Calculation of the Density and Detonation Properties of C, H, N, O and F Compounds: Use in the Design and Synthesis of New Energetic Materials
DOI:
https://doi.org/10.29356/jmcs.v53i3.991Keywords:
Density, Detonation Pressure, Detonation Velocity, Specific Impulse, Energetic Materials, Synthesis, Energetic Polymers, Cubanes, Nitramines, Furazans, TetrazolesAbstract
The estimation of the density and detonation properties of C, H, N, O, F explosives is discussed. A simple computer program, “Energy”, first developed at the Naval Weapons Center-China Lake in the early 1980’s is presented in an updated form. This program allows the rapid calculation of the estimated properties of both known and hypothetical energetic materials. A review of the use of this program in the synthesis of new energetic materials is given.
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References
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72. Bottaro, J. L.; Schmitt, R. J.; Penwell, P. A.; Ross, D. S. U. S. Patent 5198204, 1993.
73. Eaton, P. E.; Zhang, M.X.; Gilardi, R.; Gilbert, N.; Iyer, S.; Surapaneni, R. Propellents, Explosives, Pyrotechnics 2002, 27, 1-6.
74. Willer, R. L.; Day, R. S.; Gilardi, R.; George, C. J. Hetero. Chem. 1992, 29, 1835-1838.
75. Tselinskii, I. V.; Mel’nikova, S. F.; Vergizov, S. N. Zh. Organich. Khimii 1995, 31, 1125-1127.
76. Willer, R. L.; Day, R. S.; Park, D. J. U. S. Patent 5,460,669, 1995.
77. Williams, G. K.; Brill, T. B. Combustion Flame 1998, 114, 569576.
78. Gilardi, R.; George, C. Naval Research Laboratory, unpublished results.
79. Solodyuk, G. D.; Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev, V. D. J. Org. Chem. USSR 1981, 17, 861-865.
80. Novikova, T. S.; Melnikova, T. M.; Kharitonova, O. V.; Kulagina, V. O.; Aleksandrova, N. S.; Sheremetev, A. B.; Pivina, T. S.; Khmelnitskii, L. I.; Novikov, S.S. Mendeleev Commun. 1994, 230.
81. Schmidt, R. D., LLNL, unpublished results.
82. Willer, R. L.; Hashemi, A. B., Fluorochem, Inc., unpublished.
83. Gasco, A. M.; Cena, C.; Di Stilo, A.; Ermondi, G.; Medana, C.; Gasco, A. Helv. Chim. Acta 1996, 79, 1803-1817.
84. Meyer, K. G. Org. Prep. Proced. Int. 2004, 36, 361-362.
2. Exner, O. Collect. Czech. Chem. Commun., 1967, 32, 1-22.
3. Nielsen, A. T. Naval Weapons Center TP 5452, 1973.
4. Tarver, C. M.; Coon, C. L.; Guimont, J. M. SRI Report PYU 5425, 1977.
5. Tarver, C. M. J. Chem. Eng. Data, 1979, 24, 136-145.
6. Imirizi, A.; Perini, B. Acta Cryst. 1977, A33, 216-218.
7. Cady, H. H. LANL Report-7760-MS, 1979.
8. Cichra, D. A.; Holden, J. R.; Dickinson, C. NSWC TR-79-273, 1979.
9. Stine, J. R. LANL Report -8920, 1981.
10. Kamlet, M.; Jacobs, S. J. J. Chem. Phys. 1968, 48, 23-35.
11. Micro PEP computer program, Martin Marietta Corporation, 1987.
12. Rothstein, L. R.; Petersen, R. Propellants and Explosives 1979, 4, 56-60.
13. Rothstein, L. R.; Petersen, R. Propellants and Explosives 1981, 6, 91-93.
14. Rice, B. M.; Hare, J. J. J. Phys. Chem. A 2002, 106, 1770-1783.
15. Byrd, E. F. C.; Rice, B. M. J. Phys. Chem. A 2006, 110, 10051013.
16. Rice, B. M.; Hare, J. J.; Byrd, E. F. C. J. Phys. Chem. A 2007, 111, 10874-10879.
17. Kotomin, A. A.; Kozlov, A. S. Russ. J. Appl. Chem. 2006, 79, 957-966.
18. Willer, R. L.; Chafin, A. P.; Doyle, J. P. NWC Technical Memorandum 5144, August 1983.
19. Gunasekaran, A.; Jayachandran, T.; Boyer, J. H.; Trudell, M. L. J. Hetero. Chem. 1995, 32, 1405-1407.
20. Chen, O. T. ATK –Elkton, 1985.
21. Boulton, C. TLC Consultants, San Dimas, CA, 2005.
22. (a) Willer, R. L. Propellants and Explosives 1983, 8, 65. (b) Willer, R. L.; Naval Weapons Center TP-6303, 1981.
