OF ARTS AND SCIENCES. 93 



VIII. 



CONTRIBUTION FROM THE SALISBURY LABORATORY OF 

 THE WORCESTER POLYTECHNIC INSTITUTE. 



ON THE FORMATION OF THE ANHYDRIDES OF BEN- 

 ZOIC AND SUBSTITUTED BENZOIC ACIDS. 



By George D. Moore and Daniel F. O'Regan. 



Presented by Professor L P Kinnicutt, April 13, 1892. 



By the action of phosphoric anhydride upon benzoic acid and 

 an excess of benzol at 180-200°, Kollarits and Merz * obtained ben- 

 zophenone. The course of the reaction is shown by the following 

 equation : 



C 6 H 5 COOH + C 6 H 6 = C 6 H 5 COC 6 H 5 + H 2 0. 



The same result was also obtained when, instead of benzoic acid, 

 benzoic anhydride was employed : 



C 6 H 5 C0 



) + 2 C 6 H 6 = 2 C 6 H 5 COC 6 H 5 + H 2 0. 

 C 6 H 5 C0 



In a second paper f on this subject, the same authors state that 

 the formation of benzoic anhydride may possibly precede that of 

 benzophenone, and add that, if such is the case, benzophenone must 

 be formed by the direct action of benzoic anhydride upon benzol, 

 even in absence of phosphorpentoxide. This last result they were 

 unable to effect, even at temperatures ranging as high as 300°. 

 Similar negative results were likewise obtained when toluol was 

 employed instead of benzol. They therefore conclude that ben- 

 zophenone is the product of the direct action of phosphorpentoxide 

 upon benzoic acid and benzol. 



The following experiments were undertaken with a view to 

 studying more carefully the conditions of possible formation of 



* Zeitschr. fur Chemie, 1871, p. 705. Berichte, V. 447. 

 t Berichte, VI. 537. 



