Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts

Autores
Diez, Veronica Karina; Marcos, B.J.; Apesteguia, Carlos Rodolfo; Di Cosimo, Juana Isabel
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The liquid-phase cyclization of pseudoionone to ionones (α, β and γ isomers) was studied on silica-supported heteropolyacid (HPA) catalysts containing between 18.8 and 58.5% HPA. The HPA used was tungstophosphoric acid (H3PW12O40). The catalyst surface and structural properties were thoroughly characterized by several techniques. The density, chemical nature and strength distribution of the surface acid sites were determined by adsorbing and monitoring by temperature-programmed desorption and infrared spectroscopy probe molecules such as NH3 and pyridine. The pseudoionone conversion to ionones increased linearly with the Brønsted acid site density until the HPA loading approached to the monolayer saturation coverage. For higher HPA contents, the pseudoionone adsorption and conversion were hampered because of spatial constraints that diminished the reactant accessibility to the proton active sites. The highest ionone yield, 79%, was obtained on a 58.5 wt% HPA/SiO2 catalyst at 383 K and is comparable to the best values reported in literature for the homogeneously catalyzed reaction using sulfuric acid. The ionone isomer distribution was modified by varying both the temperature and the reaction time. A reaction mechanism was postulated in which ionone isomers (α, β and γ) are primary products, but γ-ionone is isomerized to α-ionone while β-ionone is not converted in the other isomers.
Fil: Diez, Veronica Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Marcos, B.J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Apesteguia, Carlos Rodolfo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Di Cosimo, Juana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Materia
Ionone
Heteropolyacid
Acid Catalysis
Tungstophosphoric Acid
Hpa
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:11336/57330
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/57330
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalystsDiez, Veronica KarinaMarcos, B.J.Apesteguia, Carlos RodolfoDi Cosimo, Juana IsabelIononeHeteropolyacidAcid CatalysisTungstophosphoric AcidHpahttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The liquid-phase cyclization of pseudoionone to ionones (α, β and γ isomers) was studied on silica-supported heteropolyacid (HPA) catalysts containing between 18.8 and 58.5% HPA. The HPA used was tungstophosphoric acid (H3PW12O40). The catalyst surface and structural properties were thoroughly characterized by several techniques. The density, chemical nature and strength distribution of the surface acid sites were determined by adsorbing and monitoring by temperature-programmed desorption and infrared spectroscopy probe molecules such as NH3 and pyridine. The pseudoionone conversion to ionones increased linearly with the Brønsted acid site density until the HPA loading approached to the monolayer saturation coverage. For higher HPA contents, the pseudoionone adsorption and conversion were hampered because of spatial constraints that diminished the reactant accessibility to the proton active sites. The highest ionone yield, 79%, was obtained on a 58.5 wt% HPA/SiO2 catalyst at 383 K and is comparable to the best values reported in literature for the homogeneously catalyzed reaction using sulfuric acid. The ionone isomer distribution was modified by varying both the temperature and the reaction time. A reaction mechanism was postulated in which ionone isomers (α, β and γ) are primary products, but γ-ionone is isomerized to α-ionone while β-ionone is not converted in the other isomers.Fil: Diez, Veronica Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; ArgentinaFil: Marcos, B.J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; ArgentinaFil: Apesteguia, Carlos Rodolfo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; ArgentinaFil: Di Cosimo, Juana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; ArgentinaElsevier Science2009-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/57330Diez, Veronica Karina; Marcos, B.J.; Apesteguia, Carlos Rodolfo; Di Cosimo, Juana Isabel; Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts; Elsevier Science; Applied Catalysis A: General; 358; 1; 4-2009; 95-1020926-860XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2009.02.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:41:02Zoai:ri.conicet.gov.ar:11336/57330instacron: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:34982025-09-29 09:41:02.912CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
title Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
spellingShingle Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
Diez, Veronica Karina
Ionone
Heteropolyacid
Acid Catalysis
Tungstophosphoric Acid
Hpa
title_short Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
title_full Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
title_fullStr Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
title_full_unstemmed Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
title_sort Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts
dc.creator.none.fl_str_mv Diez, Veronica Karina
Marcos, B.J.
