| TAZ-TFG-2018-150 |
Disolventes sostenibles: síntesis de diéteres derivados de glicerol a partir de epiclorhidrina utilizando catálisis ácida y básica
Gracia Barberán, Sara
García Laureiro, José Ignacio (dir.) ; Pires Ezquerra, Elisabet (dir.)
Universidad de Zaragoza,
CIEN,
2018
Química Orgánica department, Química Orgánica area
Graduado en Química
Tipo de Trabajo Académico: Trabajo Fin de Grado
Notas: Nowadays one of the most attractive research lines within Green Chemistry is the development of new solvents from renewable raw materials that may be capable to substitute traditional organic solvents, often polluting, hazardous and toxic. One of the most interesting starting compound for these new solvents synthesis is glycerol, a renewable raw material that can be easily obtained from vegetal oils. Amongst their derivatives we will focus on ethers, because of their chemical stability, structure versatility and low toxicity. In this dissertation a new synthesis of non-symmetric glycerol diethers from epichlorohydrin (ECH) has been developed via a two-step process. First, the synthesis of 1-alkoxy-3-chloropropan-2-ols has been carried out by reaction of epichlorohydrin and an alcohol using acid catalysis. Several heterogeneous acid catalysts have been studied, together with the influence of the nature of the different alcohols. The best results have been obtained with Nafion NR50 and K-10-H+ catalysts, which can also be easily recovered and reused in several reaction runs. Regarding reaction yield, short chain alcohols (i.e. methanol and ethanol) have been proven to be the best candidates. All the products obtained in this first reaction have been purified and characterized using 1H and 13C-NMR. Second, the 1-alkoxy-3-chloropropan-2-ols obtained from the above reactions have been made react with several alcohols in the presence of a basic catalyst (KOH). In this way, the synthesis of nine different non-symmetric glycerol diethers has been achieved with outstanding yields.
Notas: Nowadays one of the most attractive research lines within Green Chemistry is the development of new solvents from renewable raw materials that may be capable to substitute traditional organic solvents, often polluting, hazardous and toxic. One of the most interesting starting compound for these new solvents synthesis is glycerol, a renewable raw material that can be easily obtained from vegetal oils. Amongst their derivatives we will focus on ethers, because of their chemical stability, structure versatility and low toxicity. In this dissertation a new synthesis of non-symmetric glycerol diethers from epichlorohydrin (ECH) has been developed via a two-step process. First, the synthesis of 1-alkoxy-3-chloropropan-2-ols has been carried out by reaction of epichlorohydrin and an alcohol using acid catalysis. Several heterogeneous acid catalysts have been studied, together with the influence of the nature of the different alcohols. The best results have been obtained with Nafion NR50 and K-10-H+ catalysts, which can also be easily recovered and reused in several reaction runs. Regarding reaction yield, short chain alcohols (i.e. methanol and ethanol) have been proven to be the best candidates. All the products obtained in this first reaction have been purified and characterized using 1H and 13C-NMR. Second, the 1-alkoxy-3-chloropropan-2-ols obtained from the above reactions have been made react with several alcohols in the presence of a basic catalyst (KOH). In this way, the synthesis of nine different non-symmetric glycerol diethers has been achieved with outstanding yields.
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trabajos-academicos-universidad-zaragoza > centro > facultad-de-ciencias
trabajos-academicos-universidad-zaragoza > trabajos-fin-grado