Ethyl Oleate → Methyl Oleate

HRID 1510607Notes

Reaction equation

HRID 1510607 reaction equation
[C:1]([O:20][CH2:21]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]>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:1]([O:20][CH3:21])(=[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

3

Reactant 1

HCID 5363269Ethyl Oleate

Product 1

HCID 5364509Methyl Oleate

Reagents, catalysts & solvents 1

HCID 178425456HCID 178425456, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

A stainless steel autoclave with a glass liner was equipped with a magnetic stirrer bar and charged with ethyl oleate (0.34 g, 1.1 mmol) and Second Generation Grubbs Catalyst (9.3 mg, 0.11 μmol). The autoclave flushed with argon. The autoclave was evacuated and then pressurised with cis-2-butene to a pressure of 15 psi. The autoclave was heated at 60° C. with stirring overnight. The pressure was then released and ethyl vinyl ether (50 μL) added to the reaction mixture. A sample of the product was trans-esterified with methanol by conventional means and analysis of the trans-esterification product by GC showed a conversion of >85% of the oleic chains to 9-undecenoic chains.

Workup

  1. customThe autoclave flushed with argon
  2. customThe autoclave was evacuated
  3. additionethyl vinyl ether (50 μL) added to the reaction mixture

Sources & evidence

ORD record
ord-86bfe8bceb854c979bf005447f8d093b
Source dataset
uspto-grants-2012_07
Patent number
US08211989B2

Reaction notes

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