TY - JOUR
T1 - The Nitrolysis Mechanism of 3,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane
AU - Liu, Wen Jin
AU - Xu, Zhi Bin
AU - Cui, Ke Jian
AU - Xue, Min
AU - Meng, Zi Hui
AU - Huang, Xiao Chuan
AU - Ge, Zhong Xue
AU - Lin, Zhi Hui
AU - Qin, Guang Ming
N1 - Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2015/10
Y1 - 2015/10
N2 - Two intermediates, 1,5-dinitroso-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DNDS) and 1-nitroso-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane (MNX), were isolated and characterized in the synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX) from the nitrolysis of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) for the first time. When the nitrolysis of DPT was slowed down, two intermediates were detected with HPLC. It was proposed that electrophilic NO2+ and NO+ from HNO3 and N2O4 might attack nitrogen atoms at positions 3 and 7 of DPT to form the cations of the intermediates, then nucleophilic H2O attacked the bridge carbon atoms of DPT to produce the intermediates, which were oxidized to form HMX.
AB - Two intermediates, 1,5-dinitroso-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DNDS) and 1-nitroso-3,5,7-trinitro-1,3,5,7-tetraazacyclooctane (MNX), were isolated and characterized in the synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (HMX) from the nitrolysis of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) for the first time. When the nitrolysis of DPT was slowed down, two intermediates were detected with HPLC. It was proposed that electrophilic NO2+ and NO+ from HNO3 and N2O4 might attack nitrogen atoms at positions 3 and 7 of DPT to form the cations of the intermediates, then nucleophilic H2O attacked the bridge carbon atoms of DPT to produce the intermediates, which were oxidized to form HMX.
KW - DPT
KW - HMX
KW - Intermediate
KW - Mechanism
KW - Nitrolysis
UR - https://www.scopus.com/pages/publications/84944516986
U2 - 10.1002/prep.201500078
DO - 10.1002/prep.201500078
M3 - Article
AN - SCOPUS:84944516986
SN - 0721-3115
VL - 40
SP - 645
EP - 651
JO - Propellants, Explosives, Pyrotechnics
JF - Propellants, Explosives, Pyrotechnics
IS - 5
ER -