Ryan and O'Riokdan — On a-, ft-, and y- Trinitrotoluenes. 191 



It consisted of dull yellow acicular prisms, which melted at 83° C, and other- 

 wise resembled the corresponding derivative of the /3-isomcr. It gave on 

 analysis the following results : — 



0*1075 grams substance gave 10"0 c.c. moist nitrogen at 16° G. 

 and 757 m in. p. 



corresponding to N 10'8. 

 C 1 .H 16 N.. 1 O requires N 10-32. 



Summary of Results. 



The following is a summary, of the results obtained in the course of the 

 work : — 



1. The action of the aqueous alkalies on s-trinitrobenzene yields, in accord- 

 ance with Lobry de Bruyn's statement, tetranitroazoxy benzene. A small 

 amount of a substance melting about 200-220° C. was also obtained, and this 

 may possibly be hexanitrodiphenyl, which melts at 234° C. 



Tetranitroazoxybenzene resembles in its reactions the tetranitroazoxy- 

 toluene of Anschiitz and Zimmermann. 



a-trinitrotoluene yields a fairly stable compound with sodium w-butylate. 

 The analyses obtained for this compound indicate, possibly, the formation, in 

 addition to the mono-alcoholate, of a di- or tri-alcoholate in small quantities, 

 this being in agreement with the statement of Busch and Koegel, already 

 mentioned. 



With alkalies in the presence of an oxidising agent, a-trinitrotoluene yields 

 hexanitrodibenzyl. The same substance is obtained by the action of hot 

 caustic soda or sodium carbonate on a-trinitrotoluene. Hexanitrodibenzyl 

 possesses properties different from those of the tetranitroazoxytoluene of 

 Anschiitz and Zimmermann. 



/^-trinitrotoluene with alkalies yields a dinitrometacresol, melting at 

 101° C, with a large quantity of more complex products. 



■y-trinitrotoluene with alkalies gives a small quantity of a dinitrocresol 

 and also a small quantity of a crystalline substance which is insoluble in 

 alkalies, and which may possibly be a dibenzyl or stilbene derivative. 



From the products of the reaction of each of the substances mentioned 

 with alkalies dark amorphous explosive substances were isolated. 



2. a-trinitrotoluene yields brown complex products by the prolonged 

 action of aqueous ammonia. 



r3-trinitrotoluene reacts very readily with alcoholic ammonia in the cold, 

 yielding dinitrotoluidine. This is apparently at variance with Hepp's results, 



[2 C 2] 



