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Efficient metal‐free aerobic oxidation of aromatic hydrocarbons utilizing aryl‐tetrahalogenated N‐hydroxyphthalimides and 1,4‐diamino‐2,3‐dichloroanthraquinone
Author(s) -
Zhang Qiaohong,
Chen Chen,
Ma Hong,
Miao Hong,
Zhang Wei,
Sun Zhiqiang,
Xu Jie
Publication year - 2008
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.1977
Subject(s) - chemistry , acetophenone , catalysis , ethylbenzene , aryl , hydrocarbon , selectivity , indane , aromatic hydrocarbon , metal , autoxidation , organic chemistry , combinatorial chemistry , alkyl
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. Copyright © 2008 Society of Chemical Industry