Review on the Reactivity of 1,1‐Diamino‐2,2‐dinitroethylene (FOX‐7)

Abstract

Abstract1,1‐Diamino‐2,2‐dinitroethylene (FOX‐7) is a novel high‐energy insensitive material with good thermal stability and low sensitivity, and exhibits excellent application performance in the field of insensitive ammunitions and solid propellant. Although FOX‐7 is simple in molecular composition and structure, its chemical reactivity is abundant and surprising, including salification reaction, coordination reaction, nucleophilic substitution reaction, acetylate reaction, oxidizing reaction, reduction reaction, electrophilic addition reaction, among other reactions. These reactions are systemically summarized and some reaction mechanisms are analyzed in this review.

On the Mechanism of Thermal Decomposition of 1,1-Diamino-2,2-dinitroethene (FOX-7) and its Cyclic Derivatives

“…Quantum calculations as well as experimental data show that the most probable channel of the decomposition of FOX-7 and its carbocyclic homologues is channel 1, the limiting stage of which is hydrogen transfer to a carbon atom. This conclusion agrees well with the previous experimental and theoretical data on the thermal stability of these compounds [15][16][17][18][19][20].…”

“…The reactions that FOX-7 molecules can enter into have been systematized in 2 reviews [17,18], the second of which concluded that during the decomposition of aminonitroethylenes, the most likely channel of gas-phase decomposition is the formation of substituted oxazetes (such as VI, Figure 2) at the limiting stage. Along with this, based on the results of molecular dynamics and quantum calculations, it was shown [19,20] that NO 2 elimination reactions, as well as intra-and inter-molecular hydrogen transfer, could play an important role in the thermal stability of FOX-7.…”

The Effects of Metal Complexes of Nano-Graphene Oxide to Thermal Decomposition of FOX-7

“…But the sensitivity of FOX-7 is lower than that of RDX and HMX [46][47][48]. Based on these properties, FOX-7 could be used as a substitute for RDX in solid propellants [49,50]. However, FOX-7 is a new material that has rarely been reported in relation to its combustion performance.…”

Aromatic Nucleophilic Substitution of FOX‐7: Synthesis and Properties of 1‐Amino‐1‐Picrylamino‐2,2‐Dinitroethylene (APDE) and Its Potassium Salt [K(APDE)]

“…[14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Molecular structure of FOX-7 is very simple, only containing two amino groups and two nitro groups connected with an ethylene group, but its reactivity is abundant, which have been systematically summarized in a review by our group. [29] FOX-7 is a good example of a 'push-pull' alkene of the nitroenamine type, possessing a highly polarized C=C double bond whose positive and negative charges are stabilized by two amino groups and two nitro groups respectively, [30] so it presents both electrophilicity and nucleophilicity. The electrophilicity of FOX-7, which is from its positive gem-diaminocarbon, enables it to react with nucleophiles.…”