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The impact of size and shape in the performance of hydrotropes: a case-study of alkanediols

2022Journal article Open access
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dc.contributor.authorAbranches, Dinis O.
dc.contributor.authorSoares, Bruna de Paula
dc.contributor.authorFerreira, Ana M.
dc.contributor.authorShimizu, Seishi
dc.contributor.authorPinho, Simão
dc.contributor.authorCoutinho, João A.P.
dc.date.accessioned2022-05-13T10:28:41Z
dc.date.available2022-05-13T10:28:41Z
dc.date.issued2022
dc.description.abstractInspired by the recently proposed cooperative mechanism of hydrotropy, where water molecules mediate the aggregation of hydrotrope around the solute, this work studies the impact of apolar volume and polar group position on the performance of hydrotropes. To do so, the ability of two different families of alkanediols (1,2-alkanediols and 1,n-alkanediols) to increase the aqueous solubility of syringic acid is initially investigated. Interestingly, it is observed that in the dilute region (low hydrotrope concentration), the relative position of the hydroxyl groups of the alkanediols does not impact their performance. Instead, their ability to increase the solubility of syringic acid correlates remarkably well with the size of their alkyl chains. However, this is not the case for larger hydrotrope concentrations, where 1,2-alkanediols are found to perform, in general, better than 1,n-alkanediols. These seemingly contradictory findings are reconciled using theoretical and experimental techniques, namely the cooperative model of hydrotropy and chemical environment probes (Kamlet–Taft and pyrene polarity scales). It is found that the number of hydrotropes aggregated around a solute molecule does not increase linearly with the apolar volume of the former, reaching a maximum instead. This maximum is discussed in terms of competing solute–hydrotrope and hydrotrope–hydrotrope interactions. The results suggest that hydrotrope self-aggregation is more prevalent in 1,n-alkanediols, which negatively impacts their performance as hydrotropes. The results reported in this work support the cooperative model of hydrotropy and, from an application perspective, show that hydrotropes should be designed taking into consideration not only their apolar volume but also their ability to stabilize their selfaggregation in water, which negatively impacts their performance as solubility enhancers.pt_PT
dc.description.sponsorshipThis work was developed within the scope of the project CICECO-Aveiro Institute of Materials, UIDB/50011/2020 & UIDP/50011/2020, and CIMO-Mountain Research Center, UIDB/00690/2020, financed by national funds through the FCT/MEC, and when appropriate, cofinanced by FEDER under the PT2020 Partnership Agreement. B. P. S. acknowledges FCT for her PhDgrant SFRH/BD/138439/2018.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAbranches, Dinis O.; Soares, Bruna P.; Ferreira, Ana M.; Shimizu, Seishi; Pinho, Simão; Coutinho, João A.P. (2022). The impact of size and shape in the performance of hydrotropes: a case-study of alkanediols. Physical Chemistry Chemical Physics. ISSN 1463-9084. 24:13, p. 7624-7634pt_PT
dc.identifier.doi10.1039/D2CP00496Hpt_PT
dc.identifier.eissn1463-9076
dc.identifier.issn1463-9084
dc.identifier.urihttp://hdl.handle.net/10198/25439
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relationCICECO-Aveiro Institute of Materials
dc.relationCICECO-Aveiro Institute of Materials
dc.relationMountain Research Center
dc.relationEnhanced Extraction of Phenolic Compounds using Biobased Solvents as Hydrotropes
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectSolubilitypt_PT
dc.subjectSolutions;pt_PT
dc.subjectWaterpt_PT
dc.titleThe impact of size and shape in the performance of hydrotropes: a case-study of alkanediolspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleCICECO-Aveiro Institute of Materials
oaire.awardTitleMountain Research Center
oaire.awardTitleEnhanced Extraction of Phenolic Compounds using Biobased Solvents as Hydrotropes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50011%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00690%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POR_CENTRO/SFRH%2FBD%2F138439%2F2018/PT
oaire.citation.endPage7634pt_PT
oaire.citation.issue13pt_PT
oaire.citation.startPage7624pt_PT
oaire.citation.titlePhysical Chemistry Chemical Physicspt_PT
oaire.citation.volume24pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamPOR_CENTRO
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
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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