Menthylamine Synthesis via Gold-Catalyzed Hydrogenation of Menthone Oxime | Sciact - CRIS-system of Boreskov Institute of Catalysis

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 : 10 DOI: 10.1016/j.apcata.2020.117799

Tags

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

Authors

Demidova Yu.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.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, Mexico
5	Process Chemistry Centre, Åbo Akademi University, FI-20500, Turku/Åbo, Finland

Funding (2)

1	Federal Agency for Scientific Organizations	0303-2016-0012 (V.47.1.4.)
2	Russian Foundation for Basic Research	18-33-20175

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.

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 :1-10. DOI: 10.1016/j.apcata.2020.117799 WOS Scopus РИНЦ AN OpenAlex

Submitted:	May 19, 2020
Accepted:	Aug 19, 2020
Published online:	Aug 21, 2020
Published print:	Sep 5, 2020

Web of science:	WOS:000576786900001
Scopus:	2-s2.0-85090019959
Elibrary:	45326495
Chemical Abstracts:	2020:1760101
OpenAlex:	W3080984419

DB	Citing
Scopus	3
Web of science	3
Elibrary	1
OpenAlex	4