Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime

Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime Full article

Journal

Applied Catalysis A: General
ISSN: 0926-860X , E-ISSN: 1873-3875

Output data

Year: 2020, Volume: 605, Article number : 117799, Pages count : DOI: 10.1016/j.apcata.2020.117799

Tags

Biomass; Gold catalyst; Kinetics; Menthylamine; Oxime hydrogenation; Terpenoids

Authors

Demidova Y.S. ^1,2 , Mozhaitsev E.S. ³ , Suslov E.V. ³ , Nefedov A.A. ^2,3 , Saraev A.A. ^1,2 , Volcho K.P. ^2,3 , Salakhutdinov N.F. ^2,3 , Simakov A. ⁴ , Simakova I.L. ¹ , Murzin D.Y. ⁵

Affiliations

1	(Scopus) Boreskov Institute of Catalysis, pr. Lavrentieva 5, Novosibirsk, 630090, Russian Federation
2	(Scopus) Novosibirsk State University, Pirogova 2, Novosibirsk, 630090, Russian Federation
3	(Scopus) Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva 9, Novosibirsk, 630090, Russian Federation
4	(Scopus) Universidad Nacional Aut?noma de M?xico, Centro de Nanociencias y Nanotecnolog?a, km. 107 carretera Tijuana a Ensenada, Ensenada, Baja California C.P. 22860, Mexico
5	(Scopus) Process Chemistry Centre, ?bo Akademi University, Turku/?bo, FI-20500, Finland

In the current work gold nanoparticles supported on oxides (MgO, Al2O3, ZrO2, TiO2) were used for menthylamine synthesis via menthone oxime hydrogenation. An increase of the gold nanoparticles size and application of metal oxides with a strong basic character such as magnesia favored deoximation to menthone. Au/Al2O3 catalyst with the gold nanoparticles size of 2.0 nm afforded high catalytic activity and selectivity to menthylamine. The reaction kinetics including stereoselectivity to the reaction products and recyclability of the catalyst was studied using Au/Al2O3 in the temperature range 90−110 °C under hydrogen pressure of 5.5–7.5 bar. The catalytic behavior was influenced by the solvent nature, with higher selectivity to desired amine achieved using methanol. The reaction rate was pressure independent, while has first order with respect to menthone oxime concentration. Stereoselectivity to menthylamines and menthones was independent on the reaction temperature and the hydrogen pressure. © 2020 Elsevier B.V.

Demidova Y.S. , Mozhaitsev E.S. , Suslov E.V. , Nefedov A.A. , Saraev A.A. , Volcho K.P. , Salakhutdinov N.F. , Simakov A. , Simakova I.L. , Murzin D.Y.
Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime
Applied Catalysis A: General. 2020. V.605. 117799 . DOI: 10.1016/j.apcata.2020.117799 WOS Scopus РИНЦ

Published print:

Sep 1, 2020

Web of science	WOS:000576786900001
Scopus	2-s2.0-85090019959
Elibrary	45326495
OpenAlex	W3080984419