Acetic Acid → Terephthalic Acid

HRID 1883232Notes

Reaction equation

HRID 1883232 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4]C(C)=[CH:6][CH:7]=1.[OH2:9].CS(O)(=O)=[O:12].[C:15]([OH:18])(=[O:17])[CH3:16]>>[C:15]([OH:18])(=[O:17])[C:16]1[CH:4]=[CH:3][C:2]([C:1]([OH:12])=[O:9])=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6395Methanesulfonic AcidHCID 7809P-Xylene

Product 1

HCID 7489Terephthalic AcidYield 37%

Procedure

The following materials were charged to the reactor: p-xylene 10 g; water 640 g, acetic acid 0.0 g, Co(CH3CO2)2 6H2O 1.08 g, Mn(CH3CO2)2 6H2O 3.37 g, 48% aqueous HBr 6.2 g, methanesulfonic acid 2.0 mL, for a total weight of 678 g. 1.3 g (active basis) Witconate AOS-2024™ surfactant was added. The pH of the reaction mixture was approximately 1.8. The reaction was stirred at 1600 rpm. The following results were obtained: mass solids 5.99 g (37% yield of terephthalic acid based on xylene, 37% conversion of p-xylene; 1H NMR analysis shows: 100 mol % terephthalic acid}. Thus, improved results are obtained at a relatively lower pH.

Workup

  1. additionThe following materials were charged to the reactor
  2. addition1.3 g (active basis) Witconate AOS-2024™ surfactant was added
  3. customThe following results
  4. customwere obtained

Sources & evidence

ORD record
ord-5a08440f89384ef3b01e766616523a74
Source dataset
uspto-grants-2004_07
Patent number
US06759550B1

Reaction notes

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