Efficient and selective hydrogen peroxide-mediated oxidation of sulfides in batch and segmented and continuous flow using a peroxometalate-based polymer immobilised ionic liquid phase catalyst

S. Doherty*, J. G. Knight, M. A. Carroll, J. R. Ellison, S. J. Hobson, S. Stevens, C. Hardacre, P. Goodrich

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

The peroxometalate-based polymer immobilized ionic liquid phase catalyst [PO4{WO(O-2)(2)}(4)]@PIILP has been prepared by anion exchange of ring opening metathesis-derived pyrrolidinium-decorated norbornene/ cyclooctene copolymer and shown to be a remarkably efficient system for the selective oxidation of sulfides under mild conditions. A cartridge packed with a mixture of [PO4{WO(O-2)(2)}(4)]@PIILP and silica operated as a segmented or continuous flow process and gave good conversions and high selectivity for either sulfoxide (92% in methanol at 96% conversion for a residence time of 4 min) or sulfone (96% in acetonitrile at 96% conversion for a residence time of 15 min). The immobilized catalyst remained active for 8 h under continuous flow operation with a stable activity/selectivity profile that allowed 6.5 g of reactant to be processed (TON = 46 428) while a single catalyst cartridge could be used for the consecutive oxidation of multiple substrates giving activity-selectivity profiles that matched those obtained with fresh catalyst.

Original languageEnglish
Pages (from-to)1559-1571
Number of pages13
JournalGreen Chemistry
Volume17
Issue number3
Early online date08 Dec 2014
DOIs
Publication statusPublished - Mar 2015

Keywords

  • LAYERED DOUBLE HYDROXIDES
  • MILD OXIDATION
  • ROOM-TEMPERATURE
  • DEEP DESULFURIZATION
  • SULFUR HETEROCYCLES
  • SULFOXIDES
  • H2O2
  • SULFONES
  • FUELS
  • VANADIUM

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