Palmitic Acid → Stearyl Stearate

Participants

Reaction Conditions

Reaction Steps

A 2-liter round-bottom flask was charged with 142 g (0.5 mole) of rubber-maker's technical grade stearic acid, 203 g (0.75 mole) of 1-octadecanol, 11 g of p-toluenesulfonic acid and 200 ml of mixed xylenes. Rubber-maker's technical grade stearic acid typically contains approximately 56 percent by weight stearic acid, 29 percent by weight palmitic acid, 8 percent by weight oleic acid and 7 percent by weight other fatty acids. The flask was fitted with a Dean-Stark trap for water removal, a heating mantel and a thermocouple. The system was flushed with nitrogen and heated to a pot temperature of 180° C. for about 1 hour, wherein 12 ml of water were removed. Volatiles were removed under 29 inches of vacuum at 110° C. to give 342 g of a waxy solid melting at 47-55° C. and giving an infrared spectrum showing loss of hydroxyl absorption bands and formation of ester carbonyl functions.

Provenance & Evidence