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Mild Method to Synthesize TATB by Amination of 1,3,5-Trialkoxy-2,4,6-Trinitrobenzene under Phase Transfer Catalysis Conditions

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Języki publikacji
EN
Abstrakty
EN
Nucleophilic amination, as a vital step in the synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) using 1,3,5-trialkoxy-2,4,6-trinitrobenzene (TORTNB) and aqueous ammonia as the starting materials and catalyzed by phase transfer catalysis (PTCs) under mild conditions is described. Various phase transfer catalysts, such as crown ethers, tertiary amines, quaternary ammonium salts, poly ethers and cyclodextrin, and various experimental parameters, such as no. of equivalents of PTC, mole ratio of ammonium hydroxide to the starting material, reaction time, reaction temperature and cycle times of the organic phase were investigated. The crown ethers, especially 18-crown-6, show good catalytic activity and re-usability for the amination of 1,3,5-triethoxy-2,4,6-trinitrobenzene giving a yield of 96.52%. This makes for a safe process and suitable for scale-up, because the reactions are carried out under atmospheric conditions. The material synthesised by the new system was characterized by DSC, SEM and LPS.
Rocznik
Strony
47--59
Opis fizyczny
Bibliogr. 24 poz., rys., tab.
Twórcy
autor
  • Nanjing University of Science and Technology 200, Xiaolingwei St., Xuanwu District, 210094 Nanjing, Jiangsu Province, China
autor
  • Nanjing University of Science and Technology 200, Xiaolingwei St., Xuanwu District, 210094 Nanjing, Jiangsu Province, China
autor
  • Nanjing University of Science and Technology 200, Xiaolingwei St., Xuanwu District, 210094 Nanjing, Jiangsu Province, China
autor
  • Nanjing University of Science and Technology 200, Xiaolingwei St., Xuanwu District, 210094 Nanjing, Jiangsu Province, China
autor
  • Nanjing University of Science and Technology 200, Xiaolingwei St., Xuanwu District, 210094 Nanjing, Jiangsu Province, China
Bibliografia
  • [1] Dobratz, B. M. Insensitive High Explosives Triaminotrinitrobenzene (TATB): Development and Characterization, 1988 to 1994. NTIS report LA-13014-H, Los Alamos National Laboratory, Los Alamos, NM, USA, 1995.
  • [2] Wei, C. X.; Huang, H.; Duan, X. H. Structures and Properties Prediction of HMX/ TATB Co-crystal. Propellants Explos. Pyrotech. 2011, 36: 416-423.
  • [3] Kuang, F. C.; Deng, M. Z. Preparation of Insensitive Composite Explosives HMX/ TATB Using Ultrasonic Method. Chin. J. Explos. Propellants 2011, 34(1): 45-48.
  • [4] Sun, J.; Huang, H.; Zhang, Y.; Zheng, M. X.; Liu, J. L. In-situ Coating of TATB on HMX. Energ. Mater. 2006, 14(5): 330-332 (in Chinese).
  • [5] Nandi, A.K.; Ghosh, M.; Sutar, V.B. Surface Coating of Cyclotetramethylenetetranitramine (HMX) Crystals with the Insensitive High Explosive 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB). Cent. Eur. J. Energ. Mater. 2012, 9(2): 119-130.
  • [6] Hofmann, H.; Rudolf, K. Process for the Production of a Pressed Insensitive Explosive Mixture. Patent US 0216822, 2004.
  • [7] Huang, B.; Hao, X. F.; Zhang, H. B.; Yang, Z. J.; Ma, Z. G.; Li, H. Z.; Nie, F. D.; Huang, H. Ultrasonic Approach to the Synthesis of HMX@TATB Core-shell Microparticles with Improved Mechanical Sensitivity. Ultrason. Sonochem. 2014, 21: 1349-1357.
  • [8] Yang, Z. J.; Li, J. S.; Huang, B.; Liu, S. J.; Huang, Z.; Nie, F. D. Preparation and Properties Study of Core-shell CL-20/TATB Composites. Propellants Explos. Pyrotech. 2013, 35: 1-8.
  • [9] Xu, R.; Tian, Y.; Liu, C. Study on the Desensitization of CL-20 with TATB. Chinese J. Energ. Mat. 2003, 11: 219-221.
  • [10] Aekins, R. L.; Nielsen, A. T. New Method for Preparing Pentanitroaniline and Triaminotrinitrobenzenes from Trinitrotoluene. Patent US 4248798A, 1981.
  • [11] Ott, D. G.; Benziger, T. M. Preparation of 1,3,5-Triamino-2,4,6-trinitrobenzene from 3,5-Dichloranisole. Patent US 4952733A, 1990.
  • [12] Velarde, S. P.; Mancini, V. E. Methods of Producing 1,3,5-Triamino-2,4,6-trinitrobenzene. Patent US 8030521B2, 2011.
  • [13] Atkins, R. L.; Hollins, R. A.; Wilson, W. S. Synthesis of Polynitro Compounds. Hexasubstituted Benzenes. J. Org. Chem. 1986, 51: 3261-3266.
  • [14] Mitchell, A. R.; Coburn, M. D. Synthesis and Purification of 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB). Patent US 0038297A1, 2005.
  • [15] Jackson, C. L.; Wing, J. F. On the Action of Nitric Acid on Symmetric Trichlorobenzene. Amer. Chem. J. 1887, 9: 384.
  • [16] Qiu, Y. S. The New Synthetic Method of TATB. Chinese J. Explos. 1987, 3: 7-11.
  • [17] Tian, Y.; Dong, H. S.; Li B. R. Study on Production of TATB by Ammonium Carbonate (Ⅰ): Experimental Synthesis and Semiworks Production. GFB-903-970001, Chinese Academy of Engineering Physics, SiChuan, China, 1997.
  • [18] Huang, J. L.; Zhang, L. Y.; Ma, Q.; Wang, Z. Improvement of Synthesis Technology of TATB Free from Chloride. Chinese J. Energ. Mat. 2012, 20: 551-554.
  • [19] Dehmlow, E. V.; Dehmow, S. S. Phase Transfer Catalysis. 3rd ed., VCH, Weinheim, Germany, 1993.
  • [20] Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-transfer Catalysis, Fundamentals, Application and Industrial Perspectives. Chapman & Hall, New York, 1994; ISBN 0-412-04071-9.
  • [21] Sasson, Y.; Neumann, R. Handbook of Phase-Transfer Catalysis, Blackie Academic & Professional, London, 1997; ISBN 978-0-7514-0258-2.
  • [22] Halpern, M. E. Phase Transfer Catalysis. ACS Symposium Series 659, American Society, Washington, DC, 1997.
  • [23] Hashimoto, T.; Maruoka, K. Recent Development and Application of Chiral Phasetransfer Catalysts. Chem. Rev. 2007, 107: 5656-5682.
  • [24] Bellamy, A. J.; Ward S. J.; Golding P. A New Synthetic Route to 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB). Propellants Explos. Pyrotech. 2002, 27: 49-58.
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę (zadania 2017).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-2e575b1c-41ab-43ea-a656-0cfb60069e47
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