Olefin Epoxidation in Aqueous Phase Using Ionic‐Liquid Catalysts. Issue 14 (24th May 2016)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: ChemSusChem. Volume 9:Issue 14(2016:Jul.)
• Page Start: 1773
• Page End: 1776
• Publication Date: 2016-05-24
• Subjects: epoxidation -- homogeneous catalysis -- ionic liquids -- solubility -- two-phase catalysis; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201600373
• Languages: English
• ISSNs: 1864-5631

Abstract

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 H2 O2 solution, owing to perrhenate‐H2 O2 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 H2 O2 the IL catalyst forms a third phase next to the lipophilic product and water and can easily be recycled. Abstract : Right combination : Imidazolium perrhenate ionic liquids (ILs) are effective catalysts for the epoxidation of unfunctionalized olefins using hydrogen peroxide as oxidant. The catalytic activity strongly depends on the IL solubility in aqueous H2 O2, which is regulated by the nature of the cation. The IL catalysts significantly enhance the solubility of olefins into the aqueous phase, allowing for the reaction to take phase in water.