Abstract
The oxidative decarboxylation of levulinic acid (LA) by silver(I)/persulfate [Ag(I)/S2O82−] has been investigated in this paper. The effects of buffer solution, initial pH value, time and temperature and dosages of Ag(I)/S2O82− on the decarboxylation of LA were examined in batch experiments and a reaction scheme was proposed on basis of the reaction process. The experimental results showed that a solution of NaOH-KH2PO4 was comparatively suitable for the LA decarboxylation reaction by silver(I)/persulfate. Under optimum conditions (temperature 160 °C, pH 5.0, and time 0.5 h), the rate of LA conversion in NaOH-KH2PO4 solutions with an initial concentration of 0.01 mol LA reached 70.2%, 2-butanone (methyl ethyl ketone) was the single product in the gas phase and the resulted molar yield reached 44.2%.
Highlights
Levulinic acid (4-oxo-pentanoic acid), results from a series of biomass hydrolysis reactions [1,2].With its wide application profile it is an important chemical platform obtainable from renewable lignocelluloses [3,4,5] because of its molecular structure that contains a carbonyl group and a carboxyl group
Oxidative decarboxylation with various agents have been repeatedly reported as the most common pathway for the decarboxylation of carboxylic acids and their derivatives, and a variety of oxidants involved in these reactions have been extensively studied, such as porphyrin combined with manganese (Ш) [8], Schiff base complexes combined with manganese (III) [9], active hydroxyl radicals (OH) [10], peroxyl radicals [11], and high-valent metal ions [12,13,14]
It was shown that levulinic acid (LA) could be oxidatively decarboxylated by S2O82− with or without Ag(I) and leading to 2-butanone as the main gas product
Summary
Levulinic acid (4-oxo-pentanoic acid), results from a series of biomass hydrolysis reactions [1,2].With its wide application profile it is an important chemical platform obtainable from renewable lignocelluloses [3,4,5] because of its molecular structure that contains a carbonyl group and a carboxyl group. Hydrogenation of levulinic acid, can produce γ-valerolactone [6], a potentially useful polyester monomer (as γ-hydroxyvaleric acid); 1,4-pentanediol, of value in polyester production; Molecules 2011, 16 methyltetrahydrofuran, a valuable solvent or a gasoline blending component; and diphenolic acid with potential for use in polycarbonate production [7] are other significant derivatives. Oxidative decarboxylation with various agents have been repeatedly reported as the most common pathway for the decarboxylation of carboxylic acids and their derivatives, and a variety of oxidants involved in these reactions have been extensively studied, such as porphyrin combined with manganese (Ш) [8], Schiff base complexes combined with manganese (III) [9], active hydroxyl radicals (OH) [10], peroxyl radicals [11], and high-valent metal ions [12,13,14]. As for decarboxylation of LA, to the best of our knowledge until now only two reports exist; one is for the photoelectron-chemical decarboxylation of LA [15], leading to
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