Synthesis of New Energetic Materials Based on Furazan Rings and Nitro‐ <i>NNO</i> ‐azoxy Groups

Abstract

Abstract Energetic compounds 1 – 6 , consisting of one or two furazan rings linked by azo or azoxy bridges and one or two nitro‐ NNO ‐azoxy substituents, were synthesized by nitration of the corresponding tert ‐butyl‐ NNO ‐azoxy precursors with NO 2 BF 4 . Novel methods for the synthesis of 3,4‐bis( tert ‐butyl‐ NNO ‐azoxy)furazan ( 7 ) and bis‐4,4′‐( tert ‐butyl‐ NNO ‐azoxy)‐3,3′‐azoxyfurazan ( 21 ) were elaborated. The nitro‐ NNO ‐azoxy compounds obtained display high calculated detonation performance ( v D =8.07–9.40 km s −1 and P C‐J =27.4–43.4 GPa) that is superior to the corresponding nitrofurazans (DNF, DNAzF, DNAF). The replacement of nitrofurazans with the corresponding (nitro‐ NNO ‐azoxy)furazans increases the specific impulse of the model solid composite propellant formulations by 2–10 s, which is due to high calculated heats of formation (600–892 kcal kg −1 ) and positive oxygen balance (0–20 %) of the latter compounds.