SYNTHESIS AND CHARACTERIZATION OF SINGLE-CHAIN 2ND-GENERATION CLEAVABLE SURFACTANTS

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.