Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2011-03-22
2011-03-22
Davis, Brian J (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C568S587000
Reexamination Certificate
active
07910776
ABSTRACT:
Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), from alkoxy derivatives of phloroglucinol, such as 5-methoxyresorcinol, 3,5-dimethoxyphenol, or 1,3,5-trimethoxybenzene, are disclosed. The alkoxy derivatives may be exposed to and directly nitrated with a reaction mixture comprising a sulfuric acid solution and at least one nitrate salt. The nitrated alkoxy derivative of phloroglucinol may be alkoxylated and, thereafter, aminated to produce the TATB.
REFERENCES:
patent: 1380186 (1921-05-01), Brewster
patent: 1396001 (1921-11-01), MacDonald
patent: 2246963 (1941-06-01), Wilkinson
patent: 3278604 (1966-10-01), Hoffman et al.
patent: 3394183 (1968-07-01), Dacons et al.
patent: 3933926 (1976-01-01), Salter et al.
patent: 3954852 (1976-05-01), Shen et al.
patent: 4032377 (1977-06-01), Benziger
patent: 4232175 (1980-11-01), Smith et al.
patent: 4434304 (1984-02-01), DeFusco, Jr. et al.
patent: 4745232 (1988-05-01), Schmitt et al.
patent: 4952733 (1990-08-01), Ott et al.
patent: 4997987 (1991-03-01), Ott et al.
patent: 5371291 (1994-12-01), Nader
patent: 5569783 (1996-10-01), Mitchell et al.
patent: 5633406 (1997-05-01), Mitchell et al.
patent: 6069277 (2000-05-01), Mitchell et al.
patent: 7057072 (2006-06-01), Mitchell et al.
patent: 7057073 (2006-06-01), Mitchell et al.
patent: 7737308 (2010-06-01), Straessler
patent: 7763753 (2010-07-01), Paraskos et al.
patent: 2355715 (2001-05-01), None
patent: 2355714 (2004-03-01), None
patent: 9419310 (1994-09-01), None
Agrawal, J.P., et al., Organic Chemistry of Explosives, pp. 142-143, © 2007, John Wiley & Sons Ltd., West Sussex, England.
Bellamy, A., et al., “Nitration of 1,3,5-trimethoxybenzene,” J. Chem. Research (S), pp. 412-413, 2002.
Bellamy, A., et al., “Nitration of 1,3,5-trimethoxybenzene,” J. Chem. Research (M), pp. 0919-0930, 2002.
Bellamy, Anthony J., et al., “A New Synthetic Route to 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB),” Propellants, Explosives, Pyrotechnics, vol. 27, pp. 49-58, 2002.
Bellamy, Anthony J., et al., “Synthesis of Ammonium Diaminopicrate (ADAP), a New Secondary Explosive,” Propellants, Explosive, Pyrotechnics, vol. 27, pp. 59-61, 2002.
Bose, P.C., et al., “Occurrence of Dehydrorotenone in Derris uliginosa Benth,” Indian J. Chem., vol. 14B, pp. 1012-1013, Dec. 1976.
DeFusco, A.A., et al., “An Improved Preparation of Trinitrophloroglucinol,” Organic Preparations and Procedures Int., vol. 14, No. 6, pp. 393-424, 1982.
Dobratz, Brigitta M., “The Insensitive High Explosive Triaminotrinitrobenzene (TATB): Development and Characterization—1988 to 1994,” Los Alamos Nat'l. Lab., LA-13014-H, History, UC-741, 151 pages, Aug. 1995.
Dove, Michael F.A., et al., “Vanadium(v) oxytrinitrate, VO(NO3)3. A powerful reagent for the nitration of aromatic compounds at room temperature under non-acidic conditions,” J. Chem. Soc., Perkin Trans. 1, pp. 1589-1590, 1998.
Hoffman, D. Mark, et al., “Comparison of New and Legacy TATBs,” Journal of Energetic Materials, vol. 26, pp. 139-162, 2008.
Hofmann, K.A., et al., “Verbindungen von Kobaltnitriten mit p-Toluidin, Diazoaminotoluol, Hydrazin and Nitrosohydrazin,” Miteilung a. d. Chem. Laborat. D. Kgl. Akad. D. Wissenschafter zu Munchen, Eingengangen am Aug. 14, 1908, pp. 3084-3090.
Maiti, A., et al., “Solvent screening for a hard-to-dissolve molecular crystal,” Physical Chemistry Chemical Physics, vol. 10, pp. 5050-5056, 2008.
Majumdar, M.P., et al., “Nitration of Organic Compounds with Urea Nitrate-Sulphuric Acid,” Indian J. Chem., vol. 14B, pp. 1012-1013, Dec. 1976.
Mehilal, et al., “Studies on 2,4,6-trinitrophloroglucinol (TNPG)—A novel flash sensitizer,” Indian Journal of Engineering & Materials Sciences, vol. 11, pp. 59-62, Feb. 2004.
Mellor, John M., et al., “Improved Nitrations Using Metal Nitrate—Sulfuric Acid Systems,” Tetrahedron, vol. 56, pp. 8019-8024, 2000.
Mitchell, Alexander R., et al., “A New Synthesis of TATB Using Inexpensive Starting Materials and Mild Reaction Conditions,” prepared for submittal to the 27th International Annual Conference of ICT, Jun. 25-28, 1996, Karlsruhe, Federal Republic of Germany, 14 pages, Apr. 1996.
Olah, George A., et al., “New Synthetic Reagents and Reactions,” Aldrichimica Acta, vol. 12, No. 3, pp. 43-49, 1979.
Olah, George A., et al., Nitration Methods and Mechanisms, © 1989 VCH Publishers, Inc., New York, NY, p. 29.
Ott, D.G., et al., “Preparation of 1,3,5-Triamino-2,4,6-Trinitrobenzene from 3,4-Dichloroanisole,” Journal of Energetic Materials, vol. 5, pp. 343-354, 1987.
Schmidt, Robert D., et al., “New Synthesis of TATB. Process Development Studies,” prepared for submittal to the JOWOG 9 (Joint Working Group 9), Aldermaston, England, Jun. 22-26, 1998, 14 pages, May 1998.
Smith, Bengt, “The Reaction between Phenols and Orthoesters. A New Synthesis of Aryl Alkyl Ethers,” Acta Chem. Scand., vol. 10, No. 6, pp. 1006-1010, 1956.
Waller, Francis J., et al., “Lanthanide(III) and Group IV metal triflate catalysed electrophilic nitration: ‘nitrate capture’ and the role of the metal centre,” J. Chem. Soc., Perkin Trans. 1, pp. 867-871, 1999.
Zolfigol, Mohammad Ali, et al., “Nitration of Aromatic Compounds on Silica Sulfuric Acid,” Bull. Korean Chem. Soc., vol. 25, No. 9, pp. 1414-1416, 2004.
Zolfigol, Mohammad Ali, et al., “Silica Sulfuric Acid/ NaNO2 as a Novel Heterogeneous System for the Nitration of Phenols under Mild Conditions,” Molecules, vol. 7, pp. 734-742, 2002.
U.S. Appl. No. 11/744,986, filed May 7, 2007, entitled, “Methods of Producing 1,3,5-Triamino-2,4,6-Trinitrobenzene.”.
Straessler Nicholas A.
Velarde Stephen P.
Alliant Techsystems Inc.
Davis Brian J
TraskBritt
LandOfFree
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