23. Edwards, A.; Webb, G. A. J. Chem Soc., Perkins Trans. I 1977, 18, 1989-1992.
24. Lowe-Ma, C. K.; Willer, R. L. Naval Weapons Center TP-6681, 1987.
25. Willer, R. L.; Atkins, R. J. Org. Chem. 1984, 49, 5147-5150.
26. Willer, R. L. J. Org. Chem. 1984, 49, 5150-5154.
27. Lowe-Ma, C. K., Acta Cryst. C , 1990, 46, 1029-1033.
28. Nielsen, A. T. Polynitropolyazaadamatane Explosives, Proposal to the Office of Naval Research, March, 1980.
29. Nielsen, A. T.; More, D. W.; Willer, R. L. Naval Weapons Center TP-6513, 1984.
30. Nielsen, A. T.; Moore, D. W.; Chafin, A. P.; Willer, R. L. Naval Weapons Center TP-6623, 1985.
31. Willer, R. L. Naval Weapons Center IR & D Proposal, June 1982.
32. Nielsen, A. T.; Nissan, R. A.; Vanderah, D.; Coon, C. L.; Gilardi, R. D.; George, C. F.; Flippen-Anderson, J. J. Org. Chem. 1990, 55, 1459-1463.
33. Nielsen, A. T.; Chafin, A. P.; Christian, S. L.; Moore, D. W.; Nadler, M. P.; Nissan, R. A.; Vanderah, D. J. Tetrahedron 1998, 54, 11793-11812.
34. Gilbert, E. E., letter to author, dated 3 March, 1981.
35. Coburn, M. D. J. Hetero. Chem. 1968, 5, 83-87.
36. Sun, Q.; Fu, X.; Jiang, M.; Yu, D.; Du, Y. Proceding of International Symposium on Pyrotechnics and Explosives, Beijing, China, Academic Publishers, 1987, p 412.
37. (a) Willer, R. L.; Moore, D. W. J. Org. Chem. 1985, 50, 51235127. (b) Willer, R. L. NWC TP-6397, 1982. (c) Willer, R. L. NWC TP-6461, October 1983.
38. Fischer, J. W.; Nissan, R. A.; Lowe-Ma, C. K. J. Hetero. Chem. 1991, 28, 1677-1681.
39. Tselinskii, I. V.; Melnikova, S. F.; Romanova, T. V.; Pirogov, S. V.; Khisamutdinov, G. Kh.; Mratkhuzina, T. A.; Korolev, V. L.; Kondyukov, I. Z.; Abdrakhmanov, I. Sh.; Smirnov, S. P. Russ. J. Org. Chem., 1997, 33, 1656-1665.
40. Sheremetev, A. B.; Yudin, I. L. Mendeleev Commun. 1996, 247248.
41. Starchenkov, I. B.; Andrianov, V. G. Chem. Heterocycl. Compd. 1996, 32, 618-620.
42. Willer, R. L. AFOSR TR-87-0869, ADA182898, 1987.
43. Willer, R. L.; Henry, R. A. J. Org. Chem. 1988, 53, 5371-5373.
44. Ermakov, A. S.; Serkov, S. A.; Tartakovski, V. A.; Novikova, T. S.; Khmel’nitskii, L. I. Chem. Heterocycl. Compd. 1994, 30, 976979.
45. Cichra, D. A.; Adolph, H. G. Synthesis 1983, 830-833.
46. Baum, K.; Berkowitz, P. T.; Grakauskas, V.; Archibald, T. G. J. Org. Chem. 1990, 55, 2920-2924.
47. Willer, R. L.; Day, R. S.; Marchand, A. P. U. S. Patent 5,368,662, 1994.
48. Provatas, A. DSTO-TR-0966, April 2000.
49. Agrawal, J. P. Prog. Energy Combustion Sci. 1998, 24, 1-30.
50. Frankel, M. B.; Flanagan, J. E. Energetic hydroxy-terminated azido polymer, US Patent 4,268,450, 1981.
51. Willer, R. L.; Day, R. S. Proceedings of the APDA Joint International Symposium on the Compatibility of Plastics and Other Materials with Explosives, Propellants and Ingredients, American Defense Preparedness Association, Oct. 1989, 258.
