Stereoselective hydrogenation of terpenes using platinum-based catalysts

Autores
Casella, Mónica Laura; Santori, Gerardo Fabian; Moglioni, Albertina Gladys; Vetere, Virginia; Ruggera, José Fernando; Iglesias, Graciela Moltrasio; Ferretti, Osmar Alberto
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the present paper, the catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition using techniques derived from surface organometallic chemistry on metals. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. The hydrogenation of α-pinene led selectively to cis-pinane, and it was possible to observe that the modification of Pt/SiO2 with Sn caused an important decrease of the catalytic activity; this fact can be explained by combined electronic and geometrical effects. In sterically hindered terpenones (fenchone and camphor), the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. In verbenone hydrogenation, the Pt/SiO2 catalyst allowed to obtain cis-verbanone with high yield and catalysts modified with Sn led to the formation of a principal product (cis-verbanol) different than the one obtained by chemical reduction with NaBH4 (cis-verbenol). © 2006 Elsevier B.V. All rights reserved.
Fil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Santori, Gerardo Fabian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; Argentina
Fil: Moglioni, Albertina Gladys. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Iglesias, Graciela Moltrasio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; Argentina
Materia
Α-Pinene
Camphor
Hydrogenation
Platinum-Tin Catalysts
Stereoselectivity
Surface Organometallic Chemistry
Verbenone
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:11336/54135
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/54135
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Stereoselective hydrogenation of terpenes using platinum-based catalystsCasella, Mónica LauraSantori, Gerardo FabianMoglioni, Albertina GladysVetere, VirginiaRuggera, José FernandoIglesias, Graciela MoltrasioFerretti, Osmar AlbertoΑ-PineneCamphorHydrogenationPlatinum-Tin CatalystsStereoselectivitySurface Organometallic ChemistryVerbenonehttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2In the present paper, the catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition using techniques derived from surface organometallic chemistry on metals. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. The hydrogenation of α-pinene led selectively to cis-pinane, and it was possible to observe that the modification of Pt/SiO2 with Sn caused an important decrease of the catalytic activity; this fact can be explained by combined electronic and geometrical effects. In sterically hindered terpenones (fenchone and camphor), the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. In verbenone hydrogenation, the Pt/SiO2 catalyst allowed to obtain cis-verbanone with high yield and catalysts modified with Sn led to the formation of a principal product (cis-verbanol) different than the one obtained by chemical reduction with NaBH4 (cis-verbenol). © 2006 Elsevier B.V. All rights reserved.Fil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Santori, Gerardo Fabian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; ArgentinaFil: Moglioni, Albertina Gladys. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; ArgentinaFil: Iglesias, Graciela Moltrasio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; ArgentinaElsevier Science2007-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/54135Casella, Mónica Laura; Santori, Gerardo Fabian; Moglioni, Albertina Gladys; Vetere, Virginia; Ruggera, José Fernando; et al.; Stereoselective hydrogenation of terpenes using platinum-based catalysts; Elsevier Science; Applied Catalysis A: General; 318; 2-2007; 1-80926-860XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2006.10.004info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0926860X06007137info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:53:08Zoai:ri.conicet.gov.ar:11336/54135instacron: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:34982025-10-22 11:53:08.271CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereoselective hydrogenation of terpenes using platinum-based catalysts
title Stereoselective hydrogenation of terpenes using platinum-based catalysts
spellingShingle Stereoselective hydrogenation of terpenes using platinum-based catalysts
Casella, Mónica Laura
Α-Pinene
Camphor
Hydrogenation
Platinum-Tin Catalysts
Stereoselectivity
Surface Organometallic Chemistry
Verbenone
title_short Stereoselective hydrogenation of terpenes using platinum-based catalysts
title_full Stereoselective hydrogenation of terpenes using platinum-based catalysts
