Abstract
Considering the demand for organosulfur materials and the challenges associated with currently used oxidation processes, in this study, we evaluated the counter-cation of sodium chlorite (Na(+)ClO(2) (-)) with tetrabutylammonium chloride (Bu(4)N(+)Cl(-)) to synthesise tetrabutylammonium chlorite (Bu(4)N(+)ClO(2) (-)). Bu(4)N(+)ClO(2) (-) exhibited good solubility in organic solvents like chloroform (5.2 mol L(-1)) and ethyl acetate (2.8 mol L(-1)). The oxygenation reaction of organosulfides with Bu(4)N(+)ClO(2) (-) was examined in an HCl-acidic ethyl acetate solution under ambient conditions, selectively forming the corresponding sulfoxides as mono-oxygenated products. The reaction was initiated by the formation of chlorine dioxide (ClO(2)⋅) as an oxidant and an active species generated from Bu(4)N(+)ClO(2) (-) with HCl. This oxygenation method also enables the surface oxidation of sulfide polymers like polyphenylene sulfide (PPS) resins to increase their surface hydrophilicity. Therefore, the use of Bu(4)N(+)ClO(2) (-) for applications in organic solvents is an efficient, and highly selective approach for selective oxidation.