Phelps and Osborne — Esterification of Benzoic Acid. 45 











Table 



II. 



















A. 







Benzoic ester 



"D ^"^ 





Alfnhnl ™4+V. Tim 



Eeaction 





_^_ 





X> 



acid 

 grm. 



ZnCl 2 

 grm. 



J^Wj\j\±\ji 





Theory 

 grm. 



Found 

 grm. 



Per 



cent 



No. 



cm 3 . 



per cent 



hr. 



mi. 



( 1) 



50 



1 



40 

 160 



1-25 



2 





61-48 



51-58 



83-9 



( 2) 



50 



1 



40 

 260 



1-25 



3 





61-48 



56-71 



922 



( 5) 



50 



0-5 



200 



1-25 



2 





61-48 



53-26 



86-6 



( 4) 



50 



1 



200 



,1-25 





50 



61-48 



44-81 



72-9 



( 5) 



50 



1 



200 



1-25 



2 





61-48 



52-86 



86-0 



( 6) 



50 



1 



300 



1-25 



2 





61-48 



59-23 



96-3 



( 7) 



50 



1 



300 



1-25 



3 





61-48 



60-27 



98-0 



( 8 ^ 



50 



1 



200 



10 



2 





61-48 



56-73 



92-3 



( 9) 



50 



1 



200 



25 



2 





61-48 



51-48 



83-7 



(10) 



50 



10 



300 



.. 



1 



30 



61-48 



0-86 



1-4 



(11) 



50 



10 



200 



1-25 





50 



61-48 



53-42 



86-9 



(12) 



50 



1.0 



200 



1-25 



2 





61-48 



60-79 



98-9 



(13) 



50 



10 



300 



1-25 



2 



30 



61-48 



60-91 



99-1 



(14) 



50 



10 



200 



10 



2 





61-48 



53-18 



86-5 



(15) 



50 



10 



200 



25 



2 





61-48 



55-23 



89-8 



(16) 



50 



JO 



400 



1-25 



4 





61-48 



61-48 



1000 



(IV) 



50 



25 



200 



1-25 



1 



30 



61-48 



52-30 



85-1 



(18) 



50 



25 



200 



1-25 



5 





61-48 



5330 



86-7 



(19) 



50 



1 



200 



B 



1-25 



2 





61-48 



38-10 



62-0 



(20) 



50 



10 



200 



1-25 



2 





61-48 



52-40 



85-2 



(21) 



50 



10 



400 



1-25 



2 



45 



61-48 



53-33 



86-8 



(22) 



50 



10 



400 



1-25 



5 





61-48 



56-48 



91-8 



(23) 



50 



25 



200 



1-25 



2 





61-48 



52-83 



85-9 



the same amounts of alcohol containing 25 per cent of hydro- 

 chloric acid, the esterification is better by 13 - 2 per cent in one- 

 third less time. 



In studying the results recorded in Table II, a comparison 

 of experiments (4) with (5), (6) with (7), (11) with (12), (17) 

 with (18), and (21) with (22) shows that esterification is more 

 complete if the time of the reaction is reasonably prolonged. 

 It is not possible to control suitably a uniform flow of vapors 

 to the second flask if the action is very greatly prolonged. 

 The total amount of alcohol passed in a given time into the 

 second flask regulates the yield of ester, as is seen from a com- 

 parison of experiments (5) and (6). The amount of zinc 

 chloride, in the concentrations used, affects the amount of the 

 final product, as is shown in comparing (3) and (5) with (12), and 

 (4) with (11). The increase of zinc chloride to 25 grm. does 

 not seem to offer any advantage over the use of 10 grm., as is 



