Acetic Anhydride → Oleyl acetate

HRID 1607499Notes

Reaction equation

HRID 1607499 reaction equation
[CH2:1]([OH: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].[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[C:20]([O:19][CH2:1][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])(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 5284499Oleyl Alcohol2×

Product 1

HCID 5363289Oleyl acetate

Procedure

A technical grade oleyl alcohol (HD-Ocenol®90/95, iodine value 94, hydroxyl value 210) was reacted with acetic anhydride (20 mol-% excess) for 4 hours at 118° C. The reaction mixture was then poured onto ice water and the organic phase was washed repeatedly with water. The crude ester obtained was then dried and purified by distillation. The ester obtained had an iodine value of 83 and a residual hydroxyl value of 0.9.

Workup

  1. additionThe reaction mixture was then poured onto ice water
  2. washthe organic phase was washed repeatedly with water
  3. customThe crude ester obtained
  4. customwas then dried
  5. distillationpurified by distillation

Sources & evidence

ORD record
ord-c7bb567d8cf343f6a565760df74b7e95
Source dataset
uspto-grants-1989_09
Patent number
US04865774

Reaction notes

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