Mechanochemical Nitration of Aromatic Compounds

Nitration of organic compounds is necessary to produce many energetic materials, such as TNT and nitrocellulose. The conventional nitration process uses a mixture of concentrated sulfuric and nitric acids as nitrating agents and multiple solvents. The chemicals are corrosive and require special handling and disposal procedures. In this study, aromatic nitration has been achieved using solvent-free mechanochemical processing of environmentally benign precursors. Mononitrotoluene was synthesized by milling toluene with sodium nitrate and molybdenum trioxide as a Lewis acid catalyst. Several parameters affecting the desired product yield were identified and varied. A number of byproducts, i.e., dimers of toluene were also produced, but the selectivity was observed to increase with increasing mononitrotoluene yield. Both absolute mononitrotoluene yields and selectivity of its production increased with the increase in the energy transferred to the material from the milling tools.