Methanol → Formanilide

Participants

Reaction Conditions

Reaction Steps

To a 200 cc Parr reactor provided with a glass liner (actual reactor volume with liner=134 cc) and a magnetic stirrer is charged, at room temperature, 1.0 gram aniline, 20 cc methanol, 0.5 gram of BaO.CoMoO4 as catalyst and 2.5 grams of phenyl disulfide (φ2S2). The reactor is sealed and then purged with gaseous nitrogen by means of a gas inlet tube and, also at room temperature, gaseous COS (2.5 grams) is pressured into the reactor following which CO is pressured into the reactor, to provide a pressure in the reactor of about 500 psig. The molar ratio of S:aniline in this example is about 2.5:1. The pressured reactor is then heated with stirring by means of an oil bath to a temperature of 180° C., which is measured externally to the reactor. This reaction temperature is maintained for six hours after which the oil bath is cooled to about 30° C. by passing cooling water through a copper tube which is immersed in the bath. The gas in the reactor is then vented and the vent gas and the liquid product mixture in the reactor are analyzed. Methyl N-phenyl carbamate ("MPC") is found to be present in a yield of about 59 percent and in a selectivity of about 95%. No detectable formanilide is formed and the diphenyl urea yield is less than 5%.

Provenance & Evidence