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

HRID 1764083Notes

Reaction equation

HRID 1764083 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(=O)([O-])[O-].[Na+].[Na+]>>[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

4

Reactant 3

HCID 8496Isophthalic AcidHCID 10340Sodium CarbonateHCID 113200Phenol, 4,4'-(1,2-ethanediyl)bis-, 1,1'-diacetate2×

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 82 parts of isophthalic acid and 148 parts of 1,2-bis(4-acetoxyphenyl)ethane and 0.005 moles sodium carbonate per mole 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 35 to 40 parts of acetic acid distills. Thereupon the vessel is evacuated to a pressure of about 200 torr for about 5 minutes and the pressure is slowly reduced to about 1 torr while the temperature is increased to about 290° C. When the amperage on the stirrer motor increases by 0.02 to 0.04 amps, the stirrer motor is switched off and the vacuum is released with nitrogen. From 95 to 97 percent of the theoretical amount of acetic acid is collected. The polymer is extruded from the vessel under slight nitrogen pressure and is reduced in a Thomas mill to a powder of particle size in the range of about 0.1 to 0.25 mm. The inherent viscosity is about 0.3. The powder is charged to a reaction vessel which is then purged with nitrogen. The pressure is reduced to 0.1 to 0.2 torr. and the temperature is raised to about 10° to 15° C. below the melting point of the polymer. Heating is continued for 12 hours. The vessel is cooled and the crystalline polymer is discharged. The inherent viscosity of the polymer is 0.90. The polymer melts at 279°-290° C. The rate of crystallization is 2.56 min.-1.

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 200 torr for about 5 minutes
  8. temperatureis increased to about 290° C
  9. temperatureWhen the amperage on the stirrer motor increases by 0.02 to 0.04 amps
  10. customFrom 95 to 97 percent of the theoretical amount of acetic acid is collected
  11. additionThe powder is charged to a reaction vessel which
  12. customis then purged with nitrogen
  13. temperatureand the temperature is raised to about 10° to 15° C. below the melting point of the polymer
  14. temperatureHeating
  15. temperatureThe vessel is cooled
  16. customThe rate of crystallization
  17. waitis 2.56 min.

Sources & evidence

ORD record
ord-fd89168873c24d669f6a2ef708224998
Source dataset
uspto-grants-1978_09
Patent number
US04115357

Reaction notes

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