Other reactions of nitro compounds

All aromatic, nitro compounds yield chloropicrin when treated with alkaline solutions of hypochlorous acid salts. The reaction occurs at room temperature or below (the lower the temperature the higher the yields). 

The reaction was first observed by Stenhouse [146] in 1847, when treating picric acid with a hypochlorite. According to A. W. Hofmann [147], a 114 wt. % yield could be obtained in the reaction. As Gardner and Fox [148] reported, the yield could be increased up to 180 - 190%. A yield of chloropicrin amounting to about 200% can be obtained by introducing gaseous chlorine into a suspension of sodium picrate in a solution of sodium carbonate at 0°C (Orton and McKie [149]). 

It can be assumed that complete transformation of the nitro groups to chloropicrin takes place in the reaction  

C6H2(N02)30H + 11C12 + 5H20 - 3CC13N02 + 13HC1 + 3C02 (37) 

At higher temperatures side reactions occur, among others the formation of nitric acid, while the yield of chloropicrin decreases. 

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