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

Detalhes bibliográficos
Autor(a) principal: Soares, Bruna de Paula
Data de Publicação: 2018
Outros Autores: Abranches, Dinis O., Sintra, Tânia E., Leal-Duaso, Alejandro, García, José Ignacio, Pires, Elísabet, Shimizu, Seishi, Pinho, Simão, Coutinho, João A.P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10198/22307
Resumo: The 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.
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spelling Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in waterCooperativityGreen chemistryHydrotropyKirkwood-buffPhenolic acidsSetschenowThe 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.This 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.Biblioteca Digital do IPBSoares, Bruna de PaulaAbranches, Dinis O.Sintra, Tânia E.Leal-Duaso, AlejandroGarcía, José IgnacioPires, ElísabetShimizu, SeishiPinho, SimãoCoutinho, João A.P.2018-01-19T10:00:00Z20202020-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/22307engSoares, 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. 5742-574910.1021/acssuschemeng.0c01032info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-21T10:50:02Zoai:bibliotecadigital.ipb.pt:10198/22307Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:13:33.448325Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
title Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
spellingShingle Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
Soares, Bruna de Paula
Cooperativity
Green chemistry
Hydrotropy
Kirkwood-buff
Phenolic acids
Setschenow
title_short Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
title_full Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
title_fullStr Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
title_full_unstemmed Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
title_sort Glycerol ethers as hydrotropes and their use to enhance the solubility of phenolic acids in water
author Soares, Bruna de Paula
author_facet Soares, Bruna de Paula
Abranches, Dinis O.
Sintra, Tânia E.
Leal-Duaso, Alejandro
García, José Ignacio
Pires, Elísabet
Shimizu, Seishi
Pinho, Simão
Coutinho, João A.P.
author_role author
author2 Abranches, Dinis O.
Sintra, Tânia E.
Leal-Duaso, Alejandro
García, José Ignacio
Pires, Elísabet
Shimizu, Seishi
Pinho, Simão
Coutinho, João A.P.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Biblioteca Digital do IPB
dc.contributor.author.fl_str_mv Soares, Bruna de Paula
Abranches, Dinis O.
Sintra, Tânia E.
Leal-Duaso, Alejandro
García, José Ignacio
Pires, Elísabet
Shimizu, Seishi
Pinho, Simão
Coutinho, João A.P.
dc.subject.por.fl_str_mv Cooperativity
Green chemistry
Hydrotropy
Kirkwood-buff
Phenolic acids
Setschenow
topic Cooperativity
Green chemistry
Hydrotropy
Kirkwood-buff
Phenolic acids
Setschenow
description The 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.
publishDate 2018
dc.date.none.fl_str_mv 2018-01-19T10:00:00Z
2020
2020-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10198/22307
url http://hdl.handle.net/10198/22307
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Soares, 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. 5742-5749
10.1021/acssuschemeng.0c01032
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv application/pdf
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