Hydrogen Peroxide → 4-tert-Butylbenzoic acid

HRID 1166703Notes

Reaction equation

HRID 1166703 reaction equation
[CH3:1][OH:2].OC1C=C[C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=CC=1.BrBr.[OH:22]O>[Fe].O>[CH3:12][C:10]([C:13]1[CH:14]=[CH:15][C:16]([C:1]([OH:22])=[O:2])=[CH:17][CH:18]=1)([CH3:7])[CH3:11]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 887Methanol2×HCID 6623Bisphenol AHCID 24408Bromine2×

Product 1

HCID 74034-tert-Butylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A high purity 4,4′-isopropylidine-bis-(2,6-dibromophenol) characterised by ionic bromides less than 10 ppm, colour in alkaline solution from 60-100 HU, HPLC purity about 99.9%, APHA of 20% MeOH solution less than 10.0 HU, Fe less than 1.0 ppm, turbidity of 20% MeOH solution less than 5 NTU, pH of 10% slurry 6.0-7.0, size of the crystal particles, 250 to 280 microns with angle of repose lower than 30°. The product is produced by reacting Bisphenol-A with bromine in a “water-immiscible” polar solvent in the presence of hydrogen peroxide, aging the reaction products after the reaction, eliminating the excess bromine by reducing agents, washing the product layer with a combination of anionic surfactant, alkali, reducing agent and demineralised water under controlled pH conditions, partially distilling the organic solvent chilling the medium containing the product, filtering the crude product, boiling the crude product with alkali, reducing agent and demineralised water, filtering the TBBA, washing the product with demineralised water and drying to obtain the final high purity TBBA with high yield.

Workup

  1. customlower than 30°
  2. customThe product is produced
  3. customafter the reaction
  4. washwashing the product layer with a combination of anionic surfactant
  5. distillationpartially distilling the organic solvent
  6. temperaturechilling the medium
  7. additioncontaining the product
  8. filtrationfiltering the crude product
  9. filtrationfiltering the TBBA
  10. washwashing the product with demineralised water
  11. customdrying

Sources & evidence

ORD record
ord-ee799353b4604b84b62d298b09701b81
Source dataset
uspto-grants-2003_09
Patent number
US06613947B1

Reaction notes

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