Hydrolysis of 1, 3-dichloropropene in dilute aqueous solution

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.