Ethylene → 1-Decene

HRID 883832

Reaction equation

HRID 883832 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-bd544b8e4ee14d7981e8edef0c2e1ddd
Source dataset
uspto-grants-2012_08
Patent number
US08237003B2

Linked notes

Loading…