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

HRID 2195000Notes

Reaction equation

HRID 2195000 reaction equation
[CH2:1]1[O:5][CH:4]([CH:6]([OH:9])[CH2:7][OH:8])[C@@H:3]([OH:10])[CH:2]1[OH:11].[C:12](OC)(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CO.C[O-].[Na+].[PH2]([O-])=O.[Na+]>>[CH3:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]/[CH:21]=[CH:20]\[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]([O:8][CH2:7][CH:6]([OH:9])[C@H:4]1[O:5][CH2:1][C@H:2]([OH:11])[C@H:3]1[OH:10])=[O:30]

Participants

5

Reactant 4

HCID 103023(3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diolHCID 5364509Methyl Oleate2×HCID 23694274Sodium methanolate methanolHCID 178527019HCID 178527019, compound

Product 1

HCID 70693544Span #80 (Sorbitan monooleate)

Conditions

Temperature
65 °C

Procedure

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.

Workup

  1. customfitted with a stirring apparatus
  2. customwas performed at 110° C. under a nitrogen
  3. customfor 1 hour
  4. temperaturethe temperature was raised under a nitrogen stream at normal pressure to 170° C. as a reaction temperature
  5. customreached 170° C.
  6. waitwas 8 hours
  7. filtrationthe mixture was filtrated at 80° C.

Sources & evidence

ORD record
ord-4f20a92057dc497b82aa0d356b4be02b
Source dataset
uspto-grants-2012_12
Patent number
US08334397B2

Reaction notes

Loading…