Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis

Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis Full article

Journal

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Output data

Year: 2016, Volume: 420, Pages: 142-148 Pages count : 7 DOI: 10.1016/j.molcata.2016.04.013

Tags

Gold catalyst; Chemoselective hydrogenation; Carvone oxime; Dihydrocarvone; Stereoselectivity

Authors

Demidova Yu.S. ^1,2 , Suslov E.V. ³ , Simakova O.A. ⁴ , Volcho K.P. ^2,3 , Salakhutdinov N.F. ^2,3 , Simakova I.L. ^1,2 , Murzin D.Yu. ⁴

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) Novosibirsk Organ Chem Inst, Pr Lavrentieva 9, Novosibirsk 630090, Russia
4	(Данные Web of science) Abo Akad Univ, Proc Chem Ctr, FI-20500 Turku, Finland

was shown for the first time that dihydrocarvone can be selectively produced by gold-catalyzed one pot transformation of carvone oxime. This reaction was carried out at 100 degrees C under hydrogen pressure of 9 bar over 1.9 wt.% Au/TiO2 catalyst using methanol as a solvent. Dihydrocarvone synthesis was shown to occur via carvone formation with the subsequent hydrogenation of its conjugated C=C double bond. Application of Au/TiO2 catalyst for both deoximation and selective hydrogenation of olefinic C=C functional group is reported for the first time. The combination of these steps provides optimization of the synthetic method for dihydrocarvone production from carvone oxime which is a key intermediate in carvone synthesis from limonene. Despite a lower reaction rate than in the case of carvone, a significant increase in the stereoselectivity towards trans-dihydrocarvone was observed in the case of carvone oxime hydrogenation. The ratio between trans- and cis-dihydrocarvone was close to 4.0 compared to 1.8 achieved in the case of carvone hydrogenation. (C) 2016 Elsevier B.V. All rights reserved.

Demidova Y.S. , Suslov E.V. , Simakova O.A. , Volcho K.P. , Salakhutdinov N.F. , Simakova I.L. , Murzin D.Y.
Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis
Journal of Molecular Catalysis A: Chemical. 2016. V.420. P.142-148. DOI: 10.1016/j.molcata.2016.04.013 WOS Scopus РИНЦ OpenAlex

Published print:

Aug 1, 2016

Web of science:	WOS:000378366300018
Scopus:	2-s2.0-84971631176
Elibrary:	27097105
OpenAlex:	W2339504373

DB	Citing
Web of science	12
Scopus	11
Elibrary	8
OpenAlex	12