Estudio de sistemas bifuncionales para la obtención de 5-(Hidroximetil)-2-Furaldehído y Acido 5-(Hidroximetil)Furan-2-Carboxílico

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dc.contributor.advisorRojas Sarmiento, Hugo Alfonsospa
dc.contributor.advisorMartínez Zambrano, José Jobannyspa
dc.contributor.authorAguilera Palacios, Edna Ximena
dc.date.accessioned2019-05-10T21:42:05Z
dc.date.available2019-05-10T21:42:05Z
dc.date.issued2017
dc.description1 recurso en línea (102 páginas) : ilustraciones color, figuras, tablas.spa
dc.description.abstractIn this work the dehydration of fructose and glucose to 5-(hydroxymethyl)-2-furaldehyde (HMF) was studied on a bifunctional system based on LaOCl/Nb2O5 catalysts and hot compressed water. The catalysts were prepared by impregnation of LaCl3 over Nb2O5 with different loads. The solids were characterized by X-ray energy dispersion spectroscopy (EDX), thermogravimetry (TGA), N2 physisorption, pyridine and CO2 adsorption followed by Fourier transform infrared spectroscopy with diffuse reflectance (FT-IR); the acid and basic force was determined by NH3 and CO2 desorption at programmed temperature, respectively. The use of acid-base systems for the production of HMF mainly from glucose requires weak basic sites and conditions of moderate acidity which is reached with LaOCl/Nb2O5 as was confirmed by the acidity and basicity analyzes. The presence of Nb2O5 in the solids increased the yield to HMF (> 50%) and prevented the formation of undesirable products under compressed hot water conditions. With the same objective to produce HMF, a bifunctional system was developed; this is based on the design of solids with acid-basic characteristics to convert glucose to the HMF in which a step of isomerization of the glucose to the fructose supplied by the effect of the basic sites of oxides such as CeO2, La2O3 and SiO2 and a dehydration step in which the participation of acid sites derived from the functionalization of oxides with sulfonic groups -SO3H is required. The oxides were functionalized with 3-mercaptopropyltrimethoxysilane in relation to the density of hydroxyl groups chemically bound to the surface, for that purpose the amount of hydroxyl groups was determined by analysis of physisorption, thermogravimetric analysis and infrared spectroscopy by Fourier transform. The catalysts obtained were characterized by N2 physisorption, pyridine and CO2 adsorption by diffuse reflectance infrared spectroscopy with Fourier transform; desorption analysis at programmed temperature of NH3 and CO2. The results showed that the functionalization process with groups -SO3H decreases the volume of the pores and therefore their surface area due to the interaction of the oxides with organosilanes. Analyzes of the nature of the acidic sites of the solids by adsorption of pyridine showed that in all the solids there are both types of acidity; Lewis and Brönsted, the latter attributed to the acid sulfonic groups anchored to the oxides. As for its catalytic activity, the highest conversion of glucose was found when La2O3-SO3H was used as the catalyst, achieving an HMF yield of 58%. Given the importance of HMF as a platform molecule to obtain high added value compounds with pharmaceutical and polymer applications, a bifunctional system involving the use of Rh catalysts supported in reducible and non-reducible oxides and an aqueous alkaline medium to produce 5-(hydroxymethyl)furan-2-carboxylic acid (HMFCA). Synthesized catalysts were characterized by EDX, transmission electron microscopy (TEM), chemisorption and FT-IR pyridine. The results revealed that the reaction pathway did not follow the typical HMF oxidation path but followed the Cannizzaro reaction path so the main products were (furan-2,5-diyl) dimethanol (DHMF), salt of the HMFCA and some degradation products such as levulinic and formic acids as a consequence of the degradation of HMF by the effect of the alkaline medium. The oxide with the best activity was CeO2, based on these results the possible reaction mechanism was elucidated when Rh/CeO2 was used as catalyst in the presence of molecular oxygen. In addition it was shown that at lower particle sizes HMFCA yield increased.eng
