Glycerol → Triacetin

HRID 1702503Notes

Reaction equation

HRID 1702503 reaction equation
[OH:1][CH2:2][CH:3](CO)O.CC(OCC(O)CO)=O.[CH3:16][C:17]([O:19][CH2:20][CH:21]([O:24][C:25]([CH3:27])=[O:26])[CH2:22][OH:23])=[O:18]>O>[CH3:16][C:17](=[O:18])[O:19][CH2:20][CH:21]([CH2:22][O:23][C:2](=[O:1])[CH3:3])[O:24][C:25](=[O:26])[CH3:27]

Participants

5

Reactant 3

HCID 753GlycerolHCID 33510Glyceryl AcetateHCID 66021Diacetin

Product 1

HCID 5541Triacetin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

When the reaction is performed correctly, the reaction product contains only traces of glycerol, monoacetin, diacetin and water, so that the OH number normally lies below 1. Pure triacetin can be obtained readily by distillation in a rectification column of the obtained crude product, since, at atmospheric pressure, acetic acid boils at about 118° C., acetic acid anhydride boils at about 140° C., and glyceryl triacetate (triacetin) boils at about 258° C. Any catalyst that may still be present remains in the distillation residue.

Sources & evidence

ORD record
ord-103649efb762476c834ffd9e5c8d0627
Source dataset
uspto-grants-1983_04
Patent number
US04381407

Reaction notes

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