Bisphenol A → Benzene, 1,1'-(1-methylethylidene)bis[4-(2-propen-1-yloxy)-

HRID 1826098Notes

Reaction equation

HRID 1826098 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.[OH-].[K+].[CH2:20](Cl)[CH:21]=[CH2:22].[CH2:24](OCC=C)[CH:25]=[CH2:26]>C(C(C)=O)C.C1(C)C=CC=CC=1.CS(C)=O>[CH2:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:26][CH:25]=[CH2:24])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1)[CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 6623Bisphenol A2×HCID 7850Allyl chloride3×HCID 11194Diallyl etherHCID 14797Potassium Hydroxide

Product 1

HCID 77333Benzene, 1,1'-(1-methylethylidene)bis[4-(2-propen-1-yloxy)-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226399HCID 21226399, compoundSolvent

Conditions

Temperature
37.5 °C

Procedure

Bisphenol A diallyl ether was synthesized as described in U.S. Pat. No. 4,740,330. In a four-necked reactor, equipped with a condenser, stirrer, thermometer with temperature controller, and an addition funnel, were added 800 mL of bis-(2-methoxy ethyl)ether(diglyme), 400 mL of dimethyl sulfoxide (DMSO), 228 g (1 mole) bisphenol-A, and 284 g (4 moles) of 85% KOH at ambient temperature (˜25° C.). The mixture was stirred and heated to 35-40° C., and the addition of 304 g (4 moles) of allyl chloride was begun. This reaction was exothermic and was controlled at less than 45° C. by controlling the allyl chloride addition rate. The allyl chloride was added over a 4-hour period, and the reaction was continued at 45° C. for an additional 12 hours to convert the bisphenol-A into diallyl ether. The reaction mixture was cooled to ambient temperature and filtered to remove salts formed in the reaction. The filtrate was mixed with 1000 mL of 50:50 (volume:volume) methyl ethyl ketone-toluene mixture and washed four times with 200 mL portions of water. The solvents were removed from the diallyl product by rotary evaporation first at 50-60° C. and 120 mmHg and then at 120-130° C. at 10 mmHg until gas chromatography (GC) showed all the diglyme and DMSO had disappeared. The yield was 235 g (76% yield) of a light yellow product, bis A diallyl ether, with greater than 95% purity as determined by GC.

Workup

  1. customIn a four-necked reactor, equipped with a condenser, stirrer, thermometer with temperature controller, and an addition funnel
  2. customwas controlled at less than 45° C.
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. customto remove salts
  6. customformed in the reaction
  7. washwashed four times with 200 mL portions of water
  8. customThe solvents were removed from the diallyl product by rotary evaporation first at 50-60° C.
  9. customat 120-130° C.

Sources & evidence

ORD record
ord-b4571b03363b4c04a7075bf8e91a602b
Source dataset
uspto-grants-2006_05
Patent number
US07049388B2

Reaction notes

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