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 |
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| Output data | Year: 2016, Volume: 420, Pages: 142-148 Pages count : 7 DOI: 10.1016/j.molcata.2016.04.013 | ||||||||
| Tags | Carvone oxime, Chemoselective hydrogenation, Dihydrocarvone, Gold catalyst, Stereoselectivity | ||||||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Russian Foundation for Basic Research | 15-33-20198 |
Abstract:
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
Cite:
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 ANCAN OpenAlex
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 ANCAN OpenAlex
Dates:
| Submitted: | Nov 10, 2015 |
| Accepted: | Apr 15, 2016 |
| Published online: | Apr 19, 2016 |
| Published print: | Aug 1, 2016 |
Identifiers:
| Web of science: | WOS:000378366300018 |
| Scopus: | 2-s2.0-84971631176 |
| Elibrary: | 27097105 |
| Chemical Abstracts: | 2016:727005 |
| Chemical Abstracts (print): | 164:602276 |
| OpenAlex: | W2339504373 |