Decomposition of azo- and hydrazo-linked bis triazines

Journal of Energetic Materials

Volumn 27, Issue 2, 2009, Pages 63-93

  Oxley, Jimmie C ^a   Smith, James L ^a   Moran, Jesse S ^a  

^a UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

Azo bis triazines; Hydrazo bis triazines; Thermal decomposition

Indexed keywords

EID: 61449249884     PISSN: 07370652     EISSN: 15458822     Source Type: Journal    
DOI: 10.1080/07370650802405174     Document Type: Article

References (38)

1. Nielsen, A. T., A. P. Chafin, S. L. Christian, D. W. Moore, M. P. Nadler, R. A. Nissan, D. J. Vanderah, R. D. Gilardi, C. F. George, and J. L. Flippen-Anderson. 1998. Synthesis of polyazapolycyclic caged polynitramines. Tetrahedron, 54(39): 11793-11812.
2. Zhang, M.-X., P. E. Eaton, and R. Gilardi. 2000. Hepta- and octanitrocubanes. Angewandte Chemie International Edition, 39(2): 401-404.
3. Chavez, D. E., M. A. Hiskey, and R. D. Gilardi. 2000. 3,3′-Azobis(6-amino-1,2,4,5-tetrazine): A novel high-nitrogen energetic material. Angewandte Chemie International Edition, 39(10): 1791-1793.
4. Hiskey, M. A., N. Goldman, and J. R. Stine. 1998. High-nitrogen energetic materials derived from azotetrazolate. Journal of Energetic Materials, 16: 119-127.
5. Huynh, M. H.V., M. A. Hiskey, D. E. Chavez, and R. D. Galardi. 2005. Preparation, characterization, and properties of 7-nitrotetrazolo[1,5-f] furazano[4,5-b]pyridine 1-oxide. Energetic Materials, 23: 99-106.
6. Koppes, W. 2006. triazoloaminotriazinyltetrazine(TATTz) salts: Insensitive propellant ingredients. Paper presented at the 2006 Insensitive Munitions & Energetic Materials Technology Symposium.
7. Chapman, R. D., W. S. Wilson, J. W. Fronabarger, L. H. Merwin, and G. S. Ostrom. 2002. Prospects of fused polycyclic nitroazines as thermally insensitive energetic materials. Thermochimica Acta, 384(1-2): 229-243.
8. Oxley, J. C., J. L. Smith, and H. Chen. 2002. Thermal decomposition of high-nitrogen energetic compounds - Dihydrazidos-tetrazine salts. Thermochimica Acta, 384(1-2): 91-99.
9. Sivabalan, R., M. Anniyappan, S. J. Pawar, M. B. Talawar, G. M. Gore, S. Venugopalan, and B. R. Gandhe. 2006. Synthesis, characterization and thermolysis studies on triazole and tetrazole based high nitrogen content high energy materials. Journal of Hazardous Materials, 137(2): 672-680.
10. Ch, G. 1963. Syntheses with s-triazine. Angewandte Chemie International Edition, 2(6): 309-323.
11. Jurgens, B., E. Irran, J. Senker, P. Kroll, H. Muller, and W. Schnick. 2003. Melem (2,5,8-triamino-tri-s-triazine), an important intermediate during condensation of melamine rings to graphitic carbon nitride: Synthesis, structure determination by X-ray powder diffractometry, solid-state NMR, and theoretical studies. Journal of the American Chemical Society, 125(34): 10288-10300.
12. Costa, L. and G. Camino. 1988. Thermal behaviour of melamine. Journal of Thermal Analysis, 34: 423-429.
13. Smolin, E. M. and L. Rapoport. 1959. s-Triazines and Derivatives. New York: Interscience Publishers.
14. Utschig, T., M. Schwarz, G. Miehe, and E. Kroke. 2004. Synthesis of carbon nanotubes by detonation of 2,4,6-triazido-1,3,5-triazine in the presence of transition metals. Carbon, 42(4): 823-828.
15. Gillan, E. G. 2000. Synthesis of nitrogen-rich carbon nitride networks from an energetic molecular azide precursor. Chemistry of Materials, 12(12): 3906-3912.
16. Kroke, E., M. Schwarz, V. Buschmann, G. Miehe, H. Fuess, and R. Riedel. 1999. Nanotubes formed by detonation of C/N precursors. Advanced Materials, 11(2): 158-161.
17. Huynh, M. H. V., M. A. Hiskey, C. J. Pollard, D. P. Montoya, E. L. Hartline, and R. Gilardi. 2004. 4,4′,6,6′-Tetra-substituted hydrazo- and azo-1,3,5-triazines. Journal of Energetic Materials, 22(4): 217-229.
