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

Three series of single-chain, second generation cleavable surfactants, trans- [8- -5-octyl-1,3-dioxolan-4-yl)octyl]trimethylammonium methane sulfonate (1) and sodium (2) and triethanolammonium 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 micell e concentration, Krafft temperature, and dynamic laser light scatterin g measurements. Acid-catalyzed hydrolysis of surfactants 1, 2, and 3 g ives (threo-9,10-dihydroxyoctadecyl)trimethylammonium methanesulfonate (4) and sodium (6) and triethanolammonium threo-9,10-dihydroxyoctadec ane-1-sulfate (7), respectively, and a dialkyl ketone 5 (a, Me2CO; b, Et2CO; c, Pr2CO; d, Bu2CO). Cleavage of these surfactants thus gives a nother surfactant, with a higher critical micelle concentration, and a water-soluble neutral compound. Surfactants 3 were about 20 times mor e reactive than 1.