Abstract
Xylylene diamines were smoothly and selectively hydrogenated into the corresponding bis(aminomethyl)cyclohexanes in the presence of newly modified ruthenium catalysts. They were prepared by heating sodium ruthenate supported on active carbon under carbon dioxide atmosphere. Commercial ruthenium catalysts were not active enough to complete the hydrogenation in contrast with their full activity for aniline. The hydrogenation reaction of m-xylylenediamine is zero order in diamine concentration and first order in hydrogen pressure. Small quantities of m-methylbenzylamine, 1-aminomethyl-3-methylcyclohexane, and m-xylene were formed as byproducts presumably from the starting diamine through hydrogenolysis. Apparent activation energy for the formaton of 1, 3-bis(aminomethyl)cyclohexane was found to be 8.6 Kcal/mol. Though m-xylylenediamine gave predominantly cis-bis(aminomethyl)cyclohexane, almost 1 to 1 mixture of cis-and trans-isomers was obtained from p-xylylenediamine.
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