HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Toluene → Ethylene 5-norbornen-2-ol

HRID 854596
Notes
Print preview

Reaction equation

HRID 854596 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 267.8%

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 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. 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 120 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 0.831 g of ethylene/5-norbornen-2-ol co-polymer. The activity of the catalyst with respect to ethylene consumption was about 20 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-a12dc7a63ee5473294c8fa8b961bf1f9
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259214B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes