Industrial & Engineering Chemistry Research, Vol.48, No.13, 6203-6211, 2009
Reactions of Chemical Warfare Agent Simulants in the Common Ion Binary Ionic Liquid 1,2-Dimethyl-3-propylimidazolium/Copper(II) Bis(trifluoromethylsulfonyl)amide
Ionic liquids have the potential for being ideal alternatives for organic solvents in chemical warfare agent reactions and demilitarization processes. They are considered to be an excellent substitute, because of their extraordinarily wide liquid range, low melting points, chemical and thermal stability, high conductivity, and nonvolatility. In addition, many have excellent hydrophobic properties and immiscibility with water and offer the opportunity to isolate the chemical agents and reaction products from the environment. In this report, we describe a two-step process in which chemical warfare simulants are reacted with hydrogen peroxide (H2O2) followed by basic methanol in a common ion binary ionic liquid that consists of 1,2-dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)amide and copper(II) bis(trifluoromethylsulfonyl)amide. The chemical agent simulants used in this study are diisopropylfluorophosphate, bis(2-ethylhexyl) phosphite, and 2-chloroethylphenyl sulfide, which simulate agents GB, VX, and HD, respectively. Initially, H2O2 is added to the mixture of simulants and ionic liquid to remove 2-chloroethylphenyl sulfide, followed by the addition of methanolic tetramethylammonium hydroxide hydrate (TMAOH center dot 5H(2)O) (basic methanol) to eliminate diisopropylfluorophosphate and his(2-ethylhexyl) phosphite. The reactions were monitored by liquid chromatography/mass spectroscopy time-of-flight (LC/MS-TOF), coupled with ultraviolet (UV) diode array detection. Gas chromatography/mass spectroscopy (GC/MS) was used to aid in product identification.