Methyl Stearate → [2-[(2R,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] octadecanoate

Participants

Reaction Conditions

Reaction Steps

After 469 g of a 70% by weight sorbitan aqueous solution (aldehyde value of sorbitan: 7.4 ppm) and 872 g of methyl stearate were charged into a 2000 mL four-neck flask fitted with a stirring apparatus, a thermometer, and a nitrogen gas inlet, dehydration was performed at 110° C. under a nitrogen stream at normal pressure for 1 hour and further at 110° C. under a nitrogen stream at 4 kPa for 1 hour. The whole was cooled to 65° C. and, after 30.0 g of a 20% by weight sodium methoxide methanol solution and 0.06 g of sodium hypophosphite were added thereto, was heated under a nitrogen stream at normal pressure to 190° C. as a reaction temperature. After the temperature reached 190° C., pressure was reduced to 6.5 kPa and the reaction was carried out under a nitrogen stream. At the time point when the spot of methyl stearate as a raw material disappeared on thin-layer chromatography, it was judged that the reaction was completed. The reaction time was 5 hours and, after the completion of the reaction was confirmed, the mixture was filtrated at 80° C. to obtain sorbitan monostearate.

Provenance & Evidence