Isophthalic Acid → Benzene-1,3-dicarboxylic acid--4,4'-(ethane-1,2-diyl)diphenol (1/1)

HRID 2049920Notes

Reaction equation

HRID 2049920 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1.C([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31]C(=O)C)=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(=O)C>>[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1.[OH:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 8496Isophthalic AcidHCID 113200Phenol, 4,4'-(1,2-ethanediyl)bis-, 1,1'-diacetate

Product 1

HCID 6454818Benzene-1,3-dicarboxylic acid--4,4'-(ethane-1,2-diyl)diphenol (1/1)

Conditions

Temperature
250 °C

Procedure

A charge consisting of 8.2 parts of isophthalic acid and 14.8 parts of 1,2-bis(4-acetoxyphenyl)ethane is placed in a reaction vessel equipped with a stirrer, condenser and receiver. The vessel is evacuated and purged with nitrogen three times. A nitrogen blanket is maintained in the reactor while it is heated to 250° C. for about three hours during which period approximately 3.5 to 4.0 parts of acetic acid distills. Thereupon the vessel is evacuated to a pressure of about 125 mm and heating at 275° C. is continued for one half hour during which period an additional 1 to 1.5 parts of acetic acid distills. The vacuum is then increased to reduce the pressure to about 0.1 to 0.2 mm and the temperature is raised to 290° C. for an additional hour. At this point the reaction mixture becomes so viscous that further stirring is difficult. Heating is stopped, the reaction mixture is again blanketed with nitrogen and allowed to cool. The resultant polymer is light yellow in color, crystalline and demonstrates an inherent viscosity of 0.57 in the phenol-tetrachloroethane solvent.

Workup

  1. customis placed in a reaction vessel
  2. customequipped with a stirrer, condenser
  3. customThe vessel is evacuated
  4. custompurged with nitrogen three times
  5. temperatureA nitrogen blanket is maintained in the reactor while it
  6. distillationdistills
  7. customThereupon the vessel is evacuated to a pressure of about 125 mm
  8. temperatureheating at 275° C.
  9. waitis continued for one half hour during which period
  10. distillationan additional 1 to 1.5 parts of acetic acid distills
  11. temperatureThe vacuum is then increased
  12. temperaturethe temperature is raised to 290° C. for an additional hour
  13. temperatureHeating
  14. temperatureto cool

Sources & evidence

ORD record
ord-39c0a6539b85444e86be673122dd89c5
Source dataset
uspto-grants-1980_04
Patent number
US04199493

Reaction notes

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