Synthesis and Characterization of Single-Chain Second Generation Cleavable Surfactants

Article abstract of DOI:10.1021/jo00061a044

Three series of single-chain, second generation cleavable surfactants, trans-<8-(2,2-dialkyl-5-octyl-1,3-dioxolan-4-yl)octyl>trimethylammonium methanesulfonate (1) and sodium (2) and triethanolammonium trans-8-(2,2-dialkyl-5-octyl-1,3-dioxolan-4-yl)octane-1-sulfate (3) (a, R = Me; b, R = Et; c, R = Pr; d, R = Bu), were prepared.They were characterized by critical micelle concentration, Krafft temperature, and dynamic laser light scattering measurements.Acid-catalyzed hydrolysis of surfactants 1, 2, and 3 gives (threo-9,10-dihydroxyoctadecyl)trimethylammonium methanesulfonate (4) and sodium (6) and triethanolammonium threo-9,10-dihydroxyoctadecane-1-sulfate (7), respectively, and a dialkyl ketone 5 (a, Me2CO; b, Et2CO; c, Pr2CO; d, Bu2CO).Cleavage of these surfactants thus gives another surfactant, with a higher critical micelle concentration, and a water-soluble neutral compound.Surfactants 3 were about 20 times more reactive than 1.