Formic Acid → Oleic Acid

HRID 1504909Notes

Reaction equation

HRID 1504909 reaction equation
[C:1]([O:20]C)(=[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].C(O)=O.OO>>[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]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 5364509Methyl Oleate2×

Product 1

HCID 445639Oleic AcidYield 118%

Procedure

To a stirred solution of methyl oleate (MO) (200.00 g, 675 mmol) and formic acid (62.09 g, 1.35 mol) cooled in an ice bath (0° C.), H2O2 (30.0% in H2O, 306.00 mL, 2.70 mol) was added slowly. The reaction was then allowed to proceed at room temperature with vigorous stirring until LC/MS analysis indicated that MO had been consumed (around 19 hr). The reaction was then transferred to a separatory funnel, and ethyl acetate (500 mL) was added and the lower aqueous phase was removed. The organic phase was then washed with water, NaHCO3 and brine, dried with Na2SO4, filtered, concentrated using a rotary evaporator, and placed under vacuum until constant weight was achieved to yield epoxidized oleic acid (EMO) as a clear light yellow oil (225.0 g).

Workup

  1. additionwas added slowly
  2. customto proceed at room temperature
  3. customhad been consumed (around 19 hr)
  4. customThe reaction was then transferred to a separatory funnel
  5. additionethyl acetate (500 mL) was added
  6. customthe lower aqueous phase was removed
  7. washThe organic phase was then washed with water, NaHCO3 and brine
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customa rotary evaporator

Sources & evidence

ORD record
ord-d5d4b37755024de8bbdafe101c1d448d
Source dataset
uspto-grants-2015_12
Patent number
US09216940B2

Reaction notes

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