Highly selective solvent-free hydrogenation of pinenes to added-value <em>cis</em>-pinane - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Access content directly
Journal Articles Comptes Rendus. Chimie Year : 2018

Highly selective solvent-free hydrogenation of pinenes to added-value cis-pinane

Hydrogénation hautement sélective des pinènes en cis-pinane, un produit à forte valeur ajoutée, sans utilisation de solvant

Abstract

Heterogeneous catalysts based on different active metals (Pd, Pt, Ru, and Rh) and supports (carbon and alumina) were systematically tested for hydrogenation of pinenes under various reaction conditions including heating and/or sonication. Among all, Ru provided some of the best results. After sonication, Ru/C was found highly active and selective for the reduction of α-pinene alone into cis-pinane (99% selectivity at 100% conversion). However, in the absence of sonication the same catalyst was completely inactive. Alumina appeared to be a support with a beneficial chemical effect on the activity of the Ru. Indeed, Ru/Al2O3 was found very active and selective for hydrogenation of both α- and β-pinene into cis-pinane (99e100% selectivity at 100% conversion) under mild reaction conditions (room temperature, 400 Psi H2). The selectivity toward cis-pinane decreased in the following order: Ru > Rh > Pt > Pd. An extremely low leaching rate of Ru and other metals determined by inductively coupled plasma mass spectrometry confirmed the heterogeneous nature of this catalytic solvent-free hydrogenation. Ru/C was successfully recycled seven times with no decline in activity and selectivity, whereas Ru/Al2O3 could be used only once to convert pinenes to cis-pinane. Solubilization prediction tests of some natural products have revealed that pinane compares very well with n-hexane and may be an alternative to this fossil-based solvent. When compared experimentally with n-hexane, cis-pinane solubilized 42, two, and three times more of β-carotene, vanillin, and rosmarinic acid, respectively.

Dates and versions

hal-02622178 , version 1 (26-05-2020)

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Fanta J. Ndongou Moutombi, Ayyoub Selka, Anne-Sylvie Fabiano-Tixier, Delphine Foucher, Olivier Clarisse, et al.. Highly selective solvent-free hydrogenation of pinenes to added-value cis-pinane. Comptes Rendus. Chimie, 2018, 21 (11), pp.1035-1042. ⟨10.1016/j.crci.2018.09.002⟩. ⟨hal-02622178⟩
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