Toward a Critical Evaluation of DES-Based Organic Biphasic Systems: Are Deep Eutectic Solvents so Critical?

Abstract

Six biphasic systems containing heptane, ethanol, and either hydrogen bond donor compounds (HBD), glycerol, ethylene glycol, levulinic acid, or the corresponding choline chloride-based DES were studied as potential extracting systems for five natural compounds, namely, quercetin, apigenin, coumarin, β-ionone, and α-tocopherol. Phase diagrams for all biphasic systems are reported. It appears that the polarity of the HBD is the most relevant property driving the phase separation and that choline chloride has only a minor influence on the phase diagram. Measurements of the partition coefficients for the five natural compounds mentioned above reveal that the influence of choline chloride on the partition coefficient of a natural compound is only significant when the latter is present in both phases. Finally, binodal curves and partition coefficients were calculated using a conductor-like screening model for real solvents (COSMO-RS). Calculated and experimental results are in good agreement, confirming that COSMO-RS is a useful and promising tool for screening such complex biphasic systems to find the most adequate system for purifying specific natural compounds.

Molecular Modelling of Ionic Liquids: Force-Field Validation and Thermodynamic Perspective from Large-Scale Fast-Growth Solvation Free Energy Calculations

“…[1][2][3][4][5][6][7][8][9] More importantly, these functionalized solvents exhibit satisfactory solvation power for organic compounds and metallic species. [10][11][12][13] For instance, these novel solvents are applied as extractants in the separation of aromatic hydrocarbon from naphtha and in the extraction of metals. [14][15][16] Many polymeric species that are distinct from water also show satisfactorily high solubilities in these functionalized solvents.…”

Molecular Modeling of Ionic Liquids: Force‐Field Validation and Thermodynamic Perspective from Large‐Scale Fast‐Growth Solvation Free Energy Calculations

“…[1][2][3][4][5][6][7][8][9] More importantly, these functionalized solvents exhibit satisfactory solvation power for organic compounds and metallic species. [10][11][12][13] For instance, these novel solvents are applied as extractants in the separation of aromatic hydrocarbon from naphtha and in the extraction of metals. [14][15][16] Many polymeric species that are distinct from water also show satisfactorily high solubilities in these functionalized solvents.…”

Biomass Valorization Using Natural Deep Eutectic Solvents: What’s New in France?

“…In another study by Chagnoleau et al [21] six biphasic systems were investigated, as a way to optimize the purification and extractive diversity of five bio-compounds: quercetin, apigenin, coumarin, β-ionone, and α-tocopherol. The systems investigated biphasic were heptane-ethanol-(choline chloride/glycerol (1:2, mol/mol)), heptane-ethanol-(choline chloride/ethylene glycol (1:2, mol/mol)), heptane-ethanol-(choline chloride/levulinic acid (1:2, mol/mol)), heptane-ethanol glycerol, heptane-ethanol ethylene glycol, and heptaneethanol-levulinic acid.…”

“…This approach has thus demonstrated its practicality and its promising screening capacity to identify the appropriate system for the extraction and purification of the targeted biocompounds. However, to perform the COSMO-RS calculation correctly, a prior geometric optimization using the TURBOMOLE software is essential in order to be able to consider the NaDES as an individual entity [20,21].…”