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

Abstract

Two energetic compounds, 1‐amino‐1‐picrylamino‐2,2‐dinitroethylene (APDE) and its potassium salt [K(APDE)] were synthesized through an aromatic nucleophilic substitution reaction between FOX‐7 and picryl chloride. APDE and K(APDE) were characterized by elemental analysis, IR, NMR spectroscopy, and X‐ray diffraction. APDE has a 3D wavy layered stacking structure similar to FOX‐7. K(APDE) (peak temperature (Tip)=185.6 °C and impact sensitivity (IS)=19.6 J) presents better stability than APDE (tap=133.3 °C and IS=15.7 J). The reasons why the stability of APDE is lower than that of FOX‐7 and picryl chloride are analyzed. The detonation velocity (D) and detonation pressure (P) of APDE (8.36 km s−1 and 31.3 Gpa) are close to those of FOX‐7 and RDX. The thermal decomposition of K(APDE) is very violent, and its detonation performance (D=9.14 km s−1 and P=38.6 Gpa) is comparable to that of HMX, indicating that K(APDE) has good potential to be a high explosive.

Enforced Planar FOX-7-like Molecules: A Strategy for Thermally Stable and Insensitive π-Conjugated Energetic Materials

“…Molecular modification has been utilized to generate many energetic derivatives based on FOX-7 and many synthetic strategies have been developed . It is worth noting that these methods typically involve FOX-7 as a starting material . However, such an approach does not always provide competitive alternatives relative to FOX-7.…”