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Toluene → Ethylene 5-norbornen-2-ol

HRID 854598
Notes
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Reaction equation

HRID 854598 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1140Toluene2×HCID 6325Ethylene2×HCID 96066Bicyclo(2.2.1)hept-5-en-2-ol

Product 1

HCID 86594155Ethylene 5-norbornen-2-olYield 224.5%

Reagents, catalysts & solvents 2

HCID 6433264Bis(1,5-cyclooctadiene)nickelCatalyst
HCID 180
Acetone
Solvent

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 3.99 mmol; 3.00 g of 1.15 M solution in toluene) and toluene (about 18.45 g) such that the total volume of the toluene solution was about 30 mL. The glass reactor was scaled 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 produced about 0.619 g of ethylene/5-norbornen-2-ol co-polymer. The activity of the catalyst with respect to ethylene consumption was about 118 kg mol−1 h−1.

Workup

  1. customto quench
  2. customthe polymerization
  3. filtrationThe precipitated polymer was collected by filtration
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-1383596a554b482e82d3e763d81a965d
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259214B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes