Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Efficient and Mild Oxidation of α-Isophorone to Ketoisophorone Catalyzed by N-Hydroxyphthalimide and Copper Chloride

  • Chen, Lihua (School of Chemistry and Chemical Engineering, Central South University) ;
  • Tang, Ruiren (School of Chemistry and Chemical Engineering, Central South University) ;
  • Li, Zhongying (School of Chemistry and Chemical Engineering, Central South University) ;
  • Liang, Shan (School of Chemistry and Chemical Engineering, Central South University)
  • Received : 2011.10.21
  • Accepted : 2011.11.29
  • Published : 2012.02.20
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Abstract

N-hydroxyphthalimide (NHPI) and copper chloride ($CuCl_2$) were first utilized for aerobic oxidation of ${\alpha}$-isophorone (${\alpha}$-IP) to ketoisophorone (KIP) and the effects of co-catalysts, temperature, reaction time, solvent, amount of $CuCl_2$ and pressure of oxygen were investigated extensively. NHPI/$CuCl_2$ turned out to be highly efficient to this oxidation with up to 91.3% conversion and 81.0% selectivity under mild conditions. And various hydrocarbons including benzylic compounds, cycloalkene and its derivatives were also oxidized smoothly under optimized conditions. Moreover, the possible reaction mechanism was proposed and verified by FT-IR spectra.

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