Bisphenol A diglycidyl ether → Benzene-1,3-diol;ethoxyethane

HRID 5287

Reaction equation

HRID 5287 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].CC(C1C=CC(OCC2OC2)=CC=1)(C1C=C[C:15]([O:18][CH2:19][CH:20]2OC2)=[CH:14]C=1)C.C1(C=CC=C(O)C=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C1C=CC(OCC2OC2)=CC=1)(C1C=CC(OCC2OC2)=CC=1)C>C1(C)C=CC=CC=1>[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:14][CH2:15][O:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 2286Bisphenol A diglycidyl etherHCID 5054ResorcinolHCID 11776TriphenylphosphineHCID 131718118resorcinol diglycidyl ether of bisphenol A

Product 1

HCID 22234841Benzene-1,3-diol;ethoxyethane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
112 °C

Procedure

A resorcinol/diglycidyl ether of bisphenol A addition product was prepared in a 3-liter reactor equipped with an agitator, thermometer and reflux condenser. The reactor was charged with about 330.3 g. resorcinol, 1500 ml. toluene and 3.0 g. triphenylphosphine. The stirred charge was heated to reflux at about 112° C. and about 654.0 g. diglycidyl ether of bisphenol A (Ciba-Geigy Araldite GY 6004) was added dropwise in about 2.5 hours. The charge was refluxed for about one hour, devolatilized at reduced pressure and about 36.0 g. amorphous silica was added to obtain a light tan resorcinol ether compound (RE4) having a 77° C. softening point, and having a 0.45 wt. % residual oxirane oxygen.

Workup

  1. customwas prepared in a 3-liter reactor
  2. customequipped with an agitator
  3. temperaturethermometer and reflux condenser
  4. additionThe reactor was charged with about 330.3 g
  5. additionThe stirred charge
  6. temperaturewas heated
  7. temperatureThe charge was refluxed for about one hour
  8. additionamorphous silica was added

Sources & evidence

ORD record
ord-e551bf9aea5c4c649c5667d952fb6c3a
Source dataset
uspto-grants-1993_09
Patent number
US05244725

Linked notes

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