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A kind of synthetic n, the method for n'-dibenzylethylenediamine

A technology of dibenzylethylenediamine and dibenzylideneethylenediamine is applied in the field of catalytic hydrogenation to prepare N,N'-dibenzylethylenediamine, and can solve the problems of slowing down the reaction speed, side reactions, hydrogenolysis And polymerization and other problems, to achieve the effect of speeding up the reaction, good stability, and improving selectivity

Active Publication Date: 2019-05-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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. This not only slows down the reaction speed, but also easily leads to side reactions such as CN hydrogenolysis and polymerization, which is not conducive to the smooth progress of the reaction.

Method used

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  • A kind of synthetic n, the method for n'-dibenzylethylenediamine
  • A kind of synthetic n, the method for n'-dibenzylethylenediamine
  • A kind of synthetic n, the method for n'-dibenzylethylenediamine

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Embodiment 1

[0032] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 600 mesh, and the specific surface area is 1400m 2 / g, with an average pore diameter of 4nm, it was mixed with 0.6g urea uniformly, and treated at 1000°C for 5h under a nitrogen atmosphere to obtain nitrogen-doped mesoporous carbon. Then, the above-mentioned nitrogen-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 was configured into a slurry at 80°C, 10ml of 85% hydrazine hydrate solution was added dropwise, stirred for 2 hours, filtered, the filter cake was washed with deionized water until neutral, and vacuum-dried at 100°C to obtain nitrogen...

Embodiment 2

[0034] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 1000 mesh, and the specific surface area is 1200m 2 / g, the average pore size is 5nm, put it in NH 3 In , the gas flow rate is 1 L / h, and the nitrogen-doped mesoporous carbon is obtained by treating at 800 ° C for 10 h. The above nitrogen-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; The cake was prepared into a slurry at 60°C, 10ml of formaldehyde was added dropwise, stirred for 2 hours, filtered, the filter cake was washed with deionized water until neutral, and vacuum-dried at 90°C to obtain a nitrogen-doped mesoporous carbon-supported platinum catalyst.

Embodiment 3

[0036] Weigh 10g of mesoporous carbon, the particle size of mesoporous carbon is 100 mesh, and the specific surface area is 1500m 2 / g, with an average pore diameter of 10nm, mix it with 4g of melamine evenly, and treat it at 1200°C for 3h under a helium atmosphere to obtain nitrogen-doped mesoporous carbon. The above nitrogen-doped mesoporous carbon was prepared in 100ml of deionized water into 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, 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°C to obtain a nitrogen-doped mesoporous carbon-supported palladium catalyst.

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Abstract

The invention discloses a synthesis method of N,N'-dibenzylethylenediamine. The synthesis method is: in a reaction kettle, N,N'-dibenzylethylenediamine is added to nitrogen-doped mesopores. N,N'-dibenzylethylenediamine is prepared through a liquid phase catalytic hydrogenation reaction under the action of a carbon-supported precious metal catalyst; in the nitrogen-doped mesoporous carbon-supported precious metal catalyst, the precious metal is Pd or Pt, and the precious metal is The amount is 1~10wt%. The synthesis method of the present invention has the advantage of high selectivity of target products.

Description

(1) Technical field [0001] The invention relates to a method for preparing N,N'-dibenzylethylenediamine (DBE) by catalytic hydrogenation. (2) Background technology [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, and 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, ordinary Pd / C or Pt / C catalysts have the problem of poor selectivity of target products, mainly because if the activity of Pd / C or Pt / C catalysts is too high, it will lead to serious C—N hydrogenolysis. The reaction produces by-products such as monobenzylethylenediamine; if the activity of the Pd / C o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/27C07C209/52B01J23/44B01J23/42B01J27/24B01J35/10
CPCC07C209/52B01J23/42B01J23/44B01J27/24B01J35/60B01J35/64C07C211/27
Inventor 张群峰马磊卢春山丰枫许孝良李小年
Owner ZHEJIANG UNIV OF TECH
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