title_fullStr Stereoselective hydrogenation of terpenes using platinum-based catalysts
title_full_unstemmed Stereoselective hydrogenation of terpenes using platinum-based catalysts
title_sort Stereoselective hydrogenation of terpenes using platinum-based catalysts
dc.creator.none.fl_str_mv Casella, Mónica Laura
Santori, Gerardo Fabian
Moglioni, Albertina Gladys
Vetere, Virginia
Ruggera, José Fernando
Iglesias, Graciela Moltrasio
Ferretti, Osmar Alberto
author Casella, Mónica Laura
author_facet Casella, Mónica Laura
Santori, Gerardo Fabian
Moglioni, Albertina Gladys
Vetere, Virginia
Ruggera, José Fernando
Iglesias, Graciela Moltrasio
Ferretti, Osmar Alberto
author_role author
author2 Santori, Gerardo Fabian
Moglioni, Albertina Gladys
Vetere, Virginia
Ruggera, José Fernando
Iglesias, Graciela Moltrasio
Ferretti, Osmar Alberto
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Α-Pinene
Camphor
Hydrogenation
Platinum-Tin Catalysts
Stereoselectivity
Surface Organometallic Chemistry
Verbenone
topic Α-Pinene
Camphor
Hydrogenation
Platinum-Tin Catalysts
Stereoselectivity
Surface Organometallic Chemistry
Verbenone
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In the present paper, the catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition using techniques derived from surface organometallic chemistry on metals. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. The hydrogenation of α-pinene led selectively to cis-pinane, and it was possible to observe that the modification of Pt/SiO2 with Sn caused an important decrease of the catalytic activity; this fact can be explained by combined electronic and geometrical effects. In sterically hindered terpenones (fenchone and camphor), the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. In verbenone hydrogenation, the Pt/SiO2 catalyst allowed to obtain cis-verbanone with high yield and catalysts modified with Sn led to the formation of a principal product (cis-verbanol) different than the one obtained by chemical reduction with NaBH4 (cis-verbenol). © 2006 Elsevier B.V. All rights reserved.
Fil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Santori, Gerardo Fabian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; Argentina
Fil: Moglioni, Albertina Gladys. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Ruggera, José Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina
Fil: Iglesias, Graciela Moltrasio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas ; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; Argentina
description In the present paper, the catalytic hydrogenation of some terpenes is discussed. Catalysts employed were silica supported Pt and Pt modified by tin addition using techniques derived from surface organometallic chemistry on metals. Selected substrates were α-pinene, verbanone, fenchone, camphor and verbenone. The catalytic systems studied allow the control of reaction stereoselectivity. The hydrogenation of α-pinene led selectively to cis-pinane, and it was possible to observe that the modification of Pt/SiO2 with Sn caused an important decrease of the catalytic activity; this fact can be explained by combined electronic and geometrical effects. In sterically hindered terpenones (fenchone and camphor), the topography of the molecule resulted of fundamental importance in controlling the stereoselectivity of the reaction. In verbenone hydrogenation, the Pt/SiO2 catalyst allowed to obtain cis-verbanone with high yield and catalysts modified with Sn led to the formation of a principal product (cis-verbanol) different than the one obtained by chemical reduction with NaBH4 (cis-verbenol). © 2006 Elsevier B.V. All rights reserved.
publishDate 2007
dc.date.none.fl_str_mv 2007-02
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/11336/54135
Casella, Mónica Laura; Santori, Gerardo Fabian; Moglioni, Albertina Gladys; Vetere, Virginia; Ruggera, José Fernando; et al.; Stereoselective hydrogenation of terpenes using platinum-based catalysts; Elsevier Science; Applied Catalysis A: General; 318; 2-2007; 1-8
0926-860X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54135
identifier_str_mv Casella, Mónica Laura; Santori, Gerardo Fabian; Moglioni, Albertina Gladys; Vetere, Virginia; Ruggera, José Fernando; et al.; Stereoselective hydrogenation of terpenes using platinum-based catalysts; Elsevier Science; Applied Catalysis A: General; 318; 2-2007; 1-8
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.2006.10.004
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0926860X06007137
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
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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