Kansas UmvEKSiTi Quarteely. 



Vol. X, No. 3. JULY, 1901. Series A. 



ACTION OF LIQUID AMMONIA ON ACID CHLORIDS 

 AND ESTERS. 



BY EDWARD BARTOW AND DAVID F. MCFARLAND. 



The product of the action of ammonia gas or an ammonium com- 

 IDOund on an ester of an organic acid, or on an acid chlorid, is gener- 

 ally an acid amid. This fact is so well recognized that it is given as a 

 general method for the preparation of acid amids. It is stated thus in 

 Beilstein's Handbuch der Organischen Chemie, volume I, page 1232 : 

 "Die Amide entstehen bei der Einwirkung von Ammoniak auf die 

 zusammengesetzten Aether organischer Sauren. Es ist angezeigt, 

 bei moglichst niederer Temperatur zu arbeiten und freie Alkohole 

 fern zu halten ( Bonz, Ph. Ch. 2, 900). In der Kalte verlauft die re- 

 action sehr langsam, rascher beim Erhitzen unter Druck. . . . 

 Leichter erhalt man die Amide beim Behandeln der Anhydride mit 

 Ammoniak, am bequemsten aber aus den Chloriden und concentrir- 

 tem, wasserigem Ammoniak (oder trokenem Ammoniumcarbonat)." 



It seems that the ammonia used for these amid syntheses has al- 

 ways been in the form of a gas, or combined in an ammonium com- 

 pound, and that no one has published results of experiments in which 

 liquid anhydrous ammonia was used as the source of the ammonia. 

 The commercial use of liquid ammonia in the manufacture of ice has 

 so cheapened it that it is now an adjunct to every well-equipped 

 chemical laboratory, and it affords a convenient source of ammonia 

 for many experiments. Its comparative purity and freedom from 

 moisture recommend it for some syntheses, and it was particularly on 

 account of these qualities that it seemed possible to use it for the syn- 

 theses of acid amids. 



A series of experiments was undertaken, therefore, to ascertain, 

 first, whether acid amids could be obtained by the action of liquid 

 ammonia on acid chlorids; second, whether they could be obtained 

 from esters ; third, the conditions governing such reactions ; and 

 fourth, when amids are not formed, to ascertain what products are 

 formed. 



6-K.U.Qr. A-x 3 [79]-K.U.Qr.-A x 3-.Jul.v, 'CI. 



