Aerobic oxidation behavior of α-ionone catalyzed by N-hydroxyphthalimide combined with acetylacetone cobalt(II)

  • Rui-ren Tang (唐瑞仁)Email author
  • Ya-ping Zhou (周亚平)
  • Nian-hua Gong (龚年华)
  • Yu Zhao (赵瑜)


A practical catalytic method to oxidize α-ionone with molecular oxygen using N-hydroxyphthalimide(NHPI) combined with acetylacetone cobatt(II) (Co(acac)2) was developed, and the probable catalytic mechanism was proposed. The influences of the reaction conditions on conversion of α-ionone and the selectivity of the major product (5-keto-α-ionone) were investigated, and the technical parameters for 5-keto-α-ionone were optimized. The results show that the primary product is 5-keto-α-ionone, and by-products include epoxy-α-ionone, as well as rearrangement products 4-keto-β-ionone and epoxy-β-ionone, which are characterized by infrared spectra, proton nuclear magnetic resonance spectra, mass spectra and elemental analysis. The selectivity of 5-keto-α-ionone and the conversion of α-ionone are 55.0% and 97.0%, respectively, when 30%(molar fraction) NHPI, 1.0%(molar fraction) Co(acac)2 and no solvent are employed under O2 pressure of 1.0 MPa and the reaction temperature of 65 °C for 11 h. The procedure shows good reproducibility in the parallel experiments.

Key words

catalytic oxidation α-ionone 5-keto-α-ionone N-hydroxyphthalimide 


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Copyright information

© Central South University Press and Springer-Verlag GmbH 2008

Authors and Affiliations

  • Rui-ren Tang (唐瑞仁)
    • 1
    Email author
  • Ya-ping Zhou (周亚平)
    • 1
  • Nian-hua Gong (龚年华)
    • 1
  • Yu Zhao (赵瑜)
    • 2
  1. 1.School of Chemistry and Chemical EngineeringCentral South UniversityChangshaChina
  2. 2.Technology CenterChina Tobacco Hunan Industrial CorporationChangshaChina

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