The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Abstract

New derivatives of 1,1-diamino-2, 2-dinitroethene (FOX-7) are reported. These highly oxygen- and nitrogen-rich compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis (EA), and differential scanning calorimetry (DSC). X-ray structure determination of (E)-1,2-bis{(E)-2-chloro-1-(chloroimino)-2,2-dinitroethyl}diazene) (10), N1, N2-dichloro-1, 2-diazenedicarboximidamide (11), and (E,E)-N,N'-1,2-ethanediylidenebis(2, 2-dinitro-2-chloro-ethanamine) (12) was helpful in their characterization. Heats of formation (HOF) were calculated (Gaussian 03) and combined with experimental densities to estimate the detonation velocities (D) and pressures (P) of the high-energy-density materials (HEDMs) (EXPLO5, v6.01). The compounds exhibit good thermal stability, high density, positive HOF, acceptable oxygen balances, and excellent detonation properties, which often are superior to that of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX).

Furazans with Azo Linkages: Stable CHNO Energetic Materials with High Densities, Highly Energetic Performance, and Low Impact and Friction Sensitivities

“…Traditional high energy density materials (HEDMs) used for civilian and military applicationsd eveloped over the last two centuries and stillw idely used include 2,4,6-trinitrotolune (TNT), cyclo-1,3,5-trimethylene-2,4,6-trinitamine (RDX), 1, 3,5,7tetranitrotetraazacyclooctane (HMX), and pentaerythritol tetranitrate (PETN). However,t here is ongoing research and interest in the synthesis of HEDMst hat are environmentally benign and combine high performance with low sensitivity,atask which poses particularc hallenges to the synthetic organic chemist.…”

“…Therefore, seeking ab alance between high performance and stabilityi st he main challenge in the design of advanced HEDMs. The field of chemistry related to HEDMs must expand the boundaries of the energy capacity of the compounds, whichr equires new classes of functionalized compounds, [3] advanced theoreticalp redictiont echniques, [4] and new synthetic strategies. [5] Unlike the traditionally designed energetic materials, in which the fuel and oxidizing characteristics are the sole factors determining their performance, nitrogen-rich compounds have some unique properties such as high heats of formation,s ignificant gas release in the form of environmentally benign nitrogen, and commonly include moieties such as five-membered azole and six-membered azine rings.…”

Energetic Salts Based on Tetrazole N‐Oxide

“…The desirable characteristics of modern HEDMs include high density, positive heat of formation, favorable oxygen balance, high thermal stability, remarkable detonation performance, low sensitivity to external forces, and environmental friendliness . Among these properties, oxygen balance (OB) is used to represent the degree to which an explosive can be oxidized, and (OB) % for an explosive with the general formula C a H b N c O d and molecular mass M r can be calculated as: (OB) %=1600×[d−2 a− ]/ M r .…”

Insight into the acidic group-induced nitration mechanism of 2-methyl-4,6-dihydroxypyrimidine (MDP) with nitronium

“…1 Owing to its superior performances of high energy density, high explosive and most importantly, lower sensitivity towards impact and friction, FOX-7 is increasingly accepted as a kind of new insensitive energetic materials. Therefore, in recent years much attention has been paid to investigating FOX-7 from various aspects, including the synthetic method, 2-6 molecular/crystal structure, 1,7-11 thermodynamic property, [12][13][14][15] explosive performance, 16,17 thermal decomposition 18 and other performances/properties [19][20][21] in recent years. However, so far quite few references can be found focusing on the synthesis mechanism of FOX-7.…”