Crystal Engineering of Energetic Materials: Co-crystals of Ethylenedinitramine (EDNA) with Modified Performance and Improved Chemical Stability

Chemistry - A European Journal

Volumn 21, Issue 31, 2015, Pages 11029-11037

  Aakeröy, Christer B ^a   Wijethunga, Tharanga K ^a   Desper, John ^a  

^a KANSAS STATE UNIVERSITY   (United States)

Author keywords

co crystals; crystal engineering; energetic materials; ethylenedinitramine; hydrogen bonds

Indexed keywords

CRYSTAL ENGINEERING; DETONATION; ETHYLENE; EXPLOSIVES; HYDROGEN BONDS;

CHEMICAL INSTABILITY; CO-CRYSTALLIZATIONS; CO-CRYSTALS; DETONATION PROPERTIES; ENERGETIC SUBSTANCE; ETHYLENEDINITRAMINE; HYDROGEN BOND ACCEPTORS; IMPACT SENSITIVITIES;

CHEMICAL STABILITY;

EID: 85027934094     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501721     Document Type: Article

References (73)

1. D. Guo, Q. An, W. A. Goddard, S. V. Zybin, F. Huang, J. Phys. Chem. C 2014, 118, 30202-30208;
2. T. Yan, K. Wang, X. Tan, J. Liu, B. Liu, B. Zou, J. Phys. Chem. C 2014, 118, 22960-22967.
3. J. H. Urbelis, J. A. Swift, Cryst. Growth Des. 2014, 14, 1642-1649;
4. K. B. Landenberger, A. J. Matzger, Cryst. Growth Des. 2010, 10, 5341-5347.
5. D. I. A. Millar, H. E. Maynard-Casely, D. R. Allan, A. S. Cumming, A. R. Lennie, A. J. Mackay, I. D. H. Oswald, C. C. Tang, C. R. Pulham, CrystEngComm 2012, 14, 3742-3749;
6. C. Wei, H. Huang, X. Duan, C. Peia, Propellants Explos. Pyrotech. 2011, 36, 416-423;
7. C. Ma, Z. Liu, Q. Yao, Can. J. Chem. 2014, 92, 803-808.
8. C. He, J. Zhang, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A 2013, 1, 2863-2868;
9. C. J. Underwood, C. Wall, A. Provatas, L. Wallace, New J. Chem. 2012, 36, 2613-2617.
10. K. B. Landenberger, A. J. Matzger, Cryst. Growth Des. 2012, 12, 3603-3609;
11. G. H. Tao, Y. Guo, Y. H. Joo, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2008, 18, 5524-5530.
12. G. Chen, W. Shi, M. Xia, W. Lei, F. Wang, X. Gong, J. Mol. Model. 2014, 20, 2326.
13. Y. Wang, Z. Yang, H. Li, X. Zhou, Q. Zhang, J. Wang, Y. Liu, Propellants Explos. Pyrotech. 2014, 39, 590-596.
14. M. M. Qasim, B. Moore, L. Taylor, P. Honea, L. Gorb, J. Leszczynski, Int. J. Mol. Sci. 2007, 8, 1234-1264;
15. V. K. Balakrishnan, A. Halasz, J. Hawari, Environ. Sci. Technol. 2003, 37, 1838-1843;
16. J. Zhang, C. He, D. A. Parrish, J. M. Shreeve, Chem. Eur. J. 2013, 19, 8929-8936.
17. D. Fischer, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, Chem. Eur. J. 2013, 19, 4602-4613.
18. P. Vishnoi, M. G. Walawalkar, R. Murugavel, Cryst. Growth Des. 2014, 14, 5668-5673;
19. Y. Ma, A. Zhang, C. Zhang, D. Jiang, Y. Zhu, C. Zhang, Cryst. Growth Des. 2014, 14, 4703-4713;
20. H. Li, Y. Shu, S. Gao, L. Chen, Q. Ma, X. Ju, J. Mol. Model. 2013, 19, 4909-4917.
21. Y. Ma, A. Zhang, X. Xue, D. Jiang, Y. Zhu, C. Zhang, Cryst. Growth Des. 2014, 14, 6101-6114;
22. X. Liu, Z. Su, W. Ji, S. Chen, Q. Wei, G. Xie, X. Yang, S. Gao, J. Phys. Chem. C 2014, 118, 23487-23498;
23. J. P. Shen, X. H. Duan, Q. P. Luo, Y. Zhou, Q. Bao, Y. J. Ma, C. H. Pei, Cryst. Growth Des. 2011, 11, 1759-1765.
24. A. P. Agrawal, Prog. Energy Combust. Sci. 1998, 24, 1-30.
25. T. M. Klapötke, D. G. Piercey, J. Stierstorfer, Eur. J. Inorg. Chem. 2013, 1509-1517.
26. O. Bolton, A. J. Matzger, Angew. Chem. Int. Ed. 2011, 50, 8960-8963;
27. Angew. Chem. 2011, 123, 9122-9125;
28. Z. Yang, H. Li, H. Huang, X. Zhou, J. Li, F. Nie, Propellants Explos. Pyrotech. 2013, 38, 495-501.
29. S. R. Anderson, D. J. amEnde, J. S. Salan, P. Samuels, Propellants Explos. Pyrotech. 2014, 39, 637-640;
30. H. R. Li, Y. J. Shu, C. Song, L. Chen, R. J. Xu, X. H. Ju, Chin. Chem. Lett. 2014, 25, 783-786.
31. C. Guo, H. Zhang, X. Wang, X. Liu, J. Sun, J. Mater. Sci. 2013, 48, 1351-1357.
