8 THE ROYAL SOCIETY OF CANADA 



The esters with oleic acid were not satisfactorily separated as 

 their solidification points seemed very near each other and that of 

 oleic acid. After separating the excess of oleic acid the oleates could 

 only be obtained in a pasty condition at low temperatures, and rapidly 

 underwent change by hydrolysis and oxidation. 



MIXED ESTERS. 



Glycol Monochlorhydrin (C2H4 OH CI) appeared to ofïer a con- 

 venient intermediate step for preparing the mixed esters, such as the 

 chloride palmitate and chloride stéarate, as well as a second method 

 of obtaining the monoesters. Attempts to prepare it according to 

 the method described by Bouchardt^ resulted in an exceedingly small 

 yield; but by applying a suggestion in Beilstein of heating the glycol 

 to 148°C. while passing in the hydrochloric acid gas, the yield was 

 greatly increased and time saved. The hydrochloric acid was rapidly 

 absorbed by the hot glycol and the monochlorhydrin formed passed 

 over through the condenser into the receiver. The excess of hydro- 

 chloric acid in the distillate was removed by potassium carbonate, 

 and a saturated solution of the carbonate was added when the chlor- 

 hydrin with 30-40% of water floated and was removed by a separating 

 funnel. Repeated fractioning of this layer gave a waterclear liquid 

 boiling at 127°C. ; the boiling point as stated by different observers is 

 127°C. and 130-13rC. By this method the yield of the purified 

 substance was about 30% of the theoretical. 



For the preparation of the monoesters, equivalent quantities 

 of the silver salt of the respective acids (stearic and palmitic) and 

 glycol monochlorhydrin were heated for 18 hours at 105-1 15 °C. 

 The resulting mass was extracted with hot ether, filtered hot, evapor- 

 ated, and the residue taken up in alcohol. After several crystalliza- 

 tions this yielded the monoester as well as a little of the diester. 



The mixed esters described below were prepared by heating in 

 a sealed tube to 105-1 15 °C. for about 20 hours, equivalent quantities 

 of the respective acid and glycol chlorhydrin. The chlorhydrin 

 was miscible with the fused acid and the water produced by their 

 reaction separated as a lower layer. The reaction stopped with 

 18-20% of the acid remaining uncombined. The compound sought 

 was easily separated from the other components of this reaction 

 mixture (uncombined acid and a little diester) as it is much more 

 soluble in alcohol than the distearate. It crystallized readily from 

 about 90% alcohol and was comparatively easily purified. 



1 Comp. rend., 100, 453. 



