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Method used for high efficiency preparation of N,N'-dibenzylethylenediamine (DBE) through catalytic hydrogenation

A technology for dibenzylethylenediamine and dibenzylideneethylenediamine is applied in the field of efficient preparation of N,N-dibenzylethylenediamine by catalytic hydrogenation, and can solve the problem of slowing down the reaction speed, side reactions, disadvantages, etc. problem, to achieve the effect of speeding up the reaction, improving the selectivity, and not easy to drain

Active Publication Date: 2018-06-29
浙江辰阳化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, commercial Pd / C and Pt / C catalysts generally use activated carbon as the carrier. Although activated carbon has the advantages of low price and large specific surface area, the pore structure of activated carbon is mainly micropores, and the surface is neutral.
When Pd / C or Pt / C catalysts supported by activated carbon are used to prepare DBE by hydrogenation of N,N-dibenzylidene ethylenediamine, both raw materials and products have serious diffusion resistance in the micropores of activated carbon, which is Not only slows down the reaction speed, but also easily leads to side reactions such as C-N hydrogenolysis and polymerization, which is not conducive to the smooth progress of the reaction

Method used

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  • Method used for high efficiency preparation of N,N'-dibenzylethylenediamine (DBE) through catalytic hydrogenation
  • Method used for high efficiency preparation of N,N'-dibenzylethylenediamine (DBE) through catalytic hydrogenation
  • Method used for high efficiency preparation of N,N'-dibenzylethylenediamine (DBE) through catalytic hydrogenation

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Effect test

Embodiment 1

[0029] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 800 mesh, and the specific surface area is 1400m 2 / g, the average pore size is 4nm, mix it with 0.8g urea evenly, treat it at 1000℃ for 5h under nitrogen atmosphere; then pass 1L / h H 2 S, treated at 1000°C for 5h, the nitrogen / sulfur co-doped mesoporous carbon was obtained. Then, the above-mentioned nitrogen / sulfur co-doped mesoporous carbon was prepared in 100ml of deionized water to form a slurry at a temperature of 80°C, and 10ml of H 2 PdCl 4 solution (the Pd content is 0.1g / ml), stirred for 2.5h; the pH value of the solution was adjusted to 8 with 10wt% NaOH solution, and the temperature was lowered to room temperature, filtered, and the filter cake was washed to neutrality with deionized water; The filter cake is made into a slurry at 80°C, 10ml of 85% hydrazine hydrate solution is added dropwise, stirred for 2 hours, filtered, the filter cake is washed with deionized water until neutral,...

Embodiment 2

[0031] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 400 mesh, and the specific surface area is 1200m 2 / g, the average pore size is 4nm, put it in NH 3 In the process, the gas flow rate is 2L / h, the treatment is at 800°C for 10h, and then 2L / h of H 2 S, treated at 1000°C for 5h, the nitrogen / sulfur co-doped mesoporous carbon was obtained. The above nitrogen / sulfur co-doped mesoporous carbon was prepared in 100ml of deionized water to make a slurry at a temperature of 60°C, and 6ml of H 2 PtCl 6 solution (Pt content is 0.1g / ml), stirred for 2h; the pH value of the solution was adjusted to 8.5 with 10wt% KOH solution, and the temperature was lowered to room temperature, filtered, and the filter cake was washed to neutral with deionized water; Prepare the cake into a slurry at 60°C, add 10ml of formaldehyde dropwise, stir for 2 hours, filter, wash the filter cake with deionized water until neutral, and dry it in vacuum at 90°C to obtain nitrogen / su...

Embodiment 3

[0033] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 150 mesh, and the specific surface area is 1000m 2 / g, with an average pore size of 10nm, mix it with 4g of urea evenly, treat it at 1200°C for 3h under a helium atmosphere, and then pass 3L / h of H under a nitrogen atmosphere. 2 S, treated at 600°C for 5h, the nitrogen / sulfur co-doped mesoporous carbon was obtained. The above nitrogen / sulfur co-doped mesoporous carbon was prepared in 100ml of deionized water to make a slurry at a temperature of 40°C, and 10ml of Pd(NO 3 ) 2 solution (with a Pd content of 0.005g / ml), stirred for 4h; the pH value of the solution was adjusted to 9 with ammonia water, and the temperature was lowered to room temperature, filtered, and the filter cake was washed with deionized water until neutral; Prepare a slurry under water, add 30ml of formic acid dropwise, stir for 4 hours, filter, wash the filter cake with deionized water until neutral, and dry it in vacuum at 80...

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Abstract

The invention discloses a method used for high efficiency preparation of N,N'-Bis(phenylmethyl)-1,2-ethanediamine (DBE) through catalytic hydrogenation. The method comprises a following step: in a reaction vessel, N,N'-dibenzylidene ethylenediamine is subjected to liquid phase catalytic hydrogenation under the catalytic effect of a nitrogen / sulfur codoped mesoporous carbon loaded noble metal catalyst so as to obtain DBE. The method is high in target product selectivity.

Description

technical field [0001] The invention relates to a method for efficiently preparing N,N-dibenzylethylenediamine (DBE) by catalytic hydrogenation. Background technique [0002] DBE is a pharmaceutical intermediate, mainly used in the production of long-acting penicillin G, long-acting penicillin V, long-acting ampicillin, long-acting cephalosporins and other drugs. At present, DBE is mainly prepared industrially from N,N-dibenzylideneethylenediamine through catalytic hydrogenation. Among them, hydrogenation catalyst is the key technology of this process. [0003] Industrially, the catalysts used in the hydrogenation of N,N-dibenzylideneethylenediamine to prepare DBE are mainly Pd / C and Pt / C. However, common Pd / C or Pt / C catalysts have the problem of difficult balance between activity and selectivity. This is mainly because if the activity of the Pd / C or Pt / C catalyst is too low, the polymerization reaction will easily occur and generate by-products such as polybenzylethylen...

Claims

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Application Information

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IPC IPC(8): C07C209/70C07C211/27B01J27/24B01J35/10
CPCC07C209/70B01J27/24B01J35/60C07C211/27
Inventor 李小年张群峰陈燕舞赵根富彭艳婷
Owner 浙江辰阳化工有限公司
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