Toluene → Ethylene 5norbornen-2-yl acetate

HRID 1993289Notes

Reaction equation

HRID 1993289 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)(=[O:3])[CH3:2].C1(C)C=CC=CC=1.C=C>C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].CC(C)=O>[CH2:1]=[CH2:2].[C:1]([O:4][CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1140TolueneHCID 6325Ethylene2×HCID 95688Bicyclo(2.2.1)hept-5-en-2-ol, 2-acetate

Product 1

HCID 69727795Ethylene 5norbornen-2-yl acetateYield 1,471%

Reagents, catalysts & solvents 2

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A glass reactor was loaded inside a glove box with L(iPr2)Ni(η1-CH2Ph)(PMe3) (about 20 μmol; 2.00 g of 8.77 mM solution in toluene), Ni(COD)2 (about 50 μmol; 2.50 g of 17.6 mM solution in toluene), 5-norbornen-2-yl acetate (about 1.79 mmol; 3.00 g of 0.517 M solution in toluene) and toluene (about 18.45 g) such that the total volume of the solution was about 30 mL. The glass reactor was sealed inside the glove box and was attached to a vacuum/nitrogen line manifold. Ethylene was fed continuously into the reactor at about 100 psi and the pressurized reaction mixture was stirred at about 20° C. Ethylene was vented after about 60 minutes and acetone was added to quench the polymerization. The precipitated polymer was collected by filtration and dried under high vacuum overnight. About 2.373 g of ethylene/5-norbornen-2-yl acetate co-polymer was obtained. The activity of the catalyst with respect to ethylene consumption was about 70 kg mol−1 h−1.

Workup

  1. customThe glass reactor was sealed inside the glove box
  2. customto quench
  3. customthe polymerization
  4. filtrationThe precipitated polymer was collected by filtration
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-102ecd7007fb4ad6b8a5e9b9b7b8943f
Source dataset
uspto-grants-2010_01
Patent number
US07651971B2

Reaction notes

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