Acylation of phenol on solid acids: Study of the deactivation mechanism

Autores
Padro, Cristina; Apesteguia, Carlos Rodolfo
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The deactivation mechanism of the gas-phase synthesis of o-hydroxyacetophenone (o-HAP) via acylation of phenol with acetic acid was studied on Al-MCM-41 and zeolites HY, HBeta and HZSM-5. The o-HAP yield remained constant with time-on-stream on HZSM-5 but drastically decreased on the other samples because of coke formation. The origin and nature of coke precursor species were studied by employing as reactants, the key reaction intermediates and products involved in the phenol acylation reaction network. It was found that coke precursors are formed from consecutive condensation reactions and not from any ketene formation by phenyl acetate decomposition. Specifically, it is proposed that o-acetoxyacetophenone (o-AXAP), which is formed by reaction between o-HAP and acetic acid, is the key intermediate specie responsible for the formation of carbonaceous deposits and consequently, for the activity decay observed on Al-MCM-41, HY and HBeta samples. The narrow pore size structure of zeolite HZSM-5 would hinder the formation of bulky o-AXAP, thereby, decreasing drastically the formation of coke.
Fil: Padro, Cristina. 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
Materia
Acylation Reactions
Catalyst Deactivation
O-Hydroxyacetophenone Synthesis
Solid Acids
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:11336/73023
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/73023
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Acylation of phenol on solid acids: Study of the deactivation mechanismPadro, CristinaApesteguia, Carlos RodolfoAcylation ReactionsCatalyst DeactivationO-Hydroxyacetophenone SynthesisSolid Acidshttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The deactivation mechanism of the gas-phase synthesis of o-hydroxyacetophenone (o-HAP) via acylation of phenol with acetic acid was studied on Al-MCM-41 and zeolites HY, HBeta and HZSM-5. The o-HAP yield remained constant with time-on-stream on HZSM-5 but drastically decreased on the other samples because of coke formation. The origin and nature of coke precursor species were studied by employing as reactants, the key reaction intermediates and products involved in the phenol acylation reaction network. It was found that coke precursors are formed from consecutive condensation reactions and not from any ketene formation by phenyl acetate decomposition. Specifically, it is proposed that o-acetoxyacetophenone (o-AXAP), which is formed by reaction between o-HAP and acetic acid, is the key intermediate specie responsible for the formation of carbonaceous deposits and consequently, for the activity decay observed on Al-MCM-41, HY and HBeta samples. The narrow pore size structure of zeolite HZSM-5 would hinder the formation of bulky o-AXAP, thereby, decreasing drastically the formation of coke.Fil: Padro, Cristina. 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"; ArgentinaElsevier Science2005-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/73023Padro, Cristina; Apesteguia, Carlos Rodolfo; Acylation of phenol on solid acids: Study of the deactivation mechanism; Elsevier Science; Catalysis Today; 107-108; 10-2005; 258-2650920-5861CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.cattod.2005.07.078info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:58:01Zoai:ri.conicet.gov.ar:11336/73023instacron: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:34982025-09-03 09:58:01.614CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Acylation of phenol on solid acids: Study of the deactivation mechanism
title Acylation of phenol on solid acids: Study of the deactivation mechanism
spellingShingle Acylation of phenol on solid acids: Study of the deactivation mechanism
Padro, Cristina
Acylation Reactions
Catalyst Deactivation
O-Hydroxyacetophenone Synthesis
Solid Acids
title_short Acylation of phenol on solid acids: Study of the deactivation mechanism
title_full Acylation of phenol on solid acids: Study of the deactivation mechanism
title_fullStr Acylation of phenol on solid acids: Study of the deactivation mechanism
title_full_unstemmed Acylation of phenol on solid acids: Study of the deactivation mechanism
title_sort Acylation of phenol on solid acids: Study of the deactivation mechanism
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 Acylation Reactions
Catalyst Deactivation
O-Hydroxyacetophenone Synthesis
Solid Acids
topic Acylation Reactions
Catalyst Deactivation
O-Hydroxyacetophenone Synthesis
Solid Acids
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 deactivation mechanism of the gas-phase synthesis of o-hydroxyacetophenone (o-HAP) via acylation of phenol with acetic acid was studied on Al-MCM-41 and zeolites HY, HBeta and HZSM-5. The o-HAP yield remained constant with time-on-stream on HZSM-5 but drastically decreased on the other samples because of coke formation. The origin and nature of coke precursor species were studied by employing as reactants, the key reaction intermediates and products involved in the phenol acylation reaction network. It was found that coke precursors are formed from consecutive condensation reactions and not from any ketene formation by phenyl acetate decomposition. Specifically, it is proposed that o-acetoxyacetophenone (o-AXAP), which is formed by reaction between o-HAP and acetic acid, is the key intermediate specie responsible for the formation of carbonaceous deposits and consequently, for the activity decay observed on Al-MCM-41, HY and HBeta samples. The narrow pore size structure of zeolite HZSM-5 would hinder the formation of bulky o-AXAP, thereby, decreasing drastically the formation of coke.
Fil: Padro, Cristina. 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
description The deactivation mechanism of the gas-phase synthesis of o-hydroxyacetophenone (o-HAP) via acylation of phenol with acetic acid was studied on Al-MCM-41 and zeolites HY, HBeta and HZSM-5. The o-HAP yield remained constant with time-on-stream on HZSM-5 but drastically decreased on the other samples because of coke formation. The origin and nature of coke precursor species were studied by employing as reactants, the key reaction intermediates and products involved in the phenol acylation reaction network. It was found that coke precursors are formed from consecutive condensation reactions and not from any ketene formation by phenyl acetate decomposition. Specifically, it is proposed that o-acetoxyacetophenone (o-AXAP), which is formed by reaction between o-HAP and acetic acid, is the key intermediate specie responsible for the formation of carbonaceous deposits and consequently, for the activity decay observed on Al-MCM-41, HY and HBeta samples. The narrow pore size structure of zeolite HZSM-5 would hinder the formation of bulky o-AXAP, thereby, decreasing drastically the formation of coke.
publishDate 2005
dc.date.none.fl_str_mv 2005-10
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/11336/73023
Padro, Cristina; Apesteguia, Carlos Rodolfo; Acylation of phenol on solid acids: Study of the deactivation mechanism; Elsevier Science; Catalysis Today; 107-108; 10-2005; 258-265
0920-5861
CONICET Digital
CONICET
url http://hdl.handle.net/11336/73023
identifier_str_mv Padro, Cristina; Apesteguia, Carlos Rodolfo; Acylation of phenol on solid acids: Study of the deactivation mechanism; Elsevier Science; Catalysis Today; 107-108; 10-2005; 258-265
0920-5861
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.cattod.2005.07.078
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
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_ 1842269495649894400
score 13.13397

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