Surfactant-Mediated Phase Transfer as an Alternative to Propanesultone Alkylation. Formation of a New Class of Zwitterionic Surfactants

Article abstract of DOI:10.1021/jo00122a028

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 50percent 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.