Monoterpenoid oximes hydrogenation over platinum catalysts

Yu. S. Demidova*, E. S. Mozhaitsev, A. A. Munkuev, E. V. Suslov, A. A. Saraev, K. P. Volcho, N. F. Salakhutdinov, I. L. Simakova, D. Yu. Murzin

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)187-195
Number of pages9
JournalTopics in Catalysis
Volume63
Issue number1-2
DOIs
Publication statusPublished - 13 Feb 2020
MoE publication typeA1 Journal article-refereed

Keywords

  • Carvone oxime
  • Hydrogenation
  • Menthone oxime
  • Menthylamine
  • Platinum catalyst
  • Terpene

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