NEP. NITROPARAFFINE SALTS. 145 



the presence of ethylnitrolic acid and of dinitroethane in the acid 

 portion was proved as in the above case. The neutral portion was an 

 oily mixture, boiling between 105° and 130° at 30 mm. pressure. 

 The amount of material at hand was, however, insufficient lo admit of 

 its further study, although a portion boiled at ordinary pressure at 

 about 200°, and consists therefore probably of ^ diuitrobutane, 



CHsv 



C(N0,)2.* 

 C2H5/ 



The results obtained above prove that the reaction which takes place 

 on treating silver dinitroethane with alkyliodides is the following. 



I. Direct replacement of the metal (chief reaction) : 



CH3-C = NOAg + CH3I or C2H5I 



I II 

 NO2 O 



= CH3C = NOCH3 or CHg-C = NOC2H5 + Agl. 



I II I II 



NO2 O NO2 o 



A B 



The esters A and B, which are first formed, are however very un- 

 stable compounds, and just as the nitromethane salts, 



CH2 : NOM, 



II 



O 



are strong oxidizing agents. An intramolecular oxidation therefore 

 takes place, and ethylnitrolic acid and either formaldehyde or acetal- 

 dehyde is formed, according to the equation : 



CH3-C = N-CH2H or CH3-C = N-OCHHCH3 



I II I II 



NO2 O NO2 o 



= CH3-C ; NOH or CH3-C : NOH 



I I + CH2 ; O or CH3CH • O. 



NO2 NO2 



Ethylnitrolic Acid. 



The ethylnitrolic acid thus formed reacts upon silver dinitroethane, 

 present in excess, setting free dinitroethane and forming the silver salt 

 of ethylnitrolic acid, 



* V Meyer, Ber. d. chem. Ges., IX. 701. 



VOL. XXX. (N. 8. XXII. J 10 



