Phenol → endo-Dicyclopentadiene

HRID 1074915Notes

Reaction equation

HRID 1074915 reaction equation
C1(O)C=CC=CC=1.B(F)(F)F.CCOCC.[CH2:17]1[CH:21]2[CH:22]3[CH:26]=[CH:25][CH:24]([CH:20]2[CH:19]=[CH:18]1)[CH2:23]3.C1CC=CC=1.C=CC(=C)C>>[CH2:17]1[CH:21]2[C@@H:22]3[CH:26]=[CH:25][C@H:24]([CH:20]2[CH:19]=[CH:18]1)[CH2:23]3

Participants

5

Reactant 4

HCID 996PhenolHCID 6492DicyclopentadieneHCID 8000Boron trifluoride etherateHCID 22568287HCID 22568287, compound

Product 1

HCID 15618652endo-Dicyclopentadiene

Conditions

Temperature
70 °C

Procedure

To a reactor equipped with a stirrer, condenser, thermowell and heater add 1882 gms (20 moles) of phenol and 8 gms (0.4% based on total weight) of boron trifluoride etherate. Heat to 70° C. and add 132 gms (~1 mole) of a C10 diene stream containing mainly dicyclopentadiene and cyclopentadiene-isoprene codimers over a 20 minute (1200 s) period. Increase the temperature to 150° C. over a 3 hour (10,800 s) time period and hold for about 3 hours (10,800 s). Distill off unreacted phenol with a finishing temperature of 210° C. and less than 5 mm Hg. The recovered product is a dicyclopentadiene bisphenol with an average functionality of 2.07.

Workup

  1. customTo a reactor equipped with a stirrer, condenser
  2. temperatureIncrease the temperature to 150° C. over a 3 hour (10,800 s) time period
  3. custom(10,800 s)
  4. distillationDistill off unreacted phenol with a finishing temperature of 210° C. and less than 5 mm Hg

Sources & evidence

ORD record
ord-453e6f6a20a0470a916869f950673b58
Source dataset
uspto-grants-1983_07
Patent number
US04394497

Reaction notes

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