Nitro explosives tetryl

A number of important explosives contain nitramino functionality in conjunction with nitrate ester or C-nitro functionality. A-Nitrodiethanolamine dinitrate (DINA) (7) is a powerful explosive which can be melt-cast into charges. A,2,4,6-Tetranitro-A-methylaniline (tetryl) (8) exhibits high brisance (VOD 7920 m/s, d = 1.73 g/cm ) and has found application in both detonators and boosters, in addition to being a component of some composite high explosives. 

Because of their favorable elemental compositions, heteroaromatic nitro compounds represent explosives of high performance (oxygen balance, density, heat of formation and VOD) compared with analogous aromatic explosives [136-138]. With this objective, Licht and co-workers have synthesized some methylnitramine substituted pyridines and triazines, established their structures and characterized them for thermal and impact sensitivities [139]. The data on impact sensitivity, however, indicate that tetryl may not be replaced by these explosives. 

This is a powerful explosive, stronger than tetryl but weaker than cyclonite. It is, however, of no practical value chiefly because its preparation is too expensive, requiring first the conversion of methylamine into urethane and then into its nitro derivative. On hydrolysis the latter yields methylnitramine. Similarly, the hydrolysis of dinitrodimethyloxamide (p. 35) leads to the formation of methylnitramine. 

Tetryl combines with an excess of sodium sulphide to form a 13% solution. Even at room temperature the nitro groups are reduced with the formation of a non-explosive substance. This reaction is exploited for the destruction of waste tetryl. 

The explosive properties of mixtures with ammonium nitrate depend on the quantitative relationship between the oxidizing agent and the explosive or combustible substance. According to Parisot and Laffitte s [9, 47] investigations the explosive properties of mixtures of aromatic nitro compounds with ammonium nitrate vary with the change in composition of the system in an almost rectilinear manner. The graph in Fig. 69 shows how the rate of detonation depends on the composition of mixtures of tetryl or picric acid with ammonium nitrate. T. Urbanski et al. [48] also obtained a rectilinear relationship for nitrostarch mixtures with ammonium or sodium nitrate (Fig. 71, p. 265). 

Work Specific. See Specific Work Uses. Pentryl was proposed for use as a base charge in detonators in lieu of tetryl or nitro-mannite, as well as for some other purposes either alone or mixed with other explosives. Addition of an oxidizing agent(such as K chlorate) to pentryl greatly enhances its strength and is recommended by Clark as of distinct economic advantage (Refs 3,4,5,8, 9,10 11)... 

Explosive Properties Explosion Temperature 300° (Ref 4) Impact Sensitivity 20 to 35 cm vs 25 cm for tetryl 110 cm for TNT, using 2 kg wt (Ref 4) Power, by Lead Block Expansion, 380-400 cc vs 290 cc for TNT or 131 8% TNT (Ref 4) Reactivity - the nitro group in the 3 position is readily replaced Stability claimed to be as stable as TNT (Ref 4) but not found so by others. See also Ref 8 Uses. TeNAns was used in Germany in initiating and other expl mixts (Refs 3 7) but later was found to be too reactive and too sensitive for military or com) application. No information at our disposal about its uses in other countries... 

No m-nitrotetryl is produced if pure dimethylaniline is used in the usual process for the manufacture of tetryl. The amount of this impurity in the usual process depends upon the amount of monomethylaniline which may be present. A large excess of sulfuric acid tends toward the production of m-nitro compounds, but a reduction in the amount of sulfuric acid is not feasible for this increases the amount of benzene-insoluble material. m-Nitro-tetryl reacts with water, as TNA does the nitro group in the 3-position is replaced by hydroxyl, and m-hydroxytetryl or 2,4,6-trinitro-3-methylnitraminophenol, yellow crystals from water, m.p. 183°, is formed. This substance resembles picric acid and forms explosive salts. It is readily soluble in water, and... 

For mare information on this subject see individual explosives, eg, tri- and tetra-nitro aniline, ethyl enedi amine dinitrate, tetryl, etc... 

