Process Optimization for the Gas-Liquid Heterogeneous Reactive Crystallization Process Involved in the Preparation of the Insensitive High Explosive TATB

• Autorzy: Nandi A. K. , Kshirsagar A. S. , Thanigaivelan U. , Bhattacharyya S. C. , Mandal A. K. , Pandey R. K. , Bhattacharya B.
• Języki publikacji: EN

Abstrakty

EN

The thermally stable, insensitive, high explosive 1,3,5-triamino-2,4,6- trinitrobenzene (TATB) is manufactured by amination of 1,3,5-trichloro-2,4,6- trinitrobenzene (TCTNB) in toluene with NH3 gas. It is an isothermal, single-feed, semi-batch, gas-liquid heterogeneous, reaction crystallization process. The amination process is discussed by applying the chemical engineering methodology of mass transfer and reactive crystallization processes based on Two-Film Mass- Transfer (TFMT) theory. Kinetic expressions have been developed to define the chemical reactions as well as the physical phenomena (mass transfer) associated with this process. A single expression has been derived to explain the dependence of the ammonia consumption rate on various process parameters. Subsequently, the influence of various process parameters on the product quality (particle size and chloride impurity content) has been studied on the laboratory scale. Finally, the process has been established in the pilot plant, with optimized process conditions, to realize TATB of desired particle size and chloride content. The effects of feeding excess ammonia, and the presence of mercaptans/hydrogen sulphide impurities in poor quality toluene on the formation of certain undesirable by-products in TATB, are also discussed.

Słowa kluczowe

EN

TATB; TCTNB; amination; reaction crystallization; chloride impurity; particle size

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2014
• Tom: Vol. 11, no. 1
• Strony: 31--57
• Opis fizyczny: Bibliogr. 44 poz., rys., tab.

Twórcy

autor

Nandi A. K.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

autor

Kshirsagar A. S.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

autor

Thanigaivelan U.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

autor

Bhattacharyya S. C.

• Advanced Centre for Energetic Materials, Nasik-422009, India

autor

Mandal A. K.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

autor

Pandey R. K.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

autor

Bhattacharya B.

• High Energy Materials Research Laboratory, Chemical Engineering and Pilot Plant Division, Sutarwadi, Pune-411017, India

