Benzoic Acid → P-Toluic Acid

Participants

Reaction Conditions

Reaction Steps

Into an air-flow pressure reactor (or air-flow pressurizable reactor) equipped with a dehydrator similar to Dean-Stark apparatus, 300 g (2.8 mol) of p-xylene, 0.20 g (1.1 mmol) of cobalt acetate (bivalent), and 0.20 g (1.2 mmol) of manganese acetate (bivalent) were charged. Nitrogen was introduced into the reactor to raise the reactor pressure to 0.5 MPa. The mixture was heated to 150° C., and the reactor was ventilated with a mixed gas of air and nitrogen to adjust the oxygen concentration contained in off-gas to 5%. A separately prepared mixture of 0.25 g (2.2 mmol) of N-hydroxysuccinimide and 2 g of water was continuously fed in the reactor over 5 hours. Incidentally, it was assumed that the reaction was started at the time the addition of the catalyst was started, and that the reaction was completed at the time the addition of the catalyst was completed. Moreover, the reaction was carried out with trapping the produced water. After the reaction was completed, the reactor was cooled and the pressure was released. The reaction mixture was analyzed by a high-performance liquid chromatography (HPLC) to determine the conversion of the substrate and the amount and yield of the product. The conversion of p-xylene was 35.7%, and 110 g of p-toluic acid (yield 28.9%), 31 g of terephthalic acid (yield 6.68%), and 0.32 g of benzoic acid as a by-product (yield 0.094%) were obtained.

Provenance & Evidence