Hydrochloric Acid → Tetrabromobisphenol A Cyanuric Chloride

HRID 978598Notes

Reaction equation

HRID 978598 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].[Br:10][C:11]1[C:16]([OH:17])=[C:15]([Br:18])[C:14]([Br:19])=[C:13]([C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)([CH3:22])[CH3:21])[C:12]=1[Br:30].Cl>C(C(C)=O)C>[Br:10][C:11]1[C:16]([OH:17])=[C:15]([Br:18])[C:14]([Br:19])=[C:13]([C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)([CH3:22])[CH3:21])[C:12]=1[Br:30].[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7954Cyanuric chlorideHCID 542409822,3,5,6-Tetrabromo-4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Product 1

HCID 131715132Tetrabromobisphenol A Cyanuric Chloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
30 °C

Procedure

To a reaction flask equipped with a stirrer, reflux condenser, a nitrogen purge, and a temperature controlling device, were added 25.0 grams (0.136 mole) of cyanuric chloride, 331.88 grams (0.61 mole) of tetrabromobisphenol A, and a 356.88 grams of methyl ethyl ketone. While maintaining the temperature at 30° C. 34.24 grams (0.428 mole) of 50% aqueous caustic was slowly added during about 30 minutes (1800 s). The reaction mixture was stirred for an additional hour (3600 s) at 30° C., then for an additional hour (3600 s) at 60° C. The mixture was then cooled, and neutralized with hydrochloric acid, then the salt removed via water washing, then the solvent removed via vacuum distillation to about 150° C. When cooled, the product was a solid with a Mettler softening point of 126.9° C.

Workup

  1. customTo a reaction flask equipped with a stirrer
  2. temperaturereflux condenser
  3. customa nitrogen purge
  4. addition34.24 grams (0.428 mole) of 50% aqueous caustic was slowly added during about 30 minutes (1800 s)
  5. waitfor an additional hour (3600 s) at 60° C
  6. temperatureThe mixture was then cooled
  7. customthe salt removed via water washing
  8. customthe solvent removed via vacuum distillation to about 150° C
  9. temperatureWhen cooled
  10. customwith a Mettler softening point of 126.9° C.

Sources & evidence

ORD record
ord-cddb32eaad6f4c9ba396b83fa11bf89f
Source dataset
uspto-grants-1987_05
Patent number
US04665149

Reaction notes

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