1,4-Bis(trichloromethyl)benzene → Terephthalic Acid

HRID 1679310Notes

Reaction equation

HRID 1679310 reaction equation
C[O:2][C:3](=[O:14])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1.ClC(Cl)(Cl)C1C=CC(C(Cl)(Cl)Cl)=CC=1.CCl>[Mo](=O)(=O)=O>[C:8]([OH:10])(=[O:9])[C:7]1[CH:12]=[CH:13][C:4]([C:3]([OH:14])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 62331,4-Bis(trichloromethyl)benzeneHCID 6327Methyl ChlorideHCID 8441Dimethyl terephthalate

Product 1

HCID 7489Terephthalic AcidYield 234.6%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Procedure

A two-liter round flask, equipped with thermometer, magnetic stirrer, Vigreux column (40 cm), fractionating column, air cooler and receiver, was filled with 777 g (4 moles) of dimethylterephthalate, 1252 g (4 moles) of 1,4-bis-(trichloromethyl)-benzene and 4 g of molybdenum trioxide. The flask contents were maintained for 3 hours at 170° to 175° C. The escaping methyl chloride was captured in a cooling trap following the receiver. In the vacuum distillation that followed, 1559 g of terephthalic acid was obtained in a purity of 99.8% (GC). This corresponds to a yield of 95.8%.

Workup

  1. customA two-liter round flask, equipped with thermometer, magnetic stirrer, Vigreux column (40 cm), fractionating column, air cooler and receiver
  2. temperatureThe flask contents were maintained for 3 hours at 170° to 175° C
  3. distillationIn the vacuum distillation that

Sources & evidence

ORD record
ord-30b114daae7643578e7f2fba99c64c72
Source dataset
uspto-grants-1978_03
Patent number
US04080378

Reaction notes

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