Tunable Hydrophobic Eutectic Solvents Based on Terpenes and Monocarboxylic Acids

Abstract

Recently, some works claim that hydrophobic deep eutectic solvents could be prepared based on menthol and monocarboxylic acids. Despite of some promising potential applications, these systems were poorly understood, and this work addresses this issue. Here, the characterization of eutectic solvents composed of the terpenes thymol or l(−)-menthol and monocarboxylic acids is studied aiming the design of these solvents. Their solid–liquid phase diagrams were measured by differential scanning calorimetry in the whole composition range, showing that a broader composition range, and not only fixed stoichiometric proportions, can be used as solvents at low temperatures. Additionally, solvent densities and viscosities close to the eutectic compositions were measured, showing low viscosity and lower density than water. The solvatochromic parameters at the eutectic composition were also investigated aiming at better understanding their polarity. The high acidity is mainly provided by the presence of thymol in the mixture, while l(−)-menthol plays the major role on the hydrogen-bond basicity. The measured mutual solubilities with water attest to the hydrophobic character of the mixtures investigated. The experimental solid–liquid phase diagrams were described using the PC-SAFT equation of state that is shown to accurately describe the experimental data and quantify the small deviations from ideality.