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

作者：Tang Rui ren^*; Zhou Ya ping; Gong Nian hua; Zhao Yu

来源：Journal of Central South University of Technology, 2008, 15(4): 474-478.

DOI：10.1007/s11771-008-0089-5

• catalytic oxidation
• alpha-ionone
• 5-keto-alpha-ionone
• N-hydroxyphthalimide

A practical catalytic method to oxidize alpha-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 alpha-ionone and the selectivity of the major product (5-keto-alpha-ionone) were investigated, and the technical parameters for 5-keto-alpha-ionone were optimized. The results show that the primary product is 5-keto-alpha-ionone, and by-products include epoxy-alpha-ionone, as well as rearrangement products 4-keto-beta-ionone and epoxy-beta-ionone, which are characterized by infrared spectra, proton nuclear magnetic resonance spectra, mass spectra and elemental analysis. The selectivity of 5-keto-alpha-ionone and the conversion of alpha-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 O-2 pressure of 1.0 MPa and the reaction temperature of 65 degrees C for 11 h. The procedure shows good reproducibility in the parallel experiments.

• 出版日期2008-8
• 单位中南大学