2.4.6- Trinitro-mesitylene

Trinitro-mesitylene (2,4,6-Trinitro-1,3,5-trimethyl benzene). C9H9N306, mw 255.21,... 

Nitrated Solvent Naphtha (N.S.N.). As nitration of crude solvent naphtha by the usual one-stage method results in yields that are too low, because of oxidation, E. Blecher et al (Ref 3) proposed nitrating only the refined material, and in two stages. The two-stage method is described in Colver, pp 255 686—87 (Ref 4). The product consists chiefly of 2,4,6-Trinitro-mesitylene (see under Mesitylene and Deriva- tives in this Vol), and 3,5,6-trinitropseudocumene, with small quantities of the nitrated products of xylene, ethylbenzene, etc... 

N 16.47%, OB to C02 —103.4%, triclinic needles (from ale). prisms (from acet), mp 238.2°, bp expl at 415°, d 1.48g/cc. Insol in w, si sol in hot ale eth, misc in hot acet benz. Can be prepd by treating mesitylene with a mixt of. nitric sulfuric acids in the cold (Refs 2 3). Blanksma (Ref 4) prepd it by dissolving mesitylene in sulfuric acid, partial sulfonation taking place, and then adding the soln to nitric acid, with the pptn of trinitio-mesitylene. Kholevo (Ref 6) nitrated mesitylene with nitric acid 27, sulfuric acid 69, water 4% to yield white crysts. The expl power of trinitro-mesitylene is less than PA (Ref 9), and it develops a bomb press 84% that of TNT (Ref 8), Its impact sensitivity is 52% that of TNT (Ref 7), and it expls at 415° (Ref 5)... 

Thus, nitro compounds with a great number substituents, for example trinitro-mesitylene, do not give any colour reactions. Compounds with nitro groups located in the 2,4-positions, produce colours that depend to a considerable extent on the substituent in position 1. The presence of the OH or NH2 group interferes with the colour reaction. The situation remains unchanged after both of the groups have been acylated, while alkylation of a phenol restores the ability to produce colour,... 

The condensation reactions of di- and trinitro mesitylene and m-xylene also indicate that nitro groups lose their characteristic activating influence when they are flanked by two methyl groups. In the presence of piperidine, 4,6-dinitro-ra-xylene (XLVII) and 2,4,6-trinitro-m-xylene (XLVIII) will condense with benzaldehyde 22 (equations 4 and 5). When... 

During oxidn of mesitylene with nitric acid in an autoclave at 115° to give 3,5-dimethylbenzoic acid, a violent expln occurred. The reaction was attributed to local overheating, formation of a trinitro compd, 1,3,5-tri (nitromethyl) benzene, and to violent decompn of the latter. Smaller scale prepns with better temp control were uneventful (Ref 3)... 

Mesitylene, Trinitro (2,4,l -TNMes) Mo no nitrocompounds Naphthalene Pink No color See under parent compds ... 

Schultz and Gehre Explosives. G. Schultz and F. Gehre of Munich patented in Engl and the USA (1905—1906) a safety expl based on nitrated solvent naphtha, which consisted chiefly of the trinitro compds of mesitylene and pseudo-cumol. This was mixed with oxidizers, and in certain cases with finely pulverized Fe or Cu. 

Other nitro-derivatives of hydrocarhons and of phenols are used in explosive mixtures. Among the former are dinitro-benzene, chlor-dinitro-benzene, dinitro-toluene, di- or tri-nitro-den-vatives of mesitylene, pseudocumene, and xylene, dinitro-naphthalene. Trinitro-naphthalene and tetra-nitro-naphthalene have also been proposed. Of the nitro-phenols, perhaps the most important is tri-nitro-cresol, known as Cresilite in France, where it is added to Melinite. Other nitro-derivatives of the aromatic series will be mentioned in the section on detonators. 

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