Trinitro derivative of 1,3,5-trichlorobenzene

5-Trichloro-2,4,6-trinitrobenzene (m. p. 187°C) can be prepared by the nitration of 1,3,5-trichlorobenzene with anhydrous nitric acid and oleum (Jackson and Wing [42]). However, according to van Ryn [43] the yield is poor. 

the compound is of no interest as an explosive, for 1,3,5-trichlorobenzene is too expensive as a starting material. It is prepared by the chlorination of aniline followed by diazotization and reduction with alcohol. Nevertheless it may be used for the preparation of explosives with certain specially valuable properties, for example, an initiating substance - trinitrotriazidobenzene - (Vol. Ill) or for the very powerful high explosive - trinitrotrimethylnitroaminobenzene (Vol. III). It was used in Germany as an insecticide. 

Manufacture of l,3,5-trichloro-2,4,6trinitrobenzene. The I. G. Griesheim Works applied the following process for the manufacture of the above product. 

The reactor is charged with 980 kg of 30% oleum to which 100 kg of solid trichlorobenzene is added during the course of one hour. The whole is heated to 100°C for another hour and kept at this temperature for 2-3 hr longer with constant stirring. Towards the end of this operation sulphonation takes place. The reaction may be considered complete when a sample of the mixture taken from the nitrator dissolves completely in water. 

The spent acid contains 13% of HN03 and H2S04 + S03 equivalent to 90% I S04. 

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