Bioactive compounds separation with simulated moving bed technology
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Dissertação |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10773/30277 |
Resumo: | The pharmaceutical industry is developing a growing interest in natural compounds with biological and nutritional properties. Betulinic and oleanolic acids are two naturally occurring triterpenic acids, which possess such characteristics. These two compounds can be extracted from natural resources, i.e., from the bark of Eucalyptus globulus. However, their separation is difficult because these compounds present similar structures (they are constitutional isomers). In this work, the chromatographic separation of betulinic and oleanolic acids from representative extracts of E. globulus was studied. High performance liquid chromatography (HPLC) assays were initially performed using an Acclaim C30 column as stationary phase. Through these tests it was found that the mobile phase methanol/acetonitrile 50/50 (%, v/v) is the most suitable for the separation of both triterpenic acids. In order to determine the equilibrium constants () and the global linear driving force mass transfer coefficients (), several breakthrough experiments of pure acids (unary solutions) were carried out. The two parameters were correlated using experimental data and then validated by simulating the breakthrough curve of a binary mixture containing the same proportion of betulinic and oleanolic acids found in E. globulus extracts. The outcomes of all experiments were modeled using Carta’s analytical solution. In parallel, the method of moments was also used to obtain the transport parameters. The results were consistent. Lastly, the separation of betulinic and oleanolic acids by simulating moving bed (SMB) has been studied, carrying out simulations using the transport parameters obtained before from the breakthrough assays. Two different column configurations (1-1-1-1 and 2-2-2-2) and column lengths (from 10 to 25 cm) were adopted. It was concluded that using an SMB unit is able to separate betulinic and oleanolic acids with purity higher than 99 % both in extract and raffinate for all the scenarios presented. Posteriorly, the recovery of both triterpenic acids from the extract and raffinate streams of a future process was also investigated, taking advantage of their low solubility in water. Accordingly, the solubility of each triterpenic acid in solvent mixtures of increasing water concentration was experimentally measured and discussed. |
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Bioactive compounds separation with simulated moving bed technologyAdsorptionBreakthrough curvesHigh performance liquid chromatographyIsothermSimulated moving bedTriterpenic acidsThe pharmaceutical industry is developing a growing interest in natural compounds with biological and nutritional properties. Betulinic and oleanolic acids are two naturally occurring triterpenic acids, which possess such characteristics. These two compounds can be extracted from natural resources, i.e., from the bark of Eucalyptus globulus. However, their separation is difficult because these compounds present similar structures (they are constitutional isomers). In this work, the chromatographic separation of betulinic and oleanolic acids from representative extracts of E. globulus was studied. High performance liquid chromatography (HPLC) assays were initially performed using an Acclaim C30 column as stationary phase. Through these tests it was found that the mobile phase methanol/acetonitrile 50/50 (%, v/v) is the most suitable for the separation of both triterpenic acids. In order to determine the equilibrium constants () and the global linear driving force mass transfer coefficients (), several breakthrough experiments of pure acids (unary solutions) were carried out. The two parameters were correlated using experimental data and then validated by simulating the breakthrough curve of a binary mixture containing the same proportion of betulinic and oleanolic acids found in E. globulus extracts. The outcomes of all experiments were modeled using Carta’s analytical solution. In parallel, the method of moments was also used to obtain the transport parameters. The results were consistent. Lastly, the separation of betulinic and oleanolic acids by simulating moving bed (SMB) has been studied, carrying out simulations using the transport parameters obtained before from the breakthrough assays. Two different column configurations (1-1-1-1 and 2-2-2-2) and column lengths (from 10 to 25 cm) were adopted. It was concluded that using an SMB unit is able to separate betulinic and oleanolic acids with purity higher than 99 % both in extract and raffinate for all the scenarios presented. Posteriorly, the recovery of both triterpenic acids from the extract and raffinate streams of a future process was also investigated, taking advantage of their low solubility in water. Accordingly, the solubility of each triterpenic acid in solvent mixtures of increasing water concentration was experimentally measured and discussed.A indústria farmacêutica tem manifestado um crescente interesse em compostos naturais com propriedades biológicas e nutricionais. Os ácidos betulínico e oleanólico são dois ácidos triterpénicos que ocorrem naturalmente na natureza e que possuem tais características. Estes dois compostos podem ser extraídos de recursos naturais, tais como da casca do Eucalyptus globulus. No entanto, a sua separação é difícil, pois os compostos apresentam estruturas muito semelhantes (são isómeros constitucionais). Neste trabalho estudou-se a separação cromatográfica de uma amostra representativa dos extratos de E. globulus dos ácidos betulínico e oleanólico. Inicialmente foram realizados testes cromatográficos em cromatografia líquida de alta eficiência, recorrendo à fase estacionária Acclaim C30. Através destes ensaios determinou-se que a fase móvel metanol/acetonitrilo 50/50 (%, v/v) é a mais adequada para a separação destes ácidos triterpénicos. De