Acta Chimica Sinica ›› 2009, Vol. 67 ›› Issue (9): 910-916. Previous Articles     Next Articles

Original Articles

β-环糊精选择性催化氧化对甲氧基苯甲醛的研究

纪红兵* 黄丽泉 吴 犇

  

  1. (华南理工大学化学与化工学院传热强化与过程节能教育部重点实验室 广州 510640)

  • 投稿日期:2007-12-17 修回日期:2008-04-30 发布日期:2009-05-14
  • 通讯作者: 纪红兵

Selective Oxidation of p-Methoxybenzaldehyde in the Presence of β-Cyclodextrin

Ji, Hongbing* Huang, Liquan Wu, Ben   

  1. (Key Laboratory of Enhanced Heat Transfer and Energy Conservation of Ministry of Education, School of Chemistry and
    Chemical Engineering, South China University of Technology, Guangzhou 510640)
  • Received:2007-12-17 Revised:2008-04-30 Published:2009-05-14
  • Contact: Ji, Hongbing

β-Cyclodextrin can solubilize the reactants, bind substrates selectively and catalyze chemical reactions by the interaction between β-cyclodextrin and substrates. During selective oxidation of p-methoxybenzaldehyde to p-methoxyphenol under supramolecular catalysis with β-cyclodextrin using H2O2/H3BO3/H2SO4 in water, β-cyclodextrin could form inclusion complexes with p-methoxybenzaldehyde and p-methoxyphenol, which effectively prevented them from continuous reaction and promoted the reaction selectivity. Various characterization methods including 1H NMR, UV-Vis and FT-IR were adopted to analyze the interaction between β-cyclodextrin and p-methoxybenzaldehyde, showing that the stable inclusion of β-cyclodextrin and p-methoxybenzaldehyde with a molar ratio of 1∶1 can be automatically formed in water, with the stability constant of the inclusion, Ka, being 358 and the standard Gibbs function of molar reaction, Δγ (298.15 K), being -14.577 kJ•mol-1. FT-IR analysis exhibits that aldehyde groups were mainly in the narrow mouth of the β-cyclodextrin in the inclusion complexes.

Key words: β-cyclodextrin, p-methoxybenzaldehyde, p-methoxyphenol, inclusion complex