Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (10): 2039-2044.doi: 10.3866/PKU.WHXB20090935

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Asymmetric Hydrogenations of Acetophenone and Its Derivatives over Ir/HAP Modified by (1S, 2S)-DPEN

ZHANG Ding-Lin, YANG Chao-Fen, FENG Jian, FU Hai-Yan, CHEN Hua, LI Rui-Xiang, LI Xian-Jun   

  1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China|Department of Chemistry, School of Pharmacy, Third Military Medical University, Chongqing 400038, P. R. China
  • Received:2009-04-22 Revised:2009-06-19 Published:2009-09-29
  • Contact: CHEN Hua


A novel catalyst was prepared for the first time by supporting iridium on porous hydroxyapatite (Ir/HAP). The catalyst was characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy(SEM) equippedwithanenergydispersiveX-rayspectroscopy(EDS),X-rayphotoelectronspectroscopy(XPS), and Brunauer-Emmett-Teller (BET) surface area analysis. In the presence of (1S,2S)-1,2-diphenyl-1,2-ethylenediamine ((1S,2S)-DPEN), the catalytic properties of the catalyst were investigated by the asymmetric hydrogenation of aromatic ketones. Under optimum reaction conditions of temperature T=303 K, pressure p=3.0 MPa, and reaction time t=3 h, the conversion of aromatic alcohols that were produced from the hydrogenation of acetophenone and its derivatives reached 94.7%. The enantiomeric excess (ee) value for the 2'-(trifluoromethyl) phenethyl alcohol was 81.5%. Without using other ligands as stabilizers, the enantiomeric excess value was found to be higher than that reported in literature. As a catalyst carrier, hydroxyapatite is superior to SiO2 and other inorganic carriers. The catalyst is reusable with no sign of Ir leaching.

Key words: Hydroxyapatie, Iridium, Acetophenone, Asymmetric Hydrogenation, (1S,2S)-DPEN