Solubility and solvation of monosaccharides in ionic liquids

authors	Teles, ARR; Dinis, TBV; Capela, EV; Santos, LMNBF; Pinho, SP; Freire, MG; Coutinho, JAP
nationality	International
journal	PHYSICAL CHEMISTRY CHEMICAL PHYSICS
keywords	D-GLUCOSE; LIGNOCELLULOSIC MATERIALS; SUGAR ALCOHOLS; SOLID-LIQUID; D-FRUCTOSE; WATER; MIXTURES; DISSOLUTION; ENTHALPIES; ETHANOL
abstract	Herein, solubility experimental data for six monosaccharides, viz. D-(+)-glucose, D-(+)-mannose, D-(-)-fructose, D-(+)-galactose, D-(+)-xylose and L-(+)-arabinose, in four ionic liquids (ILs), at temperatures ranging from 288.2 to 348.2 K, were obtained aimed at gathering a better understanding of their solvation ability and molecular-level mechanisms which rule the dissolution process. To ascertain the chemical features that enhance the solubility of monosaccharides, ILs composed of dialkylimidazolium or tetra-alkylphosphonium cations combined with the dicyanamide, dimethylphosphate or chloride anions were investigated. It was found that the ranking of the solubility of monosaccharides depends on the IL; yet, D-(+)-xylose is always the most soluble while D-(-)-fructose is the least soluble monosaccharide. The results obtained show that both the IL cation and the anion play a major role in the solubility of monosaccharides. Finally, from the determination of the respective thermodynamic properties of solution, it was found that enthalpic contributions are dominant in the solubilization process. However, the observed differences in the solubilities of monosaccharides in 1-butyl-3-methylimidazolium dicyanamide are ruled by a change in the entropy of solution.
publisher	ROYAL SOC CHEMISTRY
issn	1463-9076
year published	2016
volume	18
issue	29
beginning page	19722
ending page	19730
digital object identifier (doi)	10.1039/c6cp03495k
web of science category	Chemistry, Physical; Physics, Atomic, Molecular & Chemical
subject category	Chemistry; Physics
unique article identifier	WOS:000380343100024