Glycerol → Glyceryl Monooleate

HRID 1166029Notes

Reaction equation

HRID 1166029 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].[OH:21][CH2:22][CH:23]([CH2:25]O)[OH:24]>O>[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][CH2:25][CH:23]([OH:24])[CH2:22][OH:21])=[O:19]

Participants

4

Reactant 2

HCID 753GlycerolHCID 445639Oleic Acid3×

Product 1

HCID 5283468Glyceryl Monooleate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of oleic acid (1.5 g=5.32 mmoles), glycerol (0.57 g=6.2 mmoles), water (70 μl) and potato protein extract (100 mg) was stirred at 50° C. and a vacuum (<50 mbar) was applied to the system using an oil pump to remove water from the mixture. For comparison a similar reaction was run without vacuum in a stoppered tube. Samples were taken from the reaction mixtures periodically for analysis by GC. Progress curves for the reactions are given in FIG. 2. In the reaction carried out under vacuum 4.43 mmoles of MG and 0.10 mmoles of DG were formed after 72 hours. 87% of the oleic acid was converted into acylglycerols. In the comparison reaction after 72 hours 3.51 mmoles of MG and 0.14 mmoles of DG were formed. The final conversion of oleic acid into acylglycerols was 71%.

Workup

  1. extractionextract (100 mg)
  2. customto remove water from the mixture
  3. customFor comparison a similar reaction
  4. customwas run without vacuum in a stoppered tube
  5. customwere formed after 72 hours
  6. customIn the comparison reaction after 72 hours 3.51 mmoles of MG and 0.14 mmoles of DG
  7. customwere formed

Sources & evidence

ORD record
ord-45b69be49a964ddeb8fd5bb5de95d4ee
Source dataset
uspto-grants-2003_09
Patent number
US06613551B2

Reaction notes

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