Abstract
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.
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Foundation item: Project(50573019) supported by the National Natural Science Foundation of China
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Tang, Rr., Zhou, Yp., Gong, Nh. et al. Aerobic oxidation behavior of α-ionone catalyzed by N-hydroxyphthalimide combined with acetylacetone cobalt(II). J. Cent. South Univ. Technol. 15, 474–478 (2008). https://doi.org/10.1007/s11771-008-0089-5
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DOI: https://doi.org/10.1007/s11771-008-0089-5