Trinitrotoluene Ethanol

The action of hydroxylamine and sodium acetate in ethanol upon picryl chloride was stated to give 4,6-dinitrobenzofuroxan, and probably some of this compound was formed, although it was later shownthat much of the original work was faulty. A report that hydroxylamine and 2,4,5-trinitrotoluene give 5-methyl-6-nitro-benzofuroxan has been found to be incorrect. Benzofuroxan has not been prepared by V-oxidation of benzofurazan, and it seems unlikely that this could be achieved, since benzofuroxan itself is oxidizable by powerful reagents to o-dinitrobenzene (Section VI, B). A report of the oxidation by nitric acid of anthraceno[l,2-c]furazan to the furoxan is incorrectlv abstracted. 

See Ethanol, Sulfuric acid, above Sulfuric acid, 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]. 

Fig. 12. The ultraviolet absorption spectrum of 2,4,6-trinitrotoluene, reproduced with permission from [93]. The solid line is the spectrum of gas-phase TNT measured at 92 °C the dotted line is the spectrum of the TNT ethanol solution measured in reference 10 of [93]. Arrows labeled as 1, 2, and 3 show die peaks corresponding to NO A 2%+(v = 0, 1, 2) X 2II(v = 0) absorption transitions, respectively.

Anhydrous sodium carbonate (30 g.) is added to a warm solution of 70 g. (0.31 mole) of 2,4,6-trinitrotoluene (Caution—-explosive substance) in 500 ml. of a mixture of equal volumes of ethanol and acetone. To the resulting mixture is added gradually (1 hour) with stirring 50 g. (0.33 mole) of p-nitrosodimethylaniline [Org. Syntheses Coll. Vol. 1, 214 (1941)]. The temperature of the reaction mixture is held below 50° during this period and for an additional hour of stirring, after which the mixture is allowed to stand for 24 hours. The solid product is removed by filtration and triturated with ethanol followed by filtration to remove the ethanol. The material is treated three times with ethanol and once with acetic acid in this manner and then is dried and powdered. (Caution—product is a dangerous explosive.)... 

Li J, Jiang Q-G, Zhcxig W-D. Persistent ethanol drinking increases liver injury induced by trinitrotoluene exposure an in-plant case-control studjy. HumExp Taxicol(l99l) 10,405-9. 

In a 50 L vessel that has double shells, 15.8 kg of trinitrotoluene is dissolved in a solution made of 14 L of acetone and 18 L of ethanol. The mixture is then stirred and heated at 50 °C until trinitrotoluene is completely dissolved. The solution is then cooled at 25 "C and stirred for three hours, followed by the vacuum filtration. Afterwards, the filtrate is washed with alcohol and dried at room temperature. The dry trinitrotoluene is passed through a 1 mm sieve. Approximately 92% of the particles in the final product should range in size from 30 to 60 pm. On the laboratory scale, 1/10 of the stated quantities could be sufficient. 

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