Synthesis of Alkanesulf onate hawing Sulfur in the β-Position of Alkyl Group

Abstract

Synthesis of β-chloroethyl alkyl sulfide via higher alkanesulfenyl chloride and Strecker reaction of the β-chloroethyl alkyl sulfide, β-chloroethyl alkyl sulf-oxide, and β-chloroethyl alkyl self one were studied.The selfone derivative reacted almost quantitatively to give alkanesulfonylethanesulfonate under following condition ; 1.2 moles of saturated aqueous solution of sodium sulfite to one mole of the chloride, 100°C, 2 hrs. Under this reaction condition, dodecyl chloride gave no dodecanesulfonate. The sulfide derivative gave alkylthioethanesulfonate in about 70% yield. The sulfoxide derivative, however, gave by-product mainly and a small amount of alkanesulfinylethanesulfonate.β-Chloroethyl alkyl sulfide was synthesized from ethylene and alkanesulfenyl chloride which was derived from alkyl mercaptan and sulfuryl chloride. The sulfoxide derivative and the sulfone derivative were synthesized from β-chloroethyl alkyl sulfide by oxidation with 30% H2O2.Sodium dodecylthioethanesulfonate thus obtained reduced the surface tension of water as low as 38-39 dyne/cm at a level of 0.02 wt%.