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

Irina L. Simakova, Yuliya S. Demidova, Andrey V. Simakov, Dmitry Yu Murzin

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Liquid-phase hydrogenation of crotonaldehyde in non-polar and polar solvents was studied on monometallic Pd, Pt, Ir, Re catalysts using mesoporous Sibunit and Al2O3 as supports. In the presence of Pd the -C=C- bond of crotonaldehyde was preferably hydrogenated to form butanal, while butanal and crotyl alcohol are formed over Ir catalysts. Crotonaldehyde hydrogenation in 1,4-dioxane did not exhibit further butanal to butanol hydrogenation. Application of Re as a catalyst leads to formation of crotyl alcohol, with activity being, however, twofold lower than of Ir catalysts. Pt/C is almost inactive in the hydrogenation of crotonaldehyde. Formation of crotyl alcohol occurs most efficiently over Ir/Al2O3 in aprotic nonpolar solvents (decane), with selectivity to crotyl alcohol increasing with temperature showing 30% at 25% conversion under 180 °C and hydrogen pressure 0.84 MPa. Crotonaldehyde hydrogenation in a polar protonic solvent (ethanol) results in butanal acetalization.

Translated title of the contributionХемоселективное гидрирование –С=О группы полиненасыщенных соединений на металлических катализаторах, нанесенных на мезопористые носители
Original languageEnglish
Pages (from-to)536-549
Number of pages14
JournalJournal of Siberian Federal University: Chemistry
Volume12
Issue number4
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • multiple unsaturated compounds
  • crotonaldehyde
  • crotyl alcohol
  • competitive hydrogenation
  • Pd
  • Pt
  • Ir
  • Re
  • alumina
  • carbon
  • SELECTIVE HYDROGENATION
  • CATALYTIC-HYDROGENATION
  • PHASE HYDROGENATION
  • CROTONALDEHYDE
  • CARBON
  • ACID
  • IR

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