Sym-trinitrotoluene

Synonyms/Trade Names 1-Methyl-2.4,6-trinitrobenzene TNT Trinitrotoluene sym-Trinitrotoluene Trinitrotoluol... 

Other Names Toluene, 2,4,6-trinitro- a-TNT 1-Methyl-2,4,6-trinitrobenzene 2,4,6-Trinitrotoluene 2-Methyl-l,3,5-trinitrobenzene 4-Methyl-l,3,5-trinitrobenzene Gradetol NSC 36949 TNT ToUt Tolite Trinitrotoluene Tritol Tritol (explosive) Trotyl Trotyl oil sym-Trinitrotoluene sym-Trinitrotoluol... 

Synonyms CCRIS 1299 EINECS 204-289-6 Entsufon 1-Methyl-2,4,6-trinitrobenzene 2-Methyl-l,3,5-trinitrobenzene NCI-C56155 NSC 36949 TNT 2,4,6-TNT a-TNT TNT-tolite Tolit Tolite Trilit Trinitrotoluene sj/ 3-Trinitrotoluene Trinitrotoluol a-Trinitrotoluol sym-Tx -nitrotoluol Tritol Triton Trotyl Trotyl oil UN 0209 UN 1356. 

Hackel and Kuboszek [30] have examined the eutectics of both forms of DEGDN with sym-trinitrobenzene and a-trinitrotoluene (Table 22). 

Symmetrical trinitrotoluene (1,3,5-trinitrotoluene,. sym-trinitrotol uenc. TNT) is manufactured by multiple-stage nitration of toluene with a mixture of nitric acid and sulfuric acid. 

Tertiary nitro compounds, of course, do not undergo tautomeric transformation, and they might be expected to be resistant to alkalis. Nevertheless aromatic nitro compounds, and polynitro-ones in particular, are very sensitive to alkalis, and undergo transformation when treated with them. For example, sym-trinitrobcnzcnc and also a- trinitrotoluene, when reacted with potassium hydroxide in methyl alcohol solution, form dark addition products (see also p. 202). Under certain conditions the nitro group can break off to form high molecular compounds. 

Nitro compounds, particularly the higher nitrated derivatives, readily enter into nucleophilic reactions. The reactions of aromatic halogenonitro compounds with bases (p. 453), as well as the addition of potassium methoxylate on to sym-trini-trobenzene resulting in the formation of an anisole derivative will be discussed below. Similar addition reactions of potassium methoxylate to trinitrotoluene (p. 301) and trinitroanisole (p. 546) are also known. These reactions were described in detail by Meisenheimer [36-38], Confirmation of such an interpretation of the reaction is provided by the fact that in the reaction of potassium ethoxylate with trinitroanisole the same dark coloured product (I) is obtained, as when potassium methoxylate is reacted with trinitrophenetole ... 

Dinitrotoluene does not give this reaction. Trinitro compounds (such as sym-trinitrobenzene and a- trinitrotoluene) also give the colour reaction but this is less typical, as the trinitro compounds give a similar colour with alcoholic NaOH alone without primary nitroparaffins. 

A detailed list of addition compounds formed by sym- trinitrobenzene, 2,4,6-trinitrotoluene, picric acid and other polynitro compounds is given in the appropriate paragraphs devoted to these nitro compounds. 

Preparation from a- trinitrotoluene. In 1893 a patent was granted to the Chemische Fabrik Griesheim [47a] for the manufacture of sym-trinitrobenzene from trinitrotoluene. The method was based on the fact observed by Tiemann [48] Mid by Claus and Becker [49], that trinitrotoluene can be oxidized with nitric acid to trinitrobenzoic acid, the latter being readily decarboxylated to form sym-trinitrobenzene ... 

The Griesheim method is generally used for the laboratory preparation of sym-trinitrobenzene. However, it is too expensive to be applied in industry. Trinitrobenzene prepared in this way is much more costly than trinitrotoluene, whereas the gain in explosive power obtained is relatively small. 

It should be mentioned that sym-trinitrobenzene is formed as a by-product of the nitration of toluene to trinitrotoluene (p. 338). 

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. 

With sodium- or potassium methoxide, trinitroanisole reacts like sym-trinitro-benzene or a- trinitrotoluene, viz. it adds on an alcoholate molecule, forming a red-coloured addition product (I) ... 

TRINITROTOLUENE (TRILITE) (TRITOL) (TRITON) (ALPHA-TRINITROTOLUENE) (SYM-TRIN1TROTOLUENE) (1,2,4,6-TRINITROTOLUENE)... 

TRINITROTOLUENE (UN 0209) (DOT) see TMN490 TRINITROTOLUENE, wetted with not <30% water, by weight (UN 1356) (DOT) see TMN490 s-TRINITROTOLUOL see TMN490 sym-TRINITROTOLUOL see TMN490... 

Trinitrobenzene (sym-ti nitrobenzene, TNB) may be prepared only with the greatest difificulty by the nitration of m-dinitrobenzene. Hepp first prepared it by this method, and Hepp and Lobry dc Bruyn improved the process, treating 60 grams of m-dinitrobenzene with a mixture of 1 kilo of fuming sulfuric acid and 500 grams of nitric acid (d. 1.52) for 1 day at 100 and for 4 days at 110 . Claus and Becker obtained trinitrobenzene by the action of concentrated nitric acid on trinitrotoluene. Trinitrobenzoic acid is formed first, and this substance in the hot liquid loses carbon dioxide from its carboxyl group. 

Forms molecular addn products with nitro compounds. Picric acid complex, mp 139 sym.trinitrobenzene complex, mp 164" trinitrotoluene complex, mp 162". 

SYNONYMS l-methyl-2,4,6-trinitrobenzene, 2-methyl-l,3,5-trinitrobenzene, hit, trinitrotoluene, sym-trinihotoluene, trinitrotoluol. 

TRINITROTOLUENE CH,C,H (NO, TNT Trinitrotoluol 2,4,6-Trinitrotoliiene sym-TrinitroColuene Strong oxidizers, ammonia, strong alkalies, oxidizable materiab Explodes ... 

Found in m-dinitro compounds examined where other additional groups, if any, were ortho to the nitro. Not found in sym-trinitro compounds but present in 2,3,4- and 2,4,5-trinitrotoluene. Absent in 3,5-dinitrobenzoic acid and 4,6-dinitro-o-cresol. It appears that a group meta to the nitro inhibits the band. 

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