SYNTHESIS, SURFACE-PROPERTIES, AND HYDROLYSIS OF CHEMODEGRADABLE ANIONIC SURFACTANTS - DIASTEREOMERICALLY PURE CIS-2,5-DISUBSTITUTED-1,3-DIOXANE AND TRANS-2,5-DISUBSTITUTED-1,3-DIOXANE

In our continuing systematic studies concerning the synthesis, surface properties, and hydrolysis of chemodegradable, diastereomerically pur e surface active 2,5-disubstituted 1,3-dioxane derivatives, two new gr oups of anionic surfactants, sodium cis-and trans(2-n-undecyl-1,3-diox an-5-yl)methyl sulfates and sodium cis-and 2-n-undecyl-1,3-dioxan-5-yl )oxy]propanesulfonates, were synthesized and investigated, Surface pro perties of these surfactants, i,e., surface excess concentration, Gamm a, surface area demand per molecule, A, effectiveness of surface tensi on reduction, Pi, critical micelle concentration, CMC, and standard fr ee energies of adsorption, Delta G(ads)(0), and of micellization, Delt a G(mic)(0), were determined, It was shown that the Irans-isomers, in which the configuration of the polar group is equatorial, are more sur face active than the cis-isomers with axial configuration of the polar group at the C-5 carbon atom of the 1,3-dioxane ring. The surfactants under study undergo easy hydrolysis reaction in DCl/D2O solution with cleavage of the 1,3-dioxane ring to nonsurface active intermediates. The trans-isomers are hydrolyzed faster than ris-isomers. (C) 1997 Aca demic Press.