Bibliografia

• [1] Dobratz B.M., The Insensitive High Explosive Triaminotrinitrobenzene (TATB): Development and Characterisation: 1888 to 1994, Report LA-13014-H, Los Alamos National Laboratory, Los Alamos, NM, 1995.
• [2] Boddu V.M., Viswanath D.S., Ghosh T.K., Damavarapu R., 2,4,6-Triamino-1,3,5- trinitrobenzene (TATB) and TATB-based Formulations − a Review, J. Hazard. Mater., 2010, 181, 1-8.
• [3] (a) Agrawal J.P., High Energy Materials: Propellants, Explosives and Pyrotechnics, Wiley, Hoboken, NJ, 2010; (b) Agrawal J.P., Hodgson R.D., Organic Chemistry of Explosives, Wiley, Hoboken, NJ, 2007.
• [4] Bellamy A.J., Ward S.J., Golding P., A New Synthesis Route to 1,3,5-Triamino- 2,4,6-trinitrobenzene (TATB), Propellants Explos. Pyrotech., 2002, 27, 49-58.
• [5] Mitchell A.R., Pagoria P.F., Schmidt R.D., A New Synthesis of TATB Using Inexpensive Starting Material and Mild Reaction Conditions, 27th Int. Annu. Conf. ICT, Karlsruhe, 1996.
• [6] Ott D.G., Benziger T.M., Preparation of 1,3,5-Triamino-2,4,6-trinitrobenzene from 3,5-Dichloroanisole, J. Energ. Mater., 1987, 5, 343-354.
• [7] Quinlin W.T., Estes V.L., Evans W.H., Schaffer C.L., Pilot Scale Synthesis of TATB, Report MHSMP-76-20, Mason and Hanger-Silas Mason Company, Pantex Plant: Amarillo, TX, 1976.
• [8] Benziger T.M., Manufacture of TATB, 12th Int. Annu. Conf. ICT, Karlsruhe, 1981, 491-503.
• [9] Ervin M., LeClaire E., Price D., Tucker N., Mahoney T., Robinson C., Sleadd B., Steinhoff L., Manufacture of Triaminotrinitrobenzene (TATB) by the Benziger Method at Holston Army Ammunition Plant, 2012 Insensitive Munitions & Energetic Material Technology Symposium (IMEMTS), Las Vegas, NV, May 14-17, 2012.
• [10] Nandi A.K., Sutar V.B., Bhattacharyya S.C., Thermal Hazards Evaluation for sym- TCB Nitration Reaction Using Thermal Screening Unit (TSU), J. Therm. Anal. Calorim., 2004, 76, 895-901.
• [11] Narasimhan V.L., Bhattacharyya S.C., Mandal A.K., Nandi A.K., Scaling Up the Process for Preparing 1,3,5-Triamino-2,4,6-trinitrobenzene (TATB), HEMRL Report 6/2006, High Energy Materials Research Laboratory, Sutarwadi, Pune, India, 2006.
• [12] Nandi A.K., Ghosh M., Sutar V.B., Mandal A.K., Pandey R.K., 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.
• [13] Nandi A.K., Kasar S.M., Thanigaivelan U., Mandal A.K., Pandey R.K., Formation of the Sensitive Impurity 1,3,5-Triamino-2-chloro-4,6-dinitrobenzene in Pilot Plant TATB Production, Org. Process. Res. Dev., 2012, 16, 2036-2042.
• [14] Nandi A.K., Sutar V.B., Jadhav V.V., Mali N.P., Mandal A.K, Pandey R.K., Bhattacharyya B., Hazardous Wastes Generated in Manufacture of High Explosive 1,3,5-Triamino-2,4,6-trinitrobenzene(TATB), J. Hazard. Toxic Radioact. Waste, 2013 (in press).
• [15] Talawar M.B., Agarwal A.P., Anniyappan M., Gore G.M., Asthana S.N., Venugopalan S., Method for Preparation of Fine TATB (2-5μm) and Its Evaluation in Plastic Bonded Explosive (PBX) Formulations, J. Hazard. Mater., 2006, B137, 1848-1852.
• [16] Cady H.H., Larson A.C., The Crystal Structure of 1,3,5-Triamino-2,4,6- trinitrobenzene, Acta Crystallogr., 1965, 18, 485-496.
• [17] Foltz M.F., Maienschein J.L., Green L.G., Particle Size Control of 1,3,5-Triamino- 2,4,6-trinitrobenzene by Recrystallization from DMSO, J. Mater. Sci., 1996, 31, 1741-1750.
• [18] Zhang H., Sun J., Kang B., Shu Y., Shu X., Liu Y., Liu X., Crystal Morphology Controlling of TATB by High Temperature Anti-Solvent Recrystallization, Propellants Explos. Pyrotech., 2012, 37, 172 -178.
• [19] Nandi A.K., Kasar S.M., Thanigaivelan U., Ghosh M., Mandal A.K., Bhattacharyya 25, 213-231.
• [20] Yang G., Nie F., Huang H., Zhao L., Pang W., Preparation and Characterization of Nano-TATB Explosive, Propellants Explos. Pyrotech., 2006, 31(5), 390-396.
