Method for synthesizing hexamethylenediamine and co-producing n-hexylamine and cyclohexylimide

A technology of cyclohexylimine and n-hexylamine, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds, etc., can solve the problems of high operation safety risk, difficult separation, long operation process, etc. The effect of risk capability and profitability, easy and safe operation, and high product yield

Active Publication Date: 2020-12-15
JIANGSU YANGNONG CHEM GROUP +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation methods of cyclohexyl imine mainly include two kinds: one is obtained by deamination and cyclization of 1,6-hexamethylenediamine. Since this process fails to completely solve the technical problem of intermolecular deamination, At present, this method has been basically eliminated; the other one uses aniline as a raw material, mixes aniline vapor and hydrogen into the reactor, and carries out hydrogenation reaction at 130°C to 170°C in the presence of a cobalt catalyst. The reaction is cooled and then distilled to obtain Finished product, but the process is complicated and the preparation cost is high
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Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] A kind of method of synthesizing hexamethylenediamine coproduction n-hexylamine and cyclohexyl imine of the present invention comprises the steps:

[0030] (1) Pump ammonia and caprolactam with a molar ratio of 30:1 into a fixed-bed reactor filled with an alumina catalyst at the same time for ammoniation reaction. The weight hourly space velocity of caprolactam is 3.0h -1 , the reaction temperature is 400°C, the reaction pressure is 1.5MPa, after the reaction, the ammoniated solution is obtained; the ammoniated solution obtained by the ammoniation reaction is quantitatively analyzed, and the results show that the single-pass conversion rate of caprolactam is 81.84%, and the selectivity of aminocapronitrile 98.12%, the selectivity of 5-hexenenitrile is 1.16%;

[0031] (2) Put the ammoniated solution obtained in step (1) into the autoclave, add the Raney nickel catalyst and solvent ethanol, and carry out the hydrogenation reaction for 5 hours at a reaction temperature of ...

Embodiment 2

[0033] A kind of method of synthesizing hexamethylenediamine coproduction n-hexylamine and cyclohexyl imine of the present invention comprises the steps:

[0034] (1) Pump ammonia and caprolactam with a molar ratio of 30:1 into a fixed-bed reactor filled with a silica catalyst at the same time to carry out ammoniation reaction. The weight hourly space velocity of caprolactam is 3.0h -1 , the reaction temperature is 400°C, and the reaction pressure is 1.5MPa. After the reaction, the ammoniated solution is obtained; the ammoniated solution obtained by the ammoniation reaction is quantitatively analyzed, and the results show that the single-pass conversion rate of caprolactam is 78.56%, and 6-aminocapronitrile The selectivity of is 95.57%, the selectivity of 5-hexenenitrile is 3.56%;

[0035] (2) Put the ammoniated solution obtained in step (1) into the autoclave, add the platinum carbon catalyst and solvent ethanol, and carry out the hydrogenation reaction for 5 hours at a react...

Embodiment 3

[0037] A kind of method of synthesizing hexamethylenediamine coproduction n-hexylamine and cyclohexyl imine of the present invention comprises the steps:

[0038] (1) Pump ammonia and caprolactam with a molar ratio of 30:1 into a fixed-bed reactor filled with alumina catalyst at the same time for ammoniation reaction. The weight hourly space velocity of caprolactam is 0.5h -1 , the reaction temperature is 400°C, and the reaction pressure is 1.5MPa. After the reaction, the ammoniated solution is obtained; the ammoniated solution obtained by the ammoniation reaction is quantitatively analyzed, and the results show that the single-pass conversion rate of caprolactam is 85.66%, and 6-aminocapronitrile The selectivity of is 95.56%, the selectivity of 5-hexenenitrile is 2.58%;

[0039] (2) Put the ammoniated solution gained in step (1) into the autoclave, add the Raney nickel catalyst and solvent methanol, and carry out hydrogenation reaction for 5h at a reaction temperature of 80°C...

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Abstract

The invention relates to a method for synthesizing hexamethylenediamine and co-producing n-hexylamine and cyclohexylimide, which comprises the following steps: simultaneously conveying ammonia gas andcaprolactam into a first reactor, and carrying out ammoniation reaction under the action of a catalyst to obtain ammoniation liquid; and putting ammoniation liquid obtained by the ammoniation reaction into a second reactor, adding a catalyst and a solvent, and carrying out hydrogenation reaction to obtain products hexamethylenediamine, n-hexylamine and cyclohexyleneimine. According to the invention, the method for co-production of three products of hexamethylenediamine, n-hexylamine and cyclohexyleneimine by the same process is innovatively designed, the problems existing in independent production of each product in the prior art are effectively overcome, the process route is simple, the operation is simple, convenient and safe, continuous production can be realized, the product yield ishigh, and the economic benefit is greatly improved; besides, by regulating and controlling the reaction conditions of the process, the proportion of three products, namely hexamethylenediamine, n-hexylamine and cyclohexyleneimine, can be regulated and controlled, so that production is matched with actual market requirements, and the anti-risk capacity and profit capacity of the process are fully improved.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a method for synthesizing hexamethylenediamine and coproducing n-hexylamine and cyclohexylimine. Background technique [0002] Hexamethylenediamine is a key raw material in the nylon industry. It is commonly used in the industry to synthesize nylon 66 and nylon 610, and then to make products such as nylon resin, nylon fiber and engineering plastics. At present, the large-scale industrialized production method of hexamethylenediamine is mainly produced by direct hydrogenation of adiponitrile under the action of a nickel-based catalyst. However, during the implementation of this process, it is generally accompanied by the production of hexamethylenediamine, which has a great impact on the quality of the synthetic nylon 66 product. Impurity diaminocyclohexane, and the impurity is extremely difficult to separate. In the prior art, patent CN107739318A discloses a me...

Claims

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Application Information

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IPC IPC(8): C07C209/48C07C211/12C07C211/07C07D223/04
CPCC07C209/48C07C253/00C07D223/04C07C211/12C07C211/07C07C255/24C07C255/30Y02P20/584
Inventor 王根林丁克鸿徐林何成义王铖王刚刘鑫殷恒志
Owner JIANGSU YANGNONG CHEM GROUP
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