Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst

Autores
Palermo, Valeria; Ruiz, Diego Manuel; Autino, Juan Carlos; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.
Fil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ruiz, Diego Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
Acid Catalysis
Chlorine-Free Organic Synthesis
Cinnamates
Keggin Heteropoly Acids
Direct Esterification
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:11336/21783
Acceder
id CONICETDig_b40511a892c84b25133bfeb1c2b1d147
oai_identifier_str oai:ri.conicet.gov.ar:11336/21783
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalystPalermo, ValeriaRuiz, Diego ManuelAutino, Juan CarlosVazquez, Patricia GracielaRomanelli, Gustavo PabloAcid CatalysisChlorine-Free Organic SynthesisCinnamatesKeggin Heteropoly AcidsDirect Esterificationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1https://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.Fil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Ruiz, Diego Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; ArgentinaFil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaDe Gruyter2012-09-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/21783Palermo, Valeria; Ruiz, Diego Manuel; Autino, Juan Carlos; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst; De Gruyter; Pure and Applied Chemistry; 84; 3; 12-9-2012; 529-5400033-4545CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1351/PAC-CON-11-06-05info:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/view/j/pac.2012.84.issue-3/pac-con-11-06-05/pac-con-11-06-05.xmlinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:07:01Zoai:ri.conicet.gov.ar:11336/21783instacron: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 10:07:01.489CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
title Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
spellingShingle Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
Palermo, Valeria
Acid Catalysis
Chlorine-Free Organic Synthesis
Cinnamates
Keggin Heteropoly Acids
Direct Esterification
title_short Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
title_full Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
title_fullStr Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
title_full_unstemmed Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
title_sort Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst
dc.creator.none.fl_str_mv Palermo, Valeria
Ruiz, Diego Manuel
Autino, Juan Carlos
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author Palermo, Valeria
author_facet Palermo, Valeria
Ruiz, Diego Manuel
Autino, Juan Carlos
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author_role author
author2 Ruiz, Diego Manuel
Autino, Juan Carlos
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author2_role author
author
author
author
dc.subject.none.fl_str_mv Acid Catalysis
Chlorine-Free Organic Synthesis
Cinnamates
Keggin Heteropoly Acids
Direct Esterification
topic Acid Catalysis
Chlorine-Free Organic Synthesis
Cinnamates
Keggin Heteropoly Acids
Direct Esterification
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.
Fil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Ruiz, Diego Manuel. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.
publishDate 2012
dc.date.none.fl_str_mv 2012-09-12
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/11336/21783
Palermo, Valeria; Ruiz, Diego Manuel; Autino, Juan Carlos; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst; De Gruyter; Pure and Applied Chemistry; 84; 3; 12-9-2012; 529-540
0033-4545
CONICET Digital
CONICET
url http://hdl.handle.net/11336/21783
identifier_str_mv Palermo, Valeria; Ruiz, Diego Manuel; Autino, Juan Carlos; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Simple halogen-free synthesis of aryl cinnamates using Mo-Keggin heteropoly acids as catalyst; De Gruyter; Pure and Applied Chemistry; 84; 3; 12-9-2012; 529-540
0033-4545
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1351/PAC-CON-11-06-05
info:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/view/j/pac.2012.84.issue-3/pac-con-11-06-05/pac-con-11-06-05.xml
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
dc.publisher.none.fl_str_mv De Gruyter
publisher.none.fl_str_mv De Gruyter
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
_version_ 1844613925582143488
score 13.070432

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