46 Dr. Debus on the Action of Nitric Acid 



Whilst the glyoxal is oxidized easily by vei-y diluted nitric acid, 

 it requires an excess of strong acid to convert the glycolic into 

 oxalic acid. 



Frequently when I employed less nitric acid in the oxidation 

 of alcohol, as mentioned in my first paper on this subject, I 

 obtained along with glyoxal a liquid which possessed many pro- 

 perties in common with glycerine, C^ H^ 0^. As it is most likely 

 to contain, like glyoxal, glycolic and glyoxylic acids, two atoms 

 of carbon, I suppose it to be homologous with glycerine. Its 

 composition would be represented by the formula C^ H^ 0^. If 

 the latter is compared with that of glyoxal, it becomes at once 

 apparent that both stand in the same relation to each other as 

 alcohol and common aldehyde, and that sethyle-glycerine, gly- 

 oxal, and glyoxylic acid, stand to each other as alcohol, aldehyde, 

 and acetic acid. 



Alcohol . 

 Aldehyde 

 Acetic acid 



= C2H'*0 

 = C2H4 0^ 



^thyle-glycerine =Q.^WO^ 

 Glyoxal . . . =C2H4 03 

 Glyoxylic acid . =G''R''0'' 



Therefore the oxidation of the alcohol by nitric acid appears not 

 to extend at once to the production of glyoxal and glyoxylic acid, 

 but the alcohol simply absorbs oxygen, and is converted into 

 another alcohol homologous with glycerine. The sethyle-glyce- 

 rine would unite with more than one atom of a monobasic acid, 

 and accordingly we find its aldehyde — the glyoxal — combining 

 with two atoms of bisulphite of ammonia, and its acid — the gly- 

 oxylic acid — bibasic or perhaps tribasic. 



Wurtz has recently produced a new alcohol which he calls 

 glycol. This alcohol would stand between sethyle-glycerine and 

 common alcohol (C^ H*'" 0), and it is not improbable that it is 

 produced by the first action of nitric acid on common alcohol. 

 If so, the oxidation of the latter would proceed thus : — 

 0^11*^0 + = C^H^O^ 



Alcohol. Glycol. 



C^H^O^ -f- = C^H^O^ 



Glycol. vEthyle-glycerine. 



C2H603 4- O = C'WO^ + H^O 



iEthyle-glycerine. Glyoxal. Water. 



C2H403 -f = C^H^O^ 



Glyoxal. Glyoxylic acid. 



C^H^O^ + O = C^tPO" 4- H^O 

 Glyoxylic acid. Oxalic acid. Water. 



