292 Phelps, Palmer and Smillie— Ester Formation. 



benzoic ester in all of the experiments of Table II, except 

 where aniline acid sulphate was the catalyzer, were recovered 

 by shaking out the ethereal solution of the impure ester from 

 the esterification flask with a solution of sodium carbonate in a 

 separating funnel containing a few pieces of ice and washing 

 with a saturated solution of sodium chloride. The sodium car- 

 bonate and the sodium chloride wash waters were each extracted 

 separately twice with fresh portions of ether to recover any 

 portions of the ester that may have been carried along with 

 them, and these ethereal solutions were added to the main mass 

 of ester. The ether was distilled oh* on a water bath, after 

 which the flask containing the ester was fitted for a vacuum dis- 

 tillation. The lower boiling impurities were removed by rais- 

 ing the temperature to 60° under a pressure of 15 mm ; the ester 

 was then distilled by heating to 140°-150° on an acid potassium 

 sulphate bath under the same pressure — 15 mm — , the receiver 

 being cooled by allowing a stream of cold water to strike it 

 continuously during the distillation. In the experiments where 

 aniline acid sulphate was used, since the aniline formed on 

 neutralization with sodium carbonate would distil over along 

 with the benzoic ester, the aniline sulphate in experiments 

 (27), (30), (31), and (32) of Table II was removed by first 

 shaking up the ethereal solution of the crude ester with water 

 in a separating funnel, and the recovery was then carried out 

 in the usual manner. In experiments (28) and (29) of Table II 

 all the material which would distil over below 150° under 15 mm 









Table I. 















Sue- 







Abso- 

 lute 

 ale oho' 



Beaction Succinic ester 





cinic 

 acid 



Catalyzer 





t 



_A ^ 



Theory 



Found 



Per 



No. 



grm. 





grm. 



cm 3 



hr. 



min. 



grm. 



grm. 



cent 



1. 



50 



H 2 S0 4 



0-5 



200 



1 



25 



73-7 



70-27 



95-3 



2. 



50 



a 



0*5 



200 



1 



30 



73-7 



70-00 



95-0 



3. 



50 



a 



0'5 



400 



1 



15 



73-7 



72 45 



98-3 



4. 



50 



a 



0-5 



400 



2 







73-7 



72-70 



98-6 



5. 



50 



a 



l'O 



200 



- 



45 



73-7 



70-55 



95-7 



6. 



50 



u 



10 



200 



1 







73-7 



70-72 



96*0 



7. 



50 



KHS0 4 



0'694 



200 



1 



10 



73-7 



33*40 



45-3 



8. 



50 



a 



2'777 



200 



1 



30 



72-7 



56-92 



77-2 



9. 



50 



a 



5*554 



200 



- 



55 



73-7 



36-74 



49-9 



10. 



50 



(NH 4 )HS0 4 



0-587 



200 



1 



10 



73-7 



39-75 



53-9 



11. 



50 



a 



2-348 



200 



1 



15 



73-7 



59-85 



81-2 



12. 



50 



it 



4-696 



200 



1 



45 



73-7 



65-85 



89-4 



13. 



50 



NaHS0 4 



4-899 



200 



1 



15 



73-7 



6925 



94-0 



14. 



50 



C 6 H 5 N.H 2 S0 4 



0-907 



200 



- 



50 



73-7 



44-35 



60-2 



15. 



50 



a 



0'907 



200 



1 







73-7 



42-85 



58-1 



16. 



50 



C 6 H,NH,H,SO 



, 0-975 



200 



1 







73-7 



1-50 



2-0 



