Transactions of The Royal Society of Canada 



SECTION III 

 Series III JUNE 1915 Vol. IX 



Fat Acid Esters of Ethylene Glycol. 

 By Dr. R. F. Ruttan, F.R.S.C, and Dr. J. R. Roebuck. 



(Read May Meeting, 1915). 

 INTRODUCTION. 



Several years ago we prepared in quantity a number of the esters 

 of ethylene glycol with the acids found in fats. Owing to the de- 

 parture of one of the authors from Montreal, the full study of the series 

 was not then completed. The work has since been resumed and the 

 more important ethylene glycol esters of the higher fat acids have been 

 prepared, and their properties and physical constants ascertained. 

 These esters were prepared with a view to comparing their rate 

 of hydrolysis with that of the true glycerides, and with the object 

 of trying feeding experiments on small animals, to ascertain whether 

 glycerides would be found to replace these compounds of glycol in the 

 liver and other tissues. 



They may all be prepared by direct esterification of glycol by 

 the desired acid at a high temperature and constant stirring as described 

 below. The separation of the mono and di derivatives can only 

 be effected by prolonged fractional crystallization in the presence of 

 large quantities of the solvent. 



They are generally harder and more crystalline and less soluble 

 in ether and alcohol, and have a higher melting point than the 

 corresponding di-glycerides. 



Since only one of the esters resulting from the union of Glycol 

 with a fat acid has been recorded, viz., the di-stearate prepared by 

 Wurtz in 1859, it was thought a careful study of the series would be of 

 value in connection with the general chemistry of fats. Our knowledge 

 of the solubilities, specific gravity, stability, etc., of the pure glycerides 

 is very limited. The work of Chittenden and Smith on the palmitins 

 published in 1886 is about the only serious study of fats since the work 

 of the French chemists Chevreul and Berthelot, early last century. 



Sec. Ill, 1915—1 



