Glycerol Ethers as Hydrotropes and Their Use to Enhance the Solubility of Phenolic Acids in Water
authors Soares, BP; Abranches, DO; Sintra, TE; Leal-Duaso, A; Garcia, JI; Pires, E; Shimizu, S; Pinho, SP; Coutinho, JAP
nationality International
journal ACS SUSTAINABLE CHEMISTRY & ENGINEERING
author keywords Green chemistry; Hydrotropy; Phenolic acids; Setschenow; Kirkwood-Buff; Cooperativity
keywords GALLIC ACID; AQUEOUS-SOLUTIONS; IONIC LIQUIDS; PLUS WATER; GREEN; SOLVENTS; MIXTURES; ALTERNATIVES; ECOTOXICITY; LIGNIN
abstract The use of glycerol ethers (with alkyl side chains ranging from one to six methyl groups) as hydrotropes to enhance the solubility of gallic and syringic acids in water was here studied. These compounds were selected due to their biological and industrial applications and for serving as model molecules for lignin solubilization. The results obtained were compared against traditional cosolvents, demonstrating the exceptional hydrotropic ability of glycerol ethers. Setschenow constants show that the hydrophobicities of both solute and hydrotrope play an important role in the solubility enhancement by hydrotropy, shedding light into its molecular mechanism. The solubility curves of gallic acid and syringic acid in the aqueous glycerol ether solutions were fitted using a recently proposed statistical thermodynamics-based model. This allowed the estimation of solute recovery from hydrotropic solution by using water as the antisolvent. Unlike what is usually claimed it is here shown that in some conditions it is impossible to recover the solute by simply adding water. This analysis paves the way for a rational design and selection of hydrotropes, in which both solubility enhancement and solute recovery are critical parameters to be taken into account.
publisher AMER CHEMICAL SOC
issn 2168-0485
year published 2020
volume 8
issue 14
beginning page 5742
ending page 5749
digital object identifier (doi) 10.1021/acssuschemeng.0c01032
web of science category Chemistry, Multidisciplinary; Green & Sustainable Science & Technology; Engineering, Chemical
subject category Chemistry; Science & Technology - Other Topics; Engineering
unique article identifier WOS:000526375000033
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journal impact factor 7.632
5 year journal impact factor 7.741
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