Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (10): 2711-2718.doi: 10.3866/PKU.WHXB20101017

• CATALYSIS AND SURFACE STRUCTURE • Previous Articles     Next Articles

Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl2(TPP)3 Supported on Hydroxyapatite Modified with Chiral Amine

ZHANG Ding-Lin1,2, YANG Chao-Fen1, SUN Ya-Ping1, FU Hai-Yan1, LI Rui-Xiang1, CHEN Hua1, LI Xian-Jun1   

  1. 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;
    2. Department of Chemistry, School of Pharmacy,The Third Military Medical University, Chongqing 400038, P. R. China
  • Received:2010-04-22 Revised:2010-06-07 Published:2010-09-27
  • Contact: CHEN Hua E-mail:scuhchen@163.com

Abstract:

Chiral amine (L-proline,D-proline, (1R,2R)-1,2 -diphenyl -1,2 -ethylene diamine sulfonate disodium ((1R, 2R)-DPENDS) and (1S,2S)-1,2 -diphenyl -1,2 -ethylene diamine sulfonate disodium ((1S,2S)-DPENDS)) modified hydroxyapatite (HAP) were prepared and characterized by Fourier transform infrared (FT -IR) spectrometry, scanning electron microscopy (SEM),X-ray diffraction (XRD), and Brunauer -Emmett -Teller (BET) surface area analysis. RuCl2 (TPP)3was supported on(1R,2R)-DPENDS modified HAP for the asymmetric hydrogenation of acetophenone. A detailed investigation about the effects of temperature, amount of alkali,H2 pressure, and concentration of DPENDS modified HAP on the activity and enantioselectivity of acetophenone hydrogenation was undertaken. Under the optimum reaction conditions of 30 oC, p(H2)=5.0 MPa, reaction time of 4 h, the conversion and enantioselectivity reached 99.9% and 77.8% enantiomeric excess (ee), respectively. The results indicated that the asymmetric hydrogenation was accomplished on the surface of the chiral amine modified HAP. The immobilized catalyst was separated from the products by simple centrifugation and reused without adding any other reagents.

 

Key words: Chiral amine, Hydroxyapatite, RuCl2(TPP)3, Acetophenone, Heterogeneous asymmetrichydrogenation

MSC2000: 

  • O643