Table 1.
Entry | Temperature (°C) |
Conversion (%) |
Selectivity (%) | |||||
---|---|---|---|---|---|---|---|---|
C6-OOH | C6-OH | C6=O | C4-(COOH)2 | C3-(COOH)2 | Total b | |||
1 c | 110 | <0.20 | N. D. d | N. D. | N. D. | N. D. | N. D. | N. D. |
2 c | 115 | <0.20 | N. D. | N. D. | N. D. | N. D. | N. D. | N. D. |
3 c | 120 | <0.20 | N. D. | N. D. | N. D. | N. D. | N. D. | N. D. |
4 c | 125 | 0.22 | 86.4 | N. D. | 13.6 | N. D. | N. D. | >99 |
5 c | 130 | 0.44 | 57.8 | 31.0 | 11.2 | N. D. | N. D. | >99 |
6 e | 120 | 4.25 | 7.0 | 33.6 | 44.6 | 10.1 | 4.7 | 85.2 |
7 f | 120 | 0.53 | 84.6 | N. D. | 15.4 | N. D. | N. D. | >99 |
8 g | 120 | 3.87 | 7.4 | 31.9 | 45.5 | 13.3 | 1.9 | 84.8 |
9 h | 120 | 0.46 | 96.4 | N. D. | 3.6 | N. D. | N. D. | >99 |
10 i | 120 | 2.22 | 39.9 | 25.6 | 26.1 | 6.9 | 1.5 | 91.6 |
11 j | 120 | 0.42 | 79.5 | 0.8 | 19.7 | N. D. | N. D. | >99 |
12 k | 120 | 2.41 | 36.5 | 35.6 | 24.1 | 3.0 | 0.8 | 96.2 |
a Reaction conditions: substrate (cyclohexane, 16.8320 g, 200 mmol), O2 (1.0 MPa in constant supply), stirring at speed of 600 rpm for 8.0 h. b Total selectivity of POX-products. c Without catalyst. d Not detected. e T(perF)PPCo as catalyst (2.5 mg, 1.2 × 10−3%, mol/mol). f T(perF)PPCu as catalyst (2.5 mg, 1.2 × 10−3%, mol/mol). g Tris(perF)P(4-CH2Cl)PPCo as catalyst (2.4 mg, 1.2 × 10−3%, mol/mol). h Tris(perF)P(4-CH2Cl)PPCu as catalyst (2.4 mg, 1.2 × 10−3%, mol/mol). i Si@Porp. Co as catalyst (20 mg, 0.10 mg/mmol, catalysts/substrate). j Si@Porp. Cu as catalyst (20 mg, 0.10 mg/mmol, catalysts/substrate). k Si@Porp. Co&Cu as catalyst (20 mg, 0.10 mg/mmol, catalysts/substrate).