To obtain further experimental evidence for a better understanding of the molecular mechanisms responsible for the soluting-out effect phenomena in ternary systems composed of an ionic liquid (IL), amino acid, and water, systematic studies on the vapor-liquid, liquid-liquid, and solid-liquid equilibrium behavior of aqueous solutions of several ILs were carried out in the presence of a range of amino acids. Water activities for binary and ternary aqueous solutions containing 1-butyl-3-methylimidazolium chloride, [Cmim]Cl, 1-hexyl-3-methylimidazolium chloride, [Cmim]Cl, 1-butyl-3-methyl-imidazolium trifluoromethanesulfonate, [Cmim][CFSO], l-Ser, Gly, Ala, and l-Pro were measured using both vapor pressure osmometry and isopiestic methods. All of the ternary IL + amino acid + water systems show negative deviations from semi-ideal behavior and therefore soluting-out effects have been observed in these systems. In the case of the [Cmim][CFSO] + amino acids aqueous systems, the IL is soluted-out by the amino acids and the soluting-out effect appears by aqueous biphasic system formation. For these systems, the phase diagram and partition coefficient of caffeine were measured at 298.15 K. However, for the [Cmim]Cl and [Cmim]Cl containing systems, the amino acids are soluted-out by the ILs and the soluting-out effect appears by precipitation of the amino acids from the solution, and the solubilities of the amino acids in the aqueous solutions decrease in the presence of [Cmim]Cl and [Cmim]Cl.

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