Synthesis of polyazapolycyclic caged polynitramines

Nielsen, Arnold T.; Chafin, Andrew P.; Christian, Stephen; Moore, Donald W.; Nadler, Melvin P.; Nissan, Robin A.; Vanderah, David J.; Gilardi, Richard; George, Clifford; Flippen‐Anderson, Judith L.

doi:10.1016/s0040-4020(98)83040-8

Cited by 412 publications

(281 citation statements)

References 63 publications

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“…The crystallographic parameters are referred from the refcode PUBMUU02 [27] and PUBMUU [27] of the Cambridge Structural Database (CSD) [28]. Considerable differences exist between the patterns and can be used to distinguish the polymorphs of HNIW.…”

Section: In-situ X-ray Powder Diffraction Analysismentioning

confidence: 99%

Thermally Induced Polymorphic Transformation of Hexanitrohexaazaisowurtzitane (HNIW) Investigated by in-situ X-ray Powder Diffraction

Liu¹,

Li²,

Ze-shan³

et al. 2016

Cent. Eur. J. Energ. Mater.

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Abstract:The ε→γ phase transition of HNIW induced by heat was investigated with in situ X-ray powder diffraction (PXRD). The effects of purity, particle size, insensitive additives and the time of isothermal heat treatment on the phase transition were evaluated. It was found that the phase transition is irreversible with changes in temperature, and the two phases can coexist in a certain temperature range. Moreover, the initial phase transition temperature increases with increasing purity and decreasing particle size of HNIW, and thus with the approximate crystal density. The addition of graphite and paraffin wax to HNIW as insensitive additives leads to a decrease in the initial phase transition temperature, but the addition of TATB does not affect the initial phase transition temperature. Thus, TATB is a suitable insensitive additive. Moreover, at the critical temperature, the isothermal time determined the efficiency of the ε-to γ-phase transition. This work lays the foundations for the choice of molding technologies, performance test methods, ammunition storage options, as well as the manufacture of HNIWbased explosive formulations.

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Section: In-situ X-ray Powder Diffraction Analysismentioning

confidence: 99%

Thermally Induced Polymorphic Transformation of Hexanitrohexaazaisowurtzitane (HNIW) Investigated by in-situ X-ray Powder Diffraction

Liu¹,

Li²,

Ze-shan³

et al. 2016

Cent. Eur. J. Energ. Mater.

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“…CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane) is a high-energy polycyclic nitramine compound with a rigid caged structure (25) (Fig. 1).…”

mentioning

confidence: 99%

Initial Reaction(s) in Biotransformation of CL-20 Is Catalyzed by Salicylate 1-Monooxygenase from Pseudomonas sp. Strain ATCC 29352

Bhushan

Halasz

Spain

et al. 2004

Appl Environ Microbiol

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“…1). Due to its higher energy and its moderate sensitivity, CL-20 is expected to replace earlier explosives (19,20,22,25). The production of CL-20 and its use in munitions and propellants can be expected to lead to environmental contamination.…”

mentioning

confidence: 99%

Biodegradation of the Nitramine Explosive CL-20

Trott¹,

Nishino²,

Hawari

et al. 2003

Appl Environ Microbiol

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The cyclic nitramine explosive CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane) was examined in soil microcosms to determine whether it is biodegradable. CL-20 was incubated with a variety of soils. The explosive disappeared in all microcosms except the controls in which microbial activity had been inhibited. CL-20 was degraded most rapidly in garden soil. After 2 days of incubation, about 80% of the initial CL-20 had disappeared. A CL-20-degrading bacterial strain, Agrobacterium sp. strain JS71, was isolated from enrichment cultures containing garden soil as an inoculum, succinate as a carbon source, and CL-20 as a nitrogen source. Growth experiments revealed that strain JS71 used 3 mol of nitrogen per mol of CL-20. 4,6,8,10,4,6,8,10,) is a new, highly energetic explosive related to the explosives RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) and HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine) (Fig. 1). Due to its higher energy and its moderate sensitivity, CL-20 is expected to replace earlier explosives (19,20,22,25). The production of CL-20 and its use in munitions and propellants can be expected to lead to environmental contamination. RDX and HMX, common contaminants in soil and groundwater at munition manufacturing sites and firing ranges, are toxic and possibly carcinogenic (7,8,11,12,16,23,27). Because of the structural similarity of CL-20 to RDX and HMX, it is likely that CL-20 has similar effects. So far, there is little information available about the properties of CL-20. In contrast to RDX and HMX, CL-20 is a caged molecule (Fig. 1). The water solubility of CL-20 is 4.8 mg/liter at 25°C (Stevens Institute of Technology [http://www.cee.stevens-tech.edu/ResProj.html]), which is lower than the solubility of the nitramines RDX and HMX (38.4 and 6.6 mg/liter at 20°C, respectively) (27).The microbial degradation of RDX and HMX under aerobic and anaerobic conditions has been extensively investigated (1, 2, 4-6, 9, 13-15, 17, 21). Under anaerobic conditions, three degradation pathways have been proposed. The first includes the production of nitroso derivatives of RDX and HMX, which are subject to further degradation (15, 21). Hawari et al. suggested a second degradation pathway which includes the direct ring cleavage of RDX and HMX without the initial reduction of the nitro groups (14, 15). The third proposed degradation pathway is based on N denitration prior to ring cleavage (1).Under aerobic conditions, RDX is degraded by a yet-unknown mechanism. The initial attack seems to be catalyzed by a cytochrome P450 (1a, 6, 24). RDX degradation by Rhodococcus sp. strain DN22 leads to the formation of nitrite, nitrous oxide, ammonia, formaldehyde, and a dead-end product with a molecular weight of 119 which was recently identified as 4-nitro-2,4-diazabutanal (1a, 5, 9). Fournier et al. proposed a degradation pathway which includes an initial denitration of RDX followed by ring cleavage to formaldehyde and the dead-end product (9).To the best of our knowledge, no biodegradation of CL-20 has...

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Synthesis of polyazapolycyclic caged polynitramines

Cited by 412 publications

References 63 publications

Thermally Induced Polymorphic Transformation of Hexanitrohexaazaisowurtzitane (HNIW) Investigated by in-situ X-ray Powder Diffraction

Thermally Induced Polymorphic Transformation of Hexanitrohexaazaisowurtzitane (HNIW) Investigated by in-situ X-ray Powder Diffraction

Initial Reaction(s) in Biotransformation of CL-20 Is Catalyzed by Salicylate 1-Monooxygenase from Pseudomonas sp. Strain ATCC 29352

Biodegradation of the Nitramine Explosive CL-20

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