Acetic Acid → P-Toluic Acid

HRID 1389534Notes

Reaction equation

HRID 1389534 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[O:10]=O.[C:12]([OH:15])(=[O:14])[CH3:13]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Co].CC1C=CC=CC=1C(O)=O.[Co]>[CH3:9][C:1]1[CH:2]=[CH:3][C:4]([C:7]([OH:14])=[O:8])=[CH:5][CH:6]=1.[C:7]([OH:8])(=[O:10])[C:4]1[CH:3]=[CH:2][C:13]([C:12]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 77254-Methylbenzaldehyde2×

Product 2

HCID 7470P-Toluic AcidHCID 7489Terephthalic Acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 104730CobaltCatalystHCID 131712030HCID 131712030, compoundCatalyst

Procedure

Into an autoclave were charged 100 g of glacial acetic acid, 20 g of p-tolualdehyde and 1 g of cobalt acetate (cobalt concentration 0.24% by weight based on the weight of the solution). The reaction was carried out at a temperature of 130° C. and an oxygen pressure of 3 kg/cm2 for 2 hours according to a batch process. The value of toluic acid/cobalt was about 20. As a result, the conversion of p-tolualdehyde was 99%, the yields of p-toluic acid and terephthalic acid were 55.4% by mole and 39.8% by mole, respectively, and the purity of terephthalic acid was 79.0%. Also, the acid value of terephthalic acid was 607.

Workup

  1. customwas carried out at a temperature of 130° C.

Sources & evidence

ORD record
ord-b295877edd3142c3a0334d0721f94f6f
Source dataset
uspto-grants-1981_01
Patent number
US04245078

Reaction notes

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