Apesteguia, Carlos Rodolfo
Di Cosimo, Juana Isabel
author Diez, Veronica Karina
author_facet Diez, Veronica Karina
Marcos, B.J.
Apesteguia, Carlos Rodolfo
Di Cosimo, Juana Isabel
author_role author
author2 Marcos, B.J.
Apesteguia, Carlos Rodolfo
Di Cosimo, Juana Isabel
author2_role author
author
author
dc.subject.none.fl_str_mv Ionone
Heteropolyacid
Acid Catalysis
Tungstophosphoric Acid
Hpa
topic Ionone
Heteropolyacid
Acid Catalysis
Tungstophosphoric Acid
Hpa
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The liquid-phase cyclization of pseudoionone to ionones (α, β and γ isomers) was studied on silica-supported heteropolyacid (HPA) catalysts containing between 18.8 and 58.5% HPA. The HPA used was tungstophosphoric acid (H3PW12O40). The catalyst surface and structural properties were thoroughly characterized by several techniques. The density, chemical nature and strength distribution of the surface acid sites were determined by adsorbing and monitoring by temperature-programmed desorption and infrared spectroscopy probe molecules such as NH3 and pyridine. The pseudoionone conversion to ionones increased linearly with the Brønsted acid site density until the HPA loading approached to the monolayer saturation coverage. For higher HPA contents, the pseudoionone adsorption and conversion were hampered because of spatial constraints that diminished the reactant accessibility to the proton active sites. The highest ionone yield, 79%, was obtained on a 58.5 wt% HPA/SiO2 catalyst at 383 K and is comparable to the best values reported in literature for the homogeneously catalyzed reaction using sulfuric acid. The ionone isomer distribution was modified by varying both the temperature and the reaction time. A reaction mechanism was postulated in which ionone isomers (α, β and γ) are primary products, but γ-ionone is isomerized to α-ionone while β-ionone is not converted in the other isomers.
Fil: Diez, Veronica Karina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Marcos, B.J.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Apesteguia, Carlos Rodolfo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
Fil: Di Cosimo, Juana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera". Universidad Nacional del Litoral. Instituto de Investigaciones en Catálisis y Petroquímica "Ing. José Miguel Parera"; Argentina
description The liquid-phase cyclization of pseudoionone to ionones (α, β and γ isomers) was studied on silica-supported heteropolyacid (HPA) catalysts containing between 18.8 and 58.5% HPA. The HPA used was tungstophosphoric acid (H3PW12O40). The catalyst surface and structural properties were thoroughly characterized by several techniques. The density, chemical nature and strength distribution of the surface acid sites were determined by adsorbing and monitoring by temperature-programmed desorption and infrared spectroscopy probe molecules such as NH3 and pyridine. The pseudoionone conversion to ionones increased linearly with the Brønsted acid site density until the HPA loading approached to the monolayer saturation coverage. For higher HPA contents, the pseudoionone adsorption and conversion were hampered because of spatial constraints that diminished the reactant accessibility to the proton active sites. The highest ionone yield, 79%, was obtained on a 58.5 wt% HPA/SiO2 catalyst at 383 K and is comparable to the best values reported in literature for the homogeneously catalyzed reaction using sulfuric acid. The ionone isomer distribution was modified by varying both the temperature and the reaction time. A reaction mechanism was postulated in which ionone isomers (α, β and γ) are primary products, but γ-ionone is isomerized to α-ionone while β-ionone is not converted in the other isomers.
publishDate 2009
dc.date.none.fl_str_mv 2009-04
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/11336/57330
Diez, Veronica Karina; Marcos, B.J.; Apesteguia, Carlos Rodolfo; Di Cosimo, Juana Isabel; Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts; Elsevier Science; Applied Catalysis A: General; 358; 1; 4-2009; 95-102
0926-860X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/57330
identifier_str_mv Diez, Veronica Karina; Marcos, B.J.; Apesteguia, Carlos Rodolfo; Di Cosimo, Juana Isabel; Ionone synthesis by cyclization of pseudoionone on silica-supported heteropolyacid catalysts; Elsevier Science; Applied Catalysis A: General; 358; 1; 4-2009; 95-102
0926-860X
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.apcata.2009.02.002
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
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 13.070432

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