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Olefin Epoxidation in Aqueous Phase Using Ionic‐Liquid Catalysts
Author(s) -
Cokoja Mirza,
Reich Robert M.,
Wilhelm Michael E.,
Kaposi Marlene,
Schäffer Johannes,
Morris Danny S.,
Münchmeyer Christian J.,
Anthofer Michael H.,
Markovits Iulius I. E.,
Kühn Fritz E.,
Herrmann Wolfgang A.,
Jess Andreas,
Love Jason B.
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600373
Subject(s) - catalysis , chemistry , ionic liquid , aqueous solution , substrate (aquarium) , hydrogen peroxide , olefin fiber , aqueous two phase system , solubility , phase (matter) , organic chemistry , inorganic chemistry , chemical engineering , oceanography , engineering , geology
Abstract Hydrophobic imidazolium‐based ionic liquids (IL) act as catalysts for the epoxidation of unfunctionalized olefins in water using hydrogen peroxide as oxidant. Although the catalysts are insoluble in both the substrate and in water, surprisingly, they are very well soluble in aqueous H 2 O 2 solution, owing to perrhenate‐H 2 O 2 interactions. Even more remarkably, the presence of the catalyst also boosts the solubility of substrate in water. This effect is crucially dependent on the cation design. Hence, the imidazolium perrhenates enable both the transfer of hydrophobic substrate into the aqueous phase, and serve as actual catalysts, which is unprecedented. At the end of the reaction and in absence of H 2 O 2 the IL catalyst forms a third phase next to the lipophilic product and water and can easily be recycled.