Preparation and Characterization of Base-Sensitive Destructible Surfactants

Article abstract of DOI:10.1021/jo00371a008

Destructible surfactants 4-n-C12H25C6H4SO2CH2CH2OC6H4X-4 (1, X = N⁺Me3, NO3^-; 2, X = SO3^-, K⁺) were prepared, and their stability/lability characteristics in aqueous micellar solutions with respect to E1cB elimination to give 4-n-C12H25C6H4SO2CH=CH2 (7) and HOC6H4X-4 (8/9) were determined by 1H NMR.In 0.001 and 0.1 M DCl, both 1 and 2 were stable for 24 h at 75 deg C.In D2O alone at 25 deg C, 1 slowly decomposed, and 2 was stable.At 25 deg C, 1 decomposed completely within 10 min in 0.1 M NaHCO3, whereas 2 was more stable in 0.1 M K2CO3.The difference in reactivities for 1 and 2 was ascribed to a combination of electronic and micellar effects.Support for the latter was found in a comparison of 2's behavior with that of 4-MeC6H4SO2CH2CH2OC6H4SO3Na-4 (10).