cis-1,3,4,6-Tetranitrooctahydroimidazo-[4,5-d]imidazole (BCHMX), its properties and initiation reactivity

Journal of Hazardous Materials

Volumn 164, Issue 2-3, 2009, Pages 954-961

  Klasovitý, Dušan ^a   Zeman, Svatopluk ^a   Růžička, Aleš ^a   Jungová, Marcela ^a   Roháč, Michal ^a  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

cis 1,3,4,6 Tetranitrooctahydroimidazo 4,5 d imidazole; Detonation; Initiation; Sensitivity; Solubility

Indexed keywords

CIS-1,3,4,6-TETRANITROOCTAHYDROIMIDAZO-[4,5-D]IMIDAZOLE; CRYSTALLOGRAPHIC STUDIES; DETONATION VELOCITIES; ETHYL ACETATES; INITIATION; NITRAMINES; NITROGEN ATOMS; NITROMETHANE; NMR CHEMICAL SHIFTS; SENSITIVITY; SHORT CONTACTS; SINGLE BONDS; SUPRAMOLECULAR ARCHITECTURES; TEMPERATURE DEPENDENCES; TETRAHYDROFURANE; THERMAL STABILITIES;

ACETONE; ACETONITRILE; CHEMICAL REACTIVITY; DIMETHYL SULFOXIDE; ELECTRIC SPARKS; ESTERS; MOLECULAR CRYSTALS; MOLYBDENUM; SOLUBILITY; TERNARY SYSTEMS; THERMODYNAMIC STABILITY;

DETONATION;

CHEMICAL REACTION; EXPERIMENTAL STUDY; SOLUBILITY; TEMPERATURE EFFECT;

ANILINE COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; EXPLOSIVE AGENTS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; NITROBENZENES; NITROGEN ISOTOPES; TEMPERATURE;

EID: 62649166916     PISSN: 03043894     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2008.08.106     Document Type: Article

References (35)

