# US 10,118,888 B2 · Method for isomerizing bis(aminomethyl) cyclohexane > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,118,888 B2 - Document ID: US10118888B2 - Status: Granted - Kind: B2 - Application number: 15/556,329 - Filed: 2016-02-25 - Published: 2018-02-15 - Granted: 2018-11-06 - Earliest claimed: 2015-03-09 - Assignees: Mitsubishi Gas Chemical Company, Inc. - Applicants: Mitsubishi Gas Chemical Company, Inc. - Inventors: Yuko Shimizu; Yoshiaki Yamamoto - Web page: https://patentgrep.com/patent/US10118888B2 ## CPC - C07C 209/68: from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton - C07C 209/86: Separation - C07C 211/18: containing at least two amino groups bound to the carbon skeleton - C07B 61/00: Other general methods - C07B 2200/07: Optical isomers - C07B 2200/09: Geometrical isomers - C07C 2601/14: The ring being saturated - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F) ## Abstract A method for isomerizing a bis(aminomethyl)cyclohexane, including isomerizing a bis(aminomethyl)cyclohexane while introducing an inert gas in a reaction solution containing a bis(aminomethyl)cyclohexane, at least one 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. ## Claims ### Claim 1 A method for isomerizing a bis(aminomethyl)cyclohexane, the method comprising isomerizing a bis(aminomethyl)cyclohexane while introducing an inert gas in a reaction solution comprising: a bis(aminomethyl)cyclohexane, at least one 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. ### Claim 2 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the inert gas is at least one selected from the group consisting of helium, argon and nitrogen. ### Claim 3 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the benzylamine compound is at least one selected from the group consisting of benzylamine, 3-methylbenzylamine, 4-methylbenzylamine, dibenzylamine, meta-xylylenediamine and para-xylylenediamine. ### Claim 4 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the benzylamine compound is 4-methylbenzylamine. ### Claim 5 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the reaction solution comprises an alkali metal-containing compound, which comprises sodium amide. ### Claim 6 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein an isomerization reaction temperature is 100 to 140° C. ### Claim 7 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the introducing of the inert gas comprises bubbling. ### Claim 8 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the bis(aminomethyl)cyclohexane is 1,4-bis(aminomethyl)cyclohexane. ### Claim 9 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the bis(aminomethyl)cyclohexane is 1,3-bis(aminomethyl)cyclohexane. ### Claim 10 (depends on 8) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 8, wherein the 1,4-bis(aminomethyl)cyclohexane is obtained in a trans-isomer content of at least 77%. ### Claim 11 (depends on 9) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 9, wherein the 1,3-bis(aminomethyl)cyclohexane is obtained in a cis-isomer content of at least 80%. ### Claim 12 (depends on 1) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 1, wherein the method comprises isomerizing the bis(aminomethyl)cyclohexane while continuously introducing the inert gas in the reaction solution. ### Claim 13 (depends on 10) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 10, wherein the method comprises isomerizing the bis(aminomethyl)cyclohexane while continuously introducing the inert gas in the reaction solution. ### Claim 14 (depends on 11) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 11, wherein the method comprises isomerizing the bis(aminomethyl)cyclohexane while continuously introducing the inert gas in the reaction solution. ### Claim 15 (depends on 12) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 12, wherein: the inert gas is at least one selected from the group consisting of helium, argon and nitrogen; the benzylamine compound is at least one selected from the group consisting of benzylamine, 3-methylbenzylamine, 4-methylbenzylamine, dibenzylamine, meta-xylylenediamine and para-xylylenediamine; the reaction solution comprises at least one of metallic sodium, sodium amide, and sodium hydride; and an amount of the benzylamine compound relative to one mole of the bis(aminomethyl)cyclohexane is 0.001 to 0.10 mol equivalents. ### Claim 16 (depends on 13) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 13, wherein: the inert gas is at least one selected from the group consisting of helium, argon and nitrogen; the benzylamine compound is at least one selected from the group consisting of benzylamine, 3-methylbenzylamine, 4-methylbenzylamine, dibenzylamine, meta-xylylenediamine and para-xylylenediamine; the reaction solution comprises at least one of metallic sodium, sodium amide, and sodium hydride; and an amount of the benzylamine compound relative to one mole of the bis(aminomethyl)cyclohexane is 0.001 to 0.10 mol equivalents. ### Claim 17 (depends on 14) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 14, wherein: the inert gas is at least one selected from the group consisting of helium, argon and nitrogen; the benzylamine compound is at least one selected from the group consisting of benzylamine, 3-methylbenzylamine, 4-methylbenzylamine, dibenzylamine, meta-xylylenediamine and para-xylylenediamine; the reaction solution comprises at least one of metallic sodium, sodium amide, and sodium hydride; and an amount of the benzylamine compound relative to one mole of the bis(aminomethyl)cyclohexane is 0.001 to 0.10 mol equivalents. ### Claim 18 (depends on 15) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 15, wherein the introducing of the inert gas comprises bubbling the inert gas in the reaction solution. ### Claim 19 (depends on 16) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 16, wherein the introducing of the inert gas comprises bubbling the inert gas in the reaction solution. ### Claim 20 (depends on 17) The method for isomerizing a bis(aminomethyl)cyclohexane according to claim 17, wherein the introducing of the inert gas comprises bubbling the inert gas in the reaction solution.