dc.description.abstractEn este trabajo se estudió la deshidratación de fructosa y glucosa a 5-(hidroximetil)-2-furaldehído (HMF) sobre un sistema bifuncional basado en catalizadores de LaOCl/ Nb2O5 y agua comprimida caliente. Los catalizadores fueron preparados por impregnación de LaCl3 sobre Nb2O5 con diferentes cargas. Los sólidos se caracterizaron por espectroscopia de dispersión de energía de rayos-X (EDX), termogravimetría (TGA), fisisorción de N2, adsorción de piridina y de CO2 seguida por espectroscopia de infrarrojo con transformada de Fourier con reflectancia difusa (FT-IR); la fuerza ácida y básica fue determinada por desorción a temperatura programada de NH3 y CO2, respectivamente. El uso de sistemas ácido-base para la producción de HMF principalmente a partir de glucosa requiere sitios básicos débiles y condiciones de acidez moderada que se alcanza con LaOCl/Nb2O5 como fue confirmado por los análisis de acidez y basicidad. La presencia de Nb2O5 en los sólidos aumentó el rendimiento de HMF (>50%) y evitó la formación de productos indeseables en condiciones de agua caliente comprimida. Con el mismo objetivo de producir HMF, se desarrolló un sistema bifuncional que consistió en el diseño de sólidos con características ácido-básicas capaces de transformar la glucosa en HMF en donde se involucra una etapa de isomerización de la glucosa a la fructosa suplida por el efecto de los sitios básicos de óxidos tales como CeO2, La2O3 y SiO2 y una etapa de deshidratación en donde se requiere la participación de sitios ácidos derivados de la funcionalización de los óxidos con grupos sulfónicos –SO3H. Los óxidos fueron funcionalizados con 3-mercaptopropiltrimetoxisilano en relación a la densidad de grupos hidroxilo unidos químicamente a la superficie, para tal fin se determinó la cantidad de grupos hidroxilo mediante análisis de fisisorción, análisis termogravimétrico y espectroscopia infrarroja con transformada de Fourier. Los catalizadores obtenidos fueron caracterizados por fisisorción de N2, adsorción de piridina y CO2 por espectroscopía infrarroja de reflectancia difusa de con transformada de Fourier; análisis de desorción a temperatura programada de NH3 y CO2. Los resultados mostraron que el proceso de funcionalización con grupos -SO3H disminuye el volumen de los poros y por lo tanto su área superficial debido a la interacción de los óxidos con organosilanos. Los análisis de la naturaleza de los sitios ácidos de los sólidos por adsorción de piridina demostraron que en todos los sólidos hay ambos tipos de acidez; Lewis y Brönsted, ésta última atribuida a los grupos sulfónicos ácidos anclados a los óxidos. En cuanto a su actividad catalítica se encontró la mayor conversión de glucosa cuando se empleó La2O3-SO3H como catalizador alcanzando un rendimiento hacia HMF del 58%. Dada la importancia del HMF como molécula plataforma para obtener compuestos de alto valor agregado con aplicaciones farmacéuticas y en la industria de polímeros, se estudió un sistema bifuncional que involucra el empleo de catalizadores de Rh soportado en óxidos reducibles y no reducibles y un medio acuoso alcalino para producir ácido 5-(hidroximetil)furan-2-carboxílico (HMFCA).. Los catalizadores sintetizados fueron caracterizados por EDX, microscopía electrónica de trasmisión (TEM), quimisorción y FT-IR de piridina. Los resultados revelan que la ruta de reacción no siguió la ruta de oxidación típica de HMF sino que siguió la ruta de reacción de Cannizzaro por lo que los principales productos fueron el (furan-2,5-diil) dimetanol (DHMF), la sal del HMFCA y algunos productos de degradación como los ácidos levulínico y fórmico como consecuencia de la degradación de HMF por efecto del medio alcalino. El óxido que mejor actividad mostró fue CeO2, con base en estos resultados se elucidó el posible mecanismo de reacción cuando se empleó Rh/CeO2 como catalizador en presencia de oxígeno molecular. Además se demostró que a menores tamaños de partícula el rendimiento a HMFCA incrementó.spa
dc.description.degreelevelMaestríaspa
dc.description.degreenameMagíster en Químicaspa
dc.description.notesBibliografía y webgrafía: páginas 89-98.spa
dc.format.mimetypeapplication/pdfspa
dc.identifier.citationAguilera Palacios, E, X. (2017). Estudio de sistemas bifuncionales para la obtención de 5-(Hidroximetil)-2-Furaldehído y Ácido 5-(Hidroximetil)Furan-2-Carboxílico. (Tesis de Maestría). Universidad Pedagógica y Tecnológica de Colombia, Tunja. http://repositorio.uptc.edu.co/handle/001/2583spa
dc.identifier.urihttp://repositorio.uptc.edu.co/handle/001/2583
dc.language.isospaspa
dc.publisherUniversidad Pedagógica y Tecnológica de Colombiaspa
dc.publisher.facultyFacultad de Ciencias. Escuela de Posgrados. Maestría en Químicaspa
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dc.rightsCopyright (c) 2017 Universidad Pedagógica y Tecnológica de Colombiaspa
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dc.rights.creativecommonsAtribución-NoComercial 4.0 Internacional (CC BY-NC 4.0)spa
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dc.subject.armarcMaestría en Química - Tesis y disertaciones académicas
dc.subject.other5-Hydroxymethylfurfural (HMF)
dc.titleEstudio de sistemas bifuncionales para la obtención de 5-(Hidroximetil)-2-Furaldehído y Acido 5-(Hidroximetil)Furan-2-Carboxílicospa
dc.typeTrabajo de grado - Maestríaspa
dc.type.coarhttp://purl.org/coar/resource_type/c_bdccspa
dc.type.coarversionhttp://purl.org/coar/version/c_970fb48d4fbd8a85spa
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