Oxygen → Cyclohexanol

Participants

Reaction Conditions

Reaction Steps

In a 350-ml autoclave made of stainless steel SUS 316 and equipped with a stirrer were placed 80 g (0.95 mol) of cyclohexane, 100 mg of N-hydroxyphthalimide, and 1.9 g of water (these formed a slurry at room temperature (25° C.)). The autoclave was hermetically sealed, pressurized to 3 MPa (gauge pressure) with a gaseous mixture of 50 percent by volume oxygen and 50 percent by volume nitrogen, and the mixture therein was stirred at 150° C. for 1 hour. As a result, 5.9 mmol of cyclohexane reacted (with a conversion of 0.7%) and thereby yielded 0.3 mmol of cyclohexanone (with a selectivity of 5.1%), 0.2 mmol of cyclohexanol (with a selectivity of 3.4%), and 3.8 mmol of cyclohexyl hydroperoxide (with a selectivity of 64.4%). The total yield of cyclohexanone, cyclohexanol, and cyclohexyl hydroperoxide was 0.45%. N-hydroxyphthalimide has a solubility in water (25° C.) of 0.01 g/100 g-H2O or less.

Provenance & Evidence