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Preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine

一种三甲基环己胺、三甲基环己酮的技术，应用在脂肪族胺的制备领域，能够解决催化剂成本提高、反应器体积增大、氨基腈低等问题

Active Publication Date: 2013-02-13
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The existing methods for preparing IPDA all have the following defects: in order to make the content of aminonitrile in the reaction product as low as possible, it is often necessary to have a higher residence time in the hydrogenation reaction stage
The use of a large amount of hydrogenation catalyst means the increase of the cost of the catalyst, but also the increase of the volume of the reactor and the investment of the reaction equipment.

Method used

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  • Preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine
  • Preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine
  • Preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] process such as figure 2 As shown, the temperature of R1 is controlled at 40°C, the temperature of R2 is controlled at 60°C, the temperature of R3-0 is controlled at 130°C, the reaction pressure of R1, R2, and R3-0 is all controlled at 15MPa, the feed rate of IPN is 80g / h, and the NH 3 The feed rate is 168g / h, and the hydrogen flow rate is 1100 standard L / h. Before the material flow enters into R2, a NaOH methanol solution with a mass concentration of 5% is added, and the feed rate is 16 g / h. The space velocity over the catalyst in each reactor is as follows:

[0055]

[0056] After the device was running for 100 hours, before the reaction mixture entered R3-0, a methanol solution of formic acid with a mass concentration of 5% was added to the reaction mixture, and the feed rate was 16 g / h. After device operation 200 hours, take a sample again from R1 reactor outlet, wherein the content of 3-cyano-3,5,5-trimethylcyclohexylimine is 95%, take a sample again from R2 ...

Embodiment 2

[0059] process such as figure 2 As shown, the temperature of R1 is controlled at 40°C, the temperature of R2 is controlled at 60°C, the temperature of R3-0, R3-1, R3-2, R3-3, and R3-4 is controlled at 130°C, and the temperature of R1, R2, R3-0, The reaction pressures of R3-1, R3-2, R3-3, and R3-4 are all controlled at 15MPa, the feed rate of IPN is 80g / h, and the NH 3 The feed rate is 168g / h, and the hydrogen flow rate is 1100 standard L / h. Before the material flow enters into R2, a NaOH methanol solution with a mass concentration of 5% is added, and the feed rate is 16 g / h. Before the reaction mixture enters the second-stage hydrogenation reactor, a methanol solution of formic acid with a mass concentration of 5% is added to the reaction mixture, and the feed rate is 16 g / h. The space velocity over the catalyst in each reactor is as follows:

[0060]

[0061]

[0062] When the test device reaches 300 hours, 400 hours, 500 hours, and 600 hours, the products that have u...

Embodiment 3

[0067] The temperature of R1 is controlled at 60°C, the temperature of R2 is controlled at 100°C, the temperature of R3-0 is controlled at 100°C, the reaction pressure of R1, R2, and R3-0 is all controlled at 20MPa, the feed rate of IPN is 80g / h, and the NH 3 The feed rate is 650g / h, and the hydrogen flow rate is 220 standard L / h. Before R2, a LiOH dimethyl ether solution with a mass concentration of 1% was added, and the feed rate was 8 g / h. Before the reaction mixture enters the R3-0, an aqueous solution of phthalic acid with a mass concentration of 1% is added to the reaction mixture, and the feed amount is 8 g / h.

[0068] After device operation 100 hours, take a sample from R1 reactor outlet, do gas chromatographic analysis, wherein the content of 3-cyano-3,5,5-trimethylcyclohexyl imine is 94%, R2 reactor outlet sampling, Do gas chromatography analysis, wherein the IPDA content is 81%, and the aminonitrile content is 14.5%.

[0069] At the beginning of the test, use R3-0...

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Abstract

The invention provides a continuous preparation method of 3-aminomethyl-3,5,5-trimethylcyclohexylamine. In the invention, a 3-cyan-3,5,5-trimethylcyclohexylimine charging flow reacts with NH3 and hydrogen in the presence of a hydrogenation catalyst. The method is characterized in that the method concretely comprises the following steps: adding an alkaline compound to the 3-cyan-3,5,5-trimethylcyclohexylimine charging flow, and adding an acidic compound to a reaction flow after partial 3-cyan-3,5,5-trimethylcyclohexylimine has been reacted in order to carry out a hydrogenation reaction to prepare the 3-aminomethyl-3,5,5-trimethylcyclohexylamine. The method has the advantages of low amino nitrile content in the product, effective reduction of the reaction stay time, and substantial reduction of the application amount of the catalyst in the hydrogenation reaction process.

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, 3-aminomethyl-3,5,5-trimethylcyclohexylamine is produced via 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile, referred to as IPN) reacts with ammonia to form 3-cyano-3,5,5-trimethylcyclohexyl imine (isophorone nitrile imine, referred to as IPNI), which is then catalytically reacted with hydrogen in the presence of ammonia. Prepared by reductive amination reaction. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/36C07C209/48
CPCC07C211/36C07C209/62C07C209/48C07C253/30C07C2101/14C07C209/52C07C2601/14C07C255/61C07C255/46
Inventor 陈长生黎源赵文娟崔洪寅华卫琦
Owner WANHUA CHEM GRP CO LTD
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