Density Functional Theory Studies on the Hydrolysis of Levoglucosenone to 5-Hydroxymethylfurfural.
J Phys Chem A
; 126(26): 4248-4254, 2022 Jul 07.
Article
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| MEDLINE
| ID: mdl-35731126
ABSTRACT
Selective conversion of lignocellulosic biomass-derived chemicals is of critical significance for sustainable fine and commodity chemical industries. Cellulose-derived levoglucosenone (LGO) has a promising potential for producing 5-hydroxymethylfurfural (HMF) with a substantial yield under acid conditions, but the mechanism is unidentified. Herein, we disclose the mechanism of LGO conversion to HMF in the aqueous phase without and with H2SO4 as a catalyst by density functional theory (DFT) calculations for the first time. Results showed that LGO first forms 6,8-dioxabicyclo[3.2.1]-octane-2,4,4-triol (DH) via two sequential hydration reactions occurring at the CâC bond and then the ketone group. The use of H2SO4 as a catalyst significantly reduced the free energy barriers of LGO and DH conversion to HMF, with a free energy barrier of 115 kJ/mol for LGO â HMF compared to that of 91 kJ/mol for DH â HMF, demonstrating that DH is easier for HMF formation.
Texto completo:
1
Base de datos:
MEDLINE
Asunto principal:
Furaldehído
Idioma:
En
Revista:
J Phys Chem A
Asunto de la revista:
QUIMICA
Año:
2022
Tipo del documento:
Article
País de afiliación:
China