278 



III, CHEMISTRY OF NEUTRAL FATS 



temperature cycle is employed; with a ratio of 1 to 1, nearly pure mono- 

 glyceride is precipitated. The glycerides prepared by alcoholysis of cotton- 

 seed oil were shown to be 1-monopalmitin and 1,3-dipalmitin, respectively. 

 The relation of reaction mixture to the products present at equilibrium are 

 shown in Figure 15. 



60 



^ 40 ^ 



2 



R 20 



Fit 



0.2 0.4 0.6 0.8 1.0 1.2 



RATIO OF FREE HYDROXY!. GROUPS TO ESTER GROUPS 



15. Calculated composition produced at equilibrium by single- 

 phase alcoholj^sis of triglycerides with glycerol. ^^ 



IVIany workers have studied glycerolysis as a method of preparing 

 monoglycerides. Most of the procedures*^''*^^ involve heating glycerol and 

 the triglyceride fat at 170-250°C. ^'arious catalysts such as xylene, caus- 

 tic soda, caustic potash, and sodium alcoholates are suggested in amounts of 

 0.05 to 0.20% of the fat used. However, in the procedure of Eckey and 

 Formo,23 a maximum temperature of 32.2°C. (90°F.) was employed. 

 The procedure has been patented by Eckey.^^^ A number of other pat- 

 ents have been issued for the commercial production of di- and mono- 

 glycerides, including those of Edeler and Richardson, ^^^ Eckey and Clark,^^^ 

 Richardson and Eckey,^^^ Christensen,^-'' and Hilditch and Rigg.^-^ 



^15 S. Kawai and S. Yamamoto, /. Soc. Chem. Ind. Japan, J,S, suppl., 219-220B(1940); 

 Chem. AbsL, 35, 1255 (1941). 



^16 E. W. Eckey, U. S. Patent No. 2,442,534 (June 1, 1948). 



^" A. Edeler and A. S. Richardson (to Procter & Gaml)l('), Canadian Patents ^ns. 

 340,803 to 340,805 (April 10, 19.34). 



4'8 E. W. Eckev and C. C. Clark (to Procter & Gamble), U. S. Patent No. 2,065,520 

 (Dec. 29, 1936). ' 



"9 A. S. Richardson and E. W. Eckey (to Procter & Gamble), U. S. Patent No. 

 2,132,437 (Oct. 11, 1938). 



^20 C. W. Christensen (to Armour), U. S. Patent No. 2,022,493 (Nov. 26, 1935). 



421 T. P. Hilditch and .J. G. Rigg (to Imperial Chemical Tiidustiies), U. S. Patent No. 

 2,073.797 (March 16, 1937). 



