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Toluene → Ethylene 5-norbornen-2-ol

HRID 1993278
Notes
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Reaction equation

HRID 1993278 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 166.9%

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(η1-CH2Ph)(PMe3) (about 20 μmol; 2.00 g of 8.77 mM solution in toluene), Ni(COD)2 (about 50 μmol; 2.5 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 about 30 mL. FIG. 11 shows this synthesis. 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 produced about 0.518 g of ethylene/5-norbornen-2-ol co-polymer. The activity of the catalyst with respect to ethylene consumption was about 105 kg mol−1 h−1.

Workup

  1. customFIG. 11 shows this synthesis
  2. customThe glass reactor was sealed inside the glove box
  3. customto quench
  4. customthe polymerization
  5. filtrationThe precipitated polymer was collected by filtration
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-b63d8a880f1b4ae0ab16f04c3940f671
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07651971B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes