Modelling of the Effect of Concentrated Nitration Conditions on the Efficiency of the Production of ,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT)

• Autorzy: Hadi Z. , Esmaeilpour K. , Damiri S. , Afzali A. , Keshavarz M. H.

Identyfikatory

DOI

10.22211/cejem/78093

• Języki publikacji: EN

Abstrakty

EN

3,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) is one of the most important intermediates in the synthesis of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX). A suitably modified Bachmann process, nitrolysis of solid hexamine in the presence of ammonium nitrate-nitric acid and acetic anhydride on a laboratory scale, is introduced to increase the efficiency, production capacity and purity of the DPT produced. Various quantitative and qualitative analytical methods were used for the identification and quality control of the product. A central composite design (CCD) of experiments was used to optimize the production process, increasing the production capacity, reducing the amount of acetic acid as the reaction medium to a suitable limit, and examining the effects of the main factors impacting on the efficiency of the nitration, e.g. the volume of ammonium nitrate-nitric acid solution, nitration temperature reactor addition time and volume of acetic anhydride. The overall results indicated that DPT was obtained with an efficiency of 64.58% and a production capacity of 20.77 (100 g·mL−1).

Słowa kluczowe

EN

DPT; CCD; optimization; production capacity; efficiency

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2018
• Tom: Vol. 15, no. 1
• Strony: 72--84
• Opis fizyczny: Bibliogr. 34 poz., rys., tab.

Twórcy

autor

Hadi Z.

• Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr P.O. Box 83145/115, Islamic Republic of Iran

autor

Esmaeilpour K.

• Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr P.O. Box 83145/115, Islamic Republic of Iran

autor

Damiri S.

• Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr P.O. Box 83145/115, Islamic Republic of Iran

autor

Afzali A.

• Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr P.O. Box 83145/115, Islamic Republic of Iran

autor

Keshavarz M. H.

• Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr P.O. Box 83145/115, Islamic Republic of Iran

Bibliografia

• [1] Agrawal, J. P. High Energy Materials: Propellants, Explosives and Pyrotechnics. WILEY-VCH, 2010; ISBN 978-3-527-32610-5.
• [2] Klapötke, T. M. Chemistry of High Energy Materials. 3rd ed., Walter de Gruyter, Berlin 2015; ISBN 978-3-11-043932-8.
• [3] McKay, A.; Wright, G. F.; Richmond, H. Nitrolysis of Hexamethylenetetramine: II. Nitrolysis of 1,5-Endomethylene-3,7-dinitro-1,3,5,7-tetraza-cyclooctane (DPT). Canad. J. Res. 1949, 27(5): 462-468.
• [4] Keshavarz, M. H. Simple Relationship for Predicting Impact Sensitivity of Nitroaromatics, Nitramines, and Nitroaliphatics. Propellants Explos. Pyrotech. 2010, 35(2): 175-181.
• [5] Keshavarz, M. H.; Moghadas, M. H.; Kavosh Tehrani, M. Relationship between the Electrostatic Sensitivity of Nitramines and their Molecular Structure. Propellants Explos. Pyrotech. 2009, 34(2): 136-141.
• [6] Keshavarz, M. H.; Hayati, M.; Ghariban-Lavasani, S.; Zohari, N. A New Method for Prediction of Friction Sensitivity of Nitramines. Cent. Eur. J. Energ. Mater. 2015, 12(2): 215-217.
• [7] Keshavarz, M. H.; Moradi, S.; Ebrahimi Saatluo, B.; Rahimi, H.; Madram, A. R. A Simple Accurate Model for Prediction of Deflagration Temperature of Energetic Compounds. J. Therm. Anal. Calorim. 2013, 112(3): 1453-1463.
• [8] Khan, R. M. Problem Solving and Data Analysis Using Minitab: A Clear and Easy Guide to Six Sigma Methodology. John Wiley & Sons, 2013; ISBN 978-1-23(5): 775-777.
• [9] Stefaniak, L.; Urbanski, T.; Witanowski, M.; Farminer, A.; Webb, G. Structural Studies on Some 1,3,5,7-Tetraazabicyclo-[3,3,1]-nonane Derivatives. Tetrahedron 1974, 30(20): 3775-3779.
• [10] Keshavarz, M. H. Approximate Prediction of Melting Point of Nitramines, Nitrate Esters, Nitrate Salts and Nitroaliphatics Energetic Compounds. J. Hazard. Mater. 2006, 138(3): 448-451.
• [11] Radhakrishnan, S.; Talawar, M.; Venugopalan, S.; Narasimhan, V. Synthesis, Characterization and Thermolysis Studies on 3,7-Dinitro-1,3,5,7- tetraazabicyclo[3,3,1]nonane (DPT): A Key Precursor in the Synthesis of Most Powerful Benchmark Energetic Materials (RDX/HMX) of Today. J. Hazard. Mater. 2008, 152(3): 1317-1324.
• [12] Solomon, I. J.; Momii, R. K.; Jarke, F. H;, Kacmarek, A. J.; Raney, J. K.; Adlaf, P. C. Proton Magnetic Resonance Data for Some Intermediates and Products of Nitrolysis of Hexamethylenetetramine. J. Chem. Eng. Data 1973, 18(3): 335-337.
• [13] Oehlert, G. W. A First Course in Design and Analysis of Experiments. W.H. Freeman and Company, 2010; ISBN 0-7167-3510-5.
• [14] Surekha, B.; Rao, D. H.; Rao, G.; Vundavilli, P. R. Parappagoudar, M. Modeling and Analysis of Resin Bonded Sand Mould System Using Design of Experiments and Central Composite Design. J. Manuf. Sci. Prod. 2012, 12(1): 31-50.
• [15] Montgomery, D. C. Design and Analysis of Experiments. 5th ed., John Wiley & Sons, 2012; ISBN 978-1-118-14692-7.
• [16] Shi, L.; Zhao, G.; Zhang, Y.; Zheng, C.; Qin, G.; Lü, J. Theoretical Investigation on the Mechanism and Design of Catalysts for Nitrolysis of Hexamine. Chin. J. Chem. 2010, 28(9): 1553-1558.
• [17] Liu, W. J.; Xu, Z. B.; Cui, K. J.; Xue, M.; Meng, Z. H.; Huang, X. C.; Ge, Z. X.; Lin, Z. H.; Qin, G. M. The Nitrolysis Mechanism of 3,7‐Dinitro‐1,3,5,7‐tetraazabicyclo[3,3,1]nonane. Propellants Explos. Pyrotech. 2015, 40(5): 645-651.
• [18] Fedoroff, B. T.; Sheffield, O. E. Encyclopedia of Explosives and Related Items. Vol. 7, Picatinny Arsenal, Dover, NJ 1975.
• [19] Vágenknecht, J.; Zeman, S. Some Characteristics of 3,7-Dinitro-3,7-dinitroso and Dinitrate Compounds Derived from 1,3,5,7-Tetraazabicyclo[3,3,1]nonane. J. Hazard. Mater. 2005, 119(1): 1-11.
• [20] Choi, C.; Bulusu, S. The Crystal Structure of Dinitropentamethylenetetramine (DPT). Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1974, 30(6): 1576-1580.
• [21] McKay, A.; Wright, G. F.; Chute, W.; Downing, D.; Myers, G. The Nitrolysis of Hexamethylenenitramine: I. The Significance of 1,5-Endomethylene-3,7-dinitro-1,3,5,7-tetrazacyclooctane (DPT). Can. J. Res. 1949, 27(4): 218-237.
• [22] Il’yasov, S.; Lobanova, A. Alkaline Decomposition of Cyclic Nitramines. Russ.J. Gen. Chem. 2005, 75(1): 118-120.
• [23] Ermolin, N.; Zarko, V. Mechanism and Kinetics of the Thermal Decomposition of Cyclic Nitramines. Combust., Explos. Shock Waves (Engl. Transl.) 1997, 33(3): 251-269.
• [24] Xue, M.; Wu, S.; Liu, W.; Zhu, Q.; Meng, Z.; Lin, Z. Solubility of 3,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane in Ethanenitrile, Methanol, 1,1-Dichloroethane, Dimethyl Sulfoxide, Acetone, and Mixed Solvents. J. Chem. Eng. Data 2015, 60(6): 1683-1687.
• [25] Kaur, N.; Kishore, D. An Insight into Hexamethylenetetramine: a Versatile Reagent in Organic Synthesis. J. Iran. Chem. Soc. 2013, 10(6): 1193-1228.
• [26] Agrawal, J. P.; Hodgson, R. Organic Chemistry of Explosives. John Wiley & Sons, 2007; ISBN 978-0-470-02967-1.
• [27] Radhakrishnan, S.; Sunil Kumar, K.; Soman, T.; Narasimhan, V. Comparative Study on the Role of DPT on the Formation of HMX in Semi-Batch and Continuous Process. J. Energ. Mater. 2008, 26(2): 102-114.
• [28] Turhan, H.; Atalar, T.; Erdem, N.; Özden, C.; Din, B.; Gül, N.; Yildiz, E.; Türker, L. Hexamethylenetetramine Dinitrate (HDN): The Precursor for RDX Production by Bachmann Process. Propellants Explos. Pyrotech. 2013, 38(5): 651-657.
• [29] Song, X.; Wang, Y.; An, C.; Guo, X.; Li, F. Dependence of Particle Morphology and Size on Mechanical Sensitivity and Thermal Stability of Octahydro-1,3,5,7- tetranitro-1,3,5,7-tetrazocine. J. Hazard. Mater. 2008, 159(2): 222-229.
• [30] Reed, R. Jr. Notes-Reaction of Hexamine and Hexamine Dinitrate with Nitric Acid and Trifluoroacetic Anhydride in Liquid Sulfur Dioxide. J. Org. Chem. 1958, 23(5): 775-777.
• [31] Liu, X.; Lu, M.; Yu, X. Improved Preparation of 3,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) from Urea. Journal of the Iranian Chemical Research 2010, 3: 133-139.
• [32] Bing, L.; Ming, L. Synthesis of 3,7-Dinitro-1,3,5,7-tetraazabicyclo[3,3,1]nonane (DPT) Using Task-Specific Ionic Liquids as Recoverable Catalysts. Journal of Chemistry 2011, 8(1): 97-100.
• [33] Strecker, R. A. Preparation of 1,5-Methylene-3,7-dinitro-1,3,5,7-tetraazacyclooctane. Patent US 4,338,442, 1982.
• [34] Afzali, A.; Esmaeilpour, K.; Damiri, S.; Zoleikha, H.; Keshavarz, M. H. Increasing the Efficiency of the Production of 1,3,5,7-Tetranitro-1,3,5,7-tetrazocane (HMX). Cent. Eur. J. Energ. Mater. 2016, 13(4): 845-858.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).