(3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diol → Span #80 (Sorbitan monooleate)

Participants

Reaction Conditions

Reaction Steps

After 469 g of a 70% by weight sorbitan aqueous solution (aldehyde value of sorbitan: 5.0 ppm) and 947 g of methyl oleate 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 51.0 g of a 10% by weight sodium methoxide methanol solution and 0.64 g of sodium hypophosphite were added thereto, the temperature was raised under a nitrogen stream at normal pressure to 170° C. as a reaction temperature. After the temperature reached 170° C., the 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 oleate as a raw material disappeared on thin-layer chromatography, it was judged that the reaction was completed. The time required for the reaction was 8 hours and, after the completion of the reaction was confirmed, the mixture was filtrated at 80° C. to obtain sorbitan monooleate.

Provenance & Evidence