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

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 : 11 DOI: 10.1007/s10562-019-02958-6

Tags

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

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	(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) Univ Nacl Autonoma Mexico, Ctr Nanociencias & Nanotecnol, Km 107 Carretera Tijuana Ensenada, Ensenada 22860, Baja California, Mexico
4	(Данные Web of science) Univ Limerick, Bernal Inst, Limerick V94 T9PX, Ireland
5	(Данные Web of science) Novosibirsk Inst Organ Chem, Pr Lavrentieva 9, Novosibirsk 630090, Russia
6	(Данные Web of science) Abo Akad Univ, Proc Chem Ctr, SF-20500 Turku, Finland

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/Al2O3 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

Published online:	Sep 19, 2019
Published print:	Dec 1, 2019

Web of science	WOS:000493659800019
Scopus	2-s2.0-85073988457
Elibrary	41815493
OpenAlex	W2974333048