Acetic Acid → P-Toluic Acid

HRID 1182328Notes

Reaction equation

HRID 1182328 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1.[C:11]([OH:14])(=[O:13])[CH3:12].C(ON1C(=O)N(OC(=O)C)C(=O)N(OC(=O)C)C1=O)(=O)C.O=O>[Ti].C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[C:8]([OH:10])(=[O:9])[C:5]1[CH:6]=[CH:7][C:12]([C:11]([OH:14])=[O:13])=[CH:3][CH:4]=1.[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 7470P-Toluic AcidHCID 113011241,3,5-Triacetoxy-hexahydro-1,3,5-triazine-2,4,6-trione

Product 2

HCID 7470P-Toluic AcidHCID 7489Terephthalic Acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalyst2×HCID 23963TitaniumCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

In a 500-ml titanium autoclave equipped with a stirrer and a pressure gauge, 15.36 g of p-toluicacid, 104.0 g of acetic acid, 0.114 g of 1,3,5-triacetoxy-hexahydro-1,3,5-triazine-2,4,6-trione (1,3,5-triacetoxyisocyanuric acid) (0.33% by mole relative to p-toluic acid), 0.112 g of cobalt (II) acetate 4 H2O and 0.277 g of manganese(II) acetate 4 H2O were placed. The autoclave was charged with 2 MPa of oxygen gas and 2 MPa of nitrogen gas and placed in a heated oil bath. The mixture was stirred at 150° C. for 1 hour. After the completion of the 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 90% yield at 93% conversion of p-toluic acid.

Workup

  1. customplaced in a heated oil bath
  2. customAfter the completion of the reaction
  3. temperatureto cool down the reaction mixture quickly

Sources & evidence

ORD record
ord-abca0c6b5bbc43b08c2a87a32187104c
Source dataset
uspto-grants-2007_10
Patent number
US07288649B2

Reaction notes

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