Acetoacetic Acid → Bisphenol A

HRID 1253075Notes

Reaction equation

[CH3:1][C:2]([CH2:4][C:5]([OH:7])=[O:6])=O.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)([CH3:17])[CH3:16])=[CH:11][CH:10]=1.C([O-])(=[O:27])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:5]([O-:7])(=[O:6])[C:4]1[CH:18]=[CH:23][C:22]([C:21]([O-:24])=[O:27])=[CH:1][CH:2]=1.[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)([CH3:17])[CH3:16])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 290 °C

Procedure

In a 0.5 liter flask equipped wiht a stirrer, thermometer, a distillation set-up and an argon inlet tube are placed 15.617 gms (0.05 mole) of the diacetate of bisphenol-A, 0.05 moles of the acetate of the monofunctional polyphenylene oxide prepared in Example 1, possessing a molecular weight of about 5,500 and having the structure: ##STR11## and 6.04 (0.037 moles) of each terephthalic and isophthalic acids. To this mixture are added about 100 ml of diphenyl ether. Heating, stirring and argon circulation are started. When the temperature reaches about 250° C. strong distillation of acetic acid is observed. The reaction mixture is gradually heated to 290° C. with continuous distillation of acetic acid and diphenyl ether. After 5 hrs a very viscous melt is obtained (290° C.). The melt is cooled and finely ground. A quantitative yield of a slightly yellow copolymer of polyphenylene oxide and the poly(iso/terephthalate) (1:1) of bisphenol-A results.

Workup

customIn a 0.5 liter flask equipped wiht a stirrer
temperatureHeating
customreaches about 250° C.
distillationstrong distillation of acetic acid
customAfter 5 hrs a very viscous melt is obtained (290° C.)
temperatureThe melt is cooled

Sources & evidence

ORD record: ord-b6c501b27de442a78b2f500dbbf59b0a
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04746709

Reaction notes

Loading…