Synthesis of Novel Amino-Picrate Derivatives of Aliphatic Nitrate Ester Explosives

Energetic materials containing the 2,4,6-trinitrobenzene functional group, including the explosive trinitrotoluene (TNT), have been investigated for decades. The trinitrobenzene functional group generally results in increased melting points and thermal stability in explosives. Addition of the trinitrobenzene group to a molecule is done via an oxygen (picrate) or nitrogen (amino picrate) bridge. Most explosives in which the trinitrobenzene group is added are aromatic materials, and investigations into aliphatic picrate materials is quite rare. Herein we report the synthesis, characterization, and explosive sensitivity of amino-picrate derivatives of aliphatic nitrate ester explosives, pentaerythritol tetranitrate (PETN), erythritol tetranitrate (ETN), nitroglycerin and ethylene glycol dinitrate (EGDN). In addition to the fully amino picrate materials, compounds containing a mixture of nitrate esters and picrate groups will be investigated. Computational analysis of the novel materials was conducted to correlate chemical properties with explosive sensitivity as well as investigate decomposition pathways of the novel materials.