Phelps and Eddy — Ester Formation. 



297 



The pure benzoic acid of commerce was used in all the work 

 recorded here. The alcohol was made as anhydrous as possi- 

 ble by repeated distillations over calcium oxide. A known 

 amount of hydrochloric acid gas, dried by passing through 

 concentrated sulphuric acid, was passed into a given- weight of 

 alcohol in the cold before diluting to definite concentration. 

 The pure zinc chloride of commerce was made anhydrous by 

 heating it to the melting point while a current of dry hydro- 

 chloric acid passed, then expelling the excess of hydrochloric 

 acid by farther heating before granulating. Potassium chlor- 

 ide was made pure by fusing potassium chlorate purified by 

 recrystallization from hot water. Pure ammonium chloride 

 was obtained by recrystallizing the product formed on treating 

 with sodium hydroxide a water solution of ammonium salt 

 precipitated in the conversion of cyanacetic ester to malonic 

 ester in the procedure described in a former paper* in this Jour- 

 nal, and collecting in pure hydrochloric acid the ammonia gas 



Table II. 



No. 



( 1) 

 ( 2) 

 (3) 



( 

 ( 

 ( 

 ( 

 ( 



( 



(10) 



(11) 

 (12) 



(13) 



(14) 



(15) 

 (16) 

 (17) 

 (18) 

 (19) 

 (20) 

 (21) 

 (22) 

 (23) 

 (24) 



Ben- 

 zoic 

 acid 

 grm. 



50 

 50 

 50 

 50 

 50 

 50 

 50 

 50 

 50 

 50 

 50 



Catalyzer 



Abs. Ale. 

 with HC1 



CaCl 

 a 



SrCL 



grm. 



1-00 



8-14 



1-16 



" ' 11-60 



BaCl 2 1-53 



" 15-30 



HgCl, 1-00 



" 1-98 



19-80 



2 3-46 



34-55 



Hg 2 Cl 



cm d 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 



per ct. 

 1.25 

 1-25 

 1--25 

 1-25 

 1-25 

 1-25 

 1-25 

 1-25 

 1-25 

 1-25 

 1-25 



Time 



lin. 

 15 



10 

 5 

 15 

 10 

 15 



15 



50 ?6H 2 6 

 50 " 



50$ MnC M 



o0 UH 2 O \ 



50 SnCJ 4 



50 



50 



50 



50 



50 



50 



50 



50 



50 



PbCl, 



u 



SbCl 3 



a 



BiCl 



1-11 



11-07 



14-60 



0-96 

 9-60 

 9-60 

 2-03 



20-31 

 1-10 



11-00 

 1-54 

 1-54 



15-40 



200 1-25 

 200 1-25 

 200 1-25 



200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 

 200 



1-25 

 1-25 

 1-25 

 1-25 



1-25 

 1-25 

 1-25 

 1-25 

 1-25 

 1-25 



20 



10 



15 

 20 



20 



20 



Theory 

 grm. 



61 

 61 

 61 

 61 

 61 

 61 

 61 

 61 

 61 

 61 

 61 



61 



Benzoic ester 



Found 

 grm. per cent 



•48 



50- 



•48 



14- 



•48 



32- 



•48 



32- 



•48 



38- 



•48 



43- 



•48 



41- 



.48 



51- 



•48 



60- 



•48 



43- 



•48 



46- 



.48 



30- 



•48 



21- 



•48 



40- 



•48 



54- 



•48 



58" 



•48 



60- 



•48 



38- 



•48 



36- 



•48 



51-< 



•48 



58'i 



•48 



36- 



•48 



51*. 



•48 



59'< 



30 

 67 

 63 

 34 

 70 

 26 

 11 

 70 

 65 

 65 

 39 



81-8 

 23-9 

 53-1 

 52-6 

 63-0 

 70-4 

 67-9 

 84-1 

 98-7 

 71-0 

 75-5 



57 49-7 

 20 34-5 

 00 65-1 



91 

 86 

 00 



70 

 58 

 98 

 80 

 93 

 35 



89-3 

 95-7 

 97-8 

 62-9 

 59'5 

 84-6 

 95-6 

 60-1 

 83-5 

 96-8 



Am. Jour. Sci. 

 21 



* This Journal, 

 ■Fourth Series, Vol. 



xxvi, 143. 

 XXVI, No. 



153. — September, 1908. 



