Abstract
Acidity of ADNBF (7-amino-4,6-dinitrobenzofuroxan) crystallized from acetic acid taken as a reaction medium was found to be 0.14–0.2%, which is not acceptable in view of the long term stability of final products. Inclusion of acetic acid during azidation reaction of the TeNA (2,3,4,6-tetranitroaniline) to ATNA (3-azido-2,4,6-trinitroaniline) and formation of ADNBF crystals from ATNA in acetic acid was found to be the main reason for the high acidity of assynthesized ADNBF crystals. In the present experiments, to reduce the acidity of ADNBF, ATNA, which is an intermediate compound, was separated from acetic acid, and ADNBF crystals were obtained by thermolysis of ATNA from various solvents. The acidity of ADNBF crystals from ethanol was found to be 0.05–0.06%, and their shape and size distribution were cubic or tetragonal and 5–30 μm, respectively, which may be suitable for applying the explosive formulations.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Wierzbowska, K. Piotrowski, J. Koralewska, N. Hutnik and A. Matynia, Korean J. Chem. Eng., 26(1), 175 (2009).
B.C. Kim, H.W. Kang and Y. H. Kim, Korean J. Chem. Eng., 23(5), 789 (2006).
W. Hyung, Y. Kim, S. Haam and K.-K. Koo, Korean J. Chem. Eng., 23(5), 819 (2006).
D. Watt, Insensitive munition: The effect of aging upon lifecycle, 2004 Insensitive Munitions & Energetic Materials Technology Symposium, San Francisco, CA, November 15–16 (2004).
R. Doherty and D. Watt, Insensitive munitions-coming of age, 35th Int. Annual Meeting of ICT, Karlsruhe, Germany, June 29–July 2 (2004).
H. Schubert, History of and experiences with insensitive explosives, Symposium Insensitive Energetic Materials, Pfinztal, Germany, March 6–7 (2007).
O.H. Johansen, K. Smith, T. Halvorsen, J.D. Kristiansen, A. Berg, R. Gjersoe and G. Nervstad, Review and update for RS-RDX and RS-HMX, Symposium Insensitive Energetic Materials, Pfinztal, Germany, March 6–7 (2007).
W. P. Norris, 7-Amino-4,6-dinitrobenzofuroxan, an insensitive high explosive, NWC TP 6522, Naval Weapons Center, China Lake, CA, USA (1984).
H. L. Ammon and D. Zhang, Acta Crystallogr. C, 42, 724 (1986).
W. P. Norris, Improved synthesis of 7-amino-4,6-dinitrofuroxan, an insensitive high explosive, NWC TP 8724, Naval Weapon Center, China Lake, CA, USA (1985).
R.M. Doherty and R. L. Simpson, A comprehensive evaluation of several insensitive high explosives, 28th Int. Annual Meeting of ICT, Karlsruhe, Germany, June 24–27 (1997).
J.-R. Cho, A new safe synthetic procedure of TeNA(2,3,4,6-Tetranitroaniline), Insensitive Munitions & Energetic Materials Technology Symposium, San Francisco, CA, November 15–16 (2004).
J. F. Weber, US Patent, 5,136,041 (1992).
G. Stedman, J. Chem. Soc., 1702 (1960).
Detailed Specification of HMX (Cyclotetramethylene tetranitramine), MIL-DTL-5444C NOT 1, US Department of Defense (2004).
E. Lieber and A. E. Thomas III, Appl. Spectrosc., 15,5, 144 (1961).
K. Nakanishi and P.H. Solomon, Infrared absorption spectroscopy, 2nd Ed., Holden-Day Inc., San Francisco, CA (1977).
E. Oliveri-Mandala and E. Calderaro, Gazz. Chim. Ital., 45,I, 311 (1915).
R. E. Schaad, US Patent, 2,557,924 (1951).
J. H. Boyer, J. Am. Chem. Soc., 73, 5248 (1951).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, JW., Kim, JK., Kim, E.J. et al. Preparation of ADNBF with low-acidity by reactive crystallization. Korean J. Chem. Eng. 27, 666–671 (2010). https://doi.org/10.1007/s11814-010-0061-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-010-0061-6