Methane → sucrose oleate

HRID 1761297Notes

Reaction equation

HRID 1761297 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CC([O:24][CH2:25][C@H:26]1[O:31][C@H:30]([O:32][C@:33]2([CH2:51][O:52]C(C)=O)[O:37][C@H:36]([CH2:38]OC(C)=O)[C@@H:35]([O:43]C(C)=O)[C@@H:34]2[O:47]C(C)=O)[C@H:29]([O:56]C(C)=O)[C@@H:28]([O:60]C(C)=O)[C@@H:27]1[O:64]C(C)=O)=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+].C>C(O)(C)C>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][CH2:38][C@H:36]1[O:37][C@:33]([O:32][C@H:30]2[O:31][C@H:26]([CH2:25][OH:24])[C@@H:27]([OH:64])[C@H:28]([OH:60])[C@H:29]2[OH:56])([CH2:51][OH:52])[C@@H:34]([OH:47])[C@@H:35]1[OH:43])=[O:19]

Participants

8

Reactant 6

HCID 297MethaneHCID 6101p-Toluenesulfonic acidHCID 8000Boron trifluoride etherateHCID 31340Sucrose octaacetateHCID 445639Oleic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 6438037sucrose oleateYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.06 mol (16.93 g) of oleic acid (Fluka Chemika, Switzerland) was weighed into a three-necked, round-bottom flask equipped with a magnetic stirrer, stopcocks, a vacuum take-off line leading to a liquid nitrogen cold-trap and a vacuum pump. 0.01 mol (6.79 g) of sucrose octaacetate, SOA, (Fluka Chemika, Switzerland) was added and the mixture was heated to 80-95 degree C. in an oil bath with continuous stirring until a homogenous solution was formed. 0.01% w/w tosylic acid (or alkyl sulfonic acid polysiloxane, or BF3.OEt2) was then added. Reaction temperature was then reduced to between 60-75 degree C. and 5-10 Torr pressure was applied. The reaction was continued for 3 to 6 hours. The product was taken up in 250 ml of iso-propanol, neutralized with aqueous 1M NaHCO3, decolourised with 2.0 g activated charcoal, and filtered. Iso-propanol was then removed by vacuum distillation. Unreacted oleic acid was extracted with 50×4 ml hexane and kept for reuse. The sucrose fatty ester was redissolved in warm iso-propanol to form 30-40% w/v solution, cool to −4 to 0 degree C. and filtered to give unreacted SOA as precipitate. The filtrate iso-propanol was then distilled off to give 70-85% pure acetylated sucrose oleate. Repeated hexane extraction and SOA precipitation gave 90-95% pure product (87% yield).

Workup

  1. customequipped with a magnetic stirrer
  2. customstopcocks, a vacuum take-off line leading to a liquid nitrogen cold-trap
  3. temperaturethe mixture was heated to 80-95 degree C
  4. customwas formed
  5. customReaction temperature
  6. customwas then reduced to between 60-75 degree C
  7. filtrationfiltered
  8. customIso-propanol was then removed by vacuum distillation
  9. extractionwas extracted with 50×4 ml hexane
  10. dissolutionThe sucrose fatty ester was redissolved in warm iso-propanol
  11. customto form 30-40% w/v solution
  12. temperaturecool to −4 to 0 degree C
  13. filtrationand filtered
  14. customto give unreacted SOA as precipitate
  15. distillationThe filtrate iso-propanol was then distilled off

Sources & evidence

ORD record
ord-207df1ba542c47b8968a7da4cbb72098
Source dataset
uspto-grants-2005_01
Patent number
US06846916B2

Reaction notes

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