Oxygen → Cyclopentanol

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 (1.14 mol) of cyclopentane, 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, 8.2 mmol of cyclopentane reacted (with a conversion of 0.7%) and thereby yielded 0.5 mmol of cyclopentanone (with a selectivity of 6.1%), 0.2 mmol of cyclopentanol (with a selectivity of 2.4%), and 5.2 mmol of cyclopentyl hydroperoxide (with a selectivity of 63.4%). The total yield of cyclopentanone, cyclopentanol, and cyclopentyl hydroperoxide was 0.52%. N-hydroxyphthalimide has a solubility in water (25° C.) of 0.01 g/100 g-H2O or less.

Provenance & Evidence