It has been an unproven paradigm that the choice of which ionic liquid to use in a chemical reaction can have a dramatic effect on the outcome of that chemical reaction. We demonstrate, for the first time, that the reaction of toluene and nitric acid in three different ionic liquids gives rise to three completely different products in high yield. Furthermore, ionic liquids can catalyze these reactions with the only byproduct being water. [reaction: see text]

This work presents the novel discovery of room-temperature ionic liquids that are mutually immiscible, some of which are also immiscible with solvents as diverse as water and alkanes; an archetypal biphasic system is trihexyltetradecylphosphonium chloride with 1-alkyl-3-methylimidazolium chloride (where the alkyl group is shorter than hexyl).

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The recently discovered class of ionic liquids--mutually immiscible ionic liquids--are explored in this work for their first practical application: the separation of aromatic and aliphatic hydrocarbons by solvent extraction. For this preliminary approach, benzene and hexane were chosen as representatives of each group of hydrocarbons; the ionic liquids 1-ethyl-3-methylimidazolium bis( (trifluoromethyl)sulfonyl)amide and trihexyl(tetradecyl)phosphonium bis( (trifluoromethyl)sulfonyl)amide, which are both liquid at room temperature and hydrophobic, were selected as potential solvents. Liquid-liquid equilibrium experiments were carried out at 25 degrees C for the quaternary system formed by the two hydrocarbons and the two ionic liquids. Typical extraction parameters were calculated and analysed in order to evaluate the possibilities of the mutual immiscible ionic liquids in accomplishing the separation target. A comparison with the case of using just one of the ionic liquids was made.

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