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Preparation method for 3-aminomethyl-3,5,5-trimethylcyclohexyl amine

A technology of trimethylcyclohexylamine and trimethylcyclohexanone, which is applied in the field of preparation of aliphatic amines, can solve the problems of reduced conversion rate, device shutdown, and increased residence time of hydrogenation catalyst loading, so as to avoid Decomposition, the effect of ensuring stable operation

Active Publication Date: 2014-12-24
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] 1) When the hydrogenation reaction solution contains IPN, the presence of such basic compounds will cause IPN to de-HCN, and HCN will shorten the service life of the hydrogenation catalyst;
[0011] 2) After most of the IPAN in the hydrogenation reaction solution is converted into IPDA, such as after 80-90% of IPAN is converted into IPDA, the existence of such basic compounds is unfavorable for the remaining IPAN to be converted into IPDA, and the conversion The rate will decrease with the increase of the concentration of such basic compounds. At this time, it is necessary to increase the loading amount of the hydrogenation catalyst or prolong the residence time of the reaction, resulting in an increase in the cost of the catalyst;
[0012] 3) After the hydrogenation reaction is finished, in the process of post-treatment, it is unavoidable that such basic compounds will be precipitated in the separation process, such as after the product is dehydrated, such basic compounds will be precipitated in the separation tower, Affect the stable operation of the separation tower, resulting in the shutdown of the device

Method used

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  • Preparation method for 3-aminomethyl-3,5,5-trimethylcyclohexyl amine
  • Preparation method for 3-aminomethyl-3,5,5-trimethylcyclohexyl amine

Examples

Experimental program
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Effect test

Embodiment 1

[0062] process such as figure 1 As shown, R1 is an imidization reactor, which uses a tubular reactor, and the catalyst inside the reactor is 75mm high and 20mm in diameter; R2 is the first-stage hydrogenation reactor, which uses a trickle bed reactor, and the catalyst is filled inside the reactor 75mm in height and 20mm in diameter; R3 is the second-stage hydrogenation reactor, which adopts a trickle bed reactor, and the catalyst inside the reactor is 75mm in height and 20mm in diameter; R4 is the auxiliary agent decomposition reactor, and the catalyst in the reactor is 400mm in height. The diameter is 20mm, and R5 is the third-stage hydrogenation reactor, which adopts a trickle bed reactor. The catalyst inside the reactor is 37.5mm high and 20mm in diameter.

[0063] R1 is filled with γ-Al with a diameter of 0.5mm 2 o 3 Balls, R2, R3, R5 are each equipped with 16-30 mesh Raney cobalt catalyst Catalloy 6400 for block fixed bed, R4 is filled with about 0.5mm α-Al 2 o 3 roun...

Embodiment 2

[0067] Other conditions are as embodiment 1, change the hydrogenation reaction auxiliary agent wherein into 5wt% tetraethylammonium hydroxide methanol solution, feed rate is 16g / h, R3 reaction temperature is changed into 100 ℃, R4 decomposition temperature is changed into At 135°C, the circulating stream 9 accounts for 4wt% of the weight of the aid decomposition reaction material 8.

[0068] Samples were taken from the outlet of the R1 reactor, and the content of IPNI in the imidization reaction material 2 was about 95 wt%, and samples were taken from the outlet of the R2 reactor, and the content of IPN in the first hydrogenation reaction material 6 was about 0.005 wt%. Sampling from the outlet of the R3 reactor, the content of IPDA in the second hydrogenation reaction material 7 is about 85wt%, and the content of IPAN is about 13.5wt%; sampling analysis from the outlet of the R4 reactor does not detect tetraethylammonium hydroxide, and reacts from R5 Sampling analysis at the ...

Embodiment 3

[0070] Other conditions are as embodiment 1, change the hydrogenation reaction auxiliary agent wherein into 1wt% tetramethylammonium hydroxide aqueous solution, feed rate is 16g / h, R4 decomposition temperature is changed into 140 DEG C, and circulation stream 9 accounts for auxiliary The agent decomposes 3wt% of reaction material 8 weights.

[0071] Samples were taken from the outlet of the R1 reactor, and the content of IPNI in the imidization reaction material 2 was about 95 wt%, and samples were taken from the outlet of the R2 reactor, and the content of IPN in the first hydrogenation reaction material 6 was about 0.004 wt%. Sampling from the outlet of the R3 reactor, the content of IPDA in the second hydrogenation reaction material 7 is about 86.5wt%, and the content of IPAN is about 12wt%; sampling and analysis from the outlet of the R4 reactor, no tetramethylammonium hydroxide is detected, and the reaction from R5 Sampling analysis at the outlet of the reactor shows that...

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Abstract

The invention provides a preparation method for 3-aminomethyl-3,5,5-trimethylcyclohexyl amine. According to the preparation method, imidization reaction materials containing 3-cyano-3,5,5-trimethylcyclohexyl imine is subjected to first-stage hydrogenation reaction under the help of a cycled material of a subsequent step, so that a first hydrogenation reaction material is obtained, and also generation of HCN-removed products is effectively inhibited, then a second-stage hydrogenation reaction is performed under the effect of a heating-degradable alkali auxiliary agent, then heating is performed to decompose the alkali auxiliary agent, a part of degraded materials is taken as the cycled material and is returned to the first-stage hydrogenation reaction as an auxiliary agent, and the residual part is subjected to third-stage hydrogenation reaction, so that 3-aminomethyl-3,5,5-trimethylcyclohexyl amine is obtained, and the content of 3-cyano-3,5,5-trimethylcyclohexyl amine and secondary amine products is effectively reduced.

Description

technical field [0001] The present invention relates to a preparation method of aliphatic amine, in particular to hydrogenation of 3-cyano-3,5,5-trimethylcyclohexanone to prepare 3-aminomethyl-3,5,5-trimethylcyclohexyl amine method. Background technique [0002] 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine, referred to as IPDA) is the preparation of 3-isocyanate group methylene-3,5,5-trimethylcyclohexyl It is a raw material for isocyanate (isophorone diisocyanate, referred to as IPDI), polyamide, etc., and it can also be used as a curing agent for epoxy resin. On an industrial scale, IPDA is obtained by combining 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile, IPN for short) with NH 3 The reaction forms 3-cyano-3,5,5-trimethylcyclohexyl imine (isophorone nitrile imine, referred to as IPNI), and IPNI is subsequently reacted with hydrogen in NH 3 In the presence of catalyzed reductive amination reaction prepared. Its reaction process is as follo...

Claims

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Application Information

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IPC IPC(8): C07C211/36C07C209/48
Inventor 陈长生姜进科陈忠英李付国李昂王坤崔娇英吕成戈赵文娟黎源
Owner WANHUA CHEM GRP CO LTD
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