Enhanced Yield of Methyl Ethyl Ketone through Levulinic Acid Decarboxylation in the AgNO3/K2S2O8 System: Mechanistic Insights and Characterization of Metallic Species

Methyl ethyl ketone (MEK) is among the most extensively utilized solvents in various industrial applications. In this study, we present a highly efficient synthesis route for MEK via the decarboxylation of biomass-derived levulinic acid, using potassium persulfate (K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>) and silver nitrate (AgNO<sub>3</sub>) as key reagents. The specific roles of AgNO<sub>3</sub> and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> were thoroughly investigated. Additional silver species, such as Ag<sub>2</sub>O and AgO, were also detected during the reaction. X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD) analyses provided evidence of the evolution of solid phases throughout the reaction. Based on these findings, we propose a radical decarboxylation mechanism initiated by the generation of sulfate radicals (SO<sub>4</sub>•⁻) through the catalytic breakdown of K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> by AgNO<sub>3</sub>. This mechanistic understanding, combined with a parametric study, enabled us to achieve an unprecedented level of levulinic acid conversion (97.9%) and MEK yield (86.6%) with this system, surpassing all previously reported results in the literature.

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Journal
Molecules
Published
2024-10-11
DOI
https://doi.org/10.3390/molecules29204822
Citations
1
Primary Topic
Mesoporous Materials and Catalysis
Type
article
Field-Weighted Citation Impact
0.12

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article

Enhanced Yield of Methyl Ethyl Ketone through Levulinic Acid Decarboxylation in the AgNO3/K2S2O8 System: Mechanistic Insights and Characterization of Metallic Species

Emeline Vedrenne, Carlos Vaca‐García, Jérôme Peydecastaing, Nydia Ileana Guzmán Barrera et al.
1 citations
Molecules
Mesoporous Materials and Catalysis
0.12
article

Enhanced Yield of Methyl Ethyl Ketone through Levulinic Acid Decarboxylation in the AgNO3/K2S2O8 System: Mechanistic Insights and Characterization of Metallic Species

Emeline Vedrenne, Carlos Vaca‐García, Jérôme Peydecastaing, Nydia Ileana Guzmán Barrera, Sophie Thiébaud‐Roux, Philippe Behra, Joël Albet, Jérôme Esvan
article en
1 citations

Abstract

Methyl ethyl ketone (MEK) is among the most extensively utilized solvents in various industrial applications. In this study, we present a highly efficient synthesis route for MEK via the decarboxylation of biomass-derived levulinic acid, using potassium persulfate (K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>) and silver nitrate (AgNO<sub>3</sub>) as key reagents. The specific roles of AgNO<sub>3</sub> and K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> were thoroughly investigated. Additional silver species, such as Ag<sub>2</sub>O and AgO, were also detected during the reaction. X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD) analyses provided evidence of the evolution of solid phases throughout the reaction. Based on these findings, we propose a radical decarboxylation mechanism initiated by the generation of sulfate radicals (SO<sub>4</sub>•⁻) through the catalytic breakdown of K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> by AgNO<sub>3</sub>. This mechanistic understanding, combined with a parametric study, enabled us to achieve an unprecedented level of levulinic acid conversion (97.9%) and MEK yield (86.6%) with this system, surpassing all previously reported results in the literature.

MoleculesVol. 29(20)
Centre National de la Recherche Scientifique (FR), Université Fédérale de Toulouse Midi-Pyrénées (FR), Institut National de Recherche pour l'Agriculture, l'Alimentation et l'Environnement (FR), Laboratoire de Chimie Agro-Industrielle (FR), Centre Interuniversitaire de Recherche et d’Ingénierie des Matériaux (FR)
European Commission
Openalex Percentile: Top 59%
Mesoporous Materials and Catalysis
0.12
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