Acetic Acid → Terephthalic Acid

Participants

Reaction Conditions

Reaction Steps

In this example, a solution of 0.1158 g (1.01 mmol) of N-hydroxysuccinimide, 0.5199 g (4.9 mmol) of p-xylene and 0.1273 g (0.511 mmol) CAT in 40 ml of acetic acid was heated to 100° C. in a Parr Hastelloy reactor fitted with temperature and pressure controllers. After the temperature reached 100° C., 860 psi of air was slowly introduced into the reactor. The mixture was stirred under pressure for one hour at 100° C., the pressure was released, and the mixture cooled to room temperature. Within roughly 15 minutes following O2 introduction, a rapid temperature rise occurred (due to heat generated by the exothermic oxidation) accompanied by a drop in reactor pressure (due to consumption of O2 in the liquid phase reaction) indicating rapid reaction. These profiles are steep and level off within minutes after induction (typical T and P profiles will be provided in the patent application). The white solid of terephthalic acid (TPA) was filtered, and the filtrate analyzed by HPLC using biphenyl as the internal standard. The solid TPA product was washed with additional acetic acid (20 ml) and dried in an oven at 120° C. for six hours to obtain 0.795 g of TPA (yield: 98% based on the initial moles of p-xylene reacted). Analysis: 97.7% TPA, 2.0% carboxybenzaldehyde (CBA), and 0.3% p-toluic acid (PTA).

Provenance & Evidence