R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods

R-(+)-limonene epoxidation has been focused from different synthesis methods. Thanks to the optically active epoxides obtained from this reaction are widely employed at industrial level, like: agrochemicals, polymers, cosmetics, pharmaceuticals. A key point found in this topic has been the asymmetri...

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Fecha de publicación:
2022
Institución:
Universidad Pedagógica y Tecnológica de Colombia
Repositorio:
RiUPTC: Repositorio Institucional UPTC
Idioma:
spa
OAI Identifier:
oai:repositorio.uptc.edu.co:001/15350
Acceso en línea:
https://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/14154
https://repositorio.uptc.edu.co/handle/001/15350
Palabra clave:
R-( )-limonene, epoxidation, catalytic oxidation, 1,2-limonene oxide, diastereomers
R-( )-limoneno, Epoxidación, Oxidación catalítica, Óxido de 1,2-limoneno, Diastereoisómeros.
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spelling 2022-07-122024-07-08T14:24:06Z2024-07-08T14:24:06Zhttps://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/1415410.19053/01217488.v13.n2.2022.14154https://repositorio.uptc.edu.co/handle/001/15350R-(+)-limonene epoxidation has been focused from different synthesis methods. Thanks to the optically active epoxides obtained from this reaction are widely employed at industrial level, like: agrochemicals, polymers, cosmetics, pharmaceuticals. A key point found in this topic has been the asymmetric induction to improve the yield to the diastereomers of 1,2-limonene oxide. Many catalysts have been developed for the diastereoselective epoxidation, but some oxidation methodology have not been so useful. The enzymes and the Jacobsen´s catalyst presented the highest selectivity towards the endocyclic epoxides diastereomers, while other catalysts like metals supported on mesoporous materials were directed to one or more oxidation products, reducing their potential industrial scaling. Also, it was evidenced that controlling the reaction parameters it allows the segregation homogeneous catalyst to a phase different from the reaction products, thus increasing its useful reutilization in several reaction cycles. This minireview confronts the different systems used for the diastereoselective epoxidation of R-(+)-limonene. Challenges, issues and trends of said chemical transformation are also discussed.  La epoxidación de R-(+)-limoneno ha sido enfocada desde diferentes métodos de síntesis. Gracias a los epóxidos ópticamente activos obtenidos de esta reacción, son ampliamente empleados a nivel industrial, como: agroquímicos, polímeros, cosméticos, farmacéuticos. Un punto clave encontrado en este tema ha sido la inducción asimétrica para mejorar el rendimiento a los diastereoisómeros del óxido de 1,2-limoneno. Se han desarrollado muchos catalizadores para la epoxidación diastereoselectiva, pero algunas metodologías de oxidación no han sido tan útiles. Las enzimas y el catalizador de Jacobsen presentaron la mayor selectividad hacia los diastereoisómeros epóxidos endocíclicos, mientras que otros catalizadores como los metales soportados sobre materiales mesoporosos se dirigieron a uno o más productos de oxidación, reduciendo su potencial escalamiento industrial. Además, se evidenció que el control de los parámetros de reacción permite la segregación del catalizador homogéneo a una fase distinta a la de los productos de reacción, aumentando así su reutilización útil en varios ciclos de reacción. Esta minirevisión confronta los diferentes sistemas utilizados para la epoxidación diastereoselectiva de R-(+)-limoneno. También se discuten los desafíos, problemas y tendencias de dicha transformación química.application/pdfspaspaUniversidad Pedagógica y Tecnológica de Colombiahttps://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/14154/12655Ciencia En Desarrollo; Vol. 13 No. 2 (2022): Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol 13, Núm.2 (2022): Julio-Diciembre; 167-184Ciencia en Desarrollo; Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol 13, Núm.2 (2022): Julio-Diciembre; 167-1842462-76580121-7488R-( )-limonene, epoxidation, catalytic oxidation, 1,2-limonene oxide, diastereomersR-( )-limoneno, Epoxidación, Oxidación catalítica, Óxido de 1,2-limoneno, Diastereoisómeros.R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methodsEpoxidación diasteroselectiva de R-(+)-limoneno: una minirevisión acerca de los métodos de sintesisinfo:eu-repo/semantics/articlehttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/access_right/c_abf2Rubio Rodríguez, Juan AlejandroJairo Antonio001/15350oai:repositorio.uptc.edu.co:001/153502025-07-18 10:56:15.343metadata.onlyhttps://repositorio.uptc.edu.coRepositorio Institucional UPTCrepositorio.uptc@uptc.edu.co
dc.title.en-US.fl_str_mv R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
dc.title.es-ES.fl_str_mv Epoxidación diasteroselectiva de R-(+)-limoneno: una minirevisión acerca de los métodos de sintesis
title R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
spellingShingle R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
R-( )-limonene, epoxidation, catalytic oxidation, 1,2-limonene oxide, diastereomers
R-( )-limoneno, Epoxidación, Oxidación catalítica, Óxido de 1,2-limoneno, Diastereoisómeros.
