Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

authors	Vilas-Boas, SM; Vieira, V; Brandao, P; Alves, RS; Coutinho, JAP; Pinho, SP; Ferreira, O
nationality	International
journal	JOURNAL OF MOLECULAR LIQUIDS
author keywords	Phenolic acids; Melting properties; NRTL-SAC; Abraham solvation model; X-ray diffraction
keywords	CRYSTALLINE NONELECTROLYTE SOLUTES; ETHANOL MIXED-SOLVENTS; ORGANIC-SOLVENTS; MATHEMATICAL CORRELATION; PHENOLIC-COMPOUNDS; THERMOCHEMICAL BEHAVIOR; 8 PURE; DESCRIPTORS; SOLVATION; WATER
abstract	The solubility of syringic acid, vanillic acid and veratric acid was measured in pure water and eleven organic solvents (methanol, ethanol, 1-propanol, 2-propanol, 2-butanone, ethyl acetate, acetonitrile, dimethylformamide, 1,2-propanediol, 1,3-propanediol and 1,3-butanediol), at 298.2 K and 313.2 K. Besides the solubility data, the melting temperatures and enthalpies of the solutes were determined by differential scanning calorimetry, while powder and single X-ray diffraction were used to resolve the solute solid structure, before and after the solubility studies. For modeling purposes, the NRTL-SAC model, also combined with the Reference Solvent Approach (RSA), and the Abraham solvation model were applied to describe the solid-liquid equilibria of the binary systems. A set of solvents was used to estimate the model parameters and afterwards, solubility predictions were carried out for binary systems not included in the correlation step. Better results were obtained using the Abraham solvation model with average relative deviations (ARD) of 15% for the correlation set and 26% for the predictions, which are more satisfactory than the results found with the NRTL-SAC model (33% for the correlation and 59% for the predictions) or the NRTL-SAC model combined with RSA (30% for the correlation and 59% for the predictions). (C) 2019 Elsevier B.V. All rights reserved.
publisher	ELSEVIER
issn	0167-7322
isbn	1873-3166
year published	2019
volume	289
digital object identifier (doi)	10.1016/j.molliq.2019.111089
web of science category	Chemistry, Physical; Physics, Atomic, Molecular & Chemical
subject category	Chemistry; Physics
unique article identifier	WOS:000482247900013