The production of energetic materials produces wastewater-containing residual levels of insensitive munition (IM) formulation constituents such as nitroguanidine (NQ) and 2,4-dinitroanisole (DNAN). Treatment of IMs using zero-valent metal or bimetal technology is well-studied, particularly iron-based treatment such as the use of zero-valent iron (ZVI). However, ZVI is usually effective only under acidic conditions. Mg-based reagents, on the other hand, remain effective without acidic conditions and offer greater reduction potential. In this work, the reductive degradation of pure NQ and DNAN in water by Mg/Cu bimetal was studied. Treatment of NQ produced two parallel reactions: nitroreduction led to aminoguanidine formation, or reduction of the encompassing nitramine group resulted in N-N bond cleavage forming guanidine. Additional byproducts identified were urea, cyanamide, formamide, and dicyandiamide. Experimental evidence on the degradation of NQ byproducts elucidated a complete reaction pathway, along with complete carbon closure from NQ byproducts. Results on conditions controlling reaction selectivity will be discussed. Conversely, treatment of DNAN in a solvent matrix resulted in subsequent nitroreduction: one nitro group was reduced (ortho or para) to form 2-amino-4-nitroanisole or 4-amino-2-nitroanisole (2-ANAN or 4-ANAN), and subsequent reduction of the other nitro group formed 2,4-diaminoanisole (DAAN). However, in an aqueous matrix, adsorption to the bimetal was significant. A fraction of DNAN partially reduced to 2-ANAN and adsorbed to the bimetal. Concurrently, DAAN formed in the liquid phase, but in insufficient amounts, i.e. resulting in an open mass balance in the liquid phase. Adsorption to the bimetal increased with oxygenation. Subsequent experiments indicated DAAN was not necessarily the final product from Mg/Cu treatment. In oxygenated systems, DAAN degraded and led to adsorption of DAAN or DAAN transformation products to the bimetal. Complete mass balance and transformation products from DNAN and DAAN degradation will be discussed.

Reductive degradation using Mg-based bimetal: Transformation and fate of 2,4-dinitroanisole (DNAN) and nitroguanidine (NQ) in wastewater

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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