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Synthesis of 14 C‐labelled octahydro‐1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocine (HMX) for use in microcosm experiments
Author(s) -
Ampleman G.,
Marois A.,
Thiboutot S.,
Hawari J.,
Greer C. W.,
Godbout J.,
Sunahara G. I.,
Shen C. F.,
Guiot S. R.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(19991230)42:13<1251::aid-jlcr281>3.0.co;2-a
Subject(s) - chemistry , hexamethylenetetramine , yield (engineering) , nitric acid , nuclear chemistry , carbon fibers , microcosm , organic chemistry , radiochemistry , environmental chemistry , thermodynamics , physics , materials science , composite number , composite material
To monitor the biodegradation of explosives in microcosm experiments, carbon‐14 labelled substrates such as 14 C‐HMX were needed. Many synthetic routes were evaluated to identify the best synthesis of 14 C‐HMX with high yield and minimal radioactive waste. To synthesize 14 C‐HMX, acetylation of labelled hexamethylenetetramine ( 14 C‐HMTA) was done yielding 3,7‐diacetyl‐1,3,5,7‐tetraazabicyclo‐[3.3.1]‐nonane ( 14 C‐DAPT) which was nitrated to obtain 1,5‐diacetyloctahydro‐3,7‐dinitro‐1,3,5,7‐tetrazocine ( 14 C‐DADN) in one step. Nitrolysis of 14 C‐DADN was achieved using a mixture of 100% nitric acid and phosphorus pentoxide to yield 14 C‐HMX. The synthesis of this carbon‐14 labelled HMX was optimized first using cold starting materials and then conducted with labelled compounds. This synthesis represents the best way of preparing high purity 14 C‐HMX with a high yield. Copyright © 1999 John Wiley & Sons, Ltd.