Base-Free Transfer Hydrogenation of Menthone by Sub- and Supercritical Alcohols Full article
| Journal |
The Journal of Supercritical Fluids
ISSN: 0896-8446 , E-ISSN: 1872-8162 |
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| Output data | Year: 2019, Volume: 145, Pages: 162-168 Pages count : 7 DOI: 10.1016/j.supflu.2018.12.011 | ||||
| Tags | Base-free Enolization Menthone Raney® nickel Supercritical alcohols Transfer hydrogenation | ||||
| Authors |
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| Affiliations |
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Funding (3)
| 1 | Federal Agency for Scientific Organizations | 0303-2016-0001 |
| 2 | Federal Agency for Scientific Organizations | V.44.1.15. |
| 3 | Russian Foundation for Basic Research | 18-29-06022 |
Abstract:
The base-free transfer hydrogenation (HTR) of menthone with six aliphatic alcohols as hydrogen source has been developed under sub- and supercritical conditions. Under sc conditions (at 350 °C and 78–210 atm) without any catalyst, all alcohols demonstrated the similar H-donor activity, which was high enough. The menthone conversion was about 64 ± 5 % for 5 hours of the reaction, whereas the selectivity on menthol reached 92–99 % for all alcohols except MeOH (73 %). The non-catalytic HTR at 250 °C was very slow and the conversion in the most active 2-PrOH was only 7.0–7.5 % for 9 hours of the reaction. Under subcritical conditions at 150 °C, the non-catalytic menthone reduction was negligible in all alcohols. But in secondary 2-PrOH and 2-BuOH, the base-free HTR catalyzed by Raney® nickel results in excellent conversion and selectivity of menthol at 150 °C, whereas no conversion of menthone was observed in primary alcohols under the same reaction conditions. A quasi-equilibrium of isomeric menthone/isomenthone mixture reached via enolization was evaluated under sub- and supercritical conditions and the Gibbs energies of the isomerization in each alcohol were calculated
Cite:
Philippov A.
, Chibiryaev A.M.
, Martyanov O.
Base-Free Transfer Hydrogenation of Menthone by Sub- and Supercritical Alcohols
The Journal of Supercritical Fluids. 2019. V.145. P.162-168. DOI: 10.1016/j.supflu.2018.12.011 WOS Scopus РИНЦ РИНЦ ANCAN OpenAlex
Base-Free Transfer Hydrogenation of Menthone by Sub- and Supercritical Alcohols
The Journal of Supercritical Fluids. 2019. V.145. P.162-168. DOI: 10.1016/j.supflu.2018.12.011 WOS Scopus РИНЦ РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | Aug 10, 2018 |
| Accepted: | Dec 7, 2018 |
| Published online: | Dec 13, 2018 |
| Published print: | Mar 1, 2019 |
Identifiers:
| Web of science: | WOS:000460071900018 |
| Scopus: | 2-s2.0-85058705730 |
| Elibrary: | 38628279 | 41798539 |
| Chemical Abstracts: | 2018:2584501 |
| Chemical Abstracts (print): | 172:25469 |
| OpenAlex: | W2904020187 |