Bisphenol A diglycidyl ether → (1,1'-Biphenyl)-2,3'-diol
Reaction equation
C[C:2]([C:15]1[CH:20]=[CH:19][C:18](OCC2OC2)=[CH:17][CH:16]=1)([C:4]1[CH:9]=[CH:8][C:7]([O:10]CC2OC2)=[CH:6]C=1)C.CCC.C(OCC1OC1)C1[O:32]C1>>[CH:17]1[CH:16]=[C:15]([C:2]2[CH:4]=[CH:9][CH:8]=[C:7]([OH:10])[CH:6]=2)[C:20]([OH:32])=[CH:19][CH:18]=1Participants
Conditions
- Temperature
- 230 fahrenheit
Procedure
To a suitable reactor were added 885 parts of the diglycidyl ether of Bisphenol A having an epoxide equivalent weight of 186 and 615 parts of 2,2'-bis(3,5-dibromo, 4-hydroxyphenyl) propane. Heat and agitation were applied raising the temperature to 230° F. When solution of the diphenol in the glycidyl ether was obtained, heating was discontinued and 30 parts of a nonionic surfactant, made by polymerizing ethylene oxide with a condensate of propylene oxide with propylene glycol (plutonic F98, obtained from Wyandotte Chemicals Corp.) were added. Deionized water, 1530 parts, was slowly added dropping the temperature to 120° F. Triphenyl phosphine, 4.15 parts, was added and heat was applied raising the temperature to 200° F. The temperature was held at 200° F., while the resinous reactants went from a taffy slurry to finely divided beads. After heating for 2 hours and 30 minutes at 200° F., the acid value of the reactants was reduced tp 0, indicating no free phenolic groups. Heating was discontinued and 2000 parts of cold water were added. The water was drawn off and the resin was washed with an additional 2000 parts of water. The resin produce was then placed on foil sheets and dried at 212° F. for 2 days. The produce had an epoxide equivalent weight of 606, a Durran's melting point of 86° C., and at 40% solids in diethylene glycol monobutyl ether, a Gardner color of 1-2 and a Gardner-Holdt viscosity at 25° C. of B-C.
Workup
- temperatureHeat
Sources & evidence
- ORD record
- ord-85dfea9f3f584c14b1e94a4cc00b506b
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04122067
Reaction notes
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