Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins

Autores
Campanella, Alejandrina; Baltanas, Miguel Angel
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Vegetable oil epoxides (oxiranes) are customarily manufactured using acetic acid (AA) as oxygen carrier and reactant source, in aqueous/organic media. Further attack of the oxirane ring by AA proceeds in this acid-catalyzed process, lowering yield. We report a study of the degradation of the ring by water-solvated AA, using Amberlite IR-120 as heterogeneous catalyst. The ring opening with solvated AA was found to be first order with respect to the concentration of epoxide groups and second order with respect to the carboxylic acid, with an activation energy of 58.7 ± 0.42 kJ mol-1. This value is within the range found in liquid-liquid systems (51.3–66.3 kJ mol-1). Yet, using IR-120, the degradation increases identically either by adding more mass of catalyst or by reducing its particle diameter while keeping the total mass constant, as both situations lead to higher external (exposed) area of the acidic catalyst (i.e., free protons associated to the sulfonic group) on the outer surface of the ion exchange resin beads. These free protons, in turn, become available to catalyze the attack on the oxirane groups of the long-chain fatty acids, which cannot enter (diffuse) into the gel phase of the resin. Despite the unavoidable presence of surface-exposed protons, the degradation can be reduced by several orders of magnitude – for similar process conditions – by using this type of heterogeneous catalysts instead of mineral acids.
Fil: Campanella, Alejandrina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Baltanas, Miguel Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Materia
Epoxidized Vegetable Oils,
Ion Exchange Resin,
Solvated Acetic Acid,
Oxirane Ring Opening.
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/27279
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/27279
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange ResinsCampanella, AlejandrinaBaltanas, Miguel AngelEpoxidized Vegetable Oils,Ion Exchange Resin,Solvated Acetic Acid,Oxirane Ring Opening.https://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2Vegetable oil epoxides (oxiranes) are customarily manufactured using acetic acid (AA) as oxygen carrier and reactant source, in aqueous/organic media. Further attack of the oxirane ring by AA proceeds in this acid-catalyzed process, lowering yield. We report a study of the degradation of the ring by water-solvated AA, using Amberlite IR-120 as heterogeneous catalyst. The ring opening with solvated AA was found to be first order with respect to the concentration of epoxide groups and second order with respect to the carboxylic acid, with an activation energy of 58.7 ± 0.42 kJ mol-1. This value is within the range found in liquid-liquid systems (51.3–66.3 kJ mol-1). Yet, using IR-120, the degradation increases identically either by adding more mass of catalyst or by reducing its particle diameter while keeping the total mass constant, as both situations lead to higher external (exposed) area of the acidic catalyst (i.e., free protons associated to the sulfonic group) on the outer surface of the ion exchange resin beads. These free protons, in turn, become available to catalyze the attack on the oxirane groups of the long-chain fatty acids, which cannot enter (diffuse) into the gel phase of the resin. Despite the unavoidable presence of surface-exposed protons, the degradation can be reduced by several orders of magnitude – for similar process conditions – by using this type of heterogeneous catalysts instead of mineral acids.Fil: Campanella, Alejandrina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Baltanas, Miguel Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaWiley VCH Verlag2004-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/27279Campanella, Alejandrina; Baltanas, Miguel Angel; Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins; Wiley VCH Verlag; European Journal of Lipid Science and Technology; 106; 8; 5-2004; 524-5301438-7697CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejlt.200400965info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejlt.200400965/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:45Zoai:ri.conicet.gov.ar:11336/27279instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:55:45.521CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
title Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
spellingShingle Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
Campanella, Alejandrina
Epoxidized Vegetable Oils,
Ion Exchange Resin,
Solvated Acetic Acid,
Oxirane Ring Opening.
title_short Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
title_full Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
title_fullStr Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
title_full_unstemmed Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
title_sort Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins
dc.creator.none.fl_str_mv Campanella, Alejandrina
Baltanas, Miguel Angel
author Campanella, Alejandrina
author_facet Campanella, Alejandrina
Baltanas, Miguel Angel
author_role author
author2 Baltanas, Miguel Angel
author2_role author
dc.subject.none.fl_str_mv Epoxidized Vegetable Oils,
Ion Exchange Resin,
Solvated Acetic Acid,
Oxirane Ring Opening.
topic Epoxidized Vegetable Oils,
Ion Exchange Resin,
Solvated Acetic Acid,
Oxirane Ring Opening.
