Method for producing bis (aminomethyl) cyclohexane

Patent metadata

Field	Value
Publication number	US-2016229792-A1
Application number	US-201415021841-A
Country	US
Kind code	A1
Filing date	Sep 17, 2014
Priority date	Sep 17, 2013
Publication date	Aug 11, 2016
Grant date	—

Abstract

A method for producing a bis(aminomethyl)cyclohexane having an isomerization step of isomerizing a cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a trans-isomer of 1,3-bis(aminomethyl)cyclohexane at the bottom part of a distillation tower to obtain a trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a cis-isomer of 1,3-bis(aminomethyl)cyclohexane; and a distillation step of separating the trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the cis-isomer of 1,3-bis(aminomethyl)cyclohexane by distillation, in the top part of the distillation tower, in which the isomerization reaction temperature in the isomerization step is 80 to 140° C., and the isomerization step and the distillation step are simultaneously carried out.

First claim

1 . A method for producing a bis(aminomethyl)cyclohexane comprising:
isomerizing a cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a trans-isomer of 1,3-bis(aminomethyl)cyclohexane at a bottom part of a distillation tower to obtain a trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or a cis-isomer of 1,3-bis(aminomethyl)cyclohexane; and separating the trans-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the cis-isomer of 1,3-bis(aminomethyl)cyclohexane by distillation, in a top part of the distillation tower, wherein an isomerization reaction temperature of the isomerizing is 80 to 140° C.; and the isomerizing and the distillation are simultaneously carried out.

2 . The method of claim 1 , wherein a content of the trans-isomer in the 1,4-bis(aminomethyl)cyclohexane obtained from the top part of the tower in the distillation is 84% or more.

3 . The method claim 1 , wherein a content of the trans-isomer in the 1,4-bis(aminomethyl)cyclohexane obtained from the top part of the tower in the distillation is 90% or more.

4 . The method of claim 1 , wherein, in the isomerizing, the cis-isomer of 1,4-bis(aminomethyl)cyclohexane and/or the trans-isomer of 1,3-bis(aminomethyl)cyclohexane are isomerized in the presence of
at least one compound selected from the group consisting of an alkali metal, an alkali metal-containing compound, an alkaline-earth metal and an alkaline-earth metal-containing compound, and a benzylamine compound.

5 . The method of claim 4 , wherein the benzylamine compound is at least one selected from the group consisting of benzylamine, 3-methylbenzylamine, 4-methylbenzylamine, dibenzylamine, metaxylylenediamine and paraxylylenediamine.

6 . The method of claim 4 , wherein the alkali metal is present and comprises metallic sodium.

7 . The method of claim 4 , wherein the alkali metal-containing compound is present and comprises at least one selected from the group consisting of an alkali metal hydride and an alkali metal amide.

8 . The method of claim 7 , wherein the alkali metal hydride is present and comprises sodium hydride.

9 . The method of claim 7 , wherein the alkali metal amide is present and comprises sodium amide.

10 . A 1,4-Bis(aminomethyl)cyclohexane comprising a trans-isomer content of 84% or more obtained by the method of claim 1 .

11 . The method of claim 1 , comprising isomerizing the cis-isomer of 1,4-bis(aminomethyl)cyclohexane.

12 . The method of claim 1 , comprising isomerizing the trans-isomer of 1,3-bis(aminomethyl)cyclohexane.

13 . The method of claim 1 , comprising isomerizing both the cis-isomer of 1,4-bis(aminomethyl)cyclohexane and the trans-isomer of 1,3-bis(aminomethyl)cyclohexane.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Yamamoto Yoshiaki
• Sameshima Yuko

Classifications

• C07C211/18

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C07C209/86

  Separation · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C209/68 Primary

  from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton · CPC title

• C07B2200/09

  Geometrical isomers · CPC title