D. Fischer, T. M. Klapötke, J. Stierstorfer
ARTICLE
Experimental Section
Acknowledgement
Financial support of this work by the Ludwig-Maximilian University
of Munich (LMU), the U.S. Army Research Laboratory (ARL), the
Armament Research, Development and Engineering Center (ARDEC),
the Strategic Environmental Research and Development Program
(SERDP) and the Office of Naval Research (ONR Global, title: “Syn-
thesis and Characterization of New High Energy Dense Oxidizers
(HEDO) - NICOP Effort” under contract nos. W911NF-09–2-0018
(ARL), W911NF-09–1-0120 (ARDEC), W011NF-09–1-0056 (AR-
DEC) and 10 WPSEED01–002 / WP-1765 (SERDP) is gratefully ac-
knowledged. The authors acknowledge collaborations with Dr. Mila
Krupka (OZM Research, Czech Republic) in the development of new
testing and evaluation methods for energetic materials and with Dr.
Muhamed Sucesca (Brodarski Institute, Croatia) in the development
of new computational codes to predict the detonation and propulsion
parameters of novel explosives. We are indebted to and thank Dr. Rob-
ert (Bob) Chapman (NAWC China Lake) for many inspired discus-
sions.
All explosive formulations consisted of 75 mg diazidoglyoxime (ex-
plosive) and 100 mg agent defeat ingredient: 100 mg RDX (reference
without fluorine and iodine), 50 mg RDX + 50 mg PTFE (PTFE as
potential fluorine source); [NH4]+[IF2O2]–, [C(NH2)3]+[IF2O2]–. The
formulation was placed in a plastic tube (diameter 5 mm, length 5 cm)
and initiated with an electrical match.
A standardized spore suspension (2 mL, MERCK, No. 1.11499.0001)
of geobacillus stearothermophilus (2.2 × 108 spores·mL–1) was loaded
in a hermetically sealed 2 L polyethylene (PE) lined detonation bomb
in the center of which the above described plastic tube containing the
agent defeat formulation was detonated. Immediately after detonation
(within 5 min) the contents of the PE lined bomb was rinsed out and
incubated for 72 hrs at 55 °C using an Agar-based medium (Merck,
No.1.07881.0500). The numbers of colonies counted are summarized
in Table 4.
Hexogen (RDX): Synthesized analog to
a literature described
procedure.[31] Urotropine (12.0 g, 86 mmol) was dissolved in 100 %
nitric acid (90 mL, 2.2 mol) at 20 °C. The solution was stirred for
40 min at room temperature and was afterwards added in small por-
tions to a mixture of sodium nitrite (1.23 g, 18 mmol) and 65 % nitric
acid (6 mL) while the temperature was kept between 50 °C and 70 °C.
After addition, the mixture was kept for further 40 min at 70 °C and
was afterwards cooled to 5 °C and poured into crushed ice (300 mL).
The precipitate was filtered, washed with water (120 mL) and dried
References
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1
yielding 15.6 g (82 %) of a colorless and crystalline solid. H NMR
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([D6]DMSO, 25 °C): δ = 6.06; 13C{1H} NMR ([D6]DMSO, 25 °C):
δ = 61.7; EA (C3H6N6O6, 222.12): calcd.: C 16.22, H 2.72, N 37.84 %;
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´
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300 mW, 25 °C): ν = 813 (100), 794 (86), 485 (14), 352 (15), 320 (19)
˜
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kept under diethyl ether. Raman (1064 nm, 300 mW, 25 °C): ν = 1017
˜
(71), 848 (83), 838 (60), 819 (100), 539 (7), 521 (5), 465 (14), 398
(10), 359 (10), 342 (18), 333 (18), 306 (18), 293 (13) cm–1.
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scribed in the literature.[8] Dichloroglyoxime[7] (784 mg, 5 mmol) was
dissolved in dimethylformamide (10 mL). At 0 °C sodium azide
(841 mg, 12.93 mmol) was added. The suspension was stirred for
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(atr): ν = 3209 (w), 2170 (w), 2123 (w), 1622 (w), 1400 (w), 1361 (w),
˜
1286 (m), 1013 (vs), 930 (m), 920 (s), 855 (s), 731 (s) cm–1; Raman
(1064 nm, 300 mW, 25 °C): = 2166 (8), 2129 (5), 2091 (3), 1621
ν
˜
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(100), 1457 (14), 1390 (12), 1216 (19), 1034 (3), 882 (20), 672 (3),
442 (6) cm–1. 1H NMR ([D6]DMSO, 25 °C): δ = 12.08; 13C{1H} NMR
([D6]DMSO, 25 °C): δ = 136.5; EA (C2H2N8O2, 170.09): calcd.:
C 14.12, H 1.19, N 65.88 %; found: C 14.38, H 1.46, N 66.01 %;
BAM drophammer: 1.5 J; friction tester: <5 N; ESD: 7 mJ.
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Z. Anorg. Allg. Chem. 2011, 660–665