Bisphenol A → HCID 178439265, compound

HRID 1632795Notes

Reaction equation

HRID 1632795 reaction equation
[N:1]#[C:2]Br.[N:4]#[C:5]Br.CC(C)=[O:9].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)([CH3:20])[CH3:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>CC(C)=O.O>[O-:9][C:2]#[N:1].[O-:11][C:5]#[N:4].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([C:21]2[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=2)([CH3:20])[CH3:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6623Bisphenol AHCID 8471Triethylamine2×HCID 10476Cyanogen BromideHCID 20148758Cyanogen bromide acetone

Product 1

HCID 178439265HCID 178439265, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

Cyanogen bromide (2.10 moles, 222.45 grams) was added to a reactor containing stirred acetone (350 milliliters) under a nitrogen atmosphere. The cyanogen bromide-acetone solution was cooled to -15° C. then Bisphenol A (1.00 mole, 228.30 grams) dissolved in chilled acetone (700 milliliters) was added to the reactor. The stirred solution was allowed to equilibrate at -5° C. then triethylamine (2.01 moles, 203.39 grams) was added to the reactor over a 125 minute (7500 s) period and so as to maintain the reaction temperature at -5° C. After completion of the triethylamine addition, the reactor was maintained at -5° C. for 30 minutes (1800 s), followed by addition of the reaction product to chilled water (650 milliliters) with agitation. After 15 minutes (900 s), the water and product mixture was multiply extracted with methylene chloride. The combined methylene chloride extracts were sequentially washed with dilute hydrochloric acid (5 percent), water, dilute hydrochloric acid, water and then dried over anhydrous magnesium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate was recovered in 91.6 percent yield (255.0 grams) as a white crystalline solid. Infrared spectrophotometric analysis confirmed the product structure for the dicyanate of Bisphenol A.

Workup

  1. additioncontaining
  2. additionwas added to the reactor
  3. customto equilibrate at -5° C.
  4. temperaturethe reactor was maintained at -5° C. for 30 minutes (1800 s)
  5. additionfollowed by addition of the reaction product
  6. extractionthe water and product mixture was multiply extracted with methylene chloride
  7. washThe combined methylene chloride extracts were sequentially washed with dilute hydrochloric acid (5 percent), water, dilute hydrochloric acid, water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. extractionThe dry methylene chloride extract
  10. filtrationwas filtered
  11. customsolvent removed by rotary evaporation under vacuum
  12. customBisphenol A dicyanate was recovered in 91.6 percent yield (255.0 grams) as a white crystalline solid

Sources & evidence

ORD record
ord-49ea5cfa75e8492abd7778b605468b1c
Source dataset
uspto-grants-1984_10
Patent number
US04477629

Reaction notes

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