Epoxidação quimio-enzimática do citronelol e B-cariofileno

Detalhes bibliográficos
Autor(a) principal: Silva, Jaqueline Maria Ramos da
Data de Publicação: 2012
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFSC
Texto Completo: http://repositorio.ufsc.br/xmlui/handle/123456789/96427
Resumo: Dissertação (mestrado) - Universidade Federal de Santa Catarina, Centro de Ciências Físicas e Matemáticas. Programa de Pós-Graduação em Química.
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spelling Universidade Federal de Santa CatarinaSilva, Jaqueline Maria Ramos daNascimento, Maria da Graça2012-10-26T11:57:09Z2012-10-26T11:57:09Z20122012301775http://repositorio.ufsc.br/xmlui/handle/123456789/96427Dissertação (mestrado) - Universidade Federal de Santa Catarina, Centro de Ciências Físicas e Matemáticas. Programa de Pós-Graduação em Química.In this work, the chemoenzymatic epoxidation of terpenes citronellol and â-caryophyllene is reported. Some experimental conditions, such as the use of different lipases and mycelia, oxidizing agents (H2O2 or UHP), reaction time, acyl donor type, temperature (15-45°C) and the influence of the organic medium, including the use of ionic liquids (ILs) were evaluated. In the epoxidation of citronellol two products were obtained; namely citronellol oxide 43 and/or citronellol epoxide ester 47. Depending on the reaction conditions, the product 43 was obtained in conv. >99%. CAL-B was the most efficient catalyst. The highest conversions were achieved for the epoxide 43 at 20 and 25 °C, with conv. of 80% and 77%. The organic medium was one of the most important parameters in this reaction. Using chloroform or dichloromethane, product 43 was obtained in conversions >99% after 24 h. Using mixtures of organic solvents and ILs, the results were dependent on both the organic solvent and the counter ion type in IL. These parameters were also evaluated when â-caryophyllene was used as the substrate. Using this substrate two products, the mono-epoxide 44 and the di-epoxide 45, were formed. The use of several lipases from different sources was also evaluated, and CAL-B was the most efficient catalyst (conv. >99% in 44). By the use of commercial lipases (Amano PS-C I, F-AP15, Amano PS-C SD, Amano PS, Amano AY 30, Amano PS IM, M Amano 10, 20 Amano AK, Amano PS-C II, A Amano 12, Lipozyme RM IM, Lipozyme IM), the conversions in product 44 were of 16-27%; by using the native lipases LAN and LRO the conversions were 20-23% and using the mycelia UEA_06 and UEA_53, the conversions were 16 and 21%, in 24 h. The best oxidizing agent was H2O2 as compared to UHP, considering that the reaction occurred in a shorter time and only a small amount of the reagent was necessary to obtain 44 or 45 as unique products in high conv. (60 ->99%). Using 2.0 mmol of H2O2, CAL-B could be reused up to 5 times with minimal loss in the conversion degrees to 44 (93-90%). The organic solvents were also selective. By using n-hexane, the preferential formation of 44 was observed with conv. >99% after 8 and 24 h reaction. When ethyl acetate and toluene were used, the conversions were of >99% on 45 after 8 and 24h. It is worth of mentioning that the chemoenzymatic methodology used mild conditions and presented selectivity, as depending on the reaction conditions only one product could be obtained in good conversion degrees.86 p.| il., grafs., tabs.porFlorianópolis, SCQuimicaEnzimasTerpeniosLipaseCompostos de EpóxiQuimica organicaEpoxidação quimio-enzimática do citronelol e B-cariofilenoinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisreponame:Repositório Institucional da UFSCinstname:Universidade Federal de Santa Catarina (UFSC)instacron:UFSCinfo:eu-repo/semantics/openAccessORIGINAL301775.pdfapplication/pdf1532162https://repositorio.ufsc.br/bitstream/123456789/96427/1/301775.pdf5f9da1e3cc2b06a41a8e3d8bbdfcb96bMD51TEXT301775.pdf.txt301775.pdf.txtExtracted Texttext/plain131615https://repositorio.ufsc.br/bitstream/123456789/96427/2/301775.pdf.txtfb7df7c33bf634bc71645079cd7307d7MD52THUMBNAIL301775.pdf.jpg301775.pdf.jpgGenerated Thumbnailimage/jpeg713https://repositorio.ufsc.br/bitstream/123456789/96427/3/301775.pdf.jpg860743d19a299b603bedb91d531f427aMD53123456789/964272013-05-04 19:57:15.108oai:repositorio.ufsc.br:123456789/96427Repositório de PublicaçõesPUBhttp://150.162.242.35/oai/requestopendoar:23732013-05-04T22:57:15Repositório Institucional da UFSC - Universidade Federal de Santa Catarina (UFSC)false
dc.title.pt_BR.fl_str_mv Epoxidação quimio-enzimática do citronelol e B-cariofileno
title Epoxidação quimio-enzimática do citronelol e B-cariofileno
spellingShingle Epoxidação quimio-enzimática do citronelol e B-cariofileno
Silva, Jaqueline Maria Ramos da
Quimica
Enzimas
Terpenios
Lipase
Compostos de Epóxi
Quimica organica
title_short Epoxidação quimio-enzimática do citronelol e B-cariofileno
title_full Epoxidação quimio-enzimática do citronelol e B-cariofileno
title_fullStr Epoxidação quimio-enzimática do citronelol e B-cariofileno
title_full_unstemmed Epoxidação quimio-enzimática do citronelol e B-cariofileno
title_sort Epoxidação quimio-enzimática do citronelol e B-cariofileno
author Silva, Jaqueline Maria Ramos da
author_facet Silva, Jaqueline Maria Ramos da
author_role author
dc.contributor.pt_BR.fl_str_mv Universidade Federal de Santa Catarina
dc.contributor.author.fl_str_mv Silva, Jaqueline Maria Ramos da
dc.contributor.advisor1.fl_str_mv Nascimento, Maria da Graça
contributor_str_mv Nascimento, Maria da Graça
dc.subject.classification.pt_BR.fl_str_mv Quimica
Enzimas
Terpenios
Lipase
Compostos de Epóxi
Quimica organica
topic Quimica
Enzimas
Terpenios
Lipase
Compostos de Epóxi
Quimica organica
description Dissertação (mestrado) - Universidade Federal de Santa Catarina, Centro de Ciências Físicas e Matemáticas. Programa de Pós-Graduação em Química.
publishDate 2012
dc.date.submitted.pt_BR.fl_str_mv 2012
dc.date.accessioned.fl_str_mv 2012-10-26T11:57:09Z
dc.date.available.fl_str_mv 2012-10-26T11:57:09Z
dc.date.issued.fl_str_mv 2012
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://repositorio.ufsc.br/xmlui/handle/123456789/96427
dc.identifier.other.pt_BR.fl_str_mv 301775
identifier_str_mv 301775
url http://repositorio.ufsc.br/xmlui/handle/123456789/96427
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 86 p.| il., grafs., tabs.
dc.publisher.none.fl_str_mv Florianópolis, SC
publisher.none.fl_str_mv Florianópolis, SC
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFSC
instname:Universidade Federal de Santa Catarina (UFSC)
instacron:UFSC
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