Electrochemical synthesis of a novel compound, 5-acetyl-2,9-decanedione, and theoretical analysis of its lithium ion complex

Abstract

Reported is the electrosynthesis of a novel liquid compound, 5-acetyl-2,9-decanedione (TK) [n³⁵_d = 1.4524 and T_m < −70 °C, T_b > 200 °C], the molecule has unique hierarchic “Y” structure with three carbonyl groups anchored at the end of each arm. The TK is formed though the electrochemical reformation of bio-derived levulinic acid in MeOH/H₂O system. The possible mechanism of formation of the TK via a side reaction of Kolbe electrolysis has been proposed. Theoretical analysis of the TK coordination with lithium ions, forming bidentate Li⁺ (TK)_Li-O1O2, or Li⁺ (TK)_Li-O2O3, or tridentate Li⁺ (TK)_Li-O1O2O3 complexes has been conducted. The results suggest that one TK can possess two Li⁺ ions, thus, it might be a competitive solvent for lithium ion batteries.