Preparation of ADNBF with low-acidity by reactive crystallization

Jun-Woo Kim; Jae-Kyeong Kim; Eui Jung Kim; Hyoun-Soo Kim; Kee-Kahb Koo

Korean Journal of Chemical Engineering, Vol.27, No.2, 666-671, February, 2010

DOI10.1007/s11814-010-0061-6 Export Citation

Preparation of ADNBF with low-acidity by reactive crystallization

Jun-Woo Kim, Jae-Kyeong Kim, Eui Jung Kim¹, Hyoun-Soo Kim², and Kee-Kahb Koo^†

Department of Chemical and Biomolecular Engineering, Sogang University, Seoul 121-742, Korea
¹Department of Chemical Engineering, University of Ulsan, Ulsan 680-742, Korea
²Agency for Defense Development, Daejeon 305-600, Korea

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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 for- mulations.

Keywords:7-Amino-4,6-dinitrobenzofuroxan;Acidity;Long-term Stability

[References]

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Kim BC, Kang HW, Kim YH, Korean J. Chem. Eng., 23(5), 789 (2006)
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Johansen OH, Smith K, Halvorsen T, Kristiansen JD, Berg A, Gjersoe R, Nervstad G, Review and update for RS-RDX and RS-HMX, Symposium Insensitive Energetic Materials, Pfinztal, Germany, March 6-7 (2007)
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[1] Wierzbowska B, Piotrowski K, Koralewska J, Hutnik N, Matynia A, Korean J. Chem. Eng., 26(1), 175 (2009)

[2] Kim BC, Kang HW, Kim YH, Korean J. Chem. Eng., 23(5), 789 (2006)

[3] Hyung W, Kim Y, Haam S, Koo KK, Korean J. Chem. Eng., 23(5), 819 (2006)

[4] Watt D, Insensitive munition: The effect of aging upon lifecycle, 2004 Insensitive Munitions & Energetic Materials Technology Symposium, San Francisco, CA, November 15-16 (2004)

[5] Doherty R, Watt D, Insensitive munitions-coming of age, 35th Int. Annual Meeting of ICT, Karlsruhe, Germany, June 29-July 2 (2004)

[6] Schubert H, History of and experiences with insensitive explosives, Symposium Insensitive Energetic Materials, Pfinztal, Germany, March 6-7 (2007)

[7] Johansen OH, Smith K, Halvorsen T, Kristiansen JD, Berg A, Gjersoe R, Nervstad G, Review and update for RS-RDX and RS-HMX, Symposium Insensitive Energetic Materials, Pfinztal, Germany, March 6-7 (2007)

[8] Norris WP, 7-Amino-4,6-dinitrobenzofuroxan, an insensitive high explosive, NWC TP 6522, Naval Weapons Center, China Lake, CA, USA (1984)

[9] Ammon HL, Zhang D, Acta Crystallogr. C, 42, 724 (1986)

[10] Norris WP, Improved synthesis of 7-amino-4,6-dinitrofuroxan, an insensitive high explosive, NWC TP 8724, Naval Weapon Center, China Lake, CA, USA (1985)

[11] Doherty RM, Simpson RL, A comprehensive evaluation of several insensitive high explosives, 28th Int. Annual Meeting of ICT, Karlsruhe, Germany, June 24-27 (1997)

[12] Cho JR, 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)

[13] Weber JF, US Patent, 5,136,041 (1992)

[14] Stedman G, J. Chem. Soc., 1702 (1960)

[15] Detailed Specification of HMX (Cyclotetramethylene tetranitramine), MIL-DTL-5444C NOT 1, US Department of Defense (2004)

[16] Lieber E, Thomas III AE, Appl. Spectrosc., 15(5), 144 (1961)

[17] Nakanishi K, Solomon PH, Infrared absorption spectroscopy, 2nd Ed., Holden-Day Inc., San Francisco, CA (1977)

[18] Oliveri-Mandala E, Calderaro E, Gazz. Chim. Ital., 45, 311 (1915)

[19] Schaad RE, US Patent, 2,557,924 (1951)

[20] Boyer JH, J. Am. Chem. Soc., 73, 5248 (1951)