Phenol → Furan-2-carbaldehyde--phenol (1/1)

HRID 370492Notes

Reaction equation

HRID 370492 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8](=[O:14])[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8](=[O:14])[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 7362FurfuralHCID 10340Sodium Carbonate

Product 1

HCID 168521Furan-2-carbaldehyde--phenol (1/1)

Conditions

Temperature
66 °C

Procedure

Into a 4 liter resin vessel equipped with a mechanical stirrer, distillation condenser, heating mantel and thermometer is placed 2000 gms (21.28 moles) of USP phenol and 1480 gms (15.25 moles) of furfural. This mixture is heated to 66° C. and 30.0 gms (0.36 mole) sodium carbonate added. The charge is then slowly heated to 121° C., at which temperature the heating mantel is removed. The reaction then becomes exothermic and the temperature continues to rise until boiling begins at 135° C. The distillate is collected in a separating device and the furfural layer is periodically drawn off and returned to the batch during the course of the reaction. Distillation is continued for 3 hours, 40 minutes with the batch temperature maintained between 133° and 139° C. The resin is then discharged from the vessel and allowed to cool to a solid which has a melting point of 89° C. (192° F.), a yield of 3230 gms, a glass transistion temperature of 330° K. (134.6° F.). This is a non-curing Novolak resin, as shown when tested on a hot plate at 330° F., but when thoroughly mixed with 10 pph of hexa, has a set time at 330° F. of 65-69 sec.

Workup

  1. customInto a 4 liter resin vessel equipped with a mechanical stirrer
  2. distillationdistillation condenser
  3. temperatureheating mantel and thermometer
  4. temperatureThe charge is then slowly heated to 121° C., at which temperature the heating mantel
  5. customis removed
  6. customThe reaction
  7. customuntil boiling begins at 135° C
  8. distillationThe distillate is collected in a separating device
  9. customreturned to the batch during the course of the reaction
  10. distillationDistillation
  11. temperaturemaintained between 133° and 139° C
  12. temperatureto cool to a solid which
  13. customa melting point of 89° C. (192° F.)
  14. customa glass transistion temperature of 330° K
  15. custom(134.6° F.)
  16. customtested on a hot plate at 330° F.
  17. additionwhen thoroughly mixed with 10 pph of hexa
  18. customat 330° F.
  19. customof 65-69 sec

Sources & evidence

ORD record
ord-da40d19913654fe3b8b3ef4133445b1e
Source dataset
uspto-grants-1985_07
Patent number
US04526924

Reaction notes

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