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...
- 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/
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|
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 |
dc.type.hasversion.spa.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.coar.spa.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
dc.type.redcol.spa.fl_str_mv |
https://purl.org/redcol/resource_type/ART |
dc.type.local.spa.fl_str_mv |
Artículo de investigación |
format |
http://purl.org/coar/resource_type/c_2df8fbb1 |
status_str |
publishedVersion |
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/ http://purl.org/coar/access_right/c_abf2 https://creativecommons.org/licenses/by-nc-sa/4.0/ |
dc.format.extent.spa.fl_str_mv |
11 |
dc.format.mimetype.spa.fl_str_mv |
application/pdf |
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 https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/2/license_rdf https://bibliotecadigital.udea.edu.co/bitstream/10495/32780/3/license.txt |
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1812173232379265024 |
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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 |