Reactivity of levulinic acid during acid catalyzed hydrolysis of Glucose, Fructose or HMF
Gajiwala, Varun Mitesh
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Levulinic acid (LA) is formed during acid-catalyzed conversion of glucose, fructose or HMF. It is stable at reaction conditions. If extra Levulinic acid is added during acid-catalyzed conversion of glucose, fructose or HMF, it does not react. In contrast, if other carbonyl-containing reagents like benzaldehyde and acetaldehyde are present, they are incorporated into the humins that form via aldol condensation involving their carbonyl group. Levulinic acid also has a carbonyl group that should be able to participate in aldol addition/condensation. Computational chemistry was used to investigate possible reactions of Levulinic acid. The results suggest that conversion of Levulinic acid to 5-hydroxy-gamma-valerolactone and two associated unsaturated lactones is energetically unfavorable. In contrast, the formation of a complex of two Levulinic acid molecules was found to be energetically favorable. This may explain the stability of Levulinic acid during acid-catalyzed hydrolysis.