Bisphenol A → HCID 131722863, compound

HRID 1596855Notes

Reaction equation

HRID 1596855 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.OS(C(F)(F)F)(=O)=O.[CH3:26][C:27]1[CH2:32][CH2:31][C@@H:30]([C:33]([CH3:35])=[CH2:34])[CH2:29][CH:28]=1.[OH-].[Na+]>O.C1(C)C(C)=CC=CC=1>[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.[CH3:26][C:27]1[CH2:32][CH2:31][C@@H:30]([C:33]([CH3:35])=[CH2:34])[CH2:29][CH:28]=1

Participants

7

Reactant 4

HCID 6623Bisphenol AHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 440917(+)-Limonene2×

Product 1

HCID 131722863HCID 131722863, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
105 °C

Procedure

A 250 ml flask with stir bar was charged with: 57 g of bisphenol-A (0.25 mole=0.50 equivalents) and 56 g (65 ml) of xylene. This was heated to 105° C. and there was then added 0.5 g of 50% triflic acid in water. Then 41 ml (34.4 g) d-limonene (99%) was added over 25 minutes at 105° C.±2° C. The reaction temperature was allowed to drop to 90° C. over 35 minutes at which time it was raised to 105° C. and an additional 40 ml of d-limonene (total of 68 g, 0.5 mols) was added over 45 minutes. After 1.5 hours at 105° C. catalyst was neutralized with 0.5 g of 15% sodium hydroxide in water. The well stirred reaction mixture was then allowed to stand overnite at room temperature. Then 176 g of liquor was separated from solid (salt), xylene, and unreacted d-limonene removed by vacuum distillation to 166° C. at 30 inches of vacuum. Yield of product and distillate was 111 g and 63 g respectively. Product was characterized by 3.8% free bisphenol-A; Mw/Mn of 310/235; and viscosity of 1250 cps (100° C.).

Workup

  1. temperaturewas raised to 105° C.
  2. stirringThe well stirred
  3. customreaction mixture
  4. customto stand overnite at room temperature
  5. customThen 176 g of liquor was separated from solid (salt), xylene, and unreacted d-limonene
  6. customremoved by vacuum distillation to 166° C. at 30 inches of vacuum
  7. customviscosity of 1250 cps (100° C.)

Sources & evidence

ORD record
ord-dbc64afa48d448d5b9f9f32b2bb0d8bf
Source dataset
uspto-grants-2001_09
Patent number
US06291723B1

Reaction notes

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