New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide

Abstract

New ionic liquids containing (2-hydroxypropyl)-functionalized imidazolium cations have been synthesized by the atom-efficient, room temperature reaction of 1-methylimidazole with acid and propylene oxide; the acid providing the anionic component of the resultant ionic liquids. The incorporation of the secondary hydroxyl-functionality in the cation causes some interesting modifications to the behavior of these ionic liquids, increasing hydrophilicity and resulting in the unprecedented formation of liquid–liquid biphases with acetone. The single crystal structure of 1-(2-hydroxypropyl)-3-methylimidazolium tetraphenylborate, prepared by metathesis of the corresponding chloride-containing ionic liquid, has also been determined.