Efficient metal-free aerobic oxidation of aromatic hydrocarbons utilizing aryl-tetrahalogenated N-hydroxyphthalimides and 1,4-diamino-2,3-dichloroanthraquinone
2008
Zhang, Qiaohong | Chen, Chen | Ma, Hong | Miao, Hong | Zhang, Wei | Sun, Zhiqiang | Xu, Jie
BACKGROUND: Hydrocarbon oxidation reactions are central to numerous processes that convert bulk chemicals into useful and higher-value products. In this investigation, an efficient metal-free catalytic system for aerobic oxidation of aromatic hydrocarbons was successfully established by synthesizing a series of aryl-tetrahalogenated N-hydroxyphthalimides and applying these compounds with 1,4-diamino-2,3-dichloroanthraquinone (DADCAQ).RESULTS: Ethylbenzene was oxidized with 82.3% conversion and 86.9% selectivity to acetophenone catalyzed by the system of TCNHPI/DADCAQ under 0.3 MPa of molecular oxygen at 100 °C for 5 h. Other hydrocarbons were oxidized with high efficiency using this catalytic system. For example, indane can be converted completely to indan-1-one with 98.0% selectivity.CONCLUSION: A highly efficient metal-free catalytic system consisting of TCNHPI and DADCAQ was developed for the oxidation of aromatic hydrocarbons with molecular oxygen. Aryl-halogen substituents served to significantly increase the activities of the catalytic system. The results in this study can form the basis for the design of an efficient hydrocarbon oxidation process.
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