Acetic Acid → Terephthalic Acid

HRID 1182343Notes

Reaction equation

HRID 1182343 reaction equation
ON1C(=O)N(O)C(=O)N(O)[C:3]1=[O:12].[C:13]([OH:16])(=[O:15])[CH3:14].[OH2:17].[CH3:18][C:19]1C=C[C:22](C)=[CH:23][CH:24]=1>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[C:3]([OH:12])(=[O:17])[C:24]1[CH:23]=[CH:22][C:14]([C:13]([OH:16])=[O:15])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962Water3×HCID 7809P-Xylene2×HCID 104197231,3,5-Trihydroxy-1,3,5-triazinane-2,4,6-trione

Product 1

HCID 7489Terephthalic AcidYield 99%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalyst

Conditions

Temperature
150 °C

Procedure

In an autoclave, 0.212 g of p-xylene, 0.011 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to p-xylene), 5 g of acetic acid, 0.003 g of cobalt(II) acetate.4 H2O, 0.003 g of manganese(II) acetate.4 H2O and 0.001 g of zirconium oxyacetate were placed. The autoclave was charged with 2 MPa of air and placed in a heated oil bath. The mixture was stirred at 150° C. for 12 hours. After the completion of reaction, the autoclave was placed on cold water to cool down the reaction mixture quickly. The resulting mixture was analyzed by high performance liquid chromatography and was found to yield terephthalic acid in 99% yield at 100% conversion of p-xylene.

Workup

  1. additionThe autoclave was charged with 2 MPa of air
  2. customplaced in a heated oil bath
  3. customAfter the completion of reaction
  4. temperatureto cool down the reaction mixture quickly

Sources & evidence

ORD record
ord-849413584eb34ae78a901248557f7093
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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