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Meerwein–Ponndorf–Verley–Oppenauer Non-catalytic Reaction of Monoterpenoids in Supercritical Fluids

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Abstract—The Meerwein–Ponndorf–Verley–Oppenauer non-catalytic reaction of cyclic monoterpenic ketones and alcohols (menthone, camphor, menthol, and borneol) was studied under supercritical conditions. It has been showed that the ketones can be reduced in supercritical isopropanol with high selectivity (89–98%) without any catalyst or base. At the same time, the conversion of menthone was 63% at 350°C, and that of camphor was 11% at 300°C for 5 h reaction. The conversions of menthol and borneol in the reverse dehydrogenation reaction in supercritical acetone were 34 and 22%, respectively, and the selectivities were 95 and 88%. Thermal dehydration is a main side reaction for all the reactions.

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ACKNOWLEDGMENTS

This work was performed within the Government Task (theme no. 0303-2016-0001). A.A. Philippov is grateful to Russian Foundation for Basic Research (project no. 18-33-00659 mol_a).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    A. A. Philippov & A. M. Chibiryaev

  2. Novosibirsk State University, 630090, Novosibirsk, Russia

    A. A. Philippov & A. M. Chibiryaev

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  1. A. A. Philippov
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  2. A. M. Chibiryaev
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Correspondence to A. A. Philippov.

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Translated by A. Tulyabaev

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Philippov, A.A., Chibiryaev, A.M. Meerwein–Ponndorf–Verley–Oppenauer Non-catalytic Reaction of Monoterpenoids in Supercritical Fluids. Russ. J. Phys. Chem. B 13, 1117–1120 (2019). https://doi.org/10.1134/S1990793119070054

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  • DOI: https://doi.org/10.1134/S1990793119070054

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