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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

Lookup NU author(s): Dr Simon DohertyORCiD, Dr Julian Knight, Dr Michael CarrollORCiD, Jack Ellison, Dr Stephen Hobson, Sam Stevens

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

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.

Publication metadata

Author(s): Doherty S, Knight JG, Carroll MA, Ellison JR, Hobson SJ, Stevens S, Hardacre C, Goodrich P

Publication type: Article

Publication status: Published

Journal: Green Chemistry

Year: 2015

Volume: 17

Issue: 3

Pages: 1559-1571

Print publication date: 01/01/2015

Online publication date: 08/12/2014

Acceptance date: 08/12/2014

Date deposited: 11/05/2015

ISSN (print): 1463-9262

ISSN (electronic): 1463-9270

Publisher: Royal Society of Chemistry Publications

URL: http://dx.doi.org/10.1039/c4gc01770f

DOI: 10.1039/c4gc01770f

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