High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ

Autores
Campanella, Alejandrina; Fontanini, Carina Guadalupe; Baltanas, Miguel Angel
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The impact of the relevant process variables on the reaction of soybean oil fatty acid methyl esters with performic acid (PFA) generated in situ using concentrated hydrogen peroxide (up to 60 wt%), to produce an epoxidized product in high yield, is studied in detail. The degree of mixing, temperature, concentration and molar ratios of reactants and/or use of a diluent were considered. Temperature increases are significantly detrimental for achieving high oxirane numbers, as the selectivity to ring-opening reactions increases. Higher concentrations of either formic acid or H2O2 are also harmful (particularly, the carboxylic acid) but much less than temperature. A proposed alternative process, employing moderate temperature (up to 40 ?C) and concentrated H2O2, compares favourably with the conventional one; higher conversion combined with high epoxide productivity and selectivity are attainable. Using economically sound reactants molar ratios, under well-mixed regimes, in which the immiscible polar and organic phases are well dispersed, the epoxidation process can be adequately described using an (equilibrated) two-phase reaction model. The model accounts for both the reversible peracid formation (in the aqueous phase) and the epoxidation reaction proper, together with the attacks on the epoxide ring by formic acid and performic acid (in the organic phase).
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: Fontanini, Carina Guadalupe. 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
Epoxidation
High Yield
Performic Acid
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/19782
Acceder
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network_name_str CONICET Digital (CONICET)
spelling High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situCampanella, AlejandrinaFontanini, Carina GuadalupeBaltanas, Miguel AngelEpoxidationHigh YieldPerformic Acidhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The impact of the relevant process variables on the reaction of soybean oil fatty acid methyl esters with performic acid (PFA) generated in situ using concentrated hydrogen peroxide (up to 60 wt%), to produce an epoxidized product in high yield, is studied in detail. The degree of mixing, temperature, concentration and molar ratios of reactants and/or use of a diluent were considered. Temperature increases are significantly detrimental for achieving high oxirane numbers, as the selectivity to ring-opening reactions increases. Higher concentrations of either formic acid or H2O2 are also harmful (particularly, the carboxylic acid) but much less than temperature. A proposed alternative process, employing moderate temperature (up to 40 ?C) and concentrated H2O2, compares favourably with the conventional one; higher conversion combined with high epoxide productivity and selectivity are attainable. Using economically sound reactants molar ratios, under well-mixed regimes, in which the immiscible polar and organic phases are well dispersed, the epoxidation process can be adequately described using an (equilibrated) two-phase reaction model. The model accounts for both the reversible peracid formation (in the aqueous phase) and the epoxidation reaction proper, together with the attacks on the epoxide ring by formic acid and performic acid (in the organic phase).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: Fontanini, Carina Guadalupe. 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; ArgentinaElsevier Science Sa2008-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/19782Campanella, Alejandrina; Fontanini, Carina Guadalupe; Baltanas, Miguel Angel; High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ; Elsevier Science Sa; Chemical Engineering Journal; 144; 3; 12-2008; 466-4751385-8947CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.cej.2008.07.016info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1385894708004154info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:10:18Zoai:ri.conicet.gov.ar:11336/19782instacron: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 10:10:19.124CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
title High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
spellingShingle High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
Campanella, Alejandrina
Epoxidation
High Yield
Performic Acid
title_short High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
title_full High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
title_fullStr High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
title_full_unstemmed High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
title_sort High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ
dc.creator.none.fl_str_mv Campanella, Alejandrina
Fontanini, Carina Guadalupe
Baltanas, Miguel Angel
author Campanella, Alejandrina
author_facet Campanella, Alejandrina
Fontanini, Carina Guadalupe
Baltanas, Miguel Angel
author_role author
author2 Fontanini, Carina Guadalupe
Baltanas, Miguel Angel
author2_role author
author
dc.subject.none.fl_str_mv Epoxidation
High Yield
Performic Acid
topic Epoxidation
High Yield
Performic Acid
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The impact of the relevant process variables on the reaction of soybean oil fatty acid methyl esters with performic acid (PFA) generated in situ using concentrated hydrogen peroxide (up to 60 wt%), to produce an epoxidized product in high yield, is studied in detail. The degree of mixing, temperature, concentration and molar ratios of reactants and/or use of a diluent were considered. Temperature increases are significantly detrimental for achieving high oxirane numbers, as the selectivity to ring-opening reactions increases. Higher concentrations of either formic acid or H2O2 are also harmful (particularly, the carboxylic acid) but much less than temperature. A proposed alternative process, employing moderate temperature (up to 40 ?C) and concentrated H2O2, compares favourably with the conventional one; higher conversion combined with high epoxide productivity and selectivity are attainable. Using economically sound reactants molar ratios, under well-mixed regimes, in which the immiscible polar and organic phases are well dispersed, the epoxidation process can be adequately described using an (equilibrated) two-phase reaction model. The model accounts for both the reversible peracid formation (in the aqueous phase) and the epoxidation reaction proper, together with the attacks on the epoxide ring by formic acid and performic acid (in the organic phase).
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: Fontanini, Carina Guadalupe. 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 The impact of the relevant process variables on the reaction of soybean oil fatty acid methyl esters with performic acid (PFA) generated in situ using concentrated hydrogen peroxide (up to 60 wt%), to produce an epoxidized product in high yield, is studied in detail. The degree of mixing, temperature, concentration and molar ratios of reactants and/or use of a diluent were considered. Temperature increases are significantly detrimental for achieving high oxirane numbers, as the selectivity to ring-opening reactions increases. Higher concentrations of either formic acid or H2O2 are also harmful (particularly, the carboxylic acid) but much less than temperature. A proposed alternative process, employing moderate temperature (up to 40 ?C) and concentrated H2O2, compares favourably with the conventional one; higher conversion combined with high epoxide productivity and selectivity are attainable. Using economically sound reactants molar ratios, under well-mixed regimes, in which the immiscible polar and organic phases are well dispersed, the epoxidation process can be adequately described using an (equilibrated) two-phase reaction model. The model accounts for both the reversible peracid formation (in the aqueous phase) and the epoxidation reaction proper, together with the attacks on the epoxide ring by formic acid and performic acid (in the organic phase).
publishDate 2008
dc.date.none.fl_str_mv 2008-12
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/11336/19782
Campanella, Alejandrina; Fontanini, Carina Guadalupe; Baltanas, Miguel Angel; High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ; Elsevier Science Sa; Chemical Engineering Journal; 144; 3; 12-2008; 466-475
1385-8947
CONICET Digital
CONICET
url http://hdl.handle.net/11336/19782
identifier_str_mv Campanella, Alejandrina; Fontanini, Carina Guadalupe; Baltanas, Miguel Angel; High Yield Epoxidation of Fatty Acid Methyl Esters with Performic Acid Generated in situ; Elsevier Science Sa; Chemical Engineering Journal; 144; 3; 12-2008; 466-475
1385-8947
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.cej.2008.07.016
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1385894708004154
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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