Forty- fifth Annual Meeting. 19 



suits exactly parallel to those of their esters, the only difference 

 being that the boiling points of the free acids were uniformly 

 about 50° higher than the boiling points of their methyl esters. 

 In other words, each and every optically active constituent boiled 

 50° higher in the one case than in the other. This shows that 

 these optically active constituents are acids which are esterifiable, 

 and marks the first distinct step toward their isolation. The sim- 

 plest interpretation of these facts is that the cause of thtj optical 

 activity resides within the naphthenic acids themselves. 



It does not necessarily follow, however, that the optically active 

 constituents present in the commercial naphthenic acids are iden- 

 tical with those originally present in the petroleum. There seems 

 to be good evidence that this is not the case, for it has been shown 

 by Albrecht^^ that the optical activity of lubricating oils is not 

 appreciably reduced by thorough refining by means of alkali. 

 This result has also been confirmed by experiments with the Kan- 

 sas oil distillates already mentioned, which retained most of their 

 optical activity after being boiled with alcoholic potash. On the 

 other hand, these experiments do not prove that no optically active 

 acids are removed by the treatment with alkali, for it is quite pos- 

 sible that both Isevorotatory and dextrorotatory acids may be re- 

 moved in approximately equal quantities. To satisfactorily settle 

 this question an experiment should be carried out at a refinery 

 upon a large quantity of oil. 



The naphthenic acids are generally believed to be the oxidation 

 products of the naphthenes, or saturated cyclic hydrocarbons of 

 the series CnH2n, which are present in most of the petroleums,, 

 but particularly in those of Russia. It is to be expected, there- 

 fore, that active acids should result from the oxidation of certain 

 active hydrocarbons. The determination of the constitution of 

 any of the active acids to be found in petroleum products would 

 thus shed light upon the constitution of the active hydrocarbons 

 from which they were formed. 



The crucial test as to the correctness of our knowledge of the 

 constitution and structure of organic compounds depends upon the 

 methods for their synthesis. But chemical synthesis is a species 

 of architecture, and just as the architect before beginning the erec- 

 tion of his structure must lay down his plans and draw his designs 

 so that each and every part shall be fitly adapted to its specific 

 use. so the chemist must first in his imagination plan the order 



14. Chemische Revue. IS. 189; 1911. See. also, "Die Polarimetrie der Erdole." M. A. 

 Rakusin, p. 39. 



