Abstract
Cu(i)-Containing room temperature ionic liquids (Cu-EnA), prepared from CuCl and ether-functionalized ionic liquids (ILs) bearing a methanesulfonate anion (EnA, n = 1, 2 or 3), were thermally stable and highly effective for the removal of alkynes such as isopropenylacetylene (IPA) and 2-butyne (2-BT) contained in dienes like isoprene (2-methyl-1,3-butadiene). Cu-EnA were found to reversibly and selectively interact with IPA and 2-BT, thereby enabling the regeneration of Cu-EnA. Fast atom bombardment (FAB)-mass spectral and computational results imply that EnA consists of an ether-functionalized imidazolium cation and a methanesulfonate-coordinated Cu(i) anion such as [CuCl(CH3SO3)]- ([CuClA]-) or [Cu(CH3SO3)2]- ([CuA2]-). Computational studies demonstrate that the preferential extraction of IPA and 2-BT to isoprene by Cu-EnA originated from the difference in the strength of the hydrogen bonding and π-complexation.
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