32. K. B. Landenberger, O. Bolton, A. J. Matzger, Angew. Chem. Int. Ed. 2013, 52, 6468-6471;
33. Angew. Chem. 2013, 125, 6596-6599.
34. C. Zhang, Z. Yang, X. Zhou, C. Zhang, Y. Ma, J. Xu, Q. Zhang, F. Nie, H. Li, Cryst. Growth Des. 2014, 14, 3923-3928.
35. C. B. Aakeröy, T. K. Wijethunga, J. Benton, J. Desper, Chem. Commun. 2015, 51, 2425-2428.
36. H. Xue, G. Ye, B. Twamley, J. M. Shreeve, Chem. Mater. 2005, 17, 191-198.
37. G. C. Hale, US Patent 2.011.578, 1935, Dover, N.J.
38. United States Department of the Army Technical Manual, Military Explosives, Department of the Army, 1989.
39. B. T. Fedoroff, O. E. Sheffield, Encyclopedia of Explosives and Related Items, Vol.6, Picatinny Arsenal, 1974.
40. M. S. Kettner, T. M. Klapötke, T. G. Müller, M. Suc'eska, Eur. J. Inorg. Chem. 2014, 4756-4771.
41. H. S. Jadhav, M. B. Talawar, R. Sivabalan, D. D. Dhavale, S. N. Asthana, V. N. Krishnamurthy, J. Hazard. Mater. 2007, 143, 192-197;
42. G. Hervé, C. Roussel, H. Graindorge, Angew. Chem. Int. Ed. 2010, 49, 3177-3181;
43. Angew. Chem. 2010, 122, 3245-3249.
44. J. C. Hinshaw, W. W. Edwards, W. W. George, J. Gilardi, Heterocycl. Chem. 1992, 29, 1721-1724.
45. L. I. Bagal, M. S. Pevzner, A. N. Frolov, N. I. Sheludyakova, Khim. Geterotsikl. Soedin. 1970, 558-562.
46. R. Meyer, J. Köhler, A. Homburg, Explosives, Wiley-VCH, Weinheim, 2008.
47. V. P. Ivshin, T. N. Ivshina, L. G. Smirnova, M. G. Ponomareva, Zh. Org. Khim. 1984, 20, 7-13.
48. M. Robert, J. Pachman, Primary Explosives, Springer, Heidelberg, 2013.
49. R.W. Millar, Lead-Free Initiator Materials for Small Electro-explosive Devices for Medium Caliber Munitions, QineiQ/FST/CR032702/1.1, 2003.
50. A. O. Franz, US 2708623A, 1955, Olin Mathieson Chemical Corporation, Virginia.
51. J. W. Turley, Acta Crystallogr. Sect. B 1968, 24, 942-946.
52. C. B. Aakeröy, S. Panikkattu, B. DeHaven, J. Desper, CrystEngComm 2013, 15, 463-470.
53. Q. L. Yan, S. Zeman, J. Šelešovský, R. Svoboda, A. Elbeih, J. Therm. Anal. Calorim. 2013, 111, 1419-1430.
54. B. Yan, N. N. Zhao, H. X. Ma, J. R. Song, F. Q. Zhao, R. Z. S. Hu, S. Afr. J. Chem. 2013, 66, 136-139;
55. M. J. Kamlet, H. Hurwitz, J. Chem. Phys. 1968, 48, 3685-3692;
56. M. J. Kamlet, S. J. Jacobs, J. Chem. Phys. 1968, 48, 23-35.
57. J. Barton, Dust Explosion Prevention and Protection, IChemE, Rugby, 2002.
58. P. Patnaik, A Comprehensive Guide to the Hazardous Properties of Chemical Substances, Wiley, New York, 2007.
59. S. Li, Q. Li, R. Li, R. Liu, K. Yang, B. Liu, B. Zou, J. Phys. Chem. C 2014, 118, 23443-23450.
60. H. Wei, H. Gao, J. M. Shreeve, Chem. Eur. J. 2014, 20, 16943-16952;
61. P. F. Pagoria, G. S. Lee, A. R. Mitchell, R. D. Schmidt, Thermochim. Acta 2002, 384, 187-204.
62. CSD ConQuest1.17, 2013 Cambridge Crystallographic Data Centre, UK.
63. D. M. Badgujar, M. B. Talawar, S. N. Asthana, P. P. Mahulikar, J. Hazard. Mater. 2008, 151, 289-305.
64. T. K. Highsmith, J. M. Hanks, S. P. Velarde, J. C. Battaro, WO02060881, 2002, Alliant Techsystems Inc, Virginia.
65. C. B. Aakeröy, T. K. Wijethunga, J. Desper, CrystEngComm 2014, 16, 28-31.
66. N. Iranpoor, H. Firouzabadi, D. Khalili, S. Motevalli, J. Org. Chem. 2008, 73, 4882-4887.
67. N. R. Ayyangar, S. N. Naik, K. V. Srinivasan, Tetrahedron Lett. 1989, 30, 7253-7256.
68. T. M. Klapötke, B. Krumm, F. X. Steemann, G. Steinhauser, Safety Sci. 2010, 48, 28-34.
69. L. W. Kissinger, M. J. Schwartz, Org. Chem. 1958, 23, 1342-1344.
70. Spartan′08, Wavefunction, Inc.
71. O. Bolton, L. R. Simke, P. F. Pagoria, A. J. Matzger, Cryst. Growth Des. 2012, 12, 4311-4314.
72. K. B. Landenberger, O. Bolton, A. J. Matzger, J. Am. Chem. Soc. 2015, 137, 5074-5079;
73. L.R. Simpson, M.F. Foltz, LLNL Small-Scale Drop-Hammer Impact Sensitivity Test, Lawrence Livennore National Laboratory.