Isophthalic Acid → Bisphenol A

HRID 27724

Reaction equation

HRID 27724 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C(=O)C)=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1)(=O)C.C(O)(=O)C1C=CC=C(C(O)=O)C=1.ClCC(Cl)(Cl)Cl.C1(O)C=CC=CC=1.CC1C=CC=C(C)C=1O.C(Cl)(Cl)Cl.C(O)C.[OH-].[K+]>>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)([CH3:13])[CH3:12])=[CH:9][CH:10]=1

Participants

6

Conditions

Temperature
290 °C

Procedure

An equimolar mixture of 2,2-bis(4-acetoxyphenyl)propane (Bisphenol A diacetate) and isophthalic acid is heated gradualy to 290° C. in a stirred vessel under gradually increasing vacuum to remove the acetic acid which is liberated. When the melt viscosity of the condensate reaches a level such that stirring becomes difficult the melt is drained from the reaction vessel and crystallized. The crystallized polymer is subjected to solid state polymerization under vacuum at 280° C. until the inherent viscosity reaches 0.65 dl/g (in 40/60 by weight tetrachloroethane/phenol solution at 25° C.). The polymer is then extruded at 350° C. and pelletized. The polymer has an inherent viscosity of 0.62 and a carboxylic acid content of 40 microequivalents per gram (μeq./g), determined by potentiometric titration of a solution of the polymer in a 2,6-dimethylphenol/chloroform/ethanol mixture with an ethanolic solution of potassium hydroxide.

Workup

  1. temperatureunder gradually increasing vacuum
  2. customto remove the acetic acid which
  3. customcrystallized
  4. customThe crystallized polymer is subjected to solid state polymerization under vacuum at 280° C. until the inherent viscosity
  5. customis then extruded at 350° C.

Sources & evidence

ORD record
ord-da044c87e1ee442cbdf8d9c420ead15b
Source dataset
uspto-grants-1980_09
Patent number
US04222932

Linked notes

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