Synthesis of CL‐20 by a Greener Method Using Nitroguanidine/HNO₃

Abstract

Abstract CL‐20 is a nitramine applied in both explosives and propellants. The traditional nitrolysis of tetraacetyldibenzylhexaazaisowurtzitane (TADB), as the key precursor for the synthesis of CL‐20, requires the use of N 2 O 4 /HNO 3 /H 2 SO 4 (so‐called mixed acid) which has its drawbacks, especially at industrial scales. Herein, the nitrolysis of TADB with a one pot method was investigated using nitroguanidine (NQ) and guanidinium nitrate (GN)/HNO 3 as new system for the synthesis of CL‐20. Positive features of these nitro‐debenzylation/nitro‐deacetylation methods include lack of mixed acids, simple work‐up and less hazardous reagents. The maximum yield of reaction (72 %) was obtained under optimized conditions (NQ (3.48 mmol) and TADB (0.58 mmol) in 98 % HNO 3 (5 mL) at 85 °C and 24 h).