Acetic Acid → Benzaldehyde

HRID 458256Notes

Reaction equation

HRID 458256 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[Na+].[C:10]([OH:13])(=[O:12])[CH3:11]>[Mn].[NH4+].[O-][V](=O)=O>[CH:7](=[O:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([OH:13])[C:11]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 1140Toluene2×HCID 253881Sodium Bromide

Product 2

HCID 240BenzaldehydeHCID 244Benzyl Alcohol

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 516859Ammonium metavanadateCatalyst

Procedure

The experiment was carried out without the addition of manganese to check its effect on the conversion and selectivity in the liquid phase oxidation of toluene with following the procedure given in Example 1. The reactor was charged with toluene 10.0 gm, ammonium metavanadate 0.131 gm, sodium bromide 0.065 gm and acetic acid 50.0 gm. After flushing with nitrogen, 5% oxygen was introduced to a pressure of 55 bar and the reaction was carried out at 120° C. In this experiment, only 2.7% conversion of toluene and 72.3% and 27.7% selectivity were obtained for benzaldehyde and benzyl alcohol, respectively.

Workup

  1. customAfter flushing with nitrogen, 5% oxygen
  2. additionwas introduced to a pressure of 55 bar
  3. customwas carried out at 120° C

Sources & evidence

ORD record
ord-be4a942948744cbc8ac0b9e6939e039b
Source dataset
uspto-grants-2007_03
Patent number
US07189882B2

Reaction notes

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