14 GIBBS. 



With concentrated sulphuric acid azophenine gives a reddish-purple resembling 

 the initial color obtained on dropping a crystal of morphine into the formal- 

 dehyde-sulphuric acid reagent, 2, 5-dianilinoquinoneanil a salmon-red 17 and 2. 5- 

 dianilinoquinone a fuchsin-red color. 



THE OXIDATION OF ANILINE. 



The oxidation of aniline with various oxidizing substances has been 

 productive of many and various reaction products. The reagents which 

 seem to have the most intimate bearing upon the reactions which ordi- 

 narily produce the coloration of aniline are oxygen, ozone and peroxides. 



Otto JS passed ozone through a solution of aniline in benzene at 15° and 50°, 

 and found the principal products to be quinone and azobenzene. 



Leeds 10 oxidized aniline acetate in acetic acid solution by means of hydrogen 

 peroxide and obtained azobenzene. 



Schunck and Marchlewski 20 and others oxidized aniline by means of hydrogen 

 peroxide in acetic acid solution and found azobenzene, dianilinoquinoneanil and 

 ammonia. They express the reaction 



4 C,;H 5 NH 2 +4 HA=C 24 rI 19 N 3 0+7H 2 0+NI-L. 



In the presence of stronger acids, indulin compounds are formed. 



Freer and Novy 2l oxidized aniline with benzoylacetyl peroxide in ether-ial 

 solution and obtained azoxybenzene as the principal oxidation product. 



Istrati -- studied the products obtained by aspirating air through boiling 



O 



ii 



aniline. Compounds to which he assigns the formulas C 



^- CA ) and 



II 

 



(C 6 H 5 -NH) 3 ; C fi H 2 • • C 6 H 2 ■ (NH-C„H 5 ) 3 are described. 



It is extremely probable that quinone condensation products which he failed to 

 identify were formed. 



EXPERIMENTAL. 



THE EFFECT OF SUNLIGHT UPON PURE, DRY ANILINE IN CONTACT WITH DRY 



ATMOSPHERIC AIR. 



Since impurities have been shown to produce a coloration of aniline, 

 and moisture often influences to a great extent the chemical action of 

 light, the effect of the sunlight upon pure, dry aniline enclosed with 

 purified, dry atmospheric air was next studied. 



Pure aniline was obtained from purified and re-crystallized acetanilid 

 by treating with potassium hydroxide solution, distilling with steam, 

 and extracting with ether. 



The etherial solution was dried over potassium hydroxide and fractioned 



"Zincke: Ber. d. deufschen chem. Ges., 1885, 18, 787, says a blood-red color. 



18 Ann. chim. et phys. (1898), 13, 138. 



19 Ber. d. deutschen chem. Ges. (1881), 14, 1382. 



w Ibid. (1892), 25, 3574. 



21 Am. Chem. Journ. (1902), 27, 178. 



"Compt. rend. Acad. sci. (1902), 135, 742. 



