TY - JOUR
T1 - Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural
T2 - A DFT study
AU - Meneses-Olmedo, Lorena Maribel
AU - Cuesta Hoyos, Sebastián
AU - Salgado Moran, Guillermo
AU - Cardona Villada, Wilson
AU - Gerli Candia, Lorena
AU - Mendoza-Huizar, Luis H.
PY - 2020/11/15
Y1 - 2020/11/15
N2 - 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.
AB - 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.
KW - Biomass
KW - Force quantum descriptor
KW - Fructose
KW - Tagatose
KW - Tautomerization
UR - http://www.scopus.com/inward/record.url?scp=85090117985&partnerID=8YFLogxK
U2 - 10.1016/j.comptc.2020.113009
DO - 10.1016/j.comptc.2020.113009
M3 - Article
AN - SCOPUS:85090117985
SN - 2210-271X
VL - 1190
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
M1 - 113009
ER -