Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones

Autores
Di Cosimo, Juana Isabel; Acosta, A.; Apesteguia, Carlos Rodolfo
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The gas-phase hydrogen transfer reduction (HTR) of mesityl oxide (MO) with 2-propanol to selectively obtain allylic alcohols was studied on MgO. MO was converted directly to 4-methyl-3-penten-2ol (UOL1) or isomerised to iso-mesityl oxide (i-MO), which consecutively formed 4-methyl-4-penten-2ol (UOL2). Significant amounts of methyl isobutyl carbinol (MIBC) were also formed by the simultaneous reduction of CC and CO groups of MO. The effect of reaction conditions on catalyst activity and selectivity was determined in order to improve total UOL yield that was about 28% under standard reaction conditions (T = 523 K, 2-propanol/MO = 5, W/FMO0 = 15 g h/mol). Total UOL yield increased continuously with contact time up to 42% but when the 2-propanol/MO ratio was varied, UOL yield reached a maximum at a reactant ratio of about 4. UOL2 yield markedly increased with temperature at expenses of MIBC. The increase of temperature also improved the catalyst stability because suppressed formation of coke intermediates. Regarding the effect of the hydrogen donor, higher total UOL yields were obtained by using secondary alcohols, such as 2-propanol and 2-butanol, than primary (1-propanol) or secondary aryl (1-penylethanol) alcohols.
Fil: Di Cosimo, Juana Isabel. 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: Acosta, A.. 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
Α,Β-Unsaturated Ketone
Basic Catalysis
Chemoselectivity
Hydrogen Transfer
Reduction
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:11336/73026
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/73026
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketonesDi Cosimo, Juana IsabelAcosta, A.Apesteguia, Carlos RodolfoΑ,Β-Unsaturated KetoneBasic CatalysisChemoselectivityHydrogen TransferReductionhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The gas-phase hydrogen transfer reduction (HTR) of mesityl oxide (MO) with 2-propanol to selectively obtain allylic alcohols was studied on MgO. MO was converted directly to 4-methyl-3-penten-2ol (UOL1) or isomerised to iso-mesityl oxide (i-MO), which consecutively formed 4-methyl-4-penten-2ol (UOL2). Significant amounts of methyl isobutyl carbinol (MIBC) were also formed by the simultaneous reduction of CC and CO groups of MO. The effect of reaction conditions on catalyst activity and selectivity was determined in order to improve total UOL yield that was about 28% under standard reaction conditions (T = 523 K, 2-propanol/MO = 5, W/FMO0 = 15 g h/mol). Total UOL yield increased continuously with contact time up to 42% but when the 2-propanol/MO ratio was varied, UOL yield reached a maximum at a reactant ratio of about 4. UOL2 yield markedly increased with temperature at expenses of MIBC. The increase of temperature also improved the catalyst stability because suppressed formation of coke intermediates. Regarding the effect of the hydrogen donor, higher total UOL yields were obtained by using secondary alcohols, such as 2-propanol and 2-butanol, than primary (1-propanol) or secondary aryl (1-penylethanol) alcohols.Fil: Di Cosimo, Juana Isabel. 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: Acosta, A.. 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 Science2005-06info: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/11336/73026Di Cosimo, Juana Isabel; Acosta, A.; Apesteguia, Carlos Rodolfo; Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 234; 1-2; 6-2005; 111-1201381-1169CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcata.2005.03.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:29Zoai:ri.conicet.gov.ar:11336/73026instacron: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 09:47:29.635CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
title Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
spellingShingle Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
Di Cosimo, Juana Isabel
Α,Β-Unsaturated Ketone
Basic Catalysis
Chemoselectivity
Hydrogen Transfer
Reduction
title_short Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
title_full Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
title_fullStr Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
title_full_unstemmed Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
title_sort Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones
dc.creator.none.fl_str_mv Di Cosimo, Juana Isabel
Acosta, A.
