Ethylene → 1-Decene

HRID 2407601Notes

Reaction equation

HRID 2407601 reaction equation
[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]\CCCCCCCC.CCCCCCCCCCCCCC.C=C>ClCCl.C(OCC)=C>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:21][O:20][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

7

Reactant 3

HCID 6325EthyleneHCID 12389TetradecaneHCID 5364509Methyl Oleate2×

Product 2

HCID 133811-DeceneYield 99%HCID 1778877Methyl 9-decenoate

Reagents, catalysts & solvents 2

HCID 8023Ethyl vinyl etherCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

The ethylenolysis of methyl oleate was used as a test to determine the activity of (PCy3)Cl2Ru(3-pentafluorophenyl-6,8-diisopropoxyinden-1-ylidene). A catalyst compound stock solution (0.1379 mM) was made by dissolving the catalyst compound in anhydrous dichloromethane. Methyl oleate (0.87 g, 1.0 mL), catalyst compound stock solution (0.906 g), dichloromethane (4.12 g), and tetradecane (0.152 g) as an internal standard were placed in a Fisher-Porter bottle equipped with a stir bar. The vessel was then filled with ethylene to 150 psig and placed in an oil bath heated to 40° C. for 3 hours. The vessel was then depressurized and 5 drops ethyl vinyl ether added to stop the reaction. A sample was analyzed by gas chromatography. The cross-metathesis reaction yielded 18.5% 1-decene and methyl-9-decenoate with 99% selectivity 1-decene and methyl-9-decenoate yields corresponded to 4300 turnovers of decene per equivalent of ruthenium.

Workup

  1. customequipped with a stir bar
  2. customplaced in an oil bath
  3. customthe reaction
  4. customThe cross-metathesis reaction

Sources & evidence

ORD record
ord-54914e5edc9046d991a31708cffc9650
Source dataset
uspto-grants-2014_08
Patent number
US08809563B2

Reaction notes

Loading…