Carbon Dioxide → Terephthalic Acid

HRID 1641604Notes

Reaction equation

HRID 1641604 reaction equation
[OH:1]N1C(=O)CCC1=O.C[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.[C:18](=[O:20])=[O:19].O=O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:14]([OH:15])(=[O:1])[C:13]1[CH:12]=[CH:11][C:10]([C:18]([OH:20])=[O:19])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 977OxygenHCID 115054-Methylbenzyl alcoholHCID 80170N-Hydroxysuccinimide

Product 1

HCID 7489Terephthalic AcidYield 96%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
22 °C

Procedure

In this example, a solution of 0.1456 g (1.26 mmol) of N-hydroxysuccinimide, 0.089 g (0.73 mmol) of 4-methylbenzyl alcohol and 0.1509 g (0.61 mmol) of cobalt acetate tetrahydrate in 40 ml of acetic acid was kept to 22° C. in a Parr Hastelloy reactor with temperature and pressure transducer. After the temperature reached 22° C., 745 psi of CO2 was introduced into the reactor, then 120 psi of O2 was added slowly to the reactor. The mixture was stirred under pressure for 24 hours at 22° C., then the pressure was released, and the mixture was cooled to room temperature. The white solid TPA was filtered, and the filtrate analyzed by HPLC using biphenyl as the internal standard. The solid TPA product was washed with acetic acid (20 ml) and dried in an oven at 120° C. for six hours to yield pure white solid terephthalic acid (96% yield).

Workup

  1. customreached 22° C.
  2. temperaturethe mixture was cooled to room temperature
  3. filtrationThe white solid TPA was filtered
  4. washThe solid TPA product was washed with acetic acid (20 ml)
  5. customdried in an oven at 120° C. for six hours

Sources & evidence

ORD record
ord-bf26233a55814ba6811deb806c56f163
Source dataset
uspto-grants-2012_02
Patent number
US08115029B2

Reaction notes

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