Methanesulfonic Acid → Distearyl Dimethyl Ammonium Methyl Sulfonate

Participants

Reaction Steps

To 500 milliliters of water was added 54 milliliters (80 grams, 0.83 mol, 3.7 eq.) of methane sulfonic acid, CH3SO3H (available from Aldrich Chemical Compoany or Eastman Kodak Company). This solution, when cooled to room temperature, was added to a suspension of distearyl dimethyl ammonium methyl sulfate (DDAMS) (150.0 grams, 0.227 mol) suspended in 600 milliliters of water. The mixture was heated (70° to 80° C.) on a hot plate with stirring for 4 hours, cooled to room temperature and allowed to stand overnight. The mixture separated into an off-white/tan solid layer atop an aqueous layer. The mixture was filtered under reduced pressure and washed with water and air dried. The crude material was recrystallized from acetone and small amounts of methylene chloride. The methylene chloride appeared to help remove an unidentified waxy/sticky impurity to afford: 110 grams (0.17 mol), m.p. 70° C. (softening), 90° C. (liquid), and a second crop 13.7 grams (0.021 mol), m.p. 70° C. (softening), 87° C. (liquid) of the desired methane sulfonate salt (DDAMES).

Provenance & Evidence