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Bis(aminomethyl)cyclohexane isomerization method

一种氨基甲基、环己烷的技术，应用在有机化学方法、从胺制备氨基化合物、氨基化合物纯化/分离等方向，能够解决难合成反式体等问题

Active Publication Date: 2017-11-28
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] It is also mostly known about the method of nuclear hydrogenation of xylylenediamine to produce bis(aminomethyl)cyclohexane, but for the nuclear hydrogenation reaction of xylylenediamine, the cis-isomer is better than the trans-isomer Easier to generate, often difficult to selectively synthesize trans isomers

Method used

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  • Bis(aminomethyl)cyclohexane isomerization method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] Add 200 g of 1,4-bis(aminomethyl)cyclohexane (cis / trans=60 / 40), 8.0 g of 4-methylbenzylamine (4-MBA), and 2.9 g of sodium amide into a 500 mL flask. A 3 mmφ pipe made of SUS316 was introduced into the liquid in the flask, and argon gas was continuously blown thereinto at a flow rate of 200 mL / min to perform isomerization reaction at 120° C. for 5 hours. The isomer composition (cis / trans) after the isomerization reaction was 18 / 82, and the recovery rate of 1,4-bis(aminomethyl)cyclohexane was 89%. The change over time of the trans isomer ratio is shown in figure 1 .

Embodiment 2

[0109] Put 200 g of 1,4-bis(aminomethyl)cyclohexane (cis / trans = 60 / 40), 9.0 g of m-xylylenediamine, and 2.9 g of sodium amide into a 500 mL flask, and introduce a 3 mmφ pipe made of SUS316 The isomerization reaction was performed at 120°C for 5 hours while continuously blowing argon gas into the liquid in the flask at a flow rate of 200 mL / min. The isomer composition (cis / trans) after the isomerization reaction was 17 / 83, and the recovery rate of 1,4-bis(aminomethyl)cyclohexane was 87%.

Embodiment 3

[0111] 200 g of 1,4-bis(aminomethyl)cyclohexane (cis / trans = 60 / 40), 7.1 g of benzylamine, and 2.9 g of sodium amide were placed in a 500 mL flask, and a 3 mmφ pipe made of SUS316 was introduced into the end of the flask. The isomerization reaction was performed at 120° C. for 5 hours while continuously blowing argon gas into the liquid at a flow rate of 200 mL / min. The isomer composition (cis / trans) after the isomerization reaction was 19 / 81, and the recovery rate of 1,4-bis(aminomethyl)cyclohexane was 96%.

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Abstract

Provided is a bis(aminomethyl)cyclohexane isomerization method wherein bis(aminomethyl)cyclohexane is isomerized while introducing an inert gas into a reaction solution that includes bis(aminomethyl)cyclohexane, at least one type of compound selected from the group consisting of alkali metals, alkali metal-containing compounds, alkali earth metals, and alkali earth metal-containing compounds, and a benzylamine compound.

Description

technical field [0001] The present invention relates to a process for the isomerization of bis(aminomethyl)cyclohexane. Background technique [0002] Bis(aminomethyl)cyclohexane is an industrially important compound used as a raw material for epoxy curing agents, polyamides, polyurethanes, and the like. Bis(aminomethyl)cyclohexane exists in two isomers, a cis-isomer and a trans-isomer derived from the cyclohexane ring. It is known that the physical properties of a polymer using bis(aminomethyl)cyclohexane vary greatly depending on the isomer ratio of the cis-isomer and the trans-isomer. [0003] For example, it is known that a polyamide using 1,4-bis(aminomethyl)cyclohexane has higher melting point and higher heat resistance as the trans-isomer content is higher (Non-Patent Document 1). In addition, it is known that polyurethane using 1,4-diisocyanatomethylcyclohexane derived from 1,4-bis(aminomethyl)cyclohexane responds to the higher the trans-isomer content. The physica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/18C07B61/00
CPCC07B61/00C07C209/86C07B2200/09C07C2601/14C07C211/18C07C209/68C07C209/90C07B2200/07
Inventor 清水裕子山本良亮
Owner MITSUBISHI GAS CHEM CO INC