188 Proceedings of the Royal Irish Academy. 



are based on the conversion of |3- trinitrotoluene into 2o-dinitro-3-inethyl- 

 phenol by the action of alkalies, and into the corresponding amine by the 

 action of ammonia. 



XIII. Action qfp-T on y-Trinitrotoluene. 



Equimolecular proportions of -/-trinitrotoluene and p-toluidine were dis- 

 solveil in benzene, and the cold solutions were mixed. The mixture was 

 allowed to evaporate in the cold, and the separated solid was washed with 

 benzene and alcohol and dried in a vacuum desiccator over calcium chloride. 

 A substance was obtained in this way which consisted of yellow needles 

 soluble in alcohol, readily soluble in benzene and pyridine. On heating it 

 turned a reddish-orange colour at 147 < '.. and melted to a red liquid at 

 1~>4 ; C It gave on analysis the following results: — 



0-1 I _ _ ms substance gave 162 c.c. moist nitrogen at 12 C. 

 and 766 in. in. p. 



corresponding to N 1717. 

 I .11 ,XA requires X 1676. 



The sal ■ an additive compound in equimolecular 



proportions of y-trinitrotoluene and p-toluidic . . 



If hot alcoholic solutions of "/-trinitrotoluene and p-toluidine be mixed, 

 the mixture on cooling quickly deposits a solid which consists mainly of 

 yellow : through which arc mixed some monoclinic platy crystals 



having an oi i .our. The yellow needle-shaped ci Ive more 



lily in alcohol than the i substance, which is, however, readily 



me or pyridine. When heated, the orange Bubstance melts 

 to a red liquid at 154' •'. It gave on analysis the following results:— 



O1140 . gave 14 - 0c.c. moist nitrogen at 12 C. 



and 774 ni.m.p. 



responding to N 1484 

 II XjO, requires X 14 



* .II ,X X 16*76. 



The su - therefore a dinitroditolylamine. According to Will 



(Ber. d. I xlvii (1014 . p. 712 . y-trinitrotoluene is con. 



2.4-dinitro-5-methylphenol. It is probable 

 therefore that the ditolyhunine has the following formula: — 