title_short R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
title_full R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
title_fullStr R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
title_full_unstemmed R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
title_sort R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods
dc.subject.en-US.fl_str_mv R-( )-limonene, epoxidation, catalytic oxidation, 1,2-limonene oxide, diastereomers
topic R-( )-limonene, epoxidation, catalytic oxidation, 1,2-limonene oxide, diastereomers
R-( )-limoneno, Epoxidación, Oxidación catalítica, Óxido de 1,2-limoneno, Diastereoisómeros.
dc.subject.es-ES.fl_str_mv R-( )-limoneno, Epoxidación, Oxidación catalítica, Óxido de 1,2-limoneno, Diastereoisómeros.
description R-(+)-limonene epoxidation has been focused from different synthesis methods. Thanks to the optically active epoxides obtained from this reaction are widely employed at industrial level, like: agrochemicals, polymers, cosmetics, pharmaceuticals. A key point found in this topic has been the asymmetric induction to improve the yield to the diastereomers of 1,2-limonene oxide. Many catalysts have been developed for the diastereoselective epoxidation, but some oxidation methodology have not been so useful. The enzymes and the Jacobsen´s catalyst presented the highest selectivity towards the endocyclic epoxides diastereomers, while other catalysts like metals supported on mesoporous materials were directed to one or more oxidation products, reducing their potential industrial scaling. Also, it was evidenced that controlling the reaction parameters it allows the segregation homogeneous catalyst to a phase different from the reaction products, thus increasing its useful reutilization in several reaction cycles. This minireview confronts the different systems used for the diastereoselective epoxidation of R-(+)-limonene. Challenges, issues and trends of said chemical transformation are also discussed.  
publishDate 2022
dc.date.accessioned.none.fl_str_mv 2024-07-08T14:24:06Z
dc.date.available.none.fl_str_mv 2024-07-08T14:24:06Z
dc.date.none.fl_str_mv 2022-07-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.identifier.none.fl_str_mv https://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/14154
10.19053/01217488.v13.n2.2022.14154
dc.identifier.uri.none.fl_str_mv https://repositorio.uptc.edu.co/handle/001/15350
url https://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/14154
https://repositorio.uptc.edu.co/handle/001/15350
identifier_str_mv 10.19053/01217488.v13.n2.2022.14154
dc.language.none.fl_str_mv spa
dc.language.iso.none.fl_str_mv spa
language spa
dc.relation.none.fl_str_mv https://revistas.uptc.edu.co/index.php/ciencia_en_desarrollo/article/view/14154/12655
dc.rights.coar.fl_str_mv http://purl.org/coar/access_right/c_abf2
rights_invalid_str_mv http://purl.org/coar/access_right/c_abf2
dc.format.none.fl_str_mv application/pdf
dc.publisher.es-ES.fl_str_mv Universidad Pedagógica y Tecnológica de Colombia
dc.source.en-US.fl_str_mv Ciencia En Desarrollo; Vol. 13 No. 2 (2022): Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol 13, Núm.2 (2022): Julio-Diciembre; 167-184
dc.source.es-ES.fl_str_mv Ciencia en Desarrollo; Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol. 13 Núm. 2 (2022): Vol 13, Núm.2 (2022): Julio-Diciembre; 167-184
dc.source.none.fl_str_mv 2462-7658
0121-7488
institution Universidad Pedagógica y Tecnológica de Colombia
repository.name.fl_str_mv Repositorio Institucional UPTC
repository.mail.fl_str_mv repositorio.uptc@uptc.edu.co
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