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

被引:71
作者
Doherty, S. [1 ]
Knight, J. G. [1 ]
Carroll, M. A. [1 ]
Ellison, J. R. [1 ]
Hobson, S. J. [1 ]
Stevens, S. [1 ]
Hardacre, C. [2 ]
Goodrich, P. [2 ]
机构
[1] Newcastle Univ, Sch Chem, NUCAT, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
[2] Queens Univ Belfast, QUILL Res Ctr, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland
关键词
MILD OXIDATION; DEEP DESULFURIZATION; SULFUR HETEROCYCLES; SULFOXIDES; SULFONES; H2O2; FUELS; THIOETHERS; LIGANDS; ALKYLATION;
D O I
10.1039/c4gc01770f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:1559 / 1571
页数:13
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