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Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water

2020Journal article Open access
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dc.contributor.authorSoares, Bruna de Paula
dc.contributor.authorAbranches, Dinis O.
dc.contributor.authorSintra, Tânia E.
dc.contributor.authorLeal-Duaso, Alejandro
dc.contributor.authorGarcía, José Ignacio
dc.contributor.authorPires, Elísabet
dc.contributor.authorShimizu, Seishi
dc.contributor.authorPinho, Simão
dc.contributor.authorCoutinho, João A.P.
dc.date.accessioned2018-02-19T10:00:00Z
dc.date.accessioned2020-06-22T10:18:29Z
dc.date.available2018-01-19T10:00:00Z
dc.date.available2020-06-22T10:18:29Z
dc.date.issued2020
dc.description.abstractThe use of glycerol ethers (with alkyl side chain 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 co-solvents, 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 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.
dc.description.sponsorshipThis work was developed within the scope of the projects CICECO-Aveiro Institute of Materials, UIDB/50011/2020 & UIDP/50011/2020, and Associate Laboratory LSRE-LCM, POCI-01-0145-FEDER-006984 (Ref. FCT UID/EQU/50020/2019), both financed by national funds through the FCT/MEC and when appropriate co-financed by FEDER under the PT2020 Partnership Agreement. The NMR spectrometers are part of the National NMR Network (PTNMR) and are partially supported by Infrastructure Project Nº 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL and FCT through PIDDAC). Financial support from Ministerio de Ciencia, Innovación (project RTI2018-093431-B-I00) and the Gobierno de Aragón (Group E37_17R) co-funded by FEDER 2014-2020 “Construyendo Europa desde Aragón” is acknowledged. Alejandro Leal-Duaso thanks the MECD for a FPU grant (FPU14/04338). B.P.S. acknowledges FCT for her Ph.D. grant SFRH/BD/138439/2018.
dc.description.versioninfo:eu-repo/semantics/publishedVersionen_EN
dc.identifier.citationSoares, Bruna P.; Abranches, Dinis O.; Sintra, Tânia E.; Leal-Duaso, Alejandro; García, José Ignacio; Pires, Elísabet; Shimizu, Seishi; Pinho, Simão P.; Coutinho, João A.P. (2020). Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water. ACS Sustainable Chemistry and Engineering. ISSN 2168-0485. 8:14, p. 5742-5749en_EN
dc.identifier.doi10.1021/acssuschemeng.0c01032en_EN
dc.identifier.urihttp://hdl.handle.net/10198/22307
dc.language.isoeng
dc.peerreviewedyesen_EN
dc.relationRTI2018-093431-B-I00
dc.subjectCooperativityen_EN
dc.subjectGreen chemistryen_EN
dc.subjectHydrotropyen_EN
dc.subjectKirkwood-buffen_EN
dc.subjectPhenolic acidsen_EN
dc.subjectSetschenowen_EN
dc.titleGlycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in wateren_EN
dc.typejournal article
dspace.entity.typePublication
person.familyNamePinho
person.givenNameSimão
person.identifier810882
person.identifier.ciencia-id481D-73AD-8D0F
person.identifier.orcid0000-0002-9211-857X
person.identifier.ridD-4148-2013
person.identifier.scopus-author-id7003570175
rcaap.rightsopenAccessen_EN
rcaap.typearticleen_EN
relation.isAuthorOfPublication8ef7789a-34f3-4915-a666-4efe26272a30
relation.isAuthorOfPublication.latestForDiscovery8ef7789a-34f3-4915-a666-4efe26272a30

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