Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate

Autores
Trasarti, Andres Fernando; González, Eduardo J.; Nieres, Pablo Daniel; Apesteguia, Carlos Rodolfo
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar re-actant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selec-tivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.
Fil: Trasarti, Andres Fernando. 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: González, Eduardo J.. 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: Nieres, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; 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
OLEOCHEMISTRY
METATHESIS
HOVEYDA GRUBBS CATALYST
METHYL OLEATE
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:11336/114009
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/114009
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl OleateTrasarti, Andres FernandoGonzález, Eduardo J.Nieres, Pablo DanielApesteguia, Carlos RodolfoOLEOCHEMISTRYMETATHESISHOVEYDA GRUBBS CATALYSTMETHYL OLEATEhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar re-actant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selec-tivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.Fil: Trasarti, Andres Fernando. 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: González, Eduardo J.. 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: Nieres, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; 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"; ArgentinaPlanta Piloto de Ingeniería Química2020-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/114009Trasarti, Andres Fernando; González, Eduardo J.; Nieres, Pablo Daniel; Apesteguia, Carlos Rodolfo; Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate; Planta Piloto de Ingeniería Química; Latin American Applied Research; 50; 2; 2-2020; 139-1440327-07931851-8796CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://laar.plapiqui.edu.ar/OJS/index.php/laar/article/view/477info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:32:26Zoai:ri.conicet.gov.ar:11336/114009instacron: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:34982025-11-12 09:32:27.147CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
title Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
spellingShingle Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
Trasarti, Andres Fernando
OLEOCHEMISTRY
METATHESIS
HOVEYDA GRUBBS CATALYST
METHYL OLEATE
title_short Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
title_full Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
title_fullStr Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
title_full_unstemmed Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
title_sort Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate
dc.creator.none.fl_str_mv Trasarti, Andres Fernando
González, Eduardo J.
Nieres, Pablo Daniel
Apesteguia, Carlos Rodolfo
author Trasarti, Andres Fernando
author_facet Trasarti, Andres Fernando
González, Eduardo J.
Nieres, Pablo Daniel
Apesteguia, Carlos Rodolfo
author_role author
author2 González, Eduardo J.
Nieres, Pablo Daniel
Apesteguia, Carlos Rodolfo
author2_role author
author
author
dc.subject.none.fl_str_mv OLEOCHEMISTRY
METATHESIS
HOVEYDA GRUBBS CATALYST
METHYL OLEATE
topic OLEOCHEMISTRY
METATHESIS
HOVEYDA GRUBBS CATALYST
METHYL OLEATE
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar re-actant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selec-tivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.
Fil: Trasarti, Andres Fernando. 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: González, Eduardo J.. 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: Nieres, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; 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 This work studies the production of high-value compounds by the cross-metathesis of methyl oleate (MO) with ethylene, cinnamonitrile and cinnamaldehyde using the 2nd generation Hoveyda-Grubbs complex (HG) as catalyst, either dissolved in toluene or supported on silica. Reactions were carried out in batch reactors between 313 and 343 K. The yield to cross-metathesis products (YC-M) for the MO cross-metathesis with cinnamonitrile and cinnamaldehyde increased with the initial molar re-actant ratio (RCN/MO, RCA/MO), reaching YC-M values of 82% and 95%, respectively, at R = 7. No catalyst deactivation took place during the 400-min catalytic runs. The liquid-phase cross-metathesis of MO with ethylene (ethenolysis) was performed over HG(10%)/SiO2 catalysts, producing 1-decene and methyl 9-decenoate, a valuable intermediate for the synthesis of pheromones. At RC2/MO = 2.5, the selec-tivity to ethenolysis products was 77% at 82% MO conversion. The MO self-metathesis was the only side reaction observed in all the catalytic tests.
publishDate 2020
dc.date.none.fl_str_mv 2020-02
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/11336/114009
Trasarti, Andres Fernando; González, Eduardo J.; Nieres, Pablo Daniel; Apesteguia, Carlos Rodolfo; Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate; Planta Piloto de Ingeniería Química; Latin American Applied Research; 50; 2; 2-2020; 139-144
0327-0793
1851-8796
CONICET Digital
CONICET
url http://hdl.handle.net/11336/114009
identifier_str_mv Trasarti, Andres Fernando; González, Eduardo J.; Nieres, Pablo Daniel; Apesteguia, Carlos Rodolfo; Plant Oil Valorization by Cross-Metathesis Reactions: Synthesis of Fine Chemicals From Methyl Oleate; Planta Piloto de Ingeniería Química; Latin American Applied Research; 50; 2; 2-2020; 139-144
0327-0793
1851-8796
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://laar.plapiqui.edu.ar/OJS/index.php/laar/article/view/477
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 Planta Piloto de Ingeniería Química
publisher.none.fl_str_mv Planta Piloto de Ingeniería Química
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
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score 12.976206

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