Terephthaloyl chloride → Adipic acid terephthalic acid

HRID 1193537

Reaction equation

HRID 1193537 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)CCCCC(Cl)=[O:19].[OH-:23].[Na+].[OH:25]C1C=CC(C2(C3C=CC(O)=CC=3)C3C=CC=CC=3C3C2=CC=CC=3)=CC=1>ClCCCl.O.[Cl-].C([N+](CC)(CC)CC)C>[C:6]([OH:19])(=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:11])=[O:23].[C:1]([OH:11])(=[O:25])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:7])=[O:23])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7488Terephthaloyl chlorideHCID 14798Sodium HydroxideHCID 61034Adipoyl chlorideHCID 767169,9-Bis(4-hydroxyphenyl)fluorene

Product 1

HCID 66662870Adipic acid terephthalic acid

Reagents, catalysts & solvents 3

HCID 5946Tetraethylammonium ChlorideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A 4.04 g amount of terephthalic acid chloride and 14.6 g of adipic acid chloride were dissolved in 300 ml of 1,2-dichloroethane. Further, 8 to 15 g of sodium hydroxide was dissolved in 1000 ml of water, followed by dissolving 35 g of 9,9-bis(4-hydroxyphenyl)fluorene and 15 g of tetraethyl ammonium chloride therein. The resultant solution was added all at once to the above-prepared organic solvent solution of the acid component while vigorously stirring, and the resultant mixture was allowed to react at room temperature for 10 to 15 hours. After completing the reaction, the aqueous phase was separated and 200 ml of 1,2-dichloroethane was added to the oily layer to lower the viscosity.

Workup

  1. customto react at room temperature for 10 to 15 hours
  2. customthe reaction
  3. customthe aqueous phase was separated
  4. addition200 ml of 1,2-dichloroethane was added to the oily layer

Sources & evidence

ORD record
ord-51f1d4c45ddc411f8c9b2698cd922079
Source dataset
uspto-grants-1989_03
Patent number
US04810771

Linked notes

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