Formaldehyde → HCID 159993, compound

HRID 1416981Notes

Reaction equation

HRID 1416981 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C(O)(=O)[C:19](O)=[O:20].C=O>C(OCCCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[CH2:19]=[O:20]

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 971Oxalic AcidHCID 6623Bisphenol A

Product 1

HCID 159993HCID 159993, compound

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent

Conditions

Temperature
140 fahrenheit

Procedure

A bisphenol A-formaldehyde novolak polymer was prepared as follows. Two thousand grams of bisphenol A and 500.0 grams of n-butyl acetate were charged into a three-necked, five-liter flask equipped with a mechanical stirrer, a condenser, a thermometer and an addition funnel to form a mixture. Using an electric mantel, the mixture was heated to 140° F. to give a homogenous mixture. Then, 10.0 grams of oxalic acid were added to the mixture and mixed for five minutes. Then, 315.8 grams of 50 weight percent formaldehyde were added dropwise through the addition funnel. An exothermic reaction took place and a gentle reflux was initiated. Addition of all formaldehyde took 60 minutes and the mixture was refluxed for 5 hours. After refluxing, water and n-butyl acetate were collected by azeotropic distillation. Free formaldehyde content of the aqueous phase of the distillate was monitored periodically. If the free formaldehyde content was more than 0.5 percent, the distillate was returned to the flask. When the free formaldehyde was less than 0.5 percent, the distillate was removed. As the distillation progressed, temperature of the resinous product in the flask rose steadily to 340° F. At this point, the resinous product was flaked. The yield of the reaction was 2,150 grams and the resin was found to have 26.5 percent free bisphenol A with a melt viscosity of 80 seconds.

Workup

  1. customequipped with a mechanical stirrer, a condenser
  2. customa thermometer and an addition funnel to form a mixture
  3. customto give a homogenous mixture
  4. additionmixed for five minutes
  5. customAn exothermic reaction
  6. temperaturea gentle reflux
  7. temperaturethe mixture was refluxed for 5 hours
  8. temperatureAfter refluxing
  9. distillationwater and n-butyl acetate were collected by azeotropic distillation
  10. customthe distillate was removed
  11. distillationAs the distillation
  12. customrose steadily to 340° F
  13. customwith a melt viscosity of 80 seconds

Sources & evidence

ORD record
ord-93446d90488d4afb824251c25cd1b0b4
Source dataset
uspto-grants-1999_06
Patent number
US05916933

Reaction notes

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