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Study on the Mechanism of the Acetolysis of Hexamethylenetetramine
Author(s) -
Ju Chen,
Shaofang Wang,
Fuping Li
Publication year - 1990
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/prep.19900150205
Subject(s) - hexamethylenetetramine , formaldehyde , yield (engineering) , chemistry , methylene , nuclear chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
The acetolysis of hexamethylenetetramine (hexamine) to give 3,7‐diacetyl‐1,3,5,7‐tetraaza‐[3.3.1]‐bicyclononane (DAPT), 1,3,5,7‐tetraacetyl‐1,3,5,7‐tetraazacyclooctane (TAT) and 1,3,5‐triacetyl‐1,3,5‐triazacyclohexane (TRAT) was studied. NMR tracing showed the courses of acetolysis, the effects of the reaction conditions on its directions, and the evidence that the methylene degraded from hexamine was the formaldehyde. Based on these results, the acetolysis mechanism was proposed. The comparison of the acetolysis with the nitrolysis of hexamine showed that the two reactions experienced the similar courses, which would be useful for searching out a way to improve the yield of 1,3,5,7‐tetranitro‐1,3,5,7‐tetraazacyclooctane (HMX) in Bachmann process.