Mar. i8, 1918 Fatty Acids ifi B litter Fat 721 



Meyer (17) employed substantially the Haller method with cotton- 

 seed oil, but increased the amount of methyl alcohol to four times the 

 weight of the oil, and obtained a yield of about 90 per cent. 



Elsdon {3, 4) employed the Haller method with coconut oil and palm- 

 kernel oil, fractionated the resulting methyl esters in vacuo, and refrac- 

 tionated to constant boiling point. He stated that the process had 

 qualitative and a considerable amount of quantitati\"e value, but was 

 too lengthy for ordinary use. 



Kailan {16) found that ether, benzene, and carbon tetrachlorid did 

 not accelerate the esterification of benzoic acid with absolute alcohol 

 and hydrochloric acid or with dilute alcohol and acid. 



Wolff and Scholze (50) used a dilute sodium-bicarbonate solution to 

 purify the esters when shaking out with ether. 



Abderhalden and Kautzsch (j) esterified the silver salt of an amino 

 acid by boiling with an excess of ethyl iodide. 



Grandmougin, Havas, and Guyot (6) showed how an organic acid after 

 treatment with sodium methylate might be converted by means of an 

 excess of dimethyl sulphate into the methyl ester of the organic acid and 

 sodium methyl sulphate. 



Possibly methyl sulfonic acid might be substituted in some instances 

 for dimethyl sulphate or methyl halide as indicated by an English patent, 

 No. 9359-^ 



Hauser and Klotz {12) esterified organic acids with alcohols by pass- 

 ing the vapors over glucinum oxide heated to 310° C. 



Permissible space does not allow one to do justice to the articles cited. 



PRELIMINARY WORK 



Further study of esterification was undertaken with a view of secur- 

 ing a method for determining the percentage of another insoluble acid 

 besides stearic and oleic in butter fat. Laurie acid was naturally the 

 most promising, on account of the lower boiling point of its esters, 

 although myristic acid was also considered a possibility. The per- 

 centage of lauric acid, together with ordinary analytical data and the 

 amount of stearic acid determined by crystallization, would permit a 

 satisfactory calculation of the remaining insoluble acids. 



Material. — At the outset the insoluble acids were employed for 

 esterification with an idea that the previous elimination of soluble acids 

 and of glycerol would be an advantage. In reality such did not prove 

 the case, as water, a limiting factor in esterification, was produced in 

 the reaction between fatty acids and alcohols, while glycerol was pro- 

 duced in the case of fats (glyceryl esters) and alcohols as shown bv the 

 following equations : 



RCOOH -f- RiOH -^catalyzer=RCOOR^-^ H.,0 

 fatty acid alcohol ester water 



(RCOO),C3H54-3RiOH-f-catalyzer=3RCOOR,-|-C3H5(OH), 

 fat alcohol ester glycerol 



' Cliem. iVhs.. v. 6. no. 4, p. 5.55. lorj. 



