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

Lorena Maribel Meneses-Olmedo, Sebastián Cuesta Hoyos, Guillermo Salgado Moran, Wilson Cardona Villada, Lorena Gerli Candia, Luis H. Mendoza-Huizar

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

1 Cita (Scopus)

Resumen

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.

Idioma originalInglés
Número de artículo113009
PublicaciónComputational and Theoretical Chemistry
Volumen1190
DOI
EstadoPublicada - 15 nov 2020

Áreas temáticas de ASJC Scopus

  • Bioquímica
  • Física de la materia condensada
  • Química física y teórica

Huella

Profundice en los temas de investigación de 'Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural: A DFT study'. En conjunto forman una huella única.

Citar esto