Hydrogen Bromide → Bisphenol A

HRID 840407Notes

Reaction equation

HRID 840407 reaction equation
Br[C:2]1[C:7]([OH:8])=[C:6](Br)[C:5](Br)=[C:4]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])[C:3]=1Br.BrBr.[Br-].[Na+].Br.Br([O-])(=O)=O.[Na+].Br>>[OH:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)([CH3:13])[CH3:12])=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 260Hydrogen BromideHCID 24408BromineHCID 23668195Sodium BromateHCID 542409822,3,5,6-Tetrabromo-4-[2-(4-hydroxyphenyl)propan-2-yl]phenolHCID 131723160HCID 131723160, compound

Product 1

HCID 6623Bisphenol A

Procedure

A highly pure and colorless tetrabromobisphenol-A (TBBPA) possessing melting point in the range of 178-182° C. is prepared in yields of 50-70% in first batch and 90-100% when the spent organic layer is recycled. In this method, the corrosive liquid bromine is displaced by sodium bromide/hydrobromic acid as brominating agent. Further, sodium bromate is used as an oxidizing as well as brominating agent to utilize the hydrobromic acid that is produced during the bromination of bisphenol-A (BPA). The reaction is conducted at 10-15° C. in a mixture of methylene chloride-water or carbon tetrachloride-water in the presence of hydrochloric acid and sodium lauryl sulfate. The crystalline product settled at the bottom of the reaction vessel is filtered, washed, dried and weighed. The spent organic layer is recycled in subsequent batches to maximize the overall yield of product recovered directly as solid and to minimize generation of organic effluent.

Workup

  1. customin the range of 178-182° C.
  2. customis prepared
  3. customin yields of 50-70% in first batch and 90-100% when the spent organic layer

Sources & evidence

ORD record
ord-4ee2d5f62d96463196ca04f6b806c260
Source dataset
uspto-grants-2002_04
Patent number
US06365786B1

Reaction notes

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