Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Yu. S. Demidova, E.V. Suslov, I.L. Simakova, E.S. Mozhajcev, D.V. Korchagina, K.P. Volcho, N.F. Salakhutdinov, A. Simakov, D. Yu. Murzin
Publication year: 2017
Journal: Journal of Molecular Catalysis A: Chemical
Volume number: 426, Part A
Start page: 60
End page: 67
eISSN: 1873-314X


Abstract

The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N2/H2 atmosphere (9 bar). The effect of hydrogen addition was explored with the aim to increase selectivity to the target amines. Hydrogen addition timing depending on myrtenol conversion and hydrogenation temperature affected selectivity to the reaction products. Hydrogen addition (1 bar) after almost complete myrtenol conversion at 100 °C increased the yield to amine up to 68% preserving Cdouble bond; length as m-dashC bond in the initial myrtenol structure. Hydrogen addition at 180 °C irrespective of the myrtenol conversion level provoked reduction of both Cdouble bond; length as m-dashC and Cdouble bond; length as m-dashN bonds with formation of two diastereomers (yield up to 93%), with trans-isomer formation being preferred when hydrogen was added at almost complete myrtenol conversion. It was shown, that in the presence of a gold catalyst controlled hydrogenation of competitive Cdouble bond; length as m-dashC and Cdouble bond; length as m-dashN groups can be performed during one-pot alcohol amination by regulation of the reaction conditions.

Last updated on 2020-02-04 at 06:26