Tetranitroaniline production

Tetranitroaniline (TNA) was used by the Russian government as a booster and fuse explosive. Aetna Powder Company produced TNA for Russian export at its plant in Noblestown, Pennsylvania. The plant exploded, ending our only source for this explosive. A new plant was built at Bound Brook, New Jersey, operated by the Calco Chemical Company. 

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Although, according to Fliirscheim, tetranitroaniline has sufficient thermal stability, even a product of the highest purity does not give a satisfactory heat test. 

According to Ingraham [19b], tetranitroaniline has shown evidence of decomposition by the heat test at 65.5°C when only a small amount of moisture was pie-sent. The main product of decompositions was II. Prolonged heating at 75°C results in loss of a nitro group. At 120°C decomposition takes place which proceeds in a way similar to that of tetryl. The initiation temperature is 231-233°C. The specific gravity of the product is 1.867 [19],... 

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. 

TNA, 2,3,4,6-tetranitroaniline (41), is a detonator in explosives. The product and the process for its synthesis were invented by the German-British chemist Bernard J. Fliirscheim, who from 1905 had investigated nitroanilines. In 1913, he sold rights to his process to Verona Chemical Company, of Newark, New Jersey. Though the process was not then adopted, the development work enabled Verona to commence the manufacture of aryl amines. The original manufacturing process for TNA was similar to those employed... 

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