Stearic Acid → Glyceryl 1,3-distearate

HRID 974161

Reaction equation

HRID 974161 reaction equation
[CH3:1][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][C:18]([O:20][CH2:21][CH:22]1[O:24][CH2:23]1)=[O:19].[C:25]([OH:44])(=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(O)C>[C:25]([O:44][CH2:23][CH:22]([CH2:21][O:20][C:18](=[O:19])[CH2:17][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:24])(=[O:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 3

HCID 5281Stearic AcidHCID 14798Sodium HydroxideHCID 62642Glycidyl stearate

Product 1

HCID 101269Glyceryl 1,3-distearate

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

1,3-Disteroylglycerol. A mixture of 171.3 g (0.5 mole) glycidol stearate, 156.5 g (0.55 mole) stearic acid, 1.0 g (0.025 mole) sodium hydroxide, and tetrabutylammonium hydrogensulfate (8.5 g, 0.025 mole) in 400 mL ethanol is heated at reflux (80° C.) for 20 hours. The solid material is removed by passage of the reaction mixture through a short column of silica gel. After evaporation, the crude solid product is subjected to centrifugal partition chromatography using a mixture of acetonitrile-hexane. Recrystallization of the resulting powder from acetone-water gives 1,3-distearoylglycerol.

Workup

  1. temperatureis heated
  2. customThe solid material is removed by passage of the reaction mixture through a short column of silica gel
  3. customAfter evaporation
  4. customto centrifugal partition chromatography
  5. additiona mixture of acetonitrile-hexane
  6. customRecrystallization of the resulting powder from acetone-water

Sources & evidence

ORD record
ord-eecbaf9c069c45028570e17526bf5173
Source dataset
uspto-grants-1991_11
Patent number
US05068119

Linked notes

Loading…