Surface-Active Imidazolium Diorganophosphates as Catalysts for Epoxidations in Water

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Schmidt, Fabian ; Drees, Markus ; Hegelmann, Markus ; Zehner, Bastian ; Jess, Andreas ; Cokoja, Mirza:
Surface-Active Imidazolium Diorganophosphates as Catalysts for Epoxidations in Water.
In: European Journal of Inorganic Chemistry. Bd. 28 (2025) Heft 16 . - e202500071.
ISSN 1099-0682
DOI: https://doi.org/10.1002/ejic.202500071

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Abstract

The synthesis and characterization of a series of imidazolium diorganophosphate-based surface-active ionic liquids (SAILs) of the general formula OMIm(RO)2PO2 (OMIm = 1-octyl-3-methylimidazolium; R = H, Me, Et, Ph, p-MeOPh) is reported. The reaction of OMIm(RO)2PO2 SAILs with hydrogen peroxide is investigated via 31P-Nuclear Magnetic Resonance (NMR) spectroscopy, showing the presence of a phosphorous-peroxo product, which is corroborated by Density Functional Theory (DFT) calculations. The sizes of the SAIL micelles in aqueous hydrogen peroxide are investigated by dynamic light scattering (DLS) before and after addition of cis-cyclooctene (COE) to study the solubilization of the organic substrate in the aqueous phase. In a model case study, the SAILs are applied as micellar catalysts for the epoxidation of COE under mild conditions.