Selectivity Control in One-Pot Myrtenol Amination over Au/ZrO2 by Molecular Hydrogen Addition | Sciact - CRIS-system of Boreskov Institute of Catalysis

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

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

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.V. ⁴ , Murzin D.Yu. ⁵

Affiliations

1	Boreskov Institute of Catalysis, pr. Lavrentieva, 5, 630090, Novosibirsk, Russia
2	Novosibirsk State University, Pirogova 2, 630090, Novosibirsk, Russia
3	Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva, 9, 630090, Novosibirsk, Russia
4	Universidad Nacional Autónoma de México, Centro de Nanociencias y Nanotecnología, km. 107 carretera Tijuana a Ensenada, C.P. 22860, Ensenada, Baja California, México
5	Process Chemistry Centre, Åbo Akademi University, FI-20500, Turku/Åbo, Finland

Funding (2)

1	National Autonomous University of Mexico National Council of Science and Technology	179619
2	Russian Foundation for Basic Research	16-33-60028

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 C C bond in the initial myrtenol structure. Hydrogen addition at 180 °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.

Demidova Y.S. , Suslov E.V. , Simakova I.L. , Mozhajcev E.S. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F. , Simakov A.V. , 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 ANCAN OpenAlex

Submitted:	Aug 20, 2016
Accepted:	Oct 12, 2016
Published online:	Nov 5, 2016
Published print:	Jan 1, 2017

Web of science:	WOS:000391076300008
Scopus:	2-s2.0-85000733340
Elibrary:	29463783
Chemical Abstracts:	2016:1822877
Chemical Abstracts (print):	166:6303
OpenAlex:	W2546909975

DB	Citing
Web of science	12
Scopus	13
Elibrary	14
OpenAlex	13