Trinitro-m-xylene

Trinitro-m-xylene [632-92-8] M 241.2, m 182.2 . Crystd from ethyl methyl ketone. 

European Commission (2005a) Summary risk assessment report (5-tert-butyl-2,4,6-trinitro-m-xylene) musk xylene, http //esis.jrc.ec.europa.eu... 

Trinitrobenzene is present in crude TNT manufactured by mixed acid nitration and results from methyl group oxidation followed by decarboxylation." In fact, a convenient method for the synthesis of 1,3,5-trinitrobenzene involves oxidation of 2,4,6-trinitrotoluene with a solution of sodium dichromate in sulfuric acid, followed by decarboxylation of the resulting 2,4,6-trinitrobenzoic acid in boiling water." 1,3,5-Trinitrobenzene is prepared from 2,4,6-trinitro-m-xylene by a similar route." 2,4,6-Trinitroanisole can be prepared from the... 

European Chemicals Agency (2009) Substance Name 5-tert-Butyl-2,4,6-trinitro-m-xylene (Musk Xylene), EC Number 201-329-4, CAS Number 81-15-2, Prioritisation and Annex XIV Background Information. European Chemicals Agency (ECHA), 14 January 2009 http //echa.europa.eu/doc/ consultations /recommendations/ prioritisations /... 

Trinitro-m-xylene, ndls (from benz +-hexane or dioxane), mp 181—84° bp—explodes on heating in a tube at 410-12°, d 1.69 was prepd by electrolysis of 2,4,6-trinitrotoluene withNa acetate in acet ac using a Pt electrode at 35—45° (Ref 3)... 

Yel crysts, mp 206°. Can be prepd by heating 2,4,6-trinitro-5-methoxy-l,3-dimethyl-benzene for 2 hours with ale NH, in a sealed tube on a water bath(Ref 2) or by heating 5-bromo-2,4,6-trinitro-m-xylene with ale NH, at 130 Ref 3)... 

For ready reference we also include a table of standard heats (enthalpies), entropies and heats of formation of a variety of explosives. This table is taken from Ref 24. All values are in KJoules. To obtain the more commonly used Kcals, divide by 4.184. TNX is 2,4,6-Trinitro-m-xylene TNM (in this table only) stands for 2,4,6-Trinitromesitylene, and TNC is 2,4,6-Trinitro-m-cresol... 

Other compounds such as 2,4-dinitrotoluene, 2,4,6-trinitro-m-xylene, 2,4,5-trinitrotoluene, hexogen, only slightly decreased the rate of crystallization (e.g. the addition of 1 mole % of 2,4-dinitrotoluene and hexogen caused a decrease in rate of crystallization of TNT at 74°C from 2.5 cm/min to 1.89 and 1.78 cm/min respectively). 

The commercial product, according to Kravchinskii [3], melts partially at 120-125°C and completely at 160-177°C, and solidifies at 160-162°C, while chemically pure 2,4,6-trinitro-m-xylene melts at 182°C. 

There are three isomeric trinitro-m-xylenes 2,4,6-trinitro-m-xylene, 2,4,5-, and 4,5,6-trinitro-m-xylene ... 

Trinitro-m-xylene crystallizes in white crystals at room temperature. It is only slightly soluble in concentrated sulphuric acid - at a temperature of 150-160°C 10% of it goes into solution. In fuming sulphuric acid the solubility is higher. 

The solubility of 2,4,6-trinitro-m-xylene in organic solvents is much lower than... 

At high temperatures 2,4,6-trinitro-m-xylene is readily dissolved by acetic acid and by aniline. 2,4,6-Trinitro-m-xylene forms eutectics with aromatic hydrocarbons and their nitro derivatives. Some of the available data are tabulated (Table 90). 

Trinitro-m-xylene is not affected by hot concentrated sulphuric and hydrochloric acids, but it reacts with alkalis in the presence of alcohol or acetone, yielding an intense blue addition product. 

Trinitro-m-xylene forms addition products less easily than a- trinitrotoluene. Undoubtedly the two methyl groups present in the ring reduce its ability to form addition compounds. 

According to Jeffemov and Tikhomirova [10], 2,4,6-trinitro-m-xylene contrary to both sym-trinitrobenzene and 2,4,6-trinitrotoluene does not combine with such hydrocarbons as acenaphthene, anthracene, phenanthrene, fluorene or naphthalene. 

The constitution of 2,4,6-trinitro-m-xylene was determined by Grevingk [13], He nitrated both 2,4- and 4,6-dinitro-m-xylene and obtained the same product. 

The isomers of 2,4,6-trinitro-m-xylene formed in the nitration process may of course be removed from the product by crystallization or by reacting with sodium sulphite, the substitution of a nitro group by a sulpho group taking place, e.g. ... 

Trinitro-m-xylene is more sensitive to impact than TNT. This can be explained by the presence of a large number of substituents on the benzene ring. As Wohler and Wenzelberg [14] found, it could explode at only about half the impact energy needed for the explosion of TNT. 

The m- xylene isolated in this way is of very high purity. When nitrated it yields a product having a melting point only slightly lower than that of chemically pure 2,4,6-trinitro-m-xylene. 

SYNS BENZENE, l-tert-BUTYL-3,5-DIMETHYL-2,4,6-TRINITRO- 5-tert-BUTYL-2,4,6-TRINITROXYLENE 5-tert-BUTYL-2,4,6-TRINITRO-m-XYLENE (DOT) MUSK XYLENE MUSK XYLENE (DOT) MUSK XYLOL ... 

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... 

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