Hydrochloric Acid → Diglycerol 1,2-distearate

HRID 481271Notes

Reaction equation

HRID 481271 reaction equation
[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.[OH2:27].Cl.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>>[C:1]([OH:19])(=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:29]([OH:32])(=[O:31])[CH2:30][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:19][CH2:1][CH:34]([CH2:33][OH:32])[OH:27].[OH:19][CH2:1][CH:34]([CH2:33][OH:32])[OH:27]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 8212Stearoyl chlorideHCID 8857Ethyl Acetate

Product 1

HCID 131720779Diglycerol 1,2-distearate

Procedure

To 42 parts by weight of the diglycerol monoisopropylidene obtained above were added 134 parts by weight of stearic acid chloride and 35 parts by weight of pyridine and the resulting mixture was stirred at room temperature for 27 hours. Then water and ethyl acetate were added to this mixture, followed by extraction. The ethyl acetate phase was separated therefrom and the ethyl acetate was distilled off under reduced pressure. 200 parts by weight of diethyl ether was added to the residue, which was dissolved therein. To the solution thus obtained was added 300 parts by weight of conc. hydrochloric acid and the resulting mixture was stirred at room temperature for 1 hour. Then the mixture was separated into two phases and the aqueous phase was eliminated. The diethyl ether phase was repeatedly washed with water until the aqueous phase became neutral. The diethyl ether phase was separated therefrom and the diethyl ether was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give diglycerol 1,2-distearate (containing about 90% by weight). (Preparation of oil-in-water type emulsion (modifier composition) b)

Workup

  1. extractionfollowed by extraction
  2. customThe ethyl acetate phase was separated
  3. distillationthe ethyl acetate was distilled off under reduced pressure
  4. addition200 parts by weight of diethyl ether was added to the residue, which
  5. dissolutionwas dissolved
  6. customTo the solution thus obtained
  7. stirringthe resulting mixture was stirred at room temperature for 1 hour
  8. customThen the mixture was separated into two phases
  9. washThe diethyl ether phase was repeatedly washed with water until the aqueous phase
  10. customThe diethyl ether phase was separated
  11. distillationthe diethyl ether was distilled off under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5bcdd68402404722acdbd8aefe89de5a
Source dataset
uspto-grants-1998_08
Patent number
US05789011

Reaction notes

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