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

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Article number113009
JournalComputational and Theoretical Chemistry
Volume1190
DOIs
Publication statusPublished - 15 Nov 2020

Keywords

  • Biomass
  • Force quantum descriptor
  • Fructose
  • Tagatose
  • Tautomerization

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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