Acetic Acid → Benzoic Acid

HRID 746300Notes

Reaction equation

HRID 746300 reaction equation
[C:1]1(C)[CH:6]=[CH:5]C=[CH:3][CH:2]=1.O=O.[C:10]([OH:13])(=[O:12])[CH3:11]>[Cr].[Co].O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Na+]>[C:10]([OH:13])(=[O:12])[C:11]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 3

HCID 176Acetic Acid2×HCID 977Oxygen2×HCID 1140Toluene

Product 1

HCID 243Benzoic AcidYield 81.9%

Reagents, catalysts & solvents 3

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 253881Sodium BromideCatalystHCID 11332432Hastelloy CCatalyst

Conditions

Temperature
23 °C

Procedure

A heated autoclave of Hastelloy C, equipped with stirrer, gas introduction tube, temperature sensor, pressure gauge and a pressurized reflux condenser was charged with 300 g of toluene, 100 g of acetic acid, 3 g of cobalt acetate tetrahydrate (Co(OAc)2.4H2O) and 1.5 g of sodium bromide. Through this mixture air was passed at 125°-130° C. and a pressure of 25 bar, with stirring, with a constant exhaust of 3 1/min. The reaction was observed by continuous measurement of the oxygen content in the exhaust gas. The end of the reaction 220 minutes later was manifested by the fact that the oxygen in the exhaust gas returned to the initial level of 21%. Then the passage of air was stopped, and, after the addition of 450 g of 50% acetic acid, the mixture was cooled to 23° C. with stirring. The crystalline target product was separated from the reaction mixture using a pressure filter, washed with 450 g of 50% acetic acid, and dried. 325.5 g of pure white benzoic acid was obtained.

Workup

  1. customwas passed at 125°-130° C.
  2. customThe end of the reaction 220 minutes
  3. stirringwith stirring
  4. customThe crystalline target product was separated from the reaction mixture
  5. filtrationfilter
  6. washwashed with 450 g of 50% acetic acid
  7. customdried

Sources & evidence

ORD record
ord-228b129346c34b2db1d25dd1ce56b06b
Source dataset
uspto-grants-1986_07
Patent number
US04603220

Reaction notes

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