modo a averiguar as constantes de equilíbrio () e os coeficientes globais de transferência de massa (), foram determinadas as curvas de rutura dos ácidos puros (soluções unárias). Estes parâmetros foram correlacionados recorrendo a dados experimentais e posteriormente validados pela simulação da curva de rutura de uma mistura binária contendo a mesma proporção de ácido betulínico e oleanólico encontrada no E. globulus. Os dados advindos deste ensaio foram modelados pela solução analítica de Carta. Paralelamente, foi também usado o método dos momentos para obter os parâmetros de transporte. Os resultados obtidos foram consistentes. Por fim, estudou-se a separação dos ácidos betulínico e oleanólico por leito móvel simulado (SMB), realizando simulações utilizando os parâmetros de transporte obtidos anteriormente pela modelação das curvas de rutura. Foram adotadas duas configurações diferentes (1-1-1-1 e 2-2-2-2) e diferentes comprimentos de coluna (variando dos 10 aos 25 cm), usando os parâmetros de transporte obtidos. Foi concluído que usando uma unidade SMB é possível separar os ácidos betulínico e oleanólico com purezas superiores a 99 % tanto no extrato como no rafinado para todos os cenários apresentados. Posteriormente, foi analisada a recuperação dos ácidos triterpénicos das correntes de extrato e rafinado de um futuro processo, tirando vantagem da sua baixa solubilidade em água. Por conseguinte, a solubilidade de cada ácido triterpénico em misturas de solventes com o aumento da concentração de água foi medida e discutida.2019-102019-10-01T00:00:00Z2021-11-11T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://hdl.handle.net/10773/30277engRibeiro, Diogo Rafael Pachecoinfo:eu-repo/semantics/embargoedAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-02-22T11:58:33Zoai:ria.ua.pt:10773/30277Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:02:26.035035Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Bioactive compounds separation with simulated moving bed technology |
title |
Bioactive compounds separation with simulated moving bed technology |
spellingShingle |
Bioactive compounds separation with simulated moving bed technology Ribeiro, Diogo Rafael Pacheco Adsorption Breakthrough curves High performance liquid chromatography Isotherm Simulated moving bed Triterpenic acids |
title_short |
Bioactive compounds separation with simulated moving bed technology |
title_full |
Bioactive compounds separation with simulated moving bed technology |
title_fullStr |
Bioactive compounds separation with simulated moving bed technology |
title_full_unstemmed |
Bioactive compounds separation with simulated moving bed technology |
title_sort |
Bioactive compounds separation with simulated moving bed technology |
author |
Ribeiro, Diogo Rafael Pacheco |
author_facet |
Ribeiro, Diogo Rafael Pacheco |
author_role |
author |
dc.contributor.author.fl_str_mv |
Ribeiro, Diogo Rafael Pacheco |
dc.subject.por.fl_str_mv |
Adsorption Breakthrough curves High performance liquid chromatography Isotherm Simulated moving bed Triterpenic acids |
topic |
Adsorption Breakthrough curves High performance liquid chromatography Isotherm Simulated moving bed Triterpenic acids |
description |
The pharmaceutical industry is developing a growing interest in natural compounds with biological and nutritional properties. Betulinic and oleanolic acids are two naturally occurring triterpenic acids, which possess such characteristics. These two compounds can be extracted from natural resources, i.e., from the bark of Eucalyptus globulus. However, their separation is difficult because these compounds present similar structures (they are constitutional isomers). In this work, the chromatographic separation of betulinic and oleanolic acids from representative extracts of E. globulus was studied. High performance liquid chromatography (HPLC) assays were initially performed using an Acclaim C30 column as stationary phase. Through these tests it was found that the mobile phase methanol/acetonitrile 50/50 (%, v/v) is the most suitable for the separation of both triterpenic acids. In order to determine the equilibrium constants () and the global linear driving force mass transfer coefficients (), several breakthrough experiments of pure acids (unary solutions) were carried out. The two parameters were correlated using experimental data and then validated by simulating the breakthrough curve of a binary mixture containing the same proportion of betulinic and oleanolic acids found in E. globulus extracts. The outcomes of all experiments were modeled using Carta’s analytical solution. In parallel, the method of moments was also used to obtain the transport parameters. The results were consistent. Lastly, the separation of betulinic and oleanolic acids by simulating moving bed (SMB) has been studied, carrying out simulations using the transport parameters obtained before from the breakthrough assays. Two different column configurations (1-1-1-1 and 2-2-2-2) and column lengths (from 10 to 25 cm) were adopted. It was concluded that using an SMB unit is able to separate betulinic and oleanolic acids with purity higher than 99 % both in extract and raffinate for all the scenarios presented. Posteriorly, the recovery of both triterpenic acids from the extract and raffinate streams of a future process was also investigated, taking advantage of their low solubility in water. Accordingly, the solubility of each triterpenic acid in solvent mixtures of increasing water concentration was experimentally measured and discussed. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-10 2019-10-01T00:00:00Z 2021-11-11T00:00:00Z |
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://hdl.handle.net/10773/30277 |
url |
http://hdl.handle.net/10773/30277 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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info:eu-repo/semantics/embargoedAccess |
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application/pdf |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799137680051666944 |