2.4.6- trinitrotoluene chemistry

In the explosives industry, precise control of temperature, mixing time, concentrations, heating, and cooling rates are maintained. Making these materials safely requires sophisticated equipment and technology to carry out the process even though the chemistry may appear simple. Under less than optimal conditions, some 2,3,5-trinitrotoluene, 3,5,6-trinitrotoluene, and 2,4,5-trinitrotoluene are produced, and they are much less stable than 2,4,6-TNT. A mixture of explosives is only as stable as its least stable... 

J.P. Davies, L.G. Blackwood, S.G. Davis, L.D. Goodrich and R.A. Larson, Design and calibration of pulsed vapor generators for 2,4,6-trinitrotoluene, cydo-l,3,5-trimethylene-2,4,6-trinitramine, and pentaerythritol tetranitrate. Analytical Chemistry 65(21) (1993) 3004-3009. 

Before anything else can be said about IEs, some rudimentary chemistry is needed. From a cookbook perspective, all explosives (be they military, commercial, or improvised) require the same chemical building blocks, which consist of a fuel and an oxidizer. Some explosives have the fuel and oxidizer as part of the same molecule, such as trinitrotoluene (TNT), and some explosives are comprised of mixtures of separate fuels and oxidizers, such as ammonium nitrate-fuel oil (ANFO). The oxidizer employed by the vast majority of explosives tends to be the NO2 (nitro) group. It is so predominant as an explosive ingredient that the primary focus of detection methods traditionally has been to look for nitro-derived properties. IEs tend to utilize a more diverse range of oxidizers. Table 3.1 gives a list of the numerous oxidizer possibilities. 

The element carbon (symbol C) is almost always found in nature covalently bonded to other carbon atoms or to a variety of other elements (most commonly H, O, and N). Due to the presence of carbon-containing compounds in all living things, the chemistry of carbon compounds is known as organic chemistry. Most high explosives are organic compounds. TNT (trinitrotoluene), for example, consists of C, H, N, and O atoms, with a molecular formula of C yH 5N P e. We will encounter other organic compounds in our study of fuels and binders in pyrotechnic mixtures. 

This annotated bibliography of the analytical chemistry of 2A,6-Trinitrotoluene, alternately referred to as a-TNT or TNT, covers a period ranging from ca 1940 to the present. Over this period, the field of analytical chemistry and, therefore, that of TNT has advanced from the simple wet chemical to the automated, computerized and highly complex instrumental methods. Because of this wide spectrum of advancements, the analytical chemistry of TNT will be formated according to the general categories of ... 

An interesting example, to further illustrate the concepts of E factors and atom efficiency is the manufacture of phloroglucinol [23]. Traditionally, it was produced from 2,4,6-trinitrotoluene (TNT) as shown in Fig. 1.2, a perfect example of nineteenth century organic chemistry. 

Acid/base chemistry is also an obvious reaction path for selective detection of a variety of materials. For example, acid/base reaction can be made to occur within a molecularly imprinted pocket to assist in differentiating the molecule of choice before deprotonating it to produce an ion pair that then interacts with the evanescent field. This approach is currently being used to selectively detect TNT to levels in the low parts-per-trillion. 2,4,6-trinitrotoluene, a potent explosive, is also a weak acid having a p/sTa of approximately 14.5 [38]. A TNT derivative is synthesized with a tether to a silane. The silane is chosen so the group can be... 

Carper, W. R., Davis, L. P. and Extine, M. W. (1982). Molecular structure of 2,4,6-trinitrotoluene. Journal of Physical Chemistry, 86,459-62. [288, 289t] Carstensen, J. T. (1977). Pharmaceutics of solids and solid dosage forms. John Wiley Sons New York. [243]... 

The almost universal adoption of trinitrotoluene as the most efficient explosive in modern warfare the development and refinement of its manufacture, and the interesting chemistry of its compounds, as well as those of the lower nitro-derivatives of toluene has prompted quite extensive research as to their composition, structure, manufacture, properties and uses. The fact that the results of these researches have been varied often quite contradictory somewhat disconnected and expressed with some confusion of terms would seem to warrant the publication of this little volume in which an attempt is made to gather together and correlate all accessible information on the subject, both theoretical and practical. 

Fuller, M.E. and Manning, J.F. (1998) Evidence of differential effects of 2,4,6-trinitrotoluene and other munitions compounds on specific sub-populations of soil microbial communities. Environmental Toxicology and Chemistry, 17, 2185-2195. 

The well known hepatotoxicity of nitroaromatic compounds such as trinitrotoluene lends suspicion to the hepatotoxicity of the nitroparaffins." Nitromethane and nitroethane produce steatosis in animal models, but there is limited evidence of hepatotoxicity of these agents in humans." Evidence for the hepatoxicity of 2-nitropropane has been raised by case reports and case series of oeeupational fatalities in settings of severe exposure. In these cases the lack of appropriate industrial hygienic measures such as adequate ventilation, and personal protective equipment contributed to the severity of the exposures. " Autopsies of the fatal cases revealed hepatocellular necrosis and fatty infiltration of the liver. No significant evidence of hepatotoxicity has been demonstrated below the ACGIH TLV of 10 ppm. Medical surveillance of workers exposed to less than 25 ppm of 2-nitropropane have not shown alterations in liver chemistries. ... 

Different configurations and chemistries have been used in SPLS continuous procedures with increased advantages over the batch procedures, since it is possible with the former to use systems that are not possible with the latter. The luminescence signal can be obtained from temporary or permanent immobilization of the analyte or reaction product in the solid phase in the case of flow-through systems. The sensing schemes for intrinsic luminescent analytes are not very common because of the lack of intrinsic luminophors, such as with PAH, polychlorinated biphenyls, or trinitrotoluene. It is much more common to use different sensing schemes to obtain a luminescent event from a nonluminescent analyte. Among others are... 

Observations Concerning the Thermal Decomposition of 2,4,5-Trinitrotoluene J. Phys. Chemistry. 74, 3035-3040. 

Isotope Effects and the Thermochemical Decomposition of Liquid 2,4,5-Trinitrotoluene Application to Mechanistic Studies Using Isothermal Differential Scanning Calorimetric Analysis J. Org. Chemistry 42, 4201-4206. 

Fernando, T. and S. D. Aust. 1991. Biodegradation of munition waste, TNT (2,4,6-trinitrotoluene), and RDX (hexahydro-l,3,5-trinitro-l,3,5-triazine) by Phanerochaete chrysosporium, p. 214-232. In D.W. Tedder and F.G. Pohland (eds.). Emerging technologies in hazardous waste management II. American Chemistry Society, Washington, D.C. 

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