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

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

Journal

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Output data

Year: 2017, Volume: 426, Pages: 60-67 Pages count : 8 DOI: 10.1016/j.molcata.2016.10.034

Tags

One-pot alcohol amination; Hydrogen borrowing; Gold; Biomass; Selectivity control; Competitive hydrogenation; Monoterpenoid

Authors

Demidova Yu.S. ^1,2 , Suslov E.V. ³ , Simakova I.L. ^1,2 , Mozhajcev E.S. ³ , Korchagina D.V. ³ , Volcho K.P. ^2,3 , Salakhutdinov N.F. ^2,3 , Simakov A. ⁴ , Murzin D.Yu. ⁵

Affiliations

1	(Данные Web of science) Boreskov Inst Catalysis, Pr Lavrentieva 5, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk Organ Chem Inst, Pr Lavrentieva 9, Novosibirsk 630090, Russia
4	(Данные Web of science) Univ Nacl Autonoma Mexico, Ctr Nanociencias & Nanotecnol, Km 107,Carretera Tijuana Ensenada, Ensenada, Baja California, Mexico
5	(Данные Web of science) Abo Akad Univ, Proc Chem Ctr, FI-20500 Turku, Finland

The one-pot myrtenol amination was studied over Au (3 wt.%)/ZrO2 catalyst under mixed N-2/H-2 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 degrees C increased the yield to amine up to 68% preserving C=C bond in the initial myrtenol structure. Hydrogen addition at 180 degrees C irrespective of the myrtenol conversion level provoked reduction of both C=C and C=N 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 C=C and C=N groups can be performed during one-pot alcohol amination by regulation of the reaction conditions. (C) 2016 Elsevier B.V. All rights reserved.

Demidova Y.S. , Suslov E.V. , Simakova I.L. , Mozhajcev E.S. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F. , Simakov A. , Murzin D.Y.
Selectivity control in one-pot myrtenol amination over Au/ZrO2 by molecular hydrogen addition
Journal of Molecular Catalysis A: Chemical. 2017. V.426. P.60-67. DOI: 10.1016/j.molcata.2016.10.034 WOS Scopus РИНЦ

Published print:

Jan 1, 2017

Web of science	WOS:000391076300008
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Elibrary	29463783
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