294 Phelps, Palmer and Smittie — Ester Formation. 









Table II. 















Ben- 







Abso- 



Reaction 



l Benzoic ester 





zoic 

 acid 







lute 

 ilcohol 



f-imo 





A 







Catalyzer 



i. 



t 



_A 



Theory 



Found 



Per 



No. 



grm. 





grm. 



cm 3 



hr. 



min. 



grin. 



grm. 



cent 



1. 



50 



KHS0 4 



1-388 



200 



1 







61-48 



2-72 



4-4 



2. 



50 





1-388 



200 



2 



45 



61*48 



9-64 



15-7 



3. 



50 





2-777 



200 



2 



15 



61-48 



13-43 



21-8 



4. 



50 





2-777 



200 



3 



15 



61-48 



19-21 



31-3 



5. 



50 





5-554 



200 



1 



40 



61-48 



11-05 



18-0 



6. 



50 





5*554 



200 



1 



45 



61-48 



5-75 



9-4 



7. 



50 





5-554 



200 



2 



20 



61-48 



7-62 



12-4 



8. 



50 





5-554 



200 



2 



30 



61-48 



10-02 



16-3 



9. 



50 



(NH 4 )HS0 4 



1-174 



200 



2 



10 



61-48 



5-48 



9-0 



10. 



50 



a. 



1-174 



200 



3 



15 



61-48 



8-69 



14-1 



11. 



50 



a 



2-349 



200 



2 



50 



61-48 



36-43 



59-3 



12. 



50 



u 



2-349 



200 



3 



50 



61-48 



4130 



67-2 



13. 



50 



a 



4-696 



200 



1 



55 



61-48 



43-83 



71-3 



14. 



50 



a 



4-696 



200 



3 







61-48 



48-56 



79-0 



15. 



50 



NaHSO, 



1-225 



200 



1 



30 



61-48 



20-99 



34-1 



16. 



50 





1-225 



200 



3 







61-48 



40-43 



65-8 



17. 



50 





2-450 



200 



1 



30 



61'48 



46-00 



74-8 



18. 



50 





2-450 



200 



3 







61-48 



58-69 



95-5 



19. 



50 





4-899 



200 



1 



15 



61-48 



56-44 



91-8 



20. 



50 





4-899 



200 



3 







61*48 



60-58 



98-5 



21. 



50 



C s H 6 N.H 2 SO, 



0-907 



200 



3 



10 



61-48 



3-13 



5-1 



22. 



50 



a 



0-907 



200 



4 







61-48 



5-00 



8-1 



23. 



50 



a 



1-814 



200 



1 



35 



61*48 



1-46 



2-4 



24. 



50 



a 



1-814 



200 



2 







61-48 



2-77 



4-5 



25. 



50 



a 



3-628 



200 



2 



20 



61-48 



3-86 



6-3 



26. 



50 



a 



3-628 



200 



3 



10 



61-48 



3-63 



5-9 



27. 



50 



C t H 5 NH a .H a S0 



4 0975 



200 



1 



50 



61*48 



1-39 



2-3 



28. 



50 



It 



0-975 



200 



2 



40 



61-48 



•56 



0-9 



29. 



50 



a 



1-950 



200 



1 



15 



61-48 



•37 



0-6 



30. 



50 



a 



1-950 



200 



3 



20 



61-48 



2-33 



3-8 



31. 



50 



a 



3*900 



200 



1 



15 



61-48 



2-60 



4-2 



32. 



50 



a 



3-900 



200 



3 



10 



61-48 



4 36 



7-1 



phates studied, when present in amounts of equal concentration 

 of acid hydrogen, are as efficient in catalytic effect as sulphuric 

 acid. Acid sodium sulphate is nearly catalytically equivalent ; 

 acid ammonium sulphate gives less effect; acid potassium sul- 

 phate considerably less ; while acid pyridine and aniline sul- 

 phates are very poor catalyzers. The acid pyridine sulphate gives 

 with succinic acid, which esteriiies readily, distinctly more 

 effect than acid aniline sulphate, but with benzoic acid, where 

 esteritication is more difficult, they give about the same effects. 

 Aside from the possibility of the acid sulphate in solution 

 being the active catalytic agent, two explanations would seem 

 obvious for the facts. First, that the catalytic effect is due in 



