Comparative theoretical kinetics and thermodynamics study on high-energy insensitive explosive 1,1-diamino-2,2-dinitroethene synthesis.
Two synthesis methods were investigated in this study in order to explore feasible reaction pathways to obtain the target DADNE product: (1) the nitration of tetrahalogen ethene and (2) the reaction of acetamidine hydrochloride with dicarbonyl dichloride. Through theoretical simulation, the findings revealed that synthesis was possible, starting from acetamidine hydrochloride in a hydrated environment, followed by subsequent reaction routes via cyclization of the methoxy-substituted acetamidine anion intermediate with oxalyl chloride to form 2-methoxy-2-methyl-imidazolan-4,5-dione, acid-catalyzed synthesis of 2-methylene-imidazolan-4,5-dione, nitration using nitric acid to obtain 2-dinitromethylene-imidazolan-4,5-dione, and hydrolysis to produce 1,1-diamino-2,2-dinitroethene. A total energy of 1048.4 kJ mol(-1) was needed to carry out the reaction according to calculation of the energy barriers at each stage, as shown by the reaction profiles.
Department of Chemical and Materials Engineering, Chung Cheng Institute of Technology, National Defense University, Taoyuan, Taiwan, Republic of China. minhsienliu@gmail.com.
Min-Hsien
MH
Liu
Department of Chemical and Materials Engineering, Chung Cheng Institute of Technology, National Defense University, Taoyuan, Taiwan, Republic of China.
Chuan-Wen
CW
Liu
1,1-diamino-2,2-dinitroethene; Acetamidine hydrochloride; Feasible pathway; Tetrahalogen ethene