Acetic Acid → Terephthalic Acid

HRID 618996Notes

Reaction equation

HRID 618996 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].ON1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=O.[O:17]=O>CC1C=CC(C)=CC=1>[C:10]([OH:17])(=[O:11])[C:9]1[CH:12]=[CH:13][C:2]([C:1]([OH:4])=[O:3])=[CH:7][CH:8]=1.[CH3:7][C:8]1[CH:9]=[CH:10][C:2]([C:1]([OH:4])=[O:3])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 10665N-Hydroxyphthalimide

Product 2

HCID 7470P-Toluic AcidYield 27%HCID 7489Terephthalic AcidYield 70%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent2×

Procedure

To 25 milliliters of acetic acid were added 1.06 grams (10 millimoles) of p-xylene, 0.16 gram (1 millimole) of N-hydroxyphthalimide and 0.018 gram (0.05 millimole) of acetylacetonatocobalt(II) Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for 12 hours. With a transformation rate of 99 percent, p-xylene was transformed into terephthalic acid (yield 70%) and p-methylbenzoic acid (yield 27%).

Sources & evidence

ORD record
ord-95c5420719a642f0aa1754b546967d7e
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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