Sorbitol → Span #80 (Sorbitan monooleate)
Reaction equation
O[CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13](O)(=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[Na+].[Na+].[PH2]([O-])=O.[Na+]>>[CH3:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]/[CH:22]=[CH:21]\[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]([O:12][CH2:11][CH:9]([OH:10])[C@H:7]1[O:8][CH2:2][C@H:3]([OH:4])[C@H:5]1[OH:6])=[O:31]Participants
Conditions
- Temperature
- 190 °C
Procedure
After 497 g of a 70% by weight sorbitol aqueous solution (aldehyde value of sorbitol: 5.0 ppm), 863 g of oleic acid, 3.0 g of sodium carbonate, and 1.7 g of sodium hypophosphite were charged into a 2000 mL four-neck flask fitted with a stirring apparatus, a thermometer, and a nitrogen gas inlet, replacement with nitrogen was performed at room temperature for 30 minutes. Thereafter, the temperature was raised stepwise to 110° C., 140° C., 190° C., and 230° C. After the temperature reached 230° C. as a reaction temperature, the reaction was carried out under a nitrogen stream at normal pressure. At the time point when the spot of oleic acid 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 product was filtrated at 80° C. to obtain sorbitan monooleate.
Workup
- customfitted with a stirring apparatus
- custom230° C
- customreached 230° C. as a reaction temperature
- waitThe reaction time was 5 hours
- filtrationthe product was filtrated at 80° C.
Sources & evidence
- ORD record
- ord-75e0675848ff406f95cebfe872b7070b
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334397B2
Reaction notes
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