Glycerol → sodium 2-(2,3-Dihydroxypropoxy)ethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a 500 mL, three neck, round bottom flask equipped with a magnetic stirring bar, modified Claisen head, condenser (set for distillation), thermometer, and temperature controller (Therm-O-Watch®, I2R) was added isethionic acid, sodium salt (Aldrich, 50.0 gm, 0.338 mol), sodium hydroxide (2.7 g, 0.0675 mol), and glycerin (Baker, 310.9 gm, 3.38 mol). The solution was heated at 190° C. under argon overnight as water distilled from the reaction mixture. A 13C-NMR(DMSO-d6) showed that the reaction was complete by the virtual disappearance of the isethionate peaks at ~53.5 ppm and ~57.4 ppm, and the emergence of product peaks at ~51.4 ppm (--CH2SO3Na) and ~67.5 ppm (CH2CH2SO3Na). The solution was cooled to ~100° C. and neutralized to pH 7 with methanesulfonic acid (Aldrich). The desired, neat material was obtained by adding 0.8 mol % of potassium phosphate, monobasic and heating on a Kugelrohr apparatus (Aldrich) at 200° C. for ~3 hr. at ~1 mm Hg to afford 77 gm of yellow waxy solid.

Provenance & Evidence