Regioselective hydroformylation of vinylarenes in aqueous media by a sol-gel entrapped rhodium catalyst

Zackaria Nairoukh, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Two methods for selective hydroformylation of vinylarenes in aqueous media are described. One method relies on the application of [Rh(cod)Cl] 2 and a tertiary phosphane entrapped within an ionic liquid-confined silica sol-gel support. The second method utilizes the same rhodium compound, encaged within ionic-liquid-free hydrophobicized sol-gel. Both methods are best carried out at 50 °C in aqueous emulsions or microemulsions that consist of the substrate, a surfactant, a co-surfactant and >89% water. The optimal H 2/CO ratio is between 1 and 1.1. Both methods allow the reuse of the heterogenized catalyst for several runs. While the regioselectivity and the yield are hardly affected by the electronic nature of the substrates, they are significantly dependent on the reaction temperature, on the surfactant employed, and on the hydrophobicity of the support of the catalyst. Despite the use of H 2 in the reactions, no transformation of the organometallic catalyst into metallic nanoparticles could be detected.

Original languageAmerican English
Pages (from-to)129-133
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume358
DOIs
StatePublished - Jun 2012

Bibliographical note

Funding Information:
We gratefully acknowledge the support of this study by the Israel Science Foundation through grant No. 299/10 .

Keywords

  • Heterogeneous catalysis
  • Hydroformylation
  • Regioselectivity
  • Rhodium
  • Sustainable chemistry

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