Ethylene → 5,6-Dihydrodicyclopentadiene Cyclopentene Ethylene

HRID 1028328Notes

Reaction equation

HRID 1028328 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH2:10][CH:9]=[CH:8][CH:7]3[CH:3]([CH2:4]2)[CH2:2]1.[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]=1.[CH2:16]([Al](CC(C)C)CC(C)C)[CH:17](C)C.C=C>C1(C)C=CC=CC=1>[CH2:2]1[CH:3]2[CH:7]3[CH2:8][CH:9]=[CH:10][CH:6]3[CH:5]([CH2:4]2)[CH2:1]1.[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]=1.[CH2:16]=[CH2:17]

Participants

6

Conditions

Temperature
70 °C

Procedure

5,6-dihydrodicyclopentadiene (2.7 g, 20 mmol), cyclopentene (1.4 g, 20 mmol) and magnetic bars were placed in a polymerization reactor in a nitrogen atmosphere, after which toluene was added thereto so as to obtain a total amount of 28 ml. This polymerization reactor was heated to 70° C. with stirring. A catalyst (0.69 mg, 2 μmol) represented by Formula 6, [Ph3C]+[B(C6F5)4]− (7.4 mg, 8 μmol) and triisobutylaluminum (160 mg, 800 μmol) were mixed with 2.0 ml of toluene in a dry box, after which the resulting mixture was added into the reactor using a syringe while being stirred at 70° C., and also ethylene gas was fed thereto at a pressure of 20 psig. After 6 min 30 sec, the ethylene gas was removed, and the reactor was opened, and thus the reaction was terminated. 30 ml of methanol was added and the reaction solution precipitated. Filtration was performed, thus obtaining powder. The powder was then decompressed to a vacuum at 100° C., so that the remaining solvent was removed from the precipitate, thereby obtaining 0.73 g of a polymer material. The polymer material thus obtained had a Tg of 18.4° C., a Mw of 76000 and a Mw/Mn of 1.6.

Workup

  1. customso as to obtain a total amount of 28 ml
  2. additionafter which the resulting mixture was added into the reactor
  3. stirringwhile being stirred at 70° C.
  4. customthe ethylene gas was removed
  5. customthus the reaction was terminated
  6. addition30 ml of methanol was added
  7. customthe reaction solution precipitated
  8. filtrationFiltration
  9. customthus obtaining powder
  10. customwas then decompressed to a vacuum at 100° C., so that the remaining solvent
  11. customwas removed from the precipitate

Sources & evidence

ORD record
ord-f20371ca23f0445ba78e4d31f3112000
Source dataset
uspto-grants-2014_05
Patent number
US08735521B2

Reaction notes

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