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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/114009
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T09:32:20Zoai: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:34982025-09-29 09:32:20.589CONICET 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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1844612986349551616 |
score |
13.070432 |