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Double salt ionic liquids prepared by mixing partially miscible ionic liquids: Tuning the solubility of lipophilic molecules

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Double Salt Ionic Liquids (DSILs) were prepared by mixing 1- ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C2mim][NTf<inf>2</inf>]) and trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide ([P<inf>66614</inf>][NTf<inf>2</inf>]) in their miscible range: [C2mim]<inf>x</inf>[P<inf>66614</inf>]<inf>(1-x)</inf>[NTf<inf>2</inf>] (0 ≤ x ≤ 0.29). <sup>1</sup>H NMR, <sup>19</sup>F NMR, and FT-IR spectroscopic studies indicated that the [NTf2]- anions preferentially interact with the [C<inf>2</inf>mim]<sup>+</sup> cations. Solubility studies showed that solutes with long alkyl chains (e.g., heptane, methyl palmitate), which have good solubility in [P<inf>66614</inf>][NTf<inf>2</inf>] but are not totally miscible, have tunable solubility in the DSILs and the presence of even minor amounts of [C<inf>2</inf>mim]<sup>+</sup> significantly decreases their solubility. However, the solubilities of benzene, toluene, 1-octanol, and poly(ethylene glycol) (PEG-300) in [C<inf>2</inf>mim]<inf>x</inf>[P<inf>66614</inf>]<sup>(1-x)</sup>[NTf<inf>2</inf>] were controlled by their miscibility with [P66614][NTf2], and can't be tuned by changing the ion concentrations within the miscibility range.

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ECS Transactions, v. 64, n. 4, p. 33-44, 2014.

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Faculdade de Ciências Farmacêuticas
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Campus: Araraquara

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