TNT 2,4,6-Trinitrotoluene

Trinitrotoluene is easily made by the reaction of HNO3 and H2SO4 with toluene. The order in which the reagents are mixed influences the output and safety of the process. It is thermally stable for over 40 h at 150°C and can be stored for 20 years at ambient temperatures. It is insensitive to shock and friction. It is slightly toxic at concentrations greater than 1.5 mg/m. Its use is extensive in the military as bombs, grenades, shells, torpedoes, and depth charges. 

The commercial product for military purposes consists of a- trinitrotoluene (2,4,6-isomer) of high purity. 

In the explosives industry it is known under various names Tolite (France) Tri, Trotyl, Tutol, Trinol. Fullpulver 1902 - abbreviation Fp02 (Germany) Tri-tolo (Italy) Trotyl and TNT (Poland) Trillit, Tolita (Spain) TNT (United Kingdom and U. S. A.) Tol, Trotil, TNT (U. S. S. R.). 

Trinitrotoluene was first mentioned in 1863. It was obtained by Wilbrand [34], who treated toluene with a mixture of nitric and sulphuric acids at a temperature 

The p- and y- isomers were obtained by Hepp [35] in 1882. The constitution of the a -isomer was determined by Claus and Becker [36] in 1883, and that of the 

CHEMICAL NAME = methyl-2,4,6-trinitrobenzene CAS NUMBER = 118-96-7 MOLECULAR FORMULA = (2HsN,0t MOLAR MASS = 227.1 g/mol 

MELTING POINT = 80. BOILING POINT = unstable, explodes at 240°C DENSITY = 1.65 g/cm3 

TNT is the abbreviation of the aromatic nitrated aromatic compound 2,4,6-trinitrotoluene. It is a pale-yellow crystalline solid that was first synthesized in 1863 by the German chemist Joseph Wilbrand (1811—1894), but it was not immediately used as an explosive. TNT is made by nitrating toluene using nitric acid, sulfuric acid, and oleum (a mixture of sulfuric acid and S03). Nitration of toluene occurs in stages, with the nitro units added sequentially in a stepwise process as the reaction proceeds. The last nitro unit is accomplished by using oleum (SO, dissolved in sulfuric acid). After nitration, unused acids are recycled, and the product is washed with sodium sulfite and water to remove impurities. 

Between World War I and II, TNT replaced picric acid as the explosive of choice in munitions. It was also mixed with other compounds to produce more powerful explosives with unique characteristics. Amatol is a mixture containing between 40% and 80% ammonium nitrate and TNT. Pentolite is a mixture of PETN (pentaerythritol tetranitrate) and TNT. Another common explosive mixture is RDX (cyclotrimethylenetrinitramine) and TNT. RDX is an abbreviation for Royal Demolition Explosive. 

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Trinitrotoluene (TNT) is made by nitration of toluene. Display electrostatic potential maps for toluene, 4-nitrotoluene (the first nitration product) and 2,4-dinitrotoluene (the second nitration product). Are the second and third nitration steps likely to be easier or more difficult than the initial nitration of toluene Explain. 

Trinitrotoluene (TNT) is reduced by the aquatic plant Myriophyllum spicatum to ami-nodinitrotoluenes (Pavlostathis et al. 1998) and, in axenic root cultures of Catharanthus roseus, the initial metabolites 2-amino-4,6-dinitrotoluene and 4-amino-2,6-dintrotoluene... 

Nitrotoluenes including 2,4,6-trinitrotoluene (TNT) are important components of explosives and several nitroarenes including the antibacterial nitrofurans have established mntagenicity (Purohit and Basu 2000). Substantial effort has been directed to the degradation of nitroarenes, and to their reduction to amines. Although nitroarene reductases, noted in Chapter 3, Part 3, are distribnted in a range of biota, the products may not necessarily represent intermediates in the degradation... 

Lewis TA, S Goszczynski, RL Crawford, RA Korns, W Adamassn (1996) Prodncts of anaerobic 2,4,6-trinitrotoluene (TNT) transformation by Clostridium bifermentans. Appl Environ Microbiol 62 4669-4674. 

Preuss A, J Fimpel, G Diekert (1993) Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch Microbiol 159 345-353. 

