182 Proceedings of the Royal Irish Academy. 



After .standing about half an hour the mixture was filtered, and the 

 residue on the filter was washed first with warm alcohol and then with 

 water. This residue was recrystallised twice from benzene. It formed 

 colourless, prismatic needles, melting at 210-213° 0. Only a very small 

 quantity of the substance was obtained in this way. 



IV. Action ofAqmciK A /In lies on a- Trinitrotoluene. 



(a) The formation of a colourless crystalline substance, melting at 212° C, 

 and probably identical with hexanitrodibenzyl, by t he action of sodium 

 carbonate on a-trinitrotoluene was observed by Dr. T. J. Nolan of Nobel's 

 Explosives Company, Ardeer, and the facl was communicated tons by the 

 Research Department of that Company. We succeeded in confirming this 

 observation by the following method, which is substantially the same as that 

 employed by Dr. Nolan. 



A. mixture of 5 _ I a-trinitrotoluene, 5 grams of dry sodium car- 



1 ate, and 150 cc. of water was heated on the water-bath for about five 



hours. The solution assumed a pale violet tint, which gradually deepened, 

 and nl t ii 1 1 ime deep red-brown. 



mixture was then cooled and filtered, and the residue was washed 

 with water until the washings were almost colourless. The residue was 

 dried, boiled with an equal weight of benzene, and tillered from a dark, 

 amorphous Bolid. On Btanding about twenty minutes, the solution deposited 

 colourless prismatic crystals, which were separated and purified by re-crystal- 

 . time-, ft benzene. The crystals melted with slight decom- 

 position -it 21G 217 0. The substance is moderately soluble in boiling 

 benzene or boiling xylene. When treated with sodium amalgam and alcohol, 



sd coloration i-< developed. It- alcoholic solution gives a brownish-red 

 coloration* with caustic soda. Since a mixture of this substance with that 

 obtained by the action of potash and iodine on trinitrotoluene melted about 

 21." c . the iv. identical 



</<> The action of aqueous caustic soda on a-trinitrotoluene yields products 

 similar to tic tied by the action of sodium carbonate. 



The black substance, which separated from the alkaline solution and was 

 not dissolved by the benzene, exploded when heated on a platinum foil. The 

 dark-coloured alkaline filtrate from the undissolved matter gave on acidifica- 

 tion, a copious evolution of nitrous fumes, a dark-coloured, slimy solid being 

 precipitated. This solid, when washed and dried, formed a black, tarry mass 

 from which ic> crystalline derivative was obtained. 



(c) Preparation of Tetranitro-Azoxytoluene. 



In the preparation of tetranitro-azoxytoluene, we followed the method of 



