Formaldehyde → Bis(2-hydroxyphenyl)methane

HRID 1608645Notes

Reaction equation

HRID 1608645 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]=[O:9]>O.O.C(O)(=O)C(O)=O>[CH:1]1[CH:2]=[C:3]([CH2:4][C:6]2[C:1]([OH:7])=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:8]([OH:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 996Phenol

Product 1

HCID 75575Bis(2-hydroxyphenyl)methaneYield 30.4%

Reagents, catalysts & solvents 1

HCID 61373Oxalic acid dihydrateCatalyst

Conditions

Temperature
70 °C

Procedure

There were mixed 2000 g of phenol and 172.5 g of 37% formalin (P/F=10) and then 5.6 g of oxalic acid dihydrate was added to the mixture, followed by reacting the mixture with heating at 70° C. for 4 hours. Then the reaction system thus obtained was heated to 160° C. under atmospheric pressure to remove the water and a small amount of phenol and further heated at a pressure of 20 mm Hg till the temperature reached 170° C. to remove unreacted phenol. Then the product was heated at 210° C. and a pressure of 6 mm Hg to further remove the remaining unreacted phenol to give 350 g of a crude bisphenol F.

Workup

  1. customThen the reaction system thus obtained
  2. temperaturewas heated to 160° C. under atmospheric pressure
  3. customto remove the water
  4. temperaturea small amount of phenol and further heated at a pressure of 20 mm Hg till the temperature
  5. customreached 170° C.
  6. customto remove unreacted phenol
  7. temperatureThen the product was heated at 210° C.
  8. customa pressure of 6 mm Hg to further remove the remaining unreacted phenol

Sources & evidence

ORD record
ord-bea3bae01adf4ec1826d323a80c852d4
Source dataset
uspto-grants-1995_03
Patent number
US05395915

Reaction notes

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