Toluene → Ethylene 5-norbornen-2-ol

HRID 854593Notes

Reaction equation

HRID 854593 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[OH:8].C1(C)C=CC=CC=1.C=C>C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].CC(C)=O>[CH2:1]=[CH2:2].[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[OH:8]

Participants

6

Conditions

Temperature
20 °C

Procedure

A glass reactor was loaded inside a glove box with L(iPr2)Ni(ηl-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-ol (about 4.49 mmol; 3.00 g of 1.30 M solution in toluene) and toluene (about 18.45 g) such that the total volume of the toluene solution was 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 20 minutes and acetone was added to quench the polymerization. The precipitated polymer was collected by filtration and dried under high vacuum overnight. The reaction provided about 0.508 g of ethylene/5-norbornen-2-ol co-polymer. The activity of the catalyst with respect to ethylene consumption was about 124 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-2eda465225f84d5c90b9cc76d35aeea2
Source dataset
uspto-grants-2007_08
Patent number
US07259214B2

Reaction notes

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