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Study on the Nitrolysis of Hexamethylenetetramine by NMR‐Spectrometry, Part IV: A Novel Mechanism of the Formation of RDX from HA
Author(s) -
Fang Zhijie,
Wang Shaofang,
Li Fuping
Publication year - 1998
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/(sici)1521-4087(199812)23:6<317::aid-prep317>3.0.co;2-p
Subject(s) - hexamethylenetetramine , chemistry , nitric acid , carbon 13 nmr , nuclear chemistry , polymer chemistry , medicinal chemistry , stereochemistry , organic chemistry
The mechanisms of the nitrolysis of hexamethylenetetramine(hexamine or HA) with nitric acid, and with the mixture of nitric acid and ammonium nitrate to form 1,3,5‐trinitro‐1,3,5‐triazacyclohexane(hexogen or RDX) were studied by NMR tracing. It was found that HA immediately disappeared, while RDX was formed gradually, which indicates the formation of some intermediates in the HA nitrolysis to give RDX. The chemical shifts of the peaks in the 1 H‐ and 13 C‐NMR tracing spectra disagreed with the possible cyclic‐structure intermediates proposed by Wright and co‐workers. Comparison of the 13 C‐NMR spectra showed that the nitrolysis fragments in K process can be used to form RDX. Based on the results, structures of intermediates were proposed. All the evidences mentioned above suggested a novel mechanism of the formation of RDX from HA, i.e., the nitrolysis of HA first gives some open‐chain methylenenitramine intermediates, and the condensation of the latter gives RDX under certain conditions.