1. Gilardi R., Flippen-Anderson J.L., and Evans R. cis-2,4,6,8-Tetranitro-1H,5H-2,4,6,8-tetraazabicyclo[3.3.0]octane, the energetic compound "bicyclo-HMX". Acta Cryst., Sect. E 58 (2002) 0972
2. Qiu L., Xiao H.-M., Ju X.-H., and Gong X.-D. Density functional theory study of solvent effects on the structure and vibrational frequencies of tetranitrotetraazabicyclooctane "bicyclo-HMX". Chin. J. Org. Chem. 63 5 (2005) 377
3. Chaykovsky M., and Koppes W.M. Synthesis of Energetic Materials. Annual Progress Rept., ADA199472, NSWC (Dec., 1987), Silver Spring, MD
4. G. Eck, M. Piteau, Process for the synthesis of 2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo (3.3.0) octane, U.S. Pat. 5,569,032 (Societe Nationale Des Poudres et Explosifs), 1997.
5. Agrawal J.P., and Hodgson R.D. Organic Chemistry of Explosives (2007), Willey & Sons, New Delhi p. 271
6. Otwinowski Z., and Minor W. Methods Enzymol. 276 (1997) 307
7. Altomare A., Cascarano G., Giacovazzo C., and Guagliardi A. Completion and refinement of crystal structures with SIR92. J. Appl. Cryst. 26 (1993) 343
8. Sheldrick G.M. SHELXL-97 (1997), University of Göttingen, Göttingen
9. Coppens P. Evaluation of absorption and extinction in single-crystal structure analysis. In: Ahmed F.R., Hall S.R., and Huber C.P. (Eds). Crystallographic Computing (1970), Munksgaard, Copenhagen 255
10. Cambridge Crystallographic Data Centre, CCDC 693279, Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EY, UK (Fax: +44-1223-336033; e-mail: deposit@ccdc.ac.uk or www: http://www.ccdc.cam.ac.uk).
11. Krupka M. Devices and equipment for testing of energetic materials. In: Vágenknecht J. (Ed). Proc. 4th Seminar "New Trends in Research of Energetic Materials" (April, 2001), Univ. Pardubice 222
12. Notice of Czech Mining Authority No. 246/1996 of Law Collect, Establishing more detailed conditions for allowing explosives, explosive objects and aids into use, and their testing, Aug. 13th, 1996, pp. 3200-3208.
13. Jarman D., Prinse W., and Bouma R. Electrostatic discharge initiation of CL-20: effect of discharge time and spark energy. Proc. 34th Int. Annual Conf. ICT. Karlsruhe, June (2003) 71/1
14. Zeman S., Friedl Z., Kočí J., Pelikán V., and Majzlík J. Electric spark sensitivity of nitramines. Part I. Aspects of molecular structure. Cent. Eur. J. Energ. Mater. 3 3 (2006) 27
15. Sućeska M. Test Methods for Explosives (1995), Springer, Heideleberg
16. C. Hochmann, B. Tipton Jr., M. Dutton, Propellant for the NASA standard initiator, Report NASA/TP-2000-210186, NASA, Lyndon B. Johnson Space Center, Houston, TX, Oct. 2000
17. Storm C.B., Stine J.R., and Kramer J.F. Sensitivity relationships in energetic materials. In: Bulusu S.N. (Ed). Chemistry and Physics of Energetic Materials (1990), Kluwer Acad. Publs., Dordrecht 605-639
18. Sitzman M.E., and Foti S.C. Solubilities of explosives. Dimethylformamide as general solvent for explosives. J. Chem. Eng. Data 20 (1975) 53
19. Zeman S., and Krupka M. New aspects of impact reactivity of polynitro compounds, Part III. Impact sensitivity as a function of the imtermolecular interactions. Propellents, Explos., Pyrotech. 28 (2003) 301
20. Kočí J., Zeman S., Majzlík J., and Strnad J. Notices to determination of the electric spark sensitivity of energetic materials. In: Vágenknecht J. (Ed). Proc. 5th Seminar "New Trends in Research of Energetic Materials" (2002), Univ. Pardubice 110
21. 15N NMR chemical shifts of nitramines. J. Energ. Mater. 17 (1999) 305
22. Kamlet M.J., and Jacobs S.J. Chemistry of detonations. I. Simple method for calculating detonation properties of carbon-hydrogen-nitrogen-oxygen explosives. J. Chem. Phys. 48 (1968) 23
23. Sinditskii V.P., Egorshev V.Y., and Berezin M.V. Study on combustion of new energetic nitramines. Proc. 32nd Annual Int. Conf. ICT. Karlsruhe (2001) 59/1
24. Eckhardt C.J., and Gavezzotti A. Computer simulations and analysis of structural and energetic features of some crystalline energetic materials. J. Phys. Chem., B 111 (2007) 3430
25. Grice M.E., Habibollahzadeh E., and Politzer P. Calculated structure, heat of formulation and decomposition energetics of 1,3-dinitro-1,3-diazacyclobutane. J. Chem. Phys. 100 (1994) 4706
26. Kohno Y., Ueda K., and Imamura A. Molecular dynamics simulations of initial decomposition process on the unique N{single bond}N bond in nitramines in the crystalline state. J. Phys. Chem. 100 (1996) 4701
27. Dickinson C., and Steward J.M. A direct determination of the crystal structure of 2,3,4,6-tetranitroaniline. Acta Cyst. 21 (1966) 663
28. Zeman S. Sensitivities of high energy compounds. In: Klapoetke T. (Ed). High Energy Density Compounds, Structure & Bonding vol. 125 (2007), Springer, Heidelberg, Germany 195-271
29. Zeman S. A study of chemical micro-mechanisms of initiation of organic polynitro compounds. In: Politzer P., and Murray J.S. (Eds). Energetic Materials. Part 2. Detonation, Combustion (2003), Elsevier B.V., Amsterdam, The Netherlands 25-52
30. Maksimov Yu.Ya., and Kogut E.N. Thermal decomposition of high-melting aromatic polynitro compounds in solution. Tr. Mosk. Khim.-Tekhnol. Inst. Mendeleeva 104 (1979) 30
31. Manelis G.B., Nazin G.M., Rubtsov Yu.I., and Strunin V.A. Thermal decomposition and combustion of explosives and powders (2003), Taylor & Francis Group, CRC Press, Boca Raton
32. Pepekin V.I., Makhov N., and Lebedev Yu.A. Teploty vzrychatogo razlozheniya individualnykh vzryvshchatykh veshchestv (heats of explosion of individual explosives). Dokl. Akad. Nauk SSSR 232 (1977) 852
33. Lebedev Yu.A., Miroshnichenko E.A., and Knobel' Yu.K. Termokhimiya Nitrosoedinenii (Thermochemistry of Nitrocompounds) (1970), Izdat Nauka, Moscow
34. Meyer R., Köhler J., and Homburg A. Explosives, 6th Compl. Rev. Ed. (2007), Wiley-VCH Verlag, Weinhem
35. Bondi A. van der Waals volumes and radii. J. Phys. Chem. 68 (1964) 441