Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system

Autores
Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprinin n-heptane as the reaction medium.The effects of the reaction parameters were studied using an experimental factorial design of threefactors and three levels with two central points. The selected experimental variables were amount ofglycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the responsevariables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, andacyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mgand T = 40-60 ◦C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprinselectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selectionof the reaction conditions is necessary not only to maximize the conversion of capric acid, but also tominimize the acyl migration reaction and the generation of undesired products. Evidence of kineticallycontrolled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.
Fil: Sanchez, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Tonetto, Gabriela Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Ferreira, María Luján. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Materia
1,3 Dag
Glycerol
Enzymatic Synthesis
Acyl Migration
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:11336/26940
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/26940
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent systemSanchez, Daniel AlbertoTonetto, Gabriela MartaFerreira, María Luján1,3 DagGlycerolEnzymatic SynthesisAcyl Migrationhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprinin n-heptane as the reaction medium.The effects of the reaction parameters were studied using an experimental factorial design of threefactors and three levels with two central points. The selected experimental variables were amount ofglycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the responsevariables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, andacyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mgand T = 40-60 ◦C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprinselectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selectionof the reaction conditions is necessary not only to maximize the conversion of capric acid, but also tominimize the acyl migration reaction and the generation of undesired products. Evidence of kineticallycontrolled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.Fil: Sanchez, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Tonetto, Gabriela Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Ferreira, María Luján. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaElsevier Science2013-11-21info: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/11336/26940Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 100; 21-11-2013; 7-181381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1381117713003391info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2013.11.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:08:35Zoai:ri.conicet.gov.ar:11336/26940instacron: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:34982025-10-22 11:08:35.591CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
title Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
spellingShingle Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
Sanchez, Daniel Alberto
1,3 Dag
Glycerol
Enzymatic Synthesis
Acyl Migration
title_short Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
title_full Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
title_fullStr Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
title_full_unstemmed Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
title_sort Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system
dc.creator.none.fl_str_mv Sanchez, Daniel Alberto
Tonetto, Gabriela Marta
Ferreira, María Luján
author Sanchez, Daniel Alberto
author_facet Sanchez, Daniel Alberto
Tonetto, Gabriela Marta
Ferreira, María Luján
author_role author
author2 Tonetto, Gabriela Marta
Ferreira, María Luján
author2_role author
author
dc.subject.none.fl_str_mv 1,3 Dag
Glycerol
Enzymatic Synthesis
Acyl Migration
topic 1,3 Dag
Glycerol
Enzymatic Synthesis
Acyl Migration
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprinin n-heptane as the reaction medium.The effects of the reaction parameters were studied using an experimental factorial design of threefactors and three levels with two central points. The selected experimental variables were amount ofglycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the responsevariables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, andacyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mgand T = 40-60 ◦C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprinselectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selectionof the reaction conditions is necessary not only to maximize the conversion of capric acid, but also tominimize the acyl migration reaction and the generation of undesired products. Evidence of kineticallycontrolled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.
Fil: Sanchez, Daniel Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Tonetto, Gabriela Marta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Ferreira, María Luján. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
description In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprinin n-heptane as the reaction medium.The effects of the reaction parameters were studied using an experimental factorial design of threefactors and three levels with two central points. The selected experimental variables were amount ofglycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the responsevariables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, andacyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mgand T = 40-60 ◦C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprinselectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selectionof the reaction conditions is necessary not only to maximize the conversion of capric acid, but also tominimize the acyl migration reaction and the generation of undesired products. Evidence of kineticallycontrolled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.
publishDate 2013
dc.date.none.fl_str_mv 2013-11-21
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/11336/26940
Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 100; 21-11-2013; 7-18
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/26940
identifier_str_mv Sanchez, Daniel Alberto; Tonetto, Gabriela Marta; Ferreira, María Luján; Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 100; 21-11-2013; 7-18
1381-1177
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://www.sciencedirect.com/science/article/pii/S1381117713003391
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2013.11.010
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
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
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score 12.982451

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