Selective One-Pot Carvone Oxime Hydrogenation over Titania Supported Gold Catalyst as a Novel Approach for Dihydrocarvone Synthesis | Sciact - CRIS-система Института катализа

Selective One-Pot Carvone Oxime Hydrogenation over Titania Supported Gold Catalyst as a Novel Approach for Dihydrocarvone Synthesis Научная публикация

Журнал

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

Вых. Данные

Год: 2016, Том: 420, Страницы: 142-148 Страниц : 7 DOI: 10.1016/j.molcata.2016.04.013

Ключевые слова

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

Авторы

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.Y. ⁴

Организации

1	Boreskov Institute of Catalysis, 630090, pr. Lavrentieva, 5, Novosibirsk, Russia
2	Novosibirsk State University, 630090, Pirogova 2, Novosibirsk, Russia
3	Novosibirsk Institute of Organic Chemistry, 630090, pr. Lavrentieva, 9, Novosibirsk, Russia
4	Process Chemistry Centre, Åbo Akademi University, FI-20500, Turku/Åbo, Finland

Информация о финансировании (1)

Российский фонд фундаментальных исследований

15-33-20198

It 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 °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 Cdouble bond; length as m-dashC double bond. Application of Au/TiO2 catalyst for both deoximation and selective hydrogenation of olefinic Cdouble bond; length as m-dashC 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

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 CAPlusCA OpenAlex

Поступила в редакцию:	10 нояб. 2015 г.
Принята к публикации:	15 апр. 2016 г.
Опубликована online:	19 апр. 2016 г.
Опубликована в печати:	1 авг. 2016 г.

Web of science:	WOS:000378366300018
Scopus:	2-s2.0-84971631176
РИНЦ:	27097105
Chemical Abstracts:	2016:727005
Chemical Abstracts (print):	164:602276
OpenAlex:	W2339504373

БД	Цитирований
Web of science	9
Scopus	12
РИНЦ	8
OpenAlex	11