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

HRID 2195003Notes

Reaction equation

HRID 2195003 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, was heated under a nitrogen stream at normal pressure to 180° C. as a reaction temperature. After the temperature reached 180° C., the reaction was carried out under a nitrogen stream at normal pressure. 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 reaction time was 12 hours and, after the completion of the reaction was confirmed, the product 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. temperaturewas heated under a nitrogen stream at normal pressure to 180° C. as a reaction temperature
  5. customreached 180° C.
  6. waitThe reaction time was 12 hours
  7. filtrationthe product was filtrated at 80° C.

Sources & evidence

ORD record
ord-c2100bb778d5405d99d3ca6ae454678e
Source dataset
uspto-grants-2012_12
Patent number
US08334397B2

Reaction notes

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