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Issue 77, 2016, Issue in Progress
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Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

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Abstract

Styrene-based peroxotungstate-modified polymer immobilized ionic liquid phase catalysts [PO4{WO(O2)2}4]@ImPIILP (Im = imidazolium) are remarkably efficient systems for the selective oxidation of sulfides under mild conditions both in batch and as a segmented or continuous flow process using ethanol as the solvent and mobile phase, respectively. The performance of these styrene-based systems has been compared against their ring opening metathesis polymerisation derived counterparts to assess their relative merits. A comparative survey revealed the catalyst supported on N-benzyl imidazolium decorated polymer immobilised ionic liquid to be the most efficient and a cartridge packed with a mixture of [PO4{WO(O2)2}4]@ImPIILP and silica operated as a segmented or continuous flow system giving good conversions and high selectivity for sulfoxide. The immobilised catalyst remained highly active for the sulfoxidation of thioanisole in ethanol with a stable conversion–selectivity profile for up to 8 h under continuous flow operation; for comparison conversions with a mixture of [NBu4]3[PO4{WO(O2)2}4] and silica dropped dramatically after only 15 min as a result of rapid leaching while [PO4{WO(O2)2}4]@ImPIILP prepared from commercially available Merrifield resin also gave consistently lower conversions; these benchmark comparisons serve to underpin the potential benefits of preparing the polymer immobilized ionic liquid supports.

Graphical abstract: Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

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Supplementary files

Article information


Submitted
29 Apr 2016
Accepted
15 Jul 2016
First published
22 Jul 2016

RSC Adv., 2016,6, 73118-73131
Article type
Paper
Author version available

Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

S. Doherty, J. G. Knight, M. A. Carroll, A. R. Clemmet, J. R. Ellison, T. Backhouse, N. Holmes, L. A. Thompson and R. A. Bourne, RSC Adv., 2016, 6, 73118
DOI: 10.1039/C6RA11157B

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