NMR study on sulfonation of internal olefins

Terminal olefins can be converted into the corresponding sulfonates by sulfonation with SO₃ followed by hydrolysis, the products are used as detergent ingredients. Although internal olefins were also expected to be good feed stocks, it was difficult to convert them into the corresponding sulfonates with as good of a yield as that of terminal olefins under the same synthesis conditions. Our studies have been carried out in order to clarify the reason for poorer conversion of the internal olefins. It was found by a nuclear magnetic resonance spectroscopic study that the major components of the sulfonated intermediate of internal olefins wereβ-sultones, the amounts of which were usually very small in sulfonated terminal olefins. A portion of theseβ-sultones was desulfonated, depending on temperature, to the original olefins and the corresponding sulfate salts during alkaline hydrolysis. The prevention of desulfonation of theβ-sultones in the hydrolysis process was one of the most important aspects for the production of internal olefin sulfonates. Finally, by keeping the hydrolysis temperature below 35°C, the conversion of internal olefins into sulfonates was achieved with the same yield as that of conventional terminal olefins.