A new chelating task-specific ionic liquid (TSIL), lutidinium-based salicylaldoxime (LSOH), and its square pyramidal vanadyl(II) complex (VO(LSO) 2 ) have been successfully synthesized and structurally characterized using elemental (CHN), spectral, and thermal analyses. The catalytic activity of the lutidinium-salicylaldoxime complex (VO(LSO) 2 ) in the alkene epoxidation reactions was studied under various reaction conditions, such as solvent effect, alkene/oxidant molar ratio, pH, reaction temperature, reaction time, and the catalyst dose. The results demonstrated that the CHCl 3 solvent, 1 : 3 of the cyclohexene/H 2 O 2 ratio, pH 8, temperature of 340 K, and catalyst dose of 0.012 mmol are assigned as the optimum conditions for achieving maximum catalytic activity for VO(LSO) 2 . Moreover, the VO(LSO) 2 complex has the potential for application in the effective and selective epoxidation of alkenes. Notably, under optimal VO(LSO) 2 conditions, cyclic alkenes convert more efficiently to their corresponding epoxides than linear alkenes.