18 Kansas Academy of Science. 



of 310°. Javanese petroleum yields vacuum fractions boiling^ 

 about 150-180° which are Isevorotatory, but the higher boiling 

 fractions are dextrorotatory.^ A sample of petroleum from Borneo 

 yielded a distillate collected between 260° and 340° under atmos- 

 pheric pressure which was Isevorotatory,^ A Isevorotatory activity 

 has also been reported in an oil from Argentine Republic.^" 



But the fractions obtained in the distillation of petroleum do 

 not represent distinct chemical individuals, but consist of more or 

 less complex mixtures. Hence it is necessary for us to make use 

 of other processes before we can isolate the optically active con- 

 stituents. The fact that the distillation products of petroleum 

 have found such a ready market without' the necessity of chemi- 

 cally transforming them has, no doubt, greatly hindered the de- 

 velopment of chemical methods for their utilization. But in re- 

 cent years competition in the refining of illuminating oils is be- 

 ginning to force the refiners to look to the utilization of their waste 

 products. In Russian refineries the alkaline sludges are now treated 

 so as to recover the so-called naphthenic acids which find a ready 

 market for the manufacture of cheap soaps. 



The fact that the naphthenic acids derived from kerosene show 

 greater optical rotation than the kerosene was first observed by 

 Rakusin.^^ The naphthenic acids derived from lubricating oils were 

 found by Marcusson^^ to be much more strongly active than those 

 derived. from kerosene. 



A study of isomeric naphthenic acids^^ has recently been made 

 in the laboratory of industrial research of the University of Kan- 

 sas. Commercial naphthenic acids, after being freed from hydro- 

 carbons, were converted into esters, which were repeatedly 

 fractionally distilled. The lowest boiling fractions were strongly 

 Isevorotatory. The succeeding fractions showed a gradual de- 

 crease until in the intermediate fractions a neutral or inactive 

 point was reached. Above this there was a gradual increase in 

 dextrorotatory activity, A portion of free naphthenic acids, which 

 were similarly puriBed, were separately fractionated and gave re- 



8. "Die neueren Ansichten uber die Entstehung des Erdols," C. Engler, Berlin, p. 55; 1907 



9. Jones and Wootton, Jr. Chem. Soc, 91, 1146; 1907. 



10. Longobardi. Petroleum VI, 552; 1911. Jr. Russ. Phys.-Chem. Soc. -iJ, 792; 1911. 



11. Die Untersuchung des Erdols und seiner Produkte, p. 178, 1906. 



12. Chemiker-Zeitung, 1907, No. 3?, p. 421. 



13. Grig. Com. 8th Internat. Cong. Appl. Chem.. VI, 57-67: 1912. 



Note.— The same isomeric naphthenic acids have since been ir.dependently isolated by the 

 method of repeated fractional crystallization of their amidee, by Gadaskin and Zavershinskaya, 

 jr. Russ. Phys.-Chem. Soc, J,5, 377, 1913. 