52. Colclough, E. Proceedings of the APDA Joint International Symposium on the Compatibility of Plastics and Other Materials with Explosives, Propellants and Ingredients, American Defense Preparedness Association, Oct. 1989, 235-240.
53. Willer, R. L.; Stern, A. G.; McGrath, D. K. CPIA Publication 550, 1991, 3, 223.
54. Willer, R. L.; Day, R. S.; Stern, A. G. US Patent 5,120.827, 1992.
55. Willer, R. L.; Day, R. S.; Stern, A. G. US Patent 5,380,777, 1995.
56. Willer, R. L.; McGrath, D. K. US Patent 5,591,936, 1997.
57. Willer, R. L.; McGrath, D. K. US Patent 5,798,480, 1997.
58. Willer, R. L.; McGrath, D. K. U. S. Patent 5,801,325, 1997.
59. Willer, R. L.; Day, R. S.; Stern, A. G. US Patent 5,162,494, 1992.
60. Willer, R. L.; Day, R. S.; Stern, A. G. US Patent 5,264,596, 1993.
61. Sanderson, A. J.; Martins, L. J.; Dewey, M. A. US Patent 6,861,501, 2005, and documents cited wherein.
62. Merritt, A. R.; Trivedi, N. J.; Ciaramitaro, D. A. ONR Molecule Synthesis Program Planning Meeting, September 9-10, 2008.
63. Eaton, P. E.; Cole, T. W. J. Am. Chem. Soc. 1964, 86, 3157-3158.
64. Alster, J.; Sandus, O. Working Group Meeting on Synthesis of High Density Energetic Materials, Hilton Head Island, SC, 1982.
65. Eaton, P. E.; Ravi Shankar, B. K.; Price, G. D.; Pluth, J. J.; Gilbert, E. E.; Alster, J.; Sandus, O. J. Org Chem. 1984, 49, 185186.
66. Eaton P. E.; Castaldi, G. J. Am. Chem. Soc. 1985, 107, 724-726.
67. Olsen, R. E., Basic Research in Solid Oxidizers, Aerojet-General Corporation, Contract No. AF04(611)-6549.
68. Cunkle, G.T.; Willer, R.L. SDIO Symposium on Innovative Science and Technology, SPIE Proceedings 1988, 872, 142.
69. Willer, R. L.; Stern, A. G. ONR Workshop on Advanced Propellants and Processing Science, Chestertown, MD, CPIA Publication 574, 1991, 15.
70. Butcher, R. J.; Gilardi, R. D.; George, C.; Flippen-Anderson, J. J. Chem. Crystal. 1996, 26, 381-388.
71. Agrawal, J. P.; Hodson, R. D. Organic Chemistry of Explosives, John Wiley and Sons, N. Y., 2007, 268.
72. Bottaro, J. L.; Schmitt, R. J.; Penwell, P. A.; Ross, D. S. U. S. Patent 5198204, 1993.
73. Eaton, P. E.; Zhang, M.X.; Gilardi, R.; Gilbert, N.; Iyer, S.; Surapaneni, R. Propellents, Explosives, Pyrotechnics 2002, 27, 1-6.
74. Willer, R. L.; Day, R. S.; Gilardi, R.; George, C. J. Hetero. Chem. 1992, 29, 1835-1838.
75. Tselinskii, I. V.; Mel’nikova, S. F.; Vergizov, S. N. Zh. Organich. Khimii 1995, 31, 1125-1127.
76. Willer, R. L.; Day, R. S.; Park, D. J. U. S. Patent 5,460,669, 1995.
77. Williams, G. K.; Brill, T. B. Combustion Flame 1998, 114, 569576.
78. Gilardi, R.; George, C. Naval Research Laboratory, unpublished results.
79. Solodyuk, G. D.; Boldyrev, M. D.; Gidaspov, B. V.; Nikolaev, V. D. J. Org. Chem. USSR 1981, 17, 861-865.
80. Novikova, T. S.; Melnikova, T. M.; Kharitonova, O. V.; Kulagina, V. O.; Aleksandrova, N. S.; Sheremetev, A. B.; Pivina, T. S.; Khmelnitskii, L. I.; Novikov, S.S. Mendeleev Commun. 1994, 230.
81. Schmidt, R. D., LLNL, unpublished results.
82. Willer, R. L.; Hashemi, A. B., Fluorochem, Inc., unpublished.
83. Gasco, A. M.; Cena, C.; Di Stilo, A.; Ermondi, G.; Medana, C.; Gasco, A. Helv. Chim. Acta 1996, 79, 1803-1817.
84. Meyer, K. G. Org. Prep. Proced. Int. 2004, 36, 361-362.
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