• [21] Estes Z.L., Chlorine Free Synthesis of TATB. Report MHSMP-77-24, Mason and Hanger-Silas Mason Company, Pantex Plant, Amarillo, TX, 1977.
• [22] Locke J.G., Estes Z.L., Emulsion Amination of TCTNB, Report MHSMP-78-26, Mason and Hanger-Silas Mason Company, Pantex Plant, Amarillo, TX, 1978.
• [23] Benziger T.M., Method for the Production of High-purity Triaminotrinitrobenzene, US Patent 4032377 A, 1977.
• [24] Benziger T.M., Method of Making Fine Grained Triaminotrinitrobenzene, US Patent 4481371, 1984.
• [25] Schaffer C.L., Quinlin W.T., Analysis of Chloronitrobenzene in TATB, Report MHSMP-82-25, Mason and Hanger-Silas Mason Company, Pantex Plant, Amarillo, TX, 1982.
• [26] Danckwerts P.V., Gas-liquid Reactions, McGraw-Hill, New York, 1970.
• [27] Lina R., Zhanga J., Bai Y., Mass Transfer of Reactive Crystallization in Synthesizing Calcite Nanocrystal, Chem. Eng. Sci., 2006, 61, 7019-7028.
• [28] Wachi S., Jones A.G., Mass Transfer with Chemical Reaction and Precipitation, Chem. Eng. Sci., 1991, 4, 1027-1033.
• [29] Perry H.R., Green D.W., Perry’s Chemical Engineers’ Handbook (7th ed.), McGraw- Hill: New York, 1997.
• [30] Mehilal, Prasad U.S., Survey R.N., Agrawal J.P., Determination of Chlorine Content in 1,3,5-Triamino-2,4,6-trinitrobenzene by Converting It into 1,3,5-Trihydroxy- 2,4,6-trinitrobenzene by Treatment with Aqueous Sodium Hydroxide, Analyst, 1998, 123, 397-398.
• [31] Rigdon P., Stephens F.B., Harrar J.E., Precise Assay of TATB by the Determination of Total Amino and Nitro Functional Group, Propellants Explos. Pyrotech., 1983, 8, 206-211.
• [32] Sykes P., A Guide Book to Mechanism in Organic Chemistry, Orient Longman Ltd., New Delhi, India, 1988.
• [33] Levenspiel O., Chemical Reaction Engineering (3rd ed.), John Wiley and Sons, New York, 1999.
• [34] Myerson A.S., Handbook of Industrial Crystallization, Butterworth-Heinemann, Boston, MA, 1993.
• [35] Mullin J.W., Crystallization (4th ed.), Butterworth-Heinemann, Oxford, 2001.
• [36] Stodinger J., Roberts P.V., A Critical Compilation of Henry’s Law Constant Temperature Dependence Relations for Organic Compounds in Dilute Aqueous Solutions, Chemosphere, 2001, 44, 561-576.
• [37] Choong K.L., Smith R., Optimization of Semi-batch Reactive Crystallization Processes, Chem. Eng. Sci., 2004, 59, 1529-1540.
• [38] Barrett P., Smith B., Worlitschek J., Bracken V., O’Sullivan B., O’Grady D., A Review of the Use of Process Analytical Technology for the Understanding and Dev., 2005, 9, 348-355.
• [39] Kim S., Lotz B., Lindrud M., Girard K., Moore T., Nagarajan K., Alvarez M., Lee T., Nikfar F., Davidovich M., Srivastava S., Kiang S., Control of the Particle Properties of a Drug Substance by Crystallization Engineering and the Effect on Drug Product Formulation, Org. Process Res. Dev., 2005, 9, 894-90.
• [40] Lindberg M., Rasmuson Å.C., Supersaturation Generation at the Feed Point in Reaction Crystallization of a Molecular Compound, Chem. Eng. Sci., 2000, 55, 1735-1746.
• [41] Zauner R., Jones A.G., Mixing Effects on Product Particle Characteristics from Semi-batch Crystal Precipitation, Chem. Eng. Res. Des., 2000, 78(A6), 894-901.
• [42] Welcher F.J., Standard Methods of Chemical Analysis (6th ed.), Vol.2: Industrial and Natural Products and Non-instrumental Methods, Part-B, Robert E. Krieger Publishing Company, Malabar, Florida, 1963.
• [43] Yasuda S.K., Simultaneous Determination of 1,3-Dinitro-2,4,6-trichlorobenzene and 1,3-Dinitro-2,4,5,6-tetrachlorobenzene in 1,3,5-Trichloro-2,4,6-trinitro-benzene, J. Chromatogr., 1972, 72, 481-486.
• [44] Narasimhan V.L., Bhattacharyya S.C., Mandal A.K., Nandi A.K., Provisional Specification for TATB, No. HEMRL/CEPP/PS/364, High Energy Materials Research Laboratory, Sutarwadi, Pune, India, 2005.