungstate and bismuth tungstate composite photocatalysts with different molar ratios, the operation steps are similar to those in Example 1, only the amount of sodium tungstate and bismuth nitrate in the composite material is changed, and the rest of the conditions are unchanged, and the sample number is Cat 2, Cat 3, Cat 4, Cat 5. See Table 1 for the composite catalyst conditions and reaction results prepared in Examples 1-5.

[0033] Table 1 Preparation conditions and reaction results of composite photocatalysts with different molar ratios

[0034]

[0035] It is found from Table 1 that the ratio of Cat 4 cadmium tungstate-bismuth tungstate makes the conversion rate of benzylamine 38.7%, the selectivity of N-benzylbutylamine is greater than 99%, and has the best photocatalytic effect.

Embodiment 6～10

[0037] According to the step 4 of the embodiment in which the molar ratio of chromium tungstate and bismuth tungstate in the reaction mixture has the best effect is 1:7.5, the remaining conditions remain unchanged, and the crystallization temperature prepared by the composite photocatalyst is changed, respectively using 100°C, 120°C, After crystallization at 140°C, 180°C, and 200°C for 24 hours, the samples were respectively coded as T 1, T 2, T 3, T 4, and T 5, and the rest of the operation steps were similar to those in Example 4. See Table 2 for the composite catalyst conditions and reaction results prepared in Examples 6-10.

[0038] Table 2 The molar ratio of chromium tungstate and bismuth tungstate is 1:7.5 and different crystallization temperature conditions and reaction results

[0039]

[0040]

[0041] It is found from Table 2 that different benzylamine conversion rates are obtained at different crystallization temperatures, and the temperature is compared with...

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Abstract

The invention provides a method for green synthesis of N-benzylidenebutyramide by highly-selective oxidation of benzylamine. The method comprises the following steps: weighing cadmium tungstate and bismuth tungstate, carrying out dissolving in an alcohol solution, and carrying out uniform mixing under stirring; subjecting the mixed solution to crystallization, and carrying out cooling, filtering, separating, drying and the like so as to prepare a cadmium tungstate-bismuth tungstate composite photocatalyst; and weighing the cadmium tungstate-bismuth tungstate composite photocatalyst, carrying out dispersing in benzylamine, introducing oxygen, and carrying out illumination so as to obtain the N-benzylidenebutyramide. The method provided by the invention can improve the conversion rate of benzylamine by controlling the ratio of a catalyst; and the N-benzylidenebutyramide prepared by using the method has selectivity larger than 99%. The method provided by the invention has the characteristics of greenness, no solvent, high efficiency, low energy consumption, simple synthetic process, etc.

Description

[0001] 【Technical field】 [0002] The invention relates to the field of photocatalytic oxidation, in particular to a method for green synthesis of N-benzylbutylamine by highly selective oxidation of benzylamine. [0003] 【Background technique】 [0004] Imines are important intermediates in organic synthesis and have important applications in the field of biomedicine. Due to the electrophilic double bond, imines can undergo important reactions with other reagents. As an important chemical product that can be used to synthesize biologically active natural products and drug candidates, N-benzylbutylamine can undergo addition reactions with esters, acid chlorides, enones, etc. to generate β-lactams, and β- The wide application of lactam antibiotics makes the oxidation of benzylamine to N-benzylbutylamine important. The traditional synthesis method adopts the condensation of primary amines and aldehydes and ketones. This method requires a heating dehydration device, the operation...

Claims

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Application Information

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IPC IPC(8): C07C249/02C07C251/24B01J23/31
CPCC07C249/02B01J23/31B01J35/39C07C251/24
Inventor 尹双凤陈鹏陈浪蒋旭曾誉刘娜
Owner HUNAN UNIV
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