Hydrolysis of 1, 3‐dichloropropene in dilute aqueous solution

Abstract Hydrolysis of [14C]‐radiolabeled 1, 3‐dichloropropene (1, 3‐D) was studied at pH 5, 7 and 9 at 10, 20 and 30°C in sterile buffered water. The rate of hydrolysis was independent of pH at each temperature, with measured half‐lives of 3‐1 (±0.l), 11.3 (±0.5) and 51 (±2.3) days at 30, 20 and 10°C, respectively. The activation energy for the hydrolysis reaction was determined to be 23.9 kcal mol−1 deg−1. One hydrolysis product was formed during the course of the study and was identified by co‐chrornatography with analytical standards, using h.p.l.c., to be 3‐chloroallyl alcohol. The alcohol appeared to be stable to further hydrolytic conversion and was formed in the same cis: trans ratio as in the initial 1, 3‐D starting material, indicating essentially identical rates of hydrolysis for the cis and trans isomers of 1, 3‐D.