INSIGHTS ON THE MECHANISM, REACTIVITY AND SELECTIVITY OF FRUCTOSE AND TAGATOSE DEHYDRATION INTO 5-HYDROXYMETHYLFURFURAL: A DFT STUDY: 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: A DFT study

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

Facultad de Ciencias Exactas y Naturales

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6 Citas (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 original	Inglés
Número de artículo	113009
Publicación	Computational and Theoretical Chemistry
Volumen	1190
DOI	https://doi.org/10.1016/j.comptc.2020.113009
Estado	Publicada - 15 nov. 2020

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© 2020 Elsevier B.V.

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Financiadores	Número del financiador
Consejo Nacional de Ciencia y Tecnología	CB-2015-257823
Universidad Autónoma del Estado de Hidalgo	123732
Sistema Nacional de Investigadores

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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: A DFT study. Computational and Theoretical Chemistry, 1190, Artículo 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: 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.",

keywords = "Biomass, Force quantum descriptor, Fructose, Tagatose, Tautomerization",

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.}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier B.V.",

year = "2020",

month = nov,

day = "15",

doi = "10.1016/j.comptc.2020.113009",

language = "English",

volume = "1190",

journal = "Computational and Theoretical Chemistry",

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publisher = "Elsevier B.V.",

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Meneses-Olmedo, LM, Cuesta Hoyos, S, Salgado Moran, G, Cardona Villada, W, Gerli Candia, L & Mendoza-Huizar, LH 2020, 'INSIGHTS ON THE MECHANISM, REACTIVITY AND SELECTIVITY OF FRUCTOSE AND TAGATOSE DEHYDRATION INTO 5-HYDROXYMETHYLFURFURAL: A DFT STUDY: A DFT study', Computational and Theoretical Chemistry, vol. 1190, 113009. https://doi.org/10.1016/j.comptc.2020.113009

INSIGHTS ON THE MECHANISM, REACTIVITY AND SELECTIVITY OF FRUCTOSE AND TAGATOSE DEHYDRATION INTO 5-HYDROXYMETHYLFURFURAL: A DFT STUDY: A DFT study. / Meneses-Olmedo, Lorena Maribel; Cuesta Hoyos, Sebastián; Salgado Moran, Guillermo et al.
En: Computational and Theoretical Chemistry, Vol. 1190, 113009, 15.11.2020.

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

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T1 - INSIGHTS ON THE MECHANISM, REACTIVITY AND SELECTIVITY OF FRUCTOSE AND TAGATOSE DEHYDRATION INTO 5-HYDROXYMETHYLFURFURAL: A DFT STUDY

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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INSIGHTS ON THE MECHANISM, REACTIVITY AND SELECTIVITY OF FRUCTOSE AND TAGATOSE DEHYDRATION INTO 5-HYDROXYMETHYLFURFURAL: A DFT STUDY: A DFT study

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