648 W. A. Drushel — Simple and Mixed Alkyl Phosphates. 



assuming that the hydrolysis is not confined to the alkyl group 

 which occurs twice in the molecule but. that in at least some of 

 the molecules the single alkyl group is hydrolyzed off, yielding in 

 the hydrolysis products acids of both types HRR'P0 4 and 

 HR 2 P0 4 . This view is in agreement with the results obtained 

 in the barium hydroxide saponification shown in Table II. 



Conclusions : — 



1. Both the simple and mixed alkyl phosphates are very 

 stable at room temperature even in decinormal hydrochloric 

 acid, but are rapidly saponified by barium hydroxide. 



2. All of the alkyl groups are hydrolyzable, although the 

 first group is much more easily attacked than the second and 

 third. 



3. In mixed alkyl phosphates the alkyl group which occurs 

 twice is not hydrolyzed to the exclusion of the single group, 

 but on the contrary the hydrolysis product contains both types 

 of dialkyl phosphoric acids, HRRT0 4 and HR 2 P0 4 , with the 

 first type probably very largely in excess of the second type. 



4. Tripropyl phosphate and triisobutyl phosphate are both 

 distillable in vacuo without decomposition. 