Apesteguia, Carlos Rodolfo
author Di Cosimo, Juana Isabel
author_facet Di Cosimo, Juana Isabel
Acosta, A.
Apesteguia, Carlos Rodolfo
author_role author
author2 Acosta, A.
Apesteguia, Carlos Rodolfo
author2_role author
author
dc.subject.none.fl_str_mv Α,Β-Unsaturated Ketone
Basic Catalysis
Chemoselectivity
Hydrogen Transfer
Reduction
topic Α,Β-Unsaturated Ketone
Basic Catalysis
Chemoselectivity
Hydrogen Transfer
Reduction
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 hydrogen transfer reduction (HTR) of mesityl oxide (MO) with 2-propanol to selectively obtain allylic alcohols was studied on MgO. MO was converted directly to 4-methyl-3-penten-2ol (UOL1) or isomerised to iso-mesityl oxide (i-MO), which consecutively formed 4-methyl-4-penten-2ol (UOL2). Significant amounts of methyl isobutyl carbinol (MIBC) were also formed by the simultaneous reduction of CC and CO groups of MO. The effect of reaction conditions on catalyst activity and selectivity was determined in order to improve total UOL yield that was about 28% under standard reaction conditions (T = 523 K, 2-propanol/MO = 5, W/FMO0 = 15 g h/mol). Total UOL yield increased continuously with contact time up to 42% but when the 2-propanol/MO ratio was varied, UOL yield reached a maximum at a reactant ratio of about 4. UOL2 yield markedly increased with temperature at expenses of MIBC. The increase of temperature also improved the catalyst stability because suppressed formation of coke intermediates. Regarding the effect of the hydrogen donor, higher total UOL yields were obtained by using secondary alcohols, such as 2-propanol and 2-butanol, than primary (1-propanol) or secondary aryl (1-penylethanol) alcohols.
Fil: Di Cosimo, Juana Isabel. 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: Acosta, A.. 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 gas-phase hydrogen transfer reduction (HTR) of mesityl oxide (MO) with 2-propanol to selectively obtain allylic alcohols was studied on MgO. MO was converted directly to 4-methyl-3-penten-2ol (UOL1) or isomerised to iso-mesityl oxide (i-MO), which consecutively formed 4-methyl-4-penten-2ol (UOL2). Significant amounts of methyl isobutyl carbinol (MIBC) were also formed by the simultaneous reduction of CC and CO groups of MO. The effect of reaction conditions on catalyst activity and selectivity was determined in order to improve total UOL yield that was about 28% under standard reaction conditions (T = 523 K, 2-propanol/MO = 5, W/FMO0 = 15 g h/mol). Total UOL yield increased continuously with contact time up to 42% but when the 2-propanol/MO ratio was varied, UOL yield reached a maximum at a reactant ratio of about 4. UOL2 yield markedly increased with temperature at expenses of MIBC. The increase of temperature also improved the catalyst stability because suppressed formation of coke intermediates. Regarding the effect of the hydrogen donor, higher total UOL yields were obtained by using secondary alcohols, such as 2-propanol and 2-butanol, than primary (1-propanol) or secondary aryl (1-penylethanol) alcohols.
publishDate 2005
dc.date.none.fl_str_mv 2005-06
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/11336/73026
Di Cosimo, Juana Isabel; Acosta, A.; Apesteguia, Carlos Rodolfo; Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 234; 1-2; 6-2005; 111-120
1381-1169
CONICET Digital
CONICET
url http://hdl.handle.net/11336/73026
identifier_str_mv Di Cosimo, Juana Isabel; Acosta, A.; Apesteguia, Carlos Rodolfo; Allylic alcohol synthesis by gas-phase hydrogen transfer reduction of unsaturated ketones; Elsevier Science; Journal of Molecular Catalysis A: Chemical; 234; 1-2; 6-2005; 111-120
1381-1169
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.molcata.2005.03.002
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_ 1842268862076157952
score 13.13397

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