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Monoterpenoid Oximes Hydrogenation Over Platinum Catalysts

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Abstract

Platinum nanoparticles supported on MgO, Al2O3, ZrO2, TiO2 were utilized for monoterpenoid oximes hydrogenation. Monocyclic menthone and carvone oximes synthesized from bio-derived monoterpenoids with a different structure were used to explore the effect of substrate structure on the reaction regularities. The oximes hydrogenation was carried out under hydrogen atmosphere at 100 °C using methanol as a solvent. Platinum catalysts were prepared by the impregnation methods. The catalysts were characterized by transmission electron microscopy, X-ray photoelectron spectroscopy, X-ray fluorescence spectroscopy, nitrogen physisorption. Hydrogenation of carvone oxime containing a conjugated oxime group and several reducible functional groups resulted in both hydrogenation and deoximation giving 5-isopropyl-2-methylcyclohexanamine and carvomenthone over Pt/Al2O3 and Pt/ZrO2 catalysts. Menthone oxime hydrogenation over Pt/Al2O3 catalysts with an average particle size of 0.8 nm provided the desired menthylamine formation with the selectivity of 90% at complete oxime conversion. Platinum catalysts based on MgO, ZrO2 and TiO2 enhanced menthone oxime deoximation to menthone.

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Acknowledgements

The authors are grateful to Dr. E.Yu. Gerasimov (TEM), I.L. Krayevskaya (XRF) and T.Ya. Efimenko (N2 physisorption) for catalysts characterization. The authors acknowledge the Multi-Access Chemical Research Center SB RAS and the Center of Collective Use «National Center of Catalyst Research» of Boreskov Institute of Catalysis for spectral and analytical measurements.

Funding

This work was supported by the Russian Foundation for Basic Research Grant No. 18–33-20175 (the synthesis of substances and the catalysts, menthone oxime hydrogenation) and by Ministry of Science and Higher Education of the Russian Federationproject No. AAAA-A17-117041710075–0 (carvone oxime hydrogenation).

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, pr. Lavrentieva 5, Novosibirsk, Russia, 630090

    Yu. S. Demidova, A. A. Saraev & I. L. Simakova

  2. Novosibirsk State University, Pirogova 2, Novosibirsk, Russia, 630090

    Yu. S. Demidova, A. A. Saraev, K. P. Volcho & N. F. Salakhutdinov

  3. Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva 9, Novosibirsk, Russia, 630090

    E. S. Mozhaitsev, A. A. Munkuev, E. V. Suslov, K. P. Volcho & N. F. Salakhutdinov

  4. Process Chemistry Centre, Åbo Akademi University, 20500, Turku, Finland

    D. Yu. Murzin

Authors
  1. Yu. S. Demidova
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  2. E. S. Mozhaitsev
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  3. A. A. Munkuev
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  4. E. V. Suslov
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  5. A. A. Saraev
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  6. K. P. Volcho
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  7. N. F. Salakhutdinov
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  8. I. L. Simakova
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  9. D. Yu. Murzin
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Correspondence to Yu. S. Demidova.

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Demidova, Y.S., Mozhaitsev, E.S., Munkuev, A.A. et al. Monoterpenoid Oximes Hydrogenation Over Platinum Catalysts. Top Catal 63, 187–195 (2020). https://doi.org/10.1007/s11244-020-01234-x

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  • DOI: https://doi.org/10.1007/s11244-020-01234-x

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