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Vegetable oil epoxides (oxiranes) are customarily manufactured using acetic acid (AA) as oxygen carrier and reactant source, in aqueous/organic media. Further attack of the oxirane ring by AA proceeds in this acid-catalyzed process, lowering yield. We report a study of the degradation of the ring by water-solvated AA, using Amberlite IR-120 as heterogeneous catalyst. The ring opening with solvated AA was found to be first order with respect to the concentration of epoxide groups and second order with respect to the carboxylic acid, with an activation energy of 58.7 ± 0.42 kJ mol-1. This value is within the range found in liquid-liquid systems (51.3–66.3 kJ mol-1). Yet, using IR-120, the degradation increases identically either by adding more mass of catalyst or by reducing its particle diameter while keeping the total mass constant, as both situations lead to higher external (exposed) area of the acidic catalyst (i.e., free protons associated to the sulfonic group) on the outer surface of the ion exchange resin beads. These free protons, in turn, become available to catalyze the attack on the oxirane groups of the long-chain fatty acids, which cannot enter (diffuse) into the gel phase of the resin. Despite the unavoidable presence of surface-exposed protons, the degradation can be reduced by several orders of magnitude – for similar process conditions – by using this type of heterogeneous catalysts instead of mineral acids.
Fil: Campanella, Alejandrina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Baltanas, Miguel Angel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
description Vegetable oil epoxides (oxiranes) are customarily manufactured using acetic acid (AA) as oxygen carrier and reactant source, in aqueous/organic media. Further attack of the oxirane ring by AA proceeds in this acid-catalyzed process, lowering yield. We report a study of the degradation of the ring by water-solvated AA, using Amberlite IR-120 as heterogeneous catalyst. The ring opening with solvated AA was found to be first order with respect to the concentration of epoxide groups and second order with respect to the carboxylic acid, with an activation energy of 58.7 ± 0.42 kJ mol-1. This value is within the range found in liquid-liquid systems (51.3–66.3 kJ mol-1). Yet, using IR-120, the degradation increases identically either by adding more mass of catalyst or by reducing its particle diameter while keeping the total mass constant, as both situations lead to higher external (exposed) area of the acidic catalyst (i.e., free protons associated to the sulfonic group) on the outer surface of the ion exchange resin beads. These free protons, in turn, become available to catalyze the attack on the oxirane groups of the long-chain fatty acids, which cannot enter (diffuse) into the gel phase of the resin. Despite the unavoidable presence of surface-exposed protons, the degradation can be reduced by several orders of magnitude – for similar process conditions – by using this type of heterogeneous catalysts instead of mineral acids.
publishDate 2004
dc.date.none.fl_str_mv 2004-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/27279
Campanella, Alejandrina; Baltanas, Miguel Angel; Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins; Wiley VCH Verlag; European Journal of Lipid Science and Technology; 106; 8; 5-2004; 524-530
1438-7697
CONICET Digital
CONICET
url http://hdl.handle.net/11336/27279
identifier_str_mv Campanella, Alejandrina; Baltanas, Miguel Angel; Degradation of the Oxirane Ring of Epoxidized Vegetable Oils with Solvated Acetic Acid Using Cation-exchange Resins; Wiley VCH Verlag; European Journal of Lipid Science and Technology; 106; 8; 5-2004; 524-530
1438-7697
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejlt.200400965
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejlt.200400965/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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