Phenol → endo-Dicyclopentadiene

HRID 1074916Notes

Reaction equation

HRID 1074916 reaction equation
C1(O)C=CC=CC=1.B(F)(F)F.[CH2:12]1[CH:16]2[CH:17]3[CH:21]=[CH:20][CH:19]([CH:15]2[CH:14]=[CH:13]1)[CH2:18]3.C=CC(=C)C.C1CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:12]1[CH:16]2[C@@H:17]3[CH:21]=[CH:20][C@H:19]([CH:15]2[CH:14]=[CH:13]1)[CH2:18]3

Participants

6

Reactant 4

HCID 996PhenolHCID 6356Boron trifluorideHCID 6492DicyclopentadieneHCID 22568287HCID 22568287, compound

Product 1

HCID 15618652endo-Dicyclopentadiene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
55 °C

Procedure

To a reactor equipped as in Example 1-A were added 2823 gms (30 moles) of phenol and 16.1 gms of BF3 etherate in 20 gms of carbon tetrachloride. The mass was heated to 55° C. and 1201.2 gms (9.09 moles) of a 99.9% reactive C10 hydrocarbon stream consisting mainly of dicyclopentadiene and cyclopentadiene isoprene codimers was added over a 4 hour (14400 s) period. The temperature of the reaction mass was 80° C. after the hydrocarbon addition period. The reactor was heated to 150° C. over a 7 hour (25200 s) period and a vacuum distillation begun. The reaction was finished at 245° C. and 1 mm Hg. The resin had an equivalent weight of 187, a melt point of 115° C. and an average functionality of 2.95.

Workup

  1. customTo a reactor equipped as in Example 1-A
  2. additionwas added over a 4 hour (14400 s) period
  3. customwas 80° C.
  4. temperatureThe reactor was heated to 150° C. over a 7 hour (25200 s) period
  5. distillationa vacuum distillation
  6. customwas finished at 245° C.
  7. customa melt point of 115° C.

Sources & evidence

ORD record
ord-09d49f36ace74070bd5c5144268d3845
Source dataset
uspto-grants-1983_07
Patent number
US04394497

Reaction notes

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