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VIII. 



THE NTTEO DEEIVATIVES OF PHENYL-2-NArHTHYLAMINE. 



By HUGH EYAN, D.Sc, and JAMES J. DEUMM, M.Sc, 

 University College, Dublin. 



Read April 22. Published Df.ce.mher 4, 1918. 



AMONGST the substances proposed for use as stabilisers for nitrocellulose 

 powders is phenyl-aceto-2-naphthalide. The nature, however, of its beneficial 

 action in such powders has not hitherto been investigated. 



As far as is known at present, stabilisers may act in various ways. The 

 substance may discharge its "role " as stabiliser by combining with the acidic 

 decomposition products of the explosive ; it may act catalytically as a negative 

 accelerative agent for the reactions involved in the disintegration of the 

 powder, or its stabilising action may simply be due to any gelatinising 

 effect it may produce when incorporated in the powder — the result of 

 gelatinisation being to render the powder less porous and, therefore, to some 

 extent protecting it from the injurious effects of atmospheric agents. The 

 nitrous and nitric acids formed during the decomposition of nitrocellulose, 

 owing to their oxidising and hydrolysihg powers, exert a deteriorating effect 

 mi the latter. Since it seemed likely that the stabilising action of phenyl- 

 aceto-2-naphthalide is due to its power of combining with nitrous and nitric 

 acids, the action on it of these substances was examined. 



Nitrogen peroxide, the nitrating constituent of dry nitrous fumes, has- 

 apparently no action on phenyl-aeeto-2-naphthalide, when the latter is free 

 from traces of moisture. In the presence of moisture a mononitro derivative 

 of phenyl-2-naphthylamine is produced ; but, as well as nitration, hydrolysis 

 of the naphthalide also occurs. This mononitro compound, which melts at 

 119° C, was also got by dissolving phenyl-aceto-2-naphthalide in cold con- 

 centrated nitric acid. The orientation of the nitro group in the compound 

 was not determined, but the following facts and considerations afford 

 indications as to the position of the nitro-group: — 



The mononitro compound melting at 119° C. cannot be 4'- or 1-nifcro- 

 phenyl-2-naphthylamine, since these compounds, which were prepared syn- 

 thetically, melt at 283° C. and 105° C. respectively. It is unlikely that the 



R.I.A. PROC, VOL,. XXXIV. SECT. B, [Z] 



