One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina | Sciact - CRIS-system of Boreskov Institute of Catalysis

One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina Full article

Journal

Catalysis Letters
ISSN: 1011-372X , E-ISSN: 1572-879X

Output data

Year: 2019, Volume: 149, Number: 12, Pages: 3454–3464 Pages count : 6 DOI: 10.1007/s10562-019-02958-6

Tags

Alcohol amination; Bimetallic catalyst; Biomass; Gold; Hydrogen borrowing; Myrtenol; One-pot; Palladium; Redox treatment effect; Terpenoids

Authors

Demidova Yu.S. ^1,2 , Simakova I.L. ^1,2 , Estrada M. ³ , Beloshapkin S. ⁴ , Suslov E.V. ⁵ , Volcho K.P. ^2,5 , Salakhutdinov N.F. ^2,5 , Simakov A. ³ , Murzin D.Yu. ⁶

Affiliations

1	Boreskov Institute of Catalysis, pr. Lavrentieva, 5, Novosibirsk, Russia 630090
2	Novosibirsk State University, Pirogova, 2, Novosibirsk, Russia 630090
3	Centro de Nanociencias y Nanotecnología, Universidad Nacional Autónoma de México, km. 107 carretera Tijuana a Ensenada, C.P. 22860 Ensenada, Baja California, Mexico
4	Bernal Institute, University of Limerick, Limerick V94 T9PX, Ireland
5	Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva, 9, Novosibirsk, Russia 630090
6	Process Chemistry Centre, Åbo Akademi University, 20500 Turku/Åbo, Finland

Funding (1)

Federal Agency for Scientific Organizations

0303-2016-0012 (V.47.1.4.)

One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9 bar) at 453 K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al O catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups.

Demidova Y.S. , Simakova I.L. , Estrada M. , Beloshapkin S. , Suslov E.V. , Volcho K.P. , Salakhutdinov N.F. , Simakov A. , Murzin D.Y.
One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina
Catalysis Letters. 2019. V.149. N12. P.3454–3464. DOI: 10.1007/s10562-019-02958-6 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Jun 5, 2019
Accepted:	Sep 12, 2019
Published online:	Sep 19, 2019
Published print:	Dec 1, 2019

Web of science:	WOS:000493659800019
Scopus:	2-s2.0-85073988457
Elibrary:	41815493
Chemical Abstracts:	2019:1834564
Chemical Abstracts (print):	171:497193
OpenAlex:	W2974333048

DB	Citing
Scopus	3
Web of science	3
Elibrary	2
OpenAlex	3