Example 1
2.5 g (30 mmol) of cyclohexane and 0.10 g of gold-supporting ceric oxide obtained in Reference Example 1 as a catalyst were put in a 12-ml autoclave, and the inside of the system was pressurized up to 1.5 MPa with oxygen at room temperature and thereafter heated up to a temperature of 120° C. and reacted for 24 hours. As a result of analyzing the reaction liquid, degree of conversion of cyclohexane was 2.0%, selectivity coefficient of cyclohexanone was 25.3% and selectivity coefficient of cyclohexanol was 35.9%.
The reaction was performed in the same manner as Example 1 except for replacing gold-supporting ceric oxide obtained in Reference Example 1 with gold-supporting MCM-41 obtained in Reference Example 2 as a catalyst. As a result of analyzing the reaction liquid, degree of conversion of cyclohexane was 1.7%, selectivity coefficient of cyclohexanone was 16.6% and selectivity coefficient of cyclohexanol was 28.5%.
Example 2
2.5 g (30 mmol) of cyclohexane and 0.10 g of gold-supporting ceric oxide obtained in Reference Example 1 as a catalyst were put in a 12-ml autoclave, to which 0.075 g (0.46 mmol) of 2,2′-azobis(isobutyronitrile) was further added as a free-radical initiator, and the inside of the system was pressurized up to 1.5 MPa with oxygen at room temperature and thereafter heated up to a temperature of 120° C. and reacted for 24 hours. As a result of analyzing the reaction liquid, degree of conversion of cyclohexane was 20.8%, selectivity coefficient of cyclohexanone was 37.8% and selectivity coefficient of cyclohexanol was 52.5%.
The reaction was performed in the same manner as Example 2 except for replacing gold-supporting ceric oxide obtained in Reference Example 1 with gold-supporting MCM-41 obtained in Reference Example 2 as a catalyst. As a result of analyzing the reaction liquid, degree of conversion of cyclohexane was 10.5%, selectivity coefficient of cyclohexanone was 31.3% and selectivity coefficient of cyclohexanol was 48.5%.
The major embodiments and the preferred embodiments of the present invention are listed below.
- [1] A method of manufacturing cycloalkanol and/or cycloalkanone wherein cycloalkane is oxidized with oxygen in the presence of a catalyst such that gold is supported on ceric oxide.
- [2] The method according to [1], wherein said oxidation is performed in the presence of a free-radical initiator.
- [3] The method according to [2], wherein the free-radical initiator is an azonitrile compound.
- [4] The method according to [2], wherein the free-radical initiator is 2,2′-azobis(isobutyronitrile).
- [5] The method according to any one of [1] to [4], wherein the cycloalkane is cyclohexane.
Example 3
The reaction was performed in the same manner as Example 2 except for pressurizing the inside of the system by using air instead of oxygen. As a result of analyzing the reaction liquid, degree of conversion of cyclohexane was 14.0%, selectivity coefficient of cyclohexanone was 28.5% and selectivity coefficient of cyclohexanol was 64.8%.
