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Design and Synthesis of Novel Energetic Oxirane Monomers Containing a Molecular Explosive Moiety
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 Title & Authors
Design and Synthesis of Novel Energetic Oxirane Monomers Containing a Molecular Explosive Moiety
Shen, Yechen; Kwon, Younghwan; Kim, Jin Seuk;
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Energetic monomers with new design concept were synthesized for energetic prepolymers. Novel energetic monomers consisted of ring-opening polymerizable oxirane and a molecular explosive moiety instead of small explosophores as energetic functional groups. According to the design concept, glycidyl dinitroazetidine (GDNAZ) and glycidyl nitroazetidinol(GNAZO) energetic monomers were synthesized, respectively, and characterized by NMR, EA and GC MS. Heat of formation and detonation performance were calculated by theoretical method to evaluate energy performance of these novel energetic monomers. The result revealed that GDANZ and GNAZO possessed high potential as new energetic monomers for synthesizing energetic prepolymers and binders in PBXs.
Energetic Monomer;Glycidyl Dinitroazetidine;Glycidyl Nitroazetidinol;
 Cited by
A. Provatas, "Energetic Polymers and Plasticisers for Explosive Formulations - A Review of Recent Advances," DSTO-TR-0966, Aeronautical and Maritime Research Laboratory (AMRL), 2000.

S. W. Ducan and D. C. Mathew, "Evaluation of 1,3,3-Trinitroazetidine (TNAZ) -A High Performance Melt-Castable Explosive," DSTO-TR-0702, Aeronautical and Maritime Research Laboratory (AMRL), 1998.

Y.-H. Kwon, J.-S. Kim, H.-S. Kim, "1-Glycidyl-3,3-dinitroazetidine Containing Explosive Moiety and Preparation Method Thereof", US Patent 7,829,729 B2, 2010.

T. G. Archibald, R. Gilardi, K. Baum, C. George, "Synthesis and X-ray Structure of 1,3,3-Trinitroazetidine," The Journal of Organic Chemistry, Vol. 22, No. 9, pp. 2920-2924, 1990.

A. R. Kartritzky, D. J. Cundy, J. Chen, "Novel Synthesis of 1,3,3-Trinitroazetidine," Journal of Heterocyclic Chemistry, Vol. 31, No. 2, pp. 271-275, 1994. crossref(new window)

A. P. Marchand, D. Rajgopal, S. G. Bott, T. G. Archibald, "A Novel Approach to the Synthesis of 1,3,3-Trinitroazetidine," The Journal of Organic Chemistry, Vol. 60, No. 15, pp. 4943-4946, 1995. crossref(new window)

M. D. Coburn, G. Buntain, B. W. Harris, K. Y. Lee and M. M. Stinecipher, "Synthesis Improvement and Characterization of 1,3,3-Trinitroazetidine (TNAZ)," Joint DOD/DOE Munitions Technology Development Preliminary Report, 1989.

R. L. McKenney Jr., T. G. Floyd, W. E. Stevens, T. G. Archibald, A. P. Marchand, G. V. M. Sharma and S. G. Bott, "Synthesis and Thermal Properties of 1,3-Dinitro-3-(1,3-dinitroazetidine-3-yl)azetidine (TNDAZ) and Its Admixtures with 1,3,3- Trinitroazetidine (TNAZ)", Journal of Energetic Materials, Vol. 16, No. 2-3, pp. 199-235, 1998. crossref(new window)

Z. Jalovy, S. Zeman, M. Suceska, P. Vavra, K. Dudek and M. Rajic, "1,3,3-Trinitroazetidine (TNAZ)- Part-I, Synthesis and Properties," Journal of Energetic Materials, Vol. 19, No. 2-3, pp. 219-239, 2001. crossref(new window)

A. P. Marchand, D. Rajagopal, S. G. Bott and T. G. Archibald, "Additions of X-Y Across the C(3)-N.sigma.-Bond in 1-Aza-3-ethylbicyclo[1.1.0]butane. Novel Routes to 3-Substituted Azetidines," The Journal of Organic Chemistry, Vol. 59, No. 18, pp. 5499-5501, 1994. crossref(new window)

M. D. Coburn, M. D. Kiskey, J. C. Oxley, J. L. Smith, W. Zheng and E. Rgers, "Synthesis and Spectra of Some $^1H-$, $^{13}C$, and $^{15}N$-labled Isomers of 1,3,3-Trinitroazetidine and 3,3-Dinitroazetidinium nitrate," Journal of Energetic Materials, Vol. 16, No. 2-3, pp. 73-99, 1998. crossref(new window)

D. L. Heywood, B. Phillips, "The Reaction of Epichlorohydrin with Secondary Amines," Journal of the American Chemical Society, Vol. 80, No. 5, pp. 1257-1259, 1958. crossref(new window)

E. Witek, A. Kochanowski and E. Bortel, "On the Reaction of Glycidol with a Secondary Amine," Macromolecular Rapid Communications, Vol. 21, No. 16, pp. 1108-1112, 2000. crossref(new window)

P. Politzer, J. S. Murray, J. M. Seminario, P. Lane, M. E. Grice and M. C. Concha, "Computational Characterization of Energetic Materials," Journal of Molecular Structure: Theochem, Vol. 573, No. 1-3, pp. 1-10, 2001. crossref(new window)

D. Habibollahzadeh, M. E. Grice, M. C. Concha, J. S. Murray and P. Politzer, "Nonlocal Density Functional Calculation of Gas Phase Heats of Formation," Journal of Computational Chemistry, Vol. 16, No. 5, pp. 654-658, 1995. crossref(new window)

M. H. Keshavarz and M. K. Tehrani, "A New Method for Determining Gas Phase Heat of Formation of Aromatic Energetic Compounds," Propellants, Explosives, Pyrotechnics, Vol. 32, No. 2, pp. 155-159, 2007. crossref(new window)

S. G. Cho, E. M. Goh, J. R. Cho and J. K. Kim, "Theoretical Studies on Molecular and Explosive Properties of 4,4,5,5-Tetranitro-2,2-bi-1H-imidazole (TNBI)," Propellants, Explosives, Pyrotechnics, Vol. 31, No. 1, pp. 33-37, 2006. crossref(new window)

J. Zhang, H. M. Xiao and X. D. Gong, "Theoretical studies on Heats of Formation for Polynitrocubanes Using the Density Functional Theory B3LYP Method and Semiempirical MO Methods," Journal of Physical Organic Chemistry, Vol. 14, No. 8, pp. 583-588, 2001. crossref(new window)

D. S. Watt and M. D. Cliff, "TNAZ based Meltcast Explosives: Technology Review and AMRL Research Directions," DSTO-TR-0702, 1998.