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IX. 

 UN ,.-. /3-, AND y-TRINITKOTOLUENES. 



By HUGH KYAN, D.Sc, AND W. M. O'EIOEDAN, M.Sc, 

 University College, Dublin. 



Read June 24. Published Deckubek 4, 1918. 



Crude n- trinitrotoluene is liable to contain small quantities of its (3- and y- 

 isomers. The three substances are very similar in physical properties and 

 are equally powerful as explosives. They differ in melting-points and in the 

 colour reactions which they give with certain substances such as ammonia. 

 Although a -trinitrotoluene is by no means a sensitive explosive, some 

 accidents have occurred with it which have not been satisfactorily explained, 

 and which indicated that the substance may sometimes contain a much more 

 sensitive body. It has generally been supposed that the sensitive body is 

 derived from a-trinitrotoluene, but it may equally well be assumed that it is 

 derived from the /3- or 7-isonier, and this assumption would be all the more 

 likely if the j3- or the ■y-isomer were chemically more reactive than the 

 a- compound. 



With a view to gaining some insight into this rather obscure field, we have 

 examined under conditions as nearly comparable as possible the behaviour of 

 the three isomers towards alkalies, amines, hydrocarbons, and aldehydes, and 

 also for comparative purposes the behaviour of alkalies towards s-trinitro- 

 benzene. 



A. — Historical Introduction. 



1. Action of Alkalies. 



J. Wilbrand (Liebig's Annalen d. Chem. cxxviii( I860), pp. 178-9), who was 

 the first to prepare <r- trinitrotoluene, mentions that it is attacked by hot 

 alkali giving a deep red solution from which acids precipitate dark Hakes. 

 Tiemann (Ber. d. Dtsch. Chem. Ges. lii (1870), pp. 217-19, 22.". -LTo states 

 that a- trinitrotoluene is coloured red by alcoholic ammonium sulphide, and 

 also that s-trinitrobenzoic acid is coloured red by excess of alkaii or by 



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