Chinese Journal of Applied Chemistry

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Preparation of Benzaldehyde through Oxidation of Styrene Catalyzed by Metallo-deuteroporphyrin Dimethyl Esters

ZHAO Donghui, HU Bingcheng*, SUN Chengguo, DENG Quanzhi   

  1. (College of Chemical Engineering,Nanjing University of Science and Technology,Nanjing 210094,China)
  • Received:2012-02-28 Revised:2012-05-17 Published:2013-01-10 Online:2013-01-10
  • Contact: Hu BingCheng
  • About author:Author: Zhao dong hui, male, a master studying in the College of Chemical Engineering, Nanjing University of Science and Technology. Research direction: organic synthesis and green catalysis. Email: zdh1949@126.com, Tel: 15295588290.

Abstract: In the presence of tert-butyl hydroperoxide(TBHP), metallo-deuteroporphyrin dimethyl esters[M(DPDME)] were used as catalysts in the oxidation of styrene. We have investigated the effects of the amount of the catalyst, the amount of the oxidant, reaction temperature, time, solvents and metallo-deuteroporphyrin dimethyl esters with different central metals on the conversion of styrene and the selectivity of benzaldehyde. The mechanism of the reaction was also discussed. The results indicated that the M(DPDME) could efficiently catalyze selective oxidation of styrene to benzaldehyde in good yields. Under the conditions of 0.002 mmol ClMn(DPDME) as the catalyst, 0.4 mmol TBHP as the oxidatant, 1 mmol styrene as the substrate, CH3CN(4 mL)/H2O(1 mL) as the solvent, reaction temperature of 75 ℃, atmospheric pressure, and a reaction time of 20 h, the conversion of styrene reached 98.3% with the benzaldehyde selectivity of 92.7%.

Key words: metallo-deuteroporphyrin dimethyl esters, styrene, catalytic oxidation

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