184 Proceedings of the Royal Irish Academy. 



Attempts to further nitrate this substance, by using (a) concentrated 

 nitric acid and glacial acetic acid ; (b) a mixture of one part of fuming nitric 

 acid, and two parts of fuming ('20 p. c. S0 3 ) sulphuric acid, were unsuccessful. 



When treated in alcohol with sodium amalgam, this substance gave a red 

 coloration similar to that got with the substance obtained in IV (a), above. 



V. Action of Aqueous Alkalies on ^-Trinitrotoluene. 



(u) Five grams of ^-trinitrotoluene were heated on the water-bath for an 

 hour with 200 ex. of 1 p. c. caustic soda. The solution quickly developed a 

 yellow colour, which gradually changed to a dec]' brown. The trinitro- 

 toluene completely. On acidifying the solution, nitrous 

 fumes were evolve. 1 and a brown solid was precipitated. This solid was 

 filtered, washed, and repeatedly extracted with boiling water. The extracts 

 on cooling gave a yellow solid, which w.i- re-crystallised from dilute alcohol, 

 melted at IOO-10J i'.. and was therefore dinitro-m-cresol (cf W.Will, 

 Bet 4 Dtech. Chem. Ges., xlvii (1914), p. 712). 



'<) Five grams of ^-trinitrotoluene \\ ere heated on the water-bath with 

 5 grams ol sodium carbonate and LOO cc of watei for three hours. The 

 solution treated as In the lasl experiment gave the same dinitro-m-cresol. 



The undissolved residue was tillered and dried. On boiling with benzene 

 the main portion dissolved, Leaving a black amorphous residue, which 

 i on heating, the benzene solution yielded only unchanged 

 /3-trinitro toluene. 



VI. .1 i / a ■ on y- Trinitrotoluene, 



Two grams of 7- trinitrotoluene were heated top three-quarters of an hour 

 with 50 cc. of 1 per cent LTie colour of the solution rapidly 



became dark brown, and amnion a was at tin- same time evolved. The brown 

 Liquid was filtered from a slight residue and acidified. The brown solid which 

 1 was filtered an ed with boiling wain. The aqueous solution 



was extracted with ethei the ethei was evaporated, and the residual solid 

 was llised from ligroiu. It consisted of pale-yellow crystals which 



melted at 72 Che dark, tarry body from which this substance had 



been separated deflagrated on heating. The crystalline solid itself was 

 evidently a dinitro-m-cres . cf. W. Will, foe. eit.). 



The residue which remained undissolved in alkali was boiled with benzene 

 and filtered from a slight residue which exploded feebly when heated "n a 



platinum foil. The benzene solution on 1 Ling gaveacicular crystals melting 



with decomposition about 190 C. In alcoholic solution ii - greenish- 



