Producción Científica Profesorado

Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural: A DFT study



Mendoza Huizar, Luis Humberto

2020

Meneses-Olmedo, L.M., Cuesta Hoyos, S., Salgado Moran, G., Cardona Villada, W., Gerli Candia, L., Mendoza-Huizar, L.H. Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural: A DFT study. Computational and Theoretical Chemistry. 2020, 1190, 113009. DOI: 10.1016/j.comptc.2020.113009


Abstract


In this study, a computational DFT study was performed to propose a new acid catalyzed mechanism to produce 5HMF from d-Fructose and d-Tagatose. The reactivity and selectivity towards 5HMF formation were analyzed, and the results revealed both saccharides present higher selectivity towards 5HMF with the first dehydration occurring on oxygen 2. Fructose seems to be more reactive than tagatose, although the dehydration process of the different hydroxyl groups on tagatose produces more unstable structures, which can undergo several side reactions. The new mechanism is proposed eliminating the tautomerization step and lowering the activation free energy of the second dehydration step in 21 kcal/mol.



Producto de Investigación




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