Chinese Journal of Applied Chemistry ›› 2011, Vol. 28 ›› Issue (11): 1256-1262.DOI: 10.3724/SP.J.1095.2011.00747

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Epoxidation of Olefins Catalyzed by Metal Phthalocyanine Tetracarboxylic Acid

LI Linqing1,2, ZHANG Aiping2, LI Jun2, DONG Xiaoli1, LV Ying2, ZHANG Yi2, GAO Shuang2*   

  1. (1.School of Chemical Engineering and Materials,Dalian Polytechnic University,Dalian;
    2.Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023)
  • Received:2010-12-17 Revised:2011-01-24 Published:2011-11-10 Online:2011-11-10
  • Contact: Shuang GAO

Abstract:

Four metal phthalocyanine tetraboxylic acid complexes(M-PTC) were synthesized and characterized by the IR, UV spectrometry and XRD. The catalytic activities of these complexes were screened using the epoxidation of olefins with molecular oxygen as oxidant. The factors including the category and amount of solvents, reaction temperature, as well as the amounts of isobutyradehyde(IBA) and catalyst were evaluated. It was found that Fe-PTC was the best catalyst. Under optimized conditions(ClCH2CH2Cl as the solvent, n(cyclooctene)∶n(catalyst)∶n(IBA)=4∶0.002 5∶16, 45 ℃, 5 h), the epoxidation of cyclooctene can give 91.1% yield, 91.1% selectivity and 1.457 turn over number(TON). Fe-PTC could be reused for 7 times without loss of catalytic activity. The IR spectra of the fresh-prepared and recovered catalysts indicated that the structure of the catalyst remained unchanged before and after reaction.

Key words: Olefin, Epoxidation, Metal Phthalocyanine Tetracarboxylic Acid, Molecular Oxygen

CLC Number: