Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent

Autores
Segobia, Dario Jobino; Trasarti, Andres Fernando; Apesteguia, Carlos Rodolfo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The effect of solvent on Ni(10.5%)/SiO2 activity and selectivity for the liquid-phase conversion of butyronitrile to butylamines was studied using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84%) and dibutylamine. Replacing ethanol by non-polar solvents (benzene, toluene, cyclohexane) caused significant changes in catalyst activity and selectivity. In particular, the selectivity to n-butylamine decreased at the expense of dibutylamine and tributylamine formation. The solvent effect on the catalyst performance was interpreted by considering: i) the solvent-catalyst interaction strength that was investigated by calorimetry, and temperature-programmed desorption of solvents characterized by mass spectrometry; ii) the solvent polarity and its ability for H-bond formation with n-butylamine.
O efeito de solvente sobre a atividade e seletividade de Ni(10.5%)/SiO2 no processo de hidrogenação em fase líquida da butironitrila a butilaminas foi estudado a 373 K e 13 bar usando-se etanol, benzeno, tolueno e cicloexano como solventes. Em etanol, um solvente prótico, o catalisador de Ni produziu n-butilamina (84%) e dibutilamina (16%). Quando solventes apolares, tais como cicloexano, tolueno ou benzeno, foram usados, a força de interação solvente-catalisador determinou a seletividade para formação de n-butilamina: quanto mais forte a interação solvente-catalisador, maior era a produção de n-butilamina. O rendimento de n-butilamina em solventes apolares variou entre 39% (cicloexano) e 63% (benzeno).
Fil: Segobia, Dario Jobino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; Argentina
Fil: Trasarti, Andres Fernando. 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
BUTYRONITRILE
BUTYLAMINES
SELECTIVE HYDROGENATION
NI CATALYSTS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/31082
Acceder
id CONICETDig_3844c2f5cde736dcaaa6ca56e78b1551
oai_identifier_str oai:ri.conicet.gov.ar:11336/31082
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of SolventSegobia, Dario JobinoTrasarti, Andres FernandoApesteguia, Carlos RodolfoBUTYRONITRILEBUTYLAMINESSELECTIVE HYDROGENATIONNI CATALYSTShttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The effect of solvent on Ni(10.5%)/SiO2 activity and selectivity for the liquid-phase conversion of butyronitrile to butylamines was studied using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84%) and dibutylamine. Replacing ethanol by non-polar solvents (benzene, toluene, cyclohexane) caused significant changes in catalyst activity and selectivity. In particular, the selectivity to n-butylamine decreased at the expense of dibutylamine and tributylamine formation. The solvent effect on the catalyst performance was interpreted by considering: i) the solvent-catalyst interaction strength that was investigated by calorimetry, and temperature-programmed desorption of solvents characterized by mass spectrometry; ii) the solvent polarity and its ability for H-bond formation with n-butylamine.O efeito de solvente sobre a atividade e seletividade de Ni(10.5%)/SiO2 no processo de hidrogenação em fase líquida da butironitrila a butilaminas foi estudado a 373 K e 13 bar usando-se etanol, benzeno, tolueno e cicloexano como solventes. Em etanol, um solvente prótico, o catalisador de Ni produziu n-butilamina (84%) e dibutilamina (16%). Quando solventes apolares, tais como cicloexano, tolueno ou benzeno, foram usados, a força de interação solvente-catalisador determinou a seletividade para formação de n-butilamina: quanto mais forte a interação solvente-catalisador, maior era a produção de n-butilamina. O rendimento de n-butilamina em solventes apolares variou entre 39% (cicloexano) e 63% (benzeno).Fil: Segobia, Dario Jobino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; ArgentinaFil: Trasarti, Andres Fernando. 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 ; ArgentinaSociedade Brasileira de Química2014-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31082Apesteguia, Carlos Rodolfo; Trasarti, Andres Fernando; Segobia, Dario Jobino; Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 25; 12; 6-2014; 2272-22790103-50531678-4790CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.5935/0103-5053.20140215info:eu-repo/semantics/altIdentifier/url/http://ref.scielo.org/vy3gtrinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:03:27Zoai:ri.conicet.gov.ar:11336/31082instacron: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 13:03:27.406CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
title Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
spellingShingle Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
Segobia, Dario Jobino
BUTYRONITRILE
BUTYLAMINES
SELECTIVE HYDROGENATION
NI CATALYSTS
title_short Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
title_full Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
title_fullStr Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
title_full_unstemmed Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
title_sort Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent
dc.creator.none.fl_str_mv Segobia, Dario Jobino
Trasarti, Andres Fernando
Apesteguia, Carlos Rodolfo
author Segobia, Dario Jobino
author_facet Segobia, Dario Jobino
Trasarti, Andres Fernando
Apesteguia, Carlos Rodolfo
author_role author
author2 Trasarti, Andres Fernando
Apesteguia, Carlos Rodolfo
author2_role author
author
dc.subject.none.fl_str_mv BUTYRONITRILE
BUTYLAMINES
SELECTIVE HYDROGENATION
NI CATALYSTS
topic BUTYRONITRILE
BUTYLAMINES
SELECTIVE HYDROGENATION
NI CATALYSTS
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 effect of solvent on Ni(10.5%)/SiO2 activity and selectivity for the liquid-phase conversion of butyronitrile to butylamines was studied using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84%) and dibutylamine. Replacing ethanol by non-polar solvents (benzene, toluene, cyclohexane) caused significant changes in catalyst activity and selectivity. In particular, the selectivity to n-butylamine decreased at the expense of dibutylamine and tributylamine formation. The solvent effect on the catalyst performance was interpreted by considering: i) the solvent-catalyst interaction strength that was investigated by calorimetry, and temperature-programmed desorption of solvents characterized by mass spectrometry; ii) the solvent polarity and its ability for H-bond formation with n-butylamine.
O efeito de solvente sobre a atividade e seletividade de Ni(10.5%)/SiO2 no processo de hidrogenação em fase líquida da butironitrila a butilaminas foi estudado a 373 K e 13 bar usando-se etanol, benzeno, tolueno e cicloexano como solventes. Em etanol, um solvente prótico, o catalisador de Ni produziu n-butilamina (84%) e dibutilamina (16%). Quando solventes apolares, tais como cicloexano, tolueno ou benzeno, foram usados, a força de interação solvente-catalisador determinou a seletividade para formação de n-butilamina: quanto mais forte a interação solvente-catalisador, maior era a produção de n-butilamina. O rendimento de n-butilamina em solventes apolares variou entre 39% (cicloexano) e 63% (benzeno).
Fil: Segobia, Dario Jobino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Investigaciones en Catálisis y Petroquímica ; Argentina
Fil: Trasarti, Andres Fernando. 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 effect of solvent on Ni(10.5%)/SiO2 activity and selectivity for the liquid-phase conversion of butyronitrile to butylamines was studied using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84%) and dibutylamine. Replacing ethanol by non-polar solvents (benzene, toluene, cyclohexane) caused significant changes in catalyst activity and selectivity. In particular, the selectivity to n-butylamine decreased at the expense of dibutylamine and tributylamine formation. The solvent effect on the catalyst performance was interpreted by considering: i) the solvent-catalyst interaction strength that was investigated by calorimetry, and temperature-programmed desorption of solvents characterized by mass spectrometry; ii) the solvent polarity and its ability for H-bond formation with n-butylamine.
publishDate 2014
dc.date.none.fl_str_mv 2014-06
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/11336/31082
Apesteguia, Carlos Rodolfo; Trasarti, Andres Fernando; Segobia, Dario Jobino; Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 25; 12; 6-2014; 2272-2279
0103-5053
1678-4790
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31082
identifier_str_mv Apesteguia, Carlos Rodolfo; Trasarti, Andres Fernando; Segobia, Dario Jobino; Synthesis of n-Butylamine from Butyronitrile on Ni/SiO2: Effect of Solvent; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 25; 12; 6-2014; 2272-2279
0103-5053
1678-4790
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.5935/0103-5053.20140215
info:eu-repo/semantics/altIdentifier/url/http://ref.scielo.org/vy3gtr
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de 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
_version_ 1842980084048199680
score 12.993085

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