Separation of carvone by batch distillation from the mixture obtained from limonene oxidation

ABSTRACT : Limonene is the main constituent of citrus oils whose oxidation produces a set of fine chemical compounds such as carvone, carveol, and limonene 1,2-epoxide. This contribution reports the results of the experimental evaluation and computational simulation of carvone separation by fraction...

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Autores:
Becerra Chalá, Jaime Andrés
Villa Holguín, Aída Luz
Tipo de recurso:
Article of investigation
Fecha de publicación:
2022
Institución:
Universidad de Antioquia
Repositorio:
Repositorio UdeA
Idioma:
eng
OAI Identifier:
oai:bibliotecadigital.udea.edu.co:10495/32780
Acceso en línea:
https://hdl.handle.net/10495/32780
https://revistas.udea.edu.co/index.php/ingenieria/article/view/342037
Palabra clave:
Esencias
Essences and essential oils
Limoneno
Limonene
Separación
Separating
Simulación
Simulation
http://aims.fao.org/aos/agrovoc/c_28446
http://aims.fao.org/aos/agrovoc/c_6973
http://aims.fao.org/aos/agrovoc/c_5209
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc-sa/2.5/co/
id UDEA2_75ddb656d4328e1c610eff70a32fe1c6
oai_identifier_str oai:bibliotecadigital.udea.edu.co:10495/32780
network_acronym_str UDEA2
network_name_str Repositorio UdeA
repository_id_str
dc.title.spa.fl_str_mv Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
dc.title.alternative.spa.fl_str_mv Separación de carvona mediante destilación discontinua de la mezcla obtenida de oxidación de limoneno
title Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
spellingShingle Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
Esencias
Essences and essential oils
Limoneno
Limonene
Separación
Separating
Simulación
Simulation
http://aims.fao.org/aos/agrovoc/c_28446
http://aims.fao.org/aos/agrovoc/c_6973
http://aims.fao.org/aos/agrovoc/c_5209
title_short Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
title_full Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
title_fullStr Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
title_full_unstemmed Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
title_sort Separation of carvone by batch distillation from the mixture obtained from limonene oxidation
dc.creator.fl_str_mv Becerra Chalá, Jaime Andrés
Villa Holguín, Aída Luz
dc.contributor.author.none.fl_str_mv Becerra Chalá, Jaime Andrés
Villa Holguín, Aída Luz
dc.subject.lemb.none.fl_str_mv Esencias
Essences and essential oils
topic Esencias
Essences and essential oils
Limoneno
Limonene
Separación
Separating
Simulación
Simulation
http://aims.fao.org/aos/agrovoc/c_28446
http://aims.fao.org/aos/agrovoc/c_6973
http://aims.fao.org/aos/agrovoc/c_5209
dc.subject.agrovoc.none.fl_str_mv Limoneno
Limonene
Separación
Separating
Simulación
Simulation
dc.subject.agrovocuri.none.fl_str_mv http://aims.fao.org/aos/agrovoc/c_28446
http://aims.fao.org/aos/agrovoc/c_6973
http://aims.fao.org/aos/agrovoc/c_5209
description ABSTRACT : Limonene is the main constituent of citrus oils whose oxidation produces a set of fine chemical compounds such as carvone, carveol, and limonene 1,2-epoxide. This contribution reports the results of the experimental evaluation and computational simulation of carvone separation by fractional distillation from the reaction mixture. Carvone was obtained from limonene oxidation over a perchlorinated iron phthalocyanine supported on modified silica catalyst (FePcCl16 − NH2 − SiO2) and t-butyl hydroperoxide (TBHP) as oxidant. Both experimental and simulation results support that fractional distillation (in batch and continuous) is a suitable technique for concentrating carvone. However, in the presence of water, the formation of immiscible L-L phases makes the experimental separation of carvone more difficult. Simulation results of the batch distillation incorporating the NRTL-RK thermodynamic model indicate that if water, acetone, and t-butanol are previously removed from the reaction mixture, carvone composition can be enriched in the reboiler from 4% up to 50%, or around 86.5% if the removal is in a third distillate cut under vacuum conditions.
publishDate 2022
dc.date.accessioned.none.fl_str_mv 2022-12-13T17:47:08Z
dc.date.available.none.fl_str_mv 2022-12-13T17:47:08Z
dc.date.issued.none.fl_str_mv 2022
dc.type.spa.fl_str_mv info:eu-repo/semantics/article
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
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dc.type.local.spa.fl_str_mv Artículo de investigación
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dc.identifier.citation.spa.fl_str_mv J. A. Becerra Chalá and A. L. Villa Holguín, “Separation of carvone by batch distillation from the mixture obtained from limonene oxidation”, Rev.Fac.Ing.Univ.Antioquia, no. 104, pp. 118–128, Aug. 2022.
dc.identifier.issn.none.fl_str_mv 0120-6230
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/10495/32780
dc.identifier.doi.none.fl_str_mv 0.17533/udea.redin.20210848
dc.identifier.eissn.none.fl_str_mv 2422-2844
dc.identifier.url.spa.fl_str_mv https://revistas.udea.edu.co/index.php/ingenieria/article/view/342037
identifier_str_mv J. A. Becerra Chalá and A. L. Villa Holguín, “Separation of carvone by batch distillation from the mixture obtained from limonene oxidation”, Rev.Fac.Ing.Univ.Antioquia, no. 104, pp. 118–128, Aug. 2022.
