Phenol → 4-Vinylphenol

HRID 436727Notes

Reaction equation

HRID 436727 reaction equation
C(C1C=CC=CC=1O)C.C1(O)C=CC=CC=1.C(C1C=C(O)C=CC=1)C.[CH2:26]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[CH3:27].C(C1C=CC=CC=1O)C.C1C=CC=CC=1.O>C1C=CC=CC=1>[CH:26]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)=[CH2:27]

Participants

7

Reactant 5

HCID 996PhenolHCID 69972-Ethylphenol2×HCID 121013-EthylphenolHCID 312424-EthylphenolHCID 86734818HCID 86734818, compound

Product 1

HCID 624534-Vinylphenol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Crude ethylphenol consisting of 2.0% phenol and m- and p-cresols, 0.2% o-ethylphenol, 55.8% m-ethylphenol and 42.0% p-ethylphenol was dissolved in benzene, and dehydrogenated at a temperature of 600° C. and LHSV of 1.0 hr-1 under atmospheric pressure using the same catalyst as in Example 1, with the ethylphenol/benzene/water molar ratio being 1/1/12. The resulting product was allowed to stand at room temperature followed by separating the water. The crude vinylphenol so separated consisted of 39.0% benzene, 4.3% phenol and m- and p-cresols, 0.1% o-ethylphenol, 22.1% m-ethylphenol, 10.4% p-ethylphenol, traces of o-vinylphenol, 10.1% m-vinylphenol, 9.5% p-vinylphenol, 0.5% oligomers of vinylphenols and 4.0% water with the p-vinylphenol/(ethylphenols+ m-vinylphenol) molar ratio being 0.61. The crude vinylphenol was directly placed in a three necked glass reactor equipped with a stirrer, and heat polymerized at 140° C. for 4 hours to afford a crude p-vinylphenol polymer consisting of 1.2% oligomers of vinylphenols, 7.5% phenol and m- and p-cresols, 0.2% o-ethylphenol, 39.0% m-ethylphenol, 18.3% p-ethylphenol, 17.4% m-vinylphenol, and 16.4% p-vinylphenol polymer.

Workup

  1. customdehydrogenated at a temperature of 600° C. and LHSV of 1.0 hr
  2. customto stand at room temperature
  3. customby separating the water
  4. customThe crude vinylphenol so separated
  5. customequipped with a stirrer
  6. temperatureheat
  7. custompolymerized at 140° C. for 4 hours

Sources & evidence

ORD record
ord-ef10bc2daaec48fca09613a3208fe7b4
Source dataset
uspto-grants-1977_06
Patent number
US04028340

Reaction notes

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