SURFACTANT-MEDIATED PHASE-TRANSFER AS AN ALTERNATIVE TO PROPANESULTONE ALKYLATION - FORMATION OF A NEW CLASS OF ZWITTERIONIC SURFACTANTS

A synthesis of propanesulfonate surfactants 5 is presented which avoids carcinogenic propanesultone 2 as an alkylating agent. A small amount of the final desired surfactant or an easily destroyed sulfate surfactant is added to a starting alcohol 3 as a phase transfer agent, the alcohol is converted to its corresponding allyl ether 4 with 50% NaOH and allyl chloride, and the allyl ether is converted to propane sulfonate 5 by air-catalyzed addition of bisulfite. Diallyl ether produced as a solvolysis byproduct is cyclized to furan sulfonate 9. Cyclization of diallylamine with bisulfite produces pyrrolidinium sulfonate 13 and diallylmethylalkylammonium salts 14 yield a new class of zwitterionic surfactants 11 which are substantially more soluble in both water and hydrocarbons than the corresponding ammonium propanesulfonates, 12. The stereochemistry of the cyclic products is consistent with a radical chain mechanism for the addition of bisulfite.