The Sundberg indole synthesis using aromatic azides as precursors of nitrenes has been used in synthesis of various indoles. Some kinds of aryl azides are readily prepared by SNAr reaction of aromatic nitro compounds with an azide ion. For example, 2,4,6-trinitrotoluene (TNT) can be converted into 2-aryl-4,6-dinitroindole, as shown in Eq. 10.60.83... 

The relevant authorities and remediation companies of many industrialized countries have made numerous efforts to develop and establish efficient and reasonable techniques for the cleanup of contaminated sites with explosives. 2,4,6-Trinitrotoluene (TNT) was the most widely produced and used explosive... 

The most serious contamination was recognized as a result of production as well as use of 2,4,6-trinitrotoluene (TNT), mainly because of vast amount of water necessary for manufacturing of this compound made it necessary to locate the factories near natural sources of water - mostly rivers. The environment around large rivers is usually characterized by sand-rich soil that allows easy seepage of rainwater. NACs are therefore... 

We concentrate our effort to phytoremediation of 2,4,6-trinitrotoluene (TNT) as the main contaminant of former and present ammunition factories and to nitroesters (PETN, NG) in the Czech Republic and in Germany. In our experiments, we studied the uptake, degradation and distribution of these compounds in plants and its degradation products in plant tissues and its subsequent utilisation for real application both for soil and waste-waters cleaning. 

Ahmad, F., and Hughes J. B., 2002, Reactivity of partially reduced arylhydroxylamine and nitrosoarene metahohtes of 2,4,6-trinitrotoluene (TNT) toward biomass and humic acids, Environ. Sci. Technol. 36 4370-4381. 

Wang, C. J., Thiele, S., and Bollag, J. M., 2002, Interaction of 2,4,6-trinitrotoluene (TNT) and 4-amino-2,6-dinitrotoluene with humic monomers in the presence of oxidative enzymes. Arch. Environ. Contam. Toxicol. 42 1-8. 

TNT, see 2,4,6-Trinitrotoluene a-TNT, see 2,4,6-Trinitrotoluene TNT-tolite, see 2,4,6-Trinitrotoluene TOCP, see Tri-o-cresyl phosphate TOFK, see Tri-o-cresyl phosphate Tolit, see 2,4,6-Trinitrotoluene Tolite, see 2,4,6-Trinitrotoluene... 

It has been known for a long time that polynitroaromatic compounds produce colored products in contact with aUcafis [1]. These color reactions have been extensively used for the identification of nitroaromatic explosives. In the Janowski reaction [7], a solution of the polynitroaromatic compound (di- or trinitroaromatic) in acetone is treated with concentrated aqueous KOH solution. 1,3,5-Trinitrobenzene (TNB) and 2,4,6-trinitrotoluene (TNT), treated with 30% aqueous KOH, produced violet-red and red colors, respectively. Many variations of the Janowski reaction were reported, using KOH or NaOH in aqueous or ethanoHc solutions as reagents, and dissolving the explosives in acetone, ethanol or acetone-ethanol mixture [3,8]. The reaction was used both for spot tests and for spraying TLC plates [9]. 

Investigated explosives included 2,4,6-trinitrotoluene (TNT), 2,4,6,N-tetranitro-N-methylaniline (tetryl), l,3,5-trinitro-l,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro-l,3,5,7-tetrazacyclooctane (HMX) and pentaerythritol tetranitrate (PETN). The temperature of the injector, cooled with liquid CO2, was —5°C for 0.3 min, programmed from —5 to 250° C, at a rate of 200°C/min, with a final hold time of 8.4 min. The column temperature was 80° C for 2 min, programmed to 250° C at 25°C/min, with a final hold of 2 min. Electron ionization (El) in the positive-ion mode was used. Figure 4 shows the mass chromatograms of a mixture of explosives (lOppb each), extracted from water by Hquid—liquid extraction and X 100 concentration. Identification was based on typical fragment ions for each one of the explosives. 

Electron-transfer-induced FQ is the most practical and efficient mechanism of signal transduction for the detection of explosives. This is because explosives, especially 2,4,6-trinitrotoluene (TNT), are often highly electron-deficient molecules that readily accept electrons from excited fluorophores. In addition, explosive devices that contain TNT also usually contain a synthetic by-product, 2,4-dinitrotoluene (DNT), which is also highly electron deficient. A basic frontier molecular orbital-based mechanism for electron transfer FQ is illustrated in Figure 3. 

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