Switchable surfactants.

Many industrial applications that rely on emulsions would benefit from an efficient, rapid method of breaking these emulsions at a specific desired stage. We report that long-chain alkyl amidine compounds can be reversibly transformed into charged surfactants by exposure to an atmosphere of carbon dioxide, thereby stabilizing water/alkane emulsions or, for the purpose of microsuspension polymerization, styrene-in-water emulsions. Bubbling nitrogen, argon, or air through the amidinium bicarbonate solutions at 65 degrees C reverses the reaction, releasing carbon dioxide and breaking the emulsion. We also find that the neutral amidines function as switchable demulsifiers of an aqueous crude oil emulsion, enhancing their practical potential.