Abstract

Compared to H2SO4, Brønsted acidic ionic liquid (BAIL, [C3SO3HMIM][HSO4]) catalyzed depolymerization of lignin yielded higher concentration of low molecular weight products under mild conditions (120°C) as proven by GC and GC–MS. To comprehend this disparity in catalytic activity among H2SO4 and BAIL (at similar H+ concentration), experimental techniques [1D(1H) NMR, 2D(15N/1H HMBC) NMR and RAMAN] have been employed. Based on these studies, it has been proven that the transfer of electron density from substrate to the electron deficient imidazolium ring via formation of hydrogen bond between OH/OCH3 (substrate) and N1C2H2N3− (cation) is possible, while the anion plays an important role. Further, density functional theory (DFT) calculations also corroborated this fact by showing a change in the bond angle and decrease in bond length (C2H2 in imidazole), due to the presence of weak and strong hydrogen bonding between the substrate and IL.

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