Health & Environmental Research Online (HERO)


Print Feedback Export to File
8157254 
Journal Article 
The Kinetics of Hydrolysis of β-Propiolactone in Acid, Neutral and Basic Solutions 
Long, FA; Purchase, M 
1950 
Yes 
Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126 
72 
7 
3267-3273 
English 
1. Data on the rate of reaction in aqueous solutions between β-propiolactone and hydroxide ion at 0.07° and 6.90° are presented. 2. Data are given on the rate of reaction between water and β-propiolactone at 11.68, 25.00 and 37.28°. Between pK values of 0 and 7 this water reaction is the only one which occurs. A preliminary study of salt effects on this reaction has been made. Sodium perchlorate and silver or potassium nitrate at concentrations up to 0.1 molar cause little or no change in rate. A large apparent effect of sodium chloride is due to entrance of a reaction of the lactone with chloride ions. 3. An acid catalyzed hydrolysis of the lactone occurs in aqueous solutions of strong acids when the acid concentration is 2 molar or higher. This reaction has been studied at 25° in solutions of perchloric, sulfuric and nitric acids. The rate of hydrolysis is accurately proportional to H0, the Hammett acidity function, and not at all to molar concentration of strong acid. The result suggests that the mechanism of the acid catalyzed hydrolysis of the β-lactone differs from that of γ-lactones and most aliphatic esters and that the reaction goes through the Aˊ-l mechanism of Day and Ingold. © 1950, American Chemical Society. All rights reserved.