Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K

Detalhes bibliográficos
Autor(a) principal: Chiavone Filho, Osvaldo
Data de Publicação: 2016
Outros Autores: Félix, Ítalla Medeiros Bezerra, Moreira, Leila Cabral, Mattedi, Silvana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFRN
Texto Completo: https://repositorio.ufrn.br/handle/123456789/44977
Resumo: Among the various types of existing antibiotics, amoxicillin stands out as a semi synthetic penicillin widely used on a world scale. The enzymatic synthesis of amoxicillin has arisen as an alternative to the drawbacks of conventional chemical synthesis. Nevertheless, to make it feasible a wide data basis of solubility is required in different conditions of industrial interest, aiming at crystallization and subsequent purification of the antibiotic. In this case, the variables such as temperature, pH and solvent composition are of fundamental importance. This work presents solubility data of amoxicillin in aqueous media using an analytical method. The solubility measurements were carried out at 283.15e298.15 K, varying the pH between 2 and 8, and ethanol composition up to 70 wt%. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. The values of pKa demonstrated to be in agreement with the solubility behavior observed experimentally. Thus, the ideal model based on pKa values has been applied as reference for the representation of the solubility data. Furthermore, the experimental solubility and pKa data sets can be used for correlation and thermodynamic modeling purposes
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spelling Chiavone Filho, OsvaldoFélix, Ítalla Medeiros BezerraMoreira, Leila CabralMattedi, Silvana2021-11-23T12:35:02Z2021-11-23T12:35:02Z2016-08-25FELIX, I.M.B.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K. Fluid Phase Equilibria, v. 422, p. 78-86, 2016. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381216301030?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2016.02.040.0378-3812https://repositorio.ufrn.br/handle/123456789/4497710.1016/j.fluid.2016.02.040ElsevierAmoxicillinSolubilityEnzymatic synthesisEthanolDissociation constantSolubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 Kinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleAmong the various types of existing antibiotics, amoxicillin stands out as a semi synthetic penicillin widely used on a world scale. The enzymatic synthesis of amoxicillin has arisen as an alternative to the drawbacks of conventional chemical synthesis. Nevertheless, to make it feasible a wide data basis of solubility is required in different conditions of industrial interest, aiming at crystallization and subsequent purification of the antibiotic. In this case, the variables such as temperature, pH and solvent composition are of fundamental importance. This work presents solubility data of amoxicillin in aqueous media using an analytical method. The solubility measurements were carried out at 283.15e298.15 K, varying the pH between 2 and 8, and ethanol composition up to 70 wt%. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. The values of pKa demonstrated to be in agreement with the solubility behavior observed experimentally. Thus, the ideal model based on pKa values has been applied as reference for the representation of the solubility data. Furthermore, the experimental solubility and pKa data sets can be used for correlation and thermodynamic modeling purposesengreponame:Repositório Institucional da UFRNinstname:Universidade Federal do Rio Grande do Norte (UFRN)instacron:UFRNinfo:eu-repo/semantics/openAccessCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.ufrn.br/bitstream/123456789/44977/2/license_rdf4d2950bda3d176f570a9f8b328dfbbefMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81484https://repositorio.ufrn.br/bitstream/123456789/44977/3/license.txte9597aa2854d128fd968be5edc8a28d9MD53123456789/449772023-02-06 15:46:55.996oai:https://repositorio.ufrn.br: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Repositório de PublicaçõesPUBhttp://repositorio.ufrn.br/oai/opendoar:2023-02-06T18:46:55Repositório Institucional da UFRN - Universidade Federal do Rio Grande do Norte (UFRN)false
dc.title.pt_BR.fl_str_mv Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
title Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
spellingShingle Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
Chiavone Filho, Osvaldo
Amoxicillin
Solubility
Enzymatic synthesis
Ethanol
Dissociation constant
title_short Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
title_full Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
title_fullStr Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
title_full_unstemmed Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
title_sort Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K
author Chiavone Filho, Osvaldo
author_facet Chiavone Filho, Osvaldo
Félix, Ítalla Medeiros Bezerra
Moreira, Leila Cabral
Mattedi, Silvana
author_role author
author2 Félix, Ítalla Medeiros Bezerra
Moreira, Leila Cabral
Mattedi, Silvana
author2_role author
author
author
dc.contributor.author.fl_str_mv Chiavone Filho, Osvaldo
Félix, Ítalla Medeiros Bezerra
Moreira, Leila Cabral
Mattedi, Silvana
dc.subject.por.fl_str_mv Amoxicillin
Solubility
Enzymatic synthesis
Ethanol
Dissociation constant
topic Amoxicillin
Solubility
Enzymatic synthesis
Ethanol
Dissociation constant
description Among the various types of existing antibiotics, amoxicillin stands out as a semi synthetic penicillin widely used on a world scale. The enzymatic synthesis of amoxicillin has arisen as an alternative to the drawbacks of conventional chemical synthesis. Nevertheless, to make it feasible a wide data basis of solubility is required in different conditions of industrial interest, aiming at crystallization and subsequent purification of the antibiotic. In this case, the variables such as temperature, pH and solvent composition are of fundamental importance. This work presents solubility data of amoxicillin in aqueous media using an analytical method. The solubility measurements were carried out at 283.15e298.15 K, varying the pH between 2 and 8, and ethanol composition up to 70 wt%. Dissociation constants have also been measured at the studied values of temperature and ethanol composition, using potentiometric titration. The values of pKa demonstrated to be in agreement with the solubility behavior observed experimentally. Thus, the ideal model based on pKa values has been applied as reference for the representation of the solubility data. Furthermore, the experimental solubility and pKa data sets can be used for correlation and thermodynamic modeling purposes
publishDate 2016
dc.date.issued.fl_str_mv 2016-08-25
dc.date.accessioned.fl_str_mv 2021-11-23T12:35:02Z
dc.date.available.fl_str_mv 2021-11-23T12:35:02Z
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.citation.fl_str_mv FELIX, I.M.B.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K. Fluid Phase Equilibria, v. 422, p. 78-86, 2016. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381216301030?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2016.02.040.
dc.identifier.uri.fl_str_mv https://repositorio.ufrn.br/handle/123456789/44977
dc.identifier.issn.none.fl_str_mv 0378-3812
dc.identifier.doi.none.fl_str_mv 10.1016/j.fluid.2016.02.040
identifier_str_mv FELIX, I.M.B.; MOREIRA, L.C.; CHIAVONE-FILHO, O.; MATTEDI, S.. Solubility measurements of amoxicillin in mixtures of water and ethanol from 283.15 to 298.15 K. Fluid Phase Equilibria, v. 422, p. 78-86, 2016. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0378381216301030?via%3Dihub. Acesso em: 29 jun. 2021. https://doi.org/10.1016/j.fluid.2016.02.040.
0378-3812
10.1016/j.fluid.2016.02.040
url https://repositorio.ufrn.br/handle/123456789/44977
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFRN
instname:Universidade Federal do Rio Grande do Norte (UFRN)
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instname_str Universidade Federal do Rio Grande do Norte (UFRN)
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institution UFRN
reponame_str Repositório Institucional da UFRN
collection Repositório Institucional da UFRN
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