18. Thurston, J. T., J. R. Dudley, D. W. Kaiser, I. Hechenbleikner, F. C. Schaefer, and D. Holm-Hansen. 1951. Cyanuric chloride derivatives. I. Aminochloro-s-triazines. Journal of the American Chemical Society, 73(7): 2981-2983.
19. Kaiser, D. W., J. T. Thurston, J. R. Dudley, F. C. Schaefer, I. Hechenbleikner, and D. Holm-Hansen. 1951. Cyanuric chloride derivatives. II. Substituted melamines. Journal of the American Chemical Society, 73(7): 2984-2986.
20. Dudley, J. R., J. T. Thurston, F. C. Schaefer, D. Holm-Hansen, C. J. Hull, and P. Adams. 1951. Cyanuric chloride derivatives. III. Alkoxy-s-triazines. Journal of the American Chemical Society, 73(7): 2986-2990.
21. Schaefer, F. C., J. T. Thurston, and J. R. Dudley. 1951. Cyanuric chloride derivatives. IV. Aryloxy-s-triazines. Journal of the American Chemical Society, 73(7): 2990-2992.
22. Dudley, J. R. 1951. Cyanuric chloride derivatives. IX. Dissociation constants of substituted melamines and related triazines. Journal of the American Chemical Society, 73(7): 3007-3008.
23. Thurston, J. T., F. C. Schaefer, J. R. Dudley, and D. Holm-Hansen. 1951. Cyanuric chloride derivatives. V. Reaction of alkoxy-s-triazines and aryloxy-s-triazines with amines. Journal of the American Chemical Society, 73(7): 2992-2996.
24. Schaefer, F. C., J. R. Dudley, and J. T. Thurston. 1951. Cyanuric chloride derivatives. VI. Rearrangement reactions of 2,4-dialkoxy-6-amino-s- triazines. Journal of the American Chemical Society, 73(7): 2996-2999.
25. Dudley, J. R., J. T. Thurston, F. C. Schaefer, C. J. Hull, D. Holm-Hansen, and P. Adams. 1951. Cyanuric chloride derivatives. VII. Transesterification reactions of alkoxy-s-triazines. Polyammelide ethers. Journal of the American Chemical Society, 73(7): 2999-3004.
26. Schaefer, F. C., J. R. Dudley, and J. T. Thurston. 1951. Cyanuric chloride derivatives. VIII. Vinylamino-s-triazines. Journal of the American Chemical Society, 73(7): 3004-3006.
27. D'Alelio, G. F. and R. H. Becker. 1960. Preparation of some sulfonylhydrazine derivatives of s-triazine. Journal of Organic Chemistry, 25: 202-205.
28. Koppes, W. M. and M. E. Sitzmann. 2004. Preparation of bis(triazolo)triazines as novel explosive and pyrotechnic agents. Patent No. US 6833454.
29. Loew, P. and C. W. Weis. 1976. Azo 1,3,5-triazines. Journal of Heterocyclic Chemistry, 13(4): 829-833.
30. Huynh, M.-H. V., M. A. Hiskey, E. L. Hartline, D. P. Montoya, and R. Gilardi. 2004. Polyazido high-nitrogen compounds: Hydrazo- and azo-1,3,5-triazine. Angewandte Chemie International Edition, 43(37): 4924-4928.
31. Li, X. T., S. H. Li, S. P. Pang, Y. Z. Yu, and Y. J. Luo. 2007. A new efficient route for the synthesis of 4,4′,6,6′-tetra(azido)azo-1,3, 5-triazine. Chinese Chemical Letters, 18(9): 1037-1039.
32. Handelsman-Benory, E., M. Botoshansky, M. Greenberg, V. Shteiman, and M. Kaftory. 2000. Methyl rearrangement of methoxy-triazines in the solid- and liquid-state. Tetrahedron, 56(36): 6887-6897.
33. Fridman, N., M. Kapon, and M. Kaftory. 2003. 2-Chloro-4,6-dimethoxy-1,3, 5-triazine. Acta Crystallographica Section C, 59(12): o685-o686.
34. Engel, P. S. 1980. Mechanism of the thermal and photo-chemical decomposition of azoalkanes. Chemical Reviews, 80(2): 99-150.
35. Neuman, R. C., R. H. Grow, G. A. Binegar, and H. J. Gunderson. 1990. cis-Diazenes. Viscosity effects, one-bond scission, and cis-trans isomerization. Journal of Organic Chemistry, 55(9): 2682-2688.
36. Patai, S.. 1971. The chemistry of the azido group. In S. Patai (ed.), The Chemistry of Azido Groups, London: Interscience Publishers.
37. Zheng, W., N. B. Wong, X. Liang, X. Long, and A. Tian. 2004. Theoretical prediction of properties of triazidotri-s-triazine and its azido-tetrazole isomerism. Journal of Physical Chemistry A, 108(5): 840-847.
38. Hammerl, A., T. M. Klapötke, and R. Rocha. 2006. Azidetetrazole ring-chain isomerism in polyazido-1,3,5-triazines, triazido-s-heptazine, and diazidotetrazines. European Journal of Inorganic Chemistry, 11: 2210-2228.