C-O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts

Kaiyou Chen, Kazuma Mori, Hideo Watanabe, Yoshinao Nakagawa, Keiichi Tomishige

Research output: Contribution to journalArticlepeer-review

143 Citations (Scopus)

Abstract

Hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol and other related substrates such as 3-hydroxytetrahydrofuran and 1,2-cyclohexanediol proceeds over Ir-ReO x/SiO 2 catalyst. TOF values are higher than those of Rh-ReO x/SiO 2, which has been reported to be an effective catalyst. The selectivity to the product, where the C-O bond neighboring the C-OH group in the substrate is dissociated, is comparable to or higher than that of Rh-ReO x/SiO 2. Hydrogenolysis of most substrates except 1,2-cyclohexanediol proceeds via the direct mechanism where hydride species formed from hydrogen molecule attacks the anti-position of C-O bond. In the case of hydrogenolysis of 1,2-cyclohexanediol where attack of anti-position of C-O bond is unfavorable, indirect mechanism involving dehydrogenation to 2-hydroxycyclohexanone is responsible for the formation of cyclohexanol.

Original languageEnglish
Pages (from-to)171-183
Number of pages13
JournalJournal of Catalysis
Volume294
DOIs
Publication statusPublished - 2012 Oct

Keywords

  • 1,2-Cyclohexanediol
  • Cyclic ethers
  • Cyclohexanol
  • Diol
  • Hydrogenolysis
  • Iridium
  • Rhenium
  • Tetrahydrofuran
  • Tetrahydropyran

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

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