Trinitrotoluene (TNT), Picric Acid (PA), Triaminotrinitrobenzene (TATB), hexanitrostilbene (HNS), 2,4,6-(trinitrophenyl)methynitramine (Tetryl), 1,3,7,9-6H-benzotriazolo[2,l-a]benzotriazol-5-ium (TACOT) and their higher order nitro derivatives, are important nitroaromatic explosives. One of the competing initial steps in the detonation of these nitroaromatics has been shown to involve... 

Explosive Nitro- DMNB DNT TNT EGDN NG PETN NC RDX HMX Tetryl Ammonium Potassium Sodium... 

Chemical properties. A chlorine atom ortho or para to a nitro group is especially reactive and is readily substituted. Numerous examples of such reactions, utilized in the preparation of explosives, are given later in the descriptions of preparation methods for dinitrophenol, dinitroanisole, hexanitrodiphenylamine, hexanitro-diphenyl sulphone, dinitroaniline, tetryl, etc. Chlorodinitrobenzene reacts with sodium sulphide and sulphur to yield sulphur dyes. The action of sodium disulphide results in the formation of tetranitrodiphenyl sulphide (p. 554). 

Apart from tetryl, which is discussed in the chapter on nitramines (Vol. Ill), the only aniline nitro derivative that has gained any considerable importance as an explosive is hexanitrodiphenylamine, or hexyl. None of the other nitro derivatives has proved of greater interest though some achieved temporary importance (as for example tetranitroaniline) or aroused a theoretical interest. 

Quite a number of other high explosives were introduced during this period nitro derivatives of aniline, anisole, diphenylamine, cresols, xylenols, etc. Some of these were used as bursting charges and some as boosters, the outstanding representative of the booster explosives being trinitrophenylmethyinitramine (Tetryl). 

DOT CLASSIFICATION EXPLOSIVE LID Label EXPLOSIVE LID SAFETY PROFILE Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. A powerful and violent explosive used as a booster explosive its use is superior to TNT. It is not as good for this purpose as tetryl, but is extremely stable and much safer to handle. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS. 

At a time when the only practicable methods for the preparation of nitrometliane were tlie interaction of metliyl iodide with silver nitrile and the Kolbe reacUon from chloracetic acid, the explosive was far too expensive to merit consideration. Tlie present cheap and large scale production of nitrometliane by the vapor-phase nitration of methane and of ethane has altered the situation profoundly. Trimethylolnitromethane tnnitrate is an explosive which can now be produced from coke, air, and natural gas. Nitro-methane too has other interest for the manufacturer of explosives. It may be used as a component of liquid explosives, and it yields on reduction methylamine which is needed for the preparation of tetryl. 

Dye intermediates were early on adapted to the production of explosives. While most modern explosives are aromatic nitro compounds, ancillary products incorporate amino groups. Of interest here are two tetranitroanilines. Tetryl (2,4,6-trinitrophenyl-A-methylnitramine, or A,2,4,6-tetranitro-iV-methylaniline) (40) is employed as a booster for TNT. It can be made from V-methylaniline (39), or the cheaper V,V-dimethylaniline (32), since the latter loses one methyl group on oxidation. An alternative route, introduced in World War II, starts with conversion of dinitrochlorobenzene into dinitro-lV-methylaniline, which is then nitrated. The explosive tetrotyl is 70% tetryl and 30% TNT. 

A relatively broad variety of aquatic toxicity studies exists for nitro-substituted phenol, toluene, and benzene explosives and related compounds, but very little toxicological information is available for tetryl, cyclic nitramines, and the other energetic compounds discussed in this chapter. Several explosives, such as tetryl, are no longer manufactured and are, therefore, of diminishing environmental concern, although their persistence and the nature, stability, and toxicity of their breakdown products is not understood in sufficient detail and should be further investigated. A variety of other energetic compounds, for example, perchlorates, are used in military operations, and due to environmental concerns with their release, additional studies on their fate and effects in aquatic systems are recommended. 

Introduction of more than two nitro groups into jV,A-dimethylaniline is no longer a smooth reaction demethylation and JV-nitration lead eventually to iV-methyl-2,4,6,Af-tetranitroaniline which is used as an explosive under the name Tetryl . 

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