Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid.
Autor(a) principal: | |
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Data de Publicação: | 2017 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/9959 https://www.sciencedirect.com/science/article/pii/S0920586116304874 |
Resumo: | The reactions of biomass-based substrates, i.e., limonene, -pinene, -pinene, terpinolene, -terpineol,nerol and linalool, with benzaldehyde in the presence of tungstophosphoric heteropoly acid H3PW12O40(HPW) supported on silica give an oxabicyclo[3.3.1]nonene compound with fragrance characteristics ingood to excellent yields. The reactions apparently involve the formation of -terpenyl carbenium ion bythe protonation of alkene or dehydration of alcohol followed by the nucleophilic attack of benzaldehyde.The subsequent oxonium-ene cyclization of the resulting oxocarbenium ion gives the oxabicyclic product.The process is an environmentally benign and heterogeneous and can be performed under mild conditionswith low catalyst amounts and no significant leaching of active components. |
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Cotta, Rafaela FerreiraRocha, Kelly Alessandra da SilvaKozhevnikova, Elena FedorovnaKozhevnikov, Ivan V.Gusevskaya, Elena Vitalievna2018-05-21T12:33:33Z2018-05-21T12:33:33Z2017COTTA, R. F. et al. Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. Catalysis Today, v. 289, p. 14-19, jul. 2017. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0920586116304874>. Acesso em: 05 abr. 2018.09205861http://www.repositorio.ufop.br/handle/123456789/9959https://www.sciencedirect.com/science/article/pii/S0920586116304874The reactions of biomass-based substrates, i.e., limonene, -pinene, -pinene, terpinolene, -terpineol,nerol and linalool, with benzaldehyde in the presence of tungstophosphoric heteropoly acid H3PW12O40(HPW) supported on silica give an oxabicyclo[3.3.1]nonene compound with fragrance characteristics ingood to excellent yields. The reactions apparently involve the formation of -terpenyl carbenium ion bythe protonation of alkene or dehydration of alcohol followed by the nucleophilic attack of benzaldehyde.The subsequent oxonium-ene cyclization of the resulting oxocarbenium ion gives the oxabicyclic product.The process is an environmentally benign and heterogeneous and can be performed under mild conditionswith low catalyst amounts and no significant leaching of active components.Biomass-based feedstockHeteropoly acidCycloadditionAcid catalysisCoupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-8924http://www.repositorio.ufop.br/bitstream/123456789/9959/2/license.txt62604f8d955274beb56c80ce1ee5dcaeMD52ORIGINALARTIGO_CouplingMonoterpenicAlkenes.pdfARTIGO_CouplingMonoterpenicAlkenes.pdfapplication/pdf394978http://www.repositorio.ufop.br/bitstream/123456789/9959/1/ARTIGO_CouplingMonoterpenicAlkenes.pdf308e5b040ae17c4c9b530c5b100c6c87MD51123456789/99592018-05-21 08:33:33.845oai:localhost: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ório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332018-05-21T12:33:33Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
title |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
spellingShingle |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. Cotta, Rafaela Ferreira Biomass-based feedstock Heteropoly acid Cycloaddition Acid catalysis |
title_short |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
title_full |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
title_fullStr |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
title_full_unstemmed |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
title_sort |
Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. |
author |
Cotta, Rafaela Ferreira |
author_facet |
Cotta, Rafaela Ferreira Rocha, Kelly Alessandra da Silva Kozhevnikova, Elena Fedorovna Kozhevnikov, Ivan V. Gusevskaya, Elena Vitalievna |
author_role |
author |
author2 |
Rocha, Kelly Alessandra da Silva Kozhevnikova, Elena Fedorovna Kozhevnikov, Ivan V. Gusevskaya, Elena Vitalievna |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Cotta, Rafaela Ferreira Rocha, Kelly Alessandra da Silva Kozhevnikova, Elena Fedorovna Kozhevnikov, Ivan V. Gusevskaya, Elena Vitalievna |
dc.subject.por.fl_str_mv |
Biomass-based feedstock Heteropoly acid Cycloaddition Acid catalysis |
topic |
Biomass-based feedstock Heteropoly acid Cycloaddition Acid catalysis |
description |
The reactions of biomass-based substrates, i.e., limonene, -pinene, -pinene, terpinolene, -terpineol,nerol and linalool, with benzaldehyde in the presence of tungstophosphoric heteropoly acid H3PW12O40(HPW) supported on silica give an oxabicyclo[3.3.1]nonene compound with fragrance characteristics ingood to excellent yields. The reactions apparently involve the formation of -terpenyl carbenium ion bythe protonation of alkene or dehydration of alcohol followed by the nucleophilic attack of benzaldehyde.The subsequent oxonium-ene cyclization of the resulting oxocarbenium ion gives the oxabicyclic product.The process is an environmentally benign and heterogeneous and can be performed under mild conditionswith low catalyst amounts and no significant leaching of active components. |
publishDate |
2017 |
dc.date.issued.fl_str_mv |
2017 |
dc.date.accessioned.fl_str_mv |
2018-05-21T12:33:33Z |
dc.date.available.fl_str_mv |
2018-05-21T12:33:33Z |
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 |
COTTA, R. F. et al. Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. Catalysis Today, v. 289, p. 14-19, jul. 2017. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0920586116304874>. Acesso em: 05 abr. 2018. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/9959 |
dc.identifier.issn.none.fl_str_mv |
09205861 |
dc.identifier.uri2.pt_BR.fl_str_mv |
https://www.sciencedirect.com/science/article/pii/S0920586116304874 |
identifier_str_mv |
COTTA, R. F. et al. Coupling of monoterpenic alkenes and alcohols with benzaldehyde catalyzed by silica-supported tungstophosphoric heteropoly acid. Catalysis Today, v. 289, p. 14-19, jul. 2017. Disponível em: <https://www.sciencedirect.com/science/article/pii/S0920586116304874>. Acesso em: 05 abr. 2018. 09205861 |
url |
http://www.repositorio.ufop.br/handle/123456789/9959 https://www.sciencedirect.com/science/article/pii/S0920586116304874 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFOP instname:Universidade Federal de Ouro Preto (UFOP) instacron:UFOP |
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Universidade Federal de Ouro Preto (UFOP) |
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UFOP |
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UFOP |
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Repositório Institucional da UFOP |
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Repositório Institucional da UFOP |
bitstream.url.fl_str_mv |
http://www.repositorio.ufop.br/bitstream/123456789/9959/2/license.txt http://www.repositorio.ufop.br/bitstream/123456789/9959/1/ARTIGO_CouplingMonoterpenicAlkenes.pdf |
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Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP) |
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repositorio@ufop.edu.br |
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