Machine element or mechanism – Gearing – Adjustable
Patent
1995-05-12
1996-10-29
Jordan, Charles T.
Machine element or mechanism
Gearing
Adjustable
564441, C07C 4500
Patent
active
055697836
ABSTRACT:
The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by:
(a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from --H, or --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen,
with an amount effective to produce DATB or TATB of 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide is selected from chloride, bromide or iodide.
in the presence of a strong base selected from sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof;
in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformide, dimethylacetamide and mixtures thereof, provided that when alcohols are present primarily DATB and picramide is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are useful specialty explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).
REFERENCES:
patent: H1078 (1992-07-01), Norris et al.
patent: H1304 (1994-04-01), Norris et al.
patent: 4032377 (1977-06-01), Benziger
patent: 4248798 (1981-02-01), Atkins
patent: 4952733 (1990-08-01), Ott
patent: 5262539 (1993-11-01), Makosza et al.
patent: 5466781 (1995-11-01), Seko
O. Westphal, "Uber die Alkylierung des Hydrazins," Ber. vol. 74 (1941), p. 759.
E. Y. Spencer, et al., "Preparation of Pyramide," Can. J. Res., vol. 24B (1946) pp. 204-207.
J. R. Holden, et al., "Head Resistant Explovies VI: Properties of 1,3-Diamino-2,4,6-Trinitrobenzene, DATB," NAVORD Report 6299 (Mar. 17, 1959).
G. M. Omietanski, et al., "The Reaction of Chloramine with Tertiary Amines. 1,1,1-Trisubstituted Hydrazinium Salts," J.ACS., vol. 78 (1956) pp. 1211-1213.
S. K. Yasuda, "Identification of 1,3,5-Triamino-2,4,6-Trinitrobenzene Impurities by Two-Dimensional Thin-Layer Chromatography," Journal of Chromatography, vol. 71 (1972), pp. 481-486.
T. Urbanski and S. K. Vasudeva, "Heat Resistant Explosives," Journal of Scientific Industrial Research, vol. 37 (May 1978), pp. 221-280.
W. P. Norris and A. P. Chatin, "CL-14, A New Dense, Insensitive, High Explosive (u)," NWC TP 6597 (May 1985).
R. L. Atkins, et al., "Synthesis of Polynitro Compounds. Hexasubstituted Benzenes," J. Org. Chem., vol. 51 (1986), pp. 3261-3266.
M. Makosza, et al., "Vicarious Nucleophilic Substitution of Hydrogen," Acc. Chem. Res., vol. 20 (1987), pp. 282-289.
W. Worthy, "Shock Sensitivity of Explosives Clarified," C&EN, Aug. 10, 1987, p. 25.
M. Makosza, "Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen," J. Org. Chem. vol. 57 (1992), pp. 4784-4885.
A. R. Mitchell, et al., "Advances in the Chemical Conversion of Energetic Materials to Higher Value Products," Presentation at Life Cycles of Energetic Materials, Del Mar, CA, Dec. 11-16, 1994.
J. G. Keay, et al., "Regiospecific synthesis of 1-substituted-1,2,4-triazoles using 4-amino-1,2,4-triazole".
Katrizky et al., J. Org. Chem. 1986, vol. 51, 5039-5040.
Katrizky et al., J. Org. Chem. 1988, vol. 53, 3978-3982.
Mitchell et al., 24th Intl. Annual. Conference of ICT, Karlsruhe, Germany, pp. 38-1-38-6. 1993.
Mitchell Alexander R.
Pagoria Philip F.
Schmidt Robert D.
Hardee John R.
Jordan Charles T.
Sartorio Henry P.
The Regents of the University of California
LandOfFree
Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6 does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6 will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1786550