Chemoselective hydrogenation of –C=O bond in multiple unsaturated compounds over metals supported on mesoporous materials

Simakova I. L., Demidova Y. S., Simakov A. V, Dmitry Murzin

    Research output: Contribution to journalArticleScientificpeer-review

    Abstract

    Liquid-phase hydrogenation of crotonaldehyde in non-polar and polar solvents was studied onmonometallic Pd, Pt, Ir, Re catalysts using mesoporous Sibunit and Al2O3 as supports. In the presenceof Pd the -C=C- bond of crotonaldehyde was preferably hydrogenated to form butanal, while butanaland crotyl alcohol are formed over Ir catalysts. Crotonaldehyde hydrogenation in 1,4-dioxane did notexhibit further butanal to butanol hydrogenation. Application of Re as a catalyst leads to formation ofcrotyl alcohol, with activity being, however, twofold lower than of Ir catalysts. Pt/C is almost inactive inthe hydrogenation of crotonaldehyde. Formation of crotyl alcohol occurs most efficiently over Ir/Al2O3in aprotic nonpolar solvents (decane), with selectivity to crotyl alcohol increasing with temperatureshowing 30% at 25% conversion under 180 °C and hydrogen pressure 0.84 MPa. Crotonaldehydehydrogenation in a polar protonic solvent (ethanol) results in butanal acetalization.

    Original languageUndefined/Unknown
    Pages (from-to)536–549
    JournalJournal of Siberian Federal University. Chemistry
    Volume12
    Issue number4
    DOIs
    Publication statusPublished - 2019
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Ir
    • Multiple unsaturated compounds
    • Crotonaldehyde
    • Crotyl alcohol
    • Re
    • PD
    • alumina
    • carbon
    • Pt
    • Competitive hydrogenation

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