Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid

Autores
Padro, Cristina; Apesteguia, Carlos Rodolfo
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The gas-phase synthesis of aromatic ketones via acylation of phenol with acetic acid was studied on SiO2–Al2O3, Al-MCM-41, zeolites HY and ZSM5, and tungstophosphoric acid (HPA) supported on MCM-41 and carbon. At contact times of 146 g h/mol, the initial conversion of phenol varied between 12.5% (HY) and 19.1% (HPA/MCM-41), and the initial selectivity to ortho-hydroxyacetophenone (o-HAP) between 37.1% (HPA/C) and 69.1% (HY). In all the cases, the formation of o-HAP was clearly favored in comparison to that of para-isomer. Zeolites HY and ZSM5, which contained strong Brønsted and Lewis acid sites, produced efficiently o-HAP via both the direct C-acylation of phenol and the acylation of phenyl acetate intermediate formed from O-acylation of phenol. HPA-based catalysts contained only Brønsted acid sites and formed o-HAP exclusively as a secondary product from phenyl acetate. The o-HAP yield remained constant with time on stream on ZSM5 but drastically decreased on the other samples because of coke formation. The superior stability of zeolite ZSM5 was interpreted by considering that coke precursor formation is avoided into the microporous structure of this zeolite.
Fil: Padro, Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; 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 ; Argentina
Materia
Aromatic Ketones
Acylation Reactions
Solid Acids
O-Hydroxyacetophenone Synthesis
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:11336/55821
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/55821
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acidPadro, CristinaApesteguia, Carlos RodolfoAromatic KetonesAcylation ReactionsSolid AcidsO-Hydroxyacetophenone Synthesishttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The gas-phase synthesis of aromatic ketones via acylation of phenol with acetic acid was studied on SiO2–Al2O3, Al-MCM-41, zeolites HY and ZSM5, and tungstophosphoric acid (HPA) supported on MCM-41 and carbon. At contact times of 146 g h/mol, the initial conversion of phenol varied between 12.5% (HY) and 19.1% (HPA/MCM-41), and the initial selectivity to ortho-hydroxyacetophenone (o-HAP) between 37.1% (HPA/C) and 69.1% (HY). In all the cases, the formation of o-HAP was clearly favored in comparison to that of para-isomer. Zeolites HY and ZSM5, which contained strong Brønsted and Lewis acid sites, produced efficiently o-HAP via both the direct C-acylation of phenol and the acylation of phenyl acetate intermediate formed from O-acylation of phenol. HPA-based catalysts contained only Brønsted acid sites and formed o-HAP exclusively as a secondary product from phenyl acetate. The o-HAP yield remained constant with time on stream on ZSM5 but drastically decreased on the other samples because of coke formation. The superior stability of zeolite ZSM5 was interpreted by considering that coke precursor formation is avoided into the microporous structure of this zeolite.Fil: Padro, Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; ArgentinaFil: Apesteguia, Carlos Rodolfo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; ArgentinaElsevier Science2004-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/55821Padro, Cristina; Apesteguia, Carlos Rodolfo; Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid; Elsevier Science; Journal of Catalysis; 226; 2; 9-2004; 308-3200021-9517CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jcat.2004.05.030info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:23:59Zoai:ri.conicet.gov.ar:11336/55821instacron: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:34982025-09-10 13:23:59.863CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
title Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
spellingShingle Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
Padro, Cristina
Aromatic Ketones
Acylation Reactions
Solid Acids
O-Hydroxyacetophenone Synthesis
title_short Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
title_full Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
title_fullStr Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
title_full_unstemmed Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
title_sort Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid
dc.creator.none.fl_str_mv Padro, Cristina
Apesteguia, Carlos Rodolfo
author Padro, Cristina
author_facet Padro, Cristina
Apesteguia, Carlos Rodolfo
author_role author
author2 Apesteguia, Carlos Rodolfo
author2_role author
dc.subject.none.fl_str_mv Aromatic Ketones
Acylation Reactions
Solid Acids
O-Hydroxyacetophenone Synthesis
topic Aromatic Ketones
Acylation Reactions
Solid Acids
O-Hydroxyacetophenone Synthesis
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 gas-phase synthesis of aromatic ketones via acylation of phenol with acetic acid was studied on SiO2–Al2O3, Al-MCM-41, zeolites HY and ZSM5, and tungstophosphoric acid (HPA) supported on MCM-41 and carbon. At contact times of 146 g h/mol, the initial conversion of phenol varied between 12.5% (HY) and 19.1% (HPA/MCM-41), and the initial selectivity to ortho-hydroxyacetophenone (o-HAP) between 37.1% (HPA/C) and 69.1% (HY). In all the cases, the formation of o-HAP was clearly favored in comparison to that of para-isomer. Zeolites HY and ZSM5, which contained strong Brønsted and Lewis acid sites, produced efficiently o-HAP via both the direct C-acylation of phenol and the acylation of phenyl acetate intermediate formed from O-acylation of phenol. HPA-based catalysts contained only Brønsted acid sites and formed o-HAP exclusively as a secondary product from phenyl acetate. The o-HAP yield remained constant with time on stream on ZSM5 but drastically decreased on the other samples because of coke formation. The superior stability of zeolite ZSM5 was interpreted by considering that coke precursor formation is avoided into the microporous structure of this zeolite.
Fil: Padro, Cristina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; 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 ; Argentina
description The gas-phase synthesis of aromatic ketones via acylation of phenol with acetic acid was studied on SiO2–Al2O3, Al-MCM-41, zeolites HY and ZSM5, and tungstophosphoric acid (HPA) supported on MCM-41 and carbon. At contact times of 146 g h/mol, the initial conversion of phenol varied between 12.5% (HY) and 19.1% (HPA/MCM-41), and the initial selectivity to ortho-hydroxyacetophenone (o-HAP) between 37.1% (HPA/C) and 69.1% (HY). In all the cases, the formation of o-HAP was clearly favored in comparison to that of para-isomer. Zeolites HY and ZSM5, which contained strong Brønsted and Lewis acid sites, produced efficiently o-HAP via both the direct C-acylation of phenol and the acylation of phenyl acetate intermediate formed from O-acylation of phenol. HPA-based catalysts contained only Brønsted acid sites and formed o-HAP exclusively as a secondary product from phenyl acetate. The o-HAP yield remained constant with time on stream on ZSM5 but drastically decreased on the other samples because of coke formation. The superior stability of zeolite ZSM5 was interpreted by considering that coke precursor formation is avoided into the microporous structure of this zeolite.
publishDate 2004
dc.date.none.fl_str_mv 2004-09
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/11336/55821
Padro, Cristina; Apesteguia, Carlos Rodolfo; Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid; Elsevier Science; Journal of Catalysis; 226; 2; 9-2004; 308-320
0021-9517
CONICET Digital
CONICET
url http://hdl.handle.net/11336/55821
identifier_str_mv Padro, Cristina; Apesteguia, Carlos Rodolfo; Gas-phase synthesis of hydroxyacetophenones by acylation of phenol with acetic acid; Elsevier Science; Journal of Catalysis; 226; 2; 9-2004; 308-320
0021-9517
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.jcat.2004.05.030
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 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
_version_ 1842981327810330624
score 12.48226

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