0120-6230
0.17533/udea.redin.20210848
2422-2844
url https://hdl.handle.net/10495/32780
https://revistas.udea.edu.co/index.php/ingenieria/article/view/342037
dc.language.iso.spa.fl_str_mv eng
language eng
dc.relation.ispartofjournalabbrev.spa.fl_str_mv Rev. Fac. Ing. Univ. Antioquia
dc.rights.spa.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/co/
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dc.rights.creativecommons.spa.fl_str_mv https://creativecommons.org/licenses/by-nc-sa/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/2.5/co/
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dc.format.extent.spa.fl_str_mv 11
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dc.publisher.spa.fl_str_mv Universidad de Antioquia, Facultad de Ingeniería
dc.publisher.group.spa.fl_str_mv Catálisis Ambiental
dc.publisher.place.spa.fl_str_mv Medellín, Colombia
institution Universidad de Antioquia
bitstream.url.fl_str_mv https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/1/BecerraJaime_2022_Separationcarvonebatch.pdf
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spelling Becerra Chalá, Jaime AndrésVilla Holguín, Aída Luz2022-12-13T17:47:08Z2022-12-13T17:47:08Z2022J. A. Becerra Chalá and A. L. Villa Holguín, “Separation of carvone by batch distillation from the mixture obtained from limonene oxidation”, Rev.Fac.Ing.Univ.Antioquia, no. 104, pp. 118–128, Aug. 2022.0120-6230https://hdl.handle.net/10495/327800.17533/udea.redin.202108482422-2844https://revistas.udea.edu.co/index.php/ingenieria/article/view/342037ABSTRACT : Limonene is the main constituent of citrus oils whose oxidation produces a set of fine chemical compounds such as carvone, carveol, and limonene 1,2-epoxide. This contribution reports the results of the experimental evaluation and computational simulation of carvone separation by fractional distillation from the reaction mixture. Carvone was obtained from limonene oxidation over a perchlorinated iron phthalocyanine supported on modified silica catalyst (FePcCl16 − NH2 − SiO2) and t-butyl hydroperoxide (TBHP) as oxidant. Both experimental and simulation results support that fractional distillation (in batch and continuous) is a suitable technique for concentrating carvone. However, in the presence of water, the formation of immiscible L-L phases makes the experimental separation of carvone more difficult. Simulation results of the batch distillation incorporating the NRTL-RK thermodynamic model indicate that if water, acetone, and t-butanol are previously removed from the reaction mixture, carvone composition can be enriched in the reboiler from 4% up to 50%, or around 86.5% if the removal is in a third distillate cut under vacuum conditions.RESUMEN : El limoneno es el principal componente de los aceites cítricos de cuya oxidación se obtienen compuestos de química fina tales como carvona, carveol y epóxido de 1,2-limoneno. En esta contribución se reportan los resultados de la evaluación experimental y mediante simulación computacional del proceso de separación de carvona mediante destilación fraccionada por lotes de la mezcla de reacción. La carvona se obtuvo a partir de la oxidación de limoneno con una ftalocianona clorada de hierro soportada en sílice modificada como catalizador heterogéneo (FePcCl16 − NH2 −SiO2) y el agente oxidante hidroperóxido de terc-butilo. A partir de los resultados experimentales y las simulaciones se infiere que la destilación fraccionada (por lotes y en continuo) es una técnica adecuada para la concentración de carvona. Sin embargo, en presencia de agua, la formación de fases L-L inmiscibles hace que la separación experimental de carvona sea más difícil. Los resultados de simulación empleando el modelo termodinámico NRTL-RK indican que si se retira previamente de la mezcla de reacción la mayor cantidad posible de agua, acetona y terc-butanol, la mezcla líquida con una fracción molar de 4% de carvona, se puede enriquecer en el rehervidor hasta un 50%, o cerca de 86,5% si se retira en una tercera fracción de destilado operando en vacío.COL000194111application/pdfengUniversidad de Antioquia, Facultad de IngenieríaCatálisis AmbientalMedellín, Colombiainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_2df8fbb1https://purl.org/redcol/resource_type/ARTArtículo de investigaciónhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/2.5/co/http://purl.org/coar/access_right/c_abf2https://creativecommons.org/licenses/by-nc-sa/4.0/Separation of carvone by batch distillation from the mixture obtained from limonene oxidationSeparación de carvona mediante destilación discontinua de la mezcla obtenida de oxidación de limonenoEsenciasEssences and essential oilsLimonenoLimoneneSeparaciónSeparatingSimulaciónSimulationhttp://aims.fao.org/aos/agrovoc/c_28446http://aims.fao.org/aos/agrovoc/c_6973http://aims.fao.org/aos/agrovoc/c_5209Rev. Fac. Ing. Univ. AntioquiaRevista Facultad de Ingeniería Universidad de Antioquia118128104Universidad de Antioquia. Vicerrectoría de investigación. Comité para el Desarrollo de la Investigación - CODIColombia. Ministerio de Ciencia Tecnología e Innovación - Minicienciasgrid.412881.6grid.433658.fORIGINALBecerraJaime_2022_Separationcarvonebatch.pdfBecerraJaime_2022_Separationcarvonebatch.pdfArtículo de investigaciónapplication/pdf628371https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/1/BecerraJaime_2022_Separationcarvonebatch.pdfb49a394920b91e77bacaee4b00a74958MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-81051https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/2/license_rdfe2060682c9c70d4d30c83c51448f4eedMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/3/license.txt8a4605be74aa9ea9d79846c1fba20a33MD5310495/32780oai:bibliotecadigital.udea.edu.co:10495/327802022-12-13 12:47:08.896Repositorio Institucional Universidad de Antioquiaandres.perez@udea.edu.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