Synthesis of 14C-Labelled Octahydro-1,3,5,7-Tetranitro-1,3,5,7-Tetrazocine (HMX) and 15N-Isotopic Hexahydro-1,3,5-Trinitro-1,3,5-Triazine (RDX) for Use in Microcosm Experiments

PDF

Authors
  1. Ampleman, G.
  2. Marois, A.
  3. Thiboutot, S.
  4. Hawari, J.
  5. Greer, C.W.
  6. and others
Corporate Authors
Defence Research Establishment Valcartier, Valcartier QUE (CAN)
Abstract
Within the framework of an R & D project on the bioremediation of soils contaminated with energetic compounds, the biodegradation of energetic nitramine products such as octogen (HMX) and hexogen (RDX) is under study. Microcosm assays can be performed with radioactive carbon-14 labelled substrates or with isotopic nitrogen-15 labelled substrates in order to ascertain and monitor their biodegradation pathways and to optimize parameters for a bioremediation process. To synthesize 14C-HMX, acetylation of labelled hexamethylenetetramine (14C-HMTA) was done yielding 3,7-diacetyl-1,3,5,7-tetraazabicyclo-(3.3.1)-nonane (14C-DAPT) which was nitrated to obtain 1,5-diacetyloctahydro-3,7-dinitro-1,3,5,7-tetrazocine (14C-DADN) in one step. Nitrolysis of 14C-DADN was achieved using a mixture of 100% nitric acid and phosphorus pentoxide to yield 14C-HMX. The synthesis of this carbon-14 labelled HMX was optimized first using cold starting materials and then conducted with labelled compounds. To synthesize 15N-RDX, nitration of nitrogen-15 hexamethylenetetramine (15N-HMTA) was done according to the Hale process. 15N-HMTA was prepared by reacting cold formaldehyde with isotopic nitrogen-15 ammonium hydroxide.
Keywords
Bioremediation;Site restoration;Chief, Research and Developmnent (CRAD);Defence Research Establishments;Defence Research and Development Branch;Soil pollution
Report Number
DREV-TR-1999-199 — Technical Report
Date of publication
25 Jan 2000
Number of Pages
34
DSTKIM No
CA000506
CANDIS No
512589
Format(s):
Hardcopy;Document Image stored on Optical Disk

Permanent link

Document 1 of 1

Date modified: