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

doi:10.1016/j.comptc.2020.113009

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

Exact Sciences School

Research output: Contribution to journal › Article › peer-review

5 Citations (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 language	English
Article number	113009
Journal	Computational and Theoretical Chemistry
Volume	1190
DOIs	https://doi.org/10.1016/j.comptc.2020.113009
Publication status	Published - 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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10.1016/j.comptc.2020.113009

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

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

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.",

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author = "Meneses-Olmedo, {Lorena Maribel} and {Cuesta Hoyos}, Sebasti{\'a}n and {Salgado Moran}, Guillermo and {Cardona Villada}, Wilson and {Gerli Candia}, Lorena and Mendoza-Huizar, {Luis H.}",

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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

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VL - 1190

JO - Computational and Theoretical Chemistry

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M1 - 113009

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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