催化学报

催化学报 ›› 2008, Vol. 29 ›› Issue (4): 351-355.

• 研究论文 • 上一篇    下一篇

SBA-15固载脯氨酸催化剂的制备及其在不对称Mannich反应中的应用

孙彩霞,李海岗,吴海虹,刘月明,吴鹏   

  1. 华东师范大学化学系上海市绿色化学与化工过程绿色化重点实验室, 上海 200062
  • 收稿日期:2008-04-25 出版日期:2008-04-25 发布日期:2012-03-22

Immobilization of L-Proline on SBA-15 and Its Application in Asymmetric Mannich Reaction

SUN Caixia, LI Haigang, WU Haihong*, LIU Yueming, WU Peng   

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, China
  • Received:2008-04-25 Online:2008-04-25 Published:2012-03-22

PDF

809

被引次数

11

摘要： 以4-羟基-L-脯氨酸为原料合成了脯氨酸衍生物,并将其固载于介孔SBA-15分子筛上制备了Pro/SBA-15催化剂. 用X射线衍射、N2吸附-脱附、扫描电镜和红外光谱等手段对Pro/SBA-15催化剂进行了表征,并考察了催化剂在不对称Mannich反应中的催化性能. 结果表明,固载脯氨酸不影响SBA-15的有序介孔结构,只是其孔径、孔体积和BET比表面积有所减小,在不对称Mannich反应中具有较高的催化活性和对映选择性. 与均相催化相比,以对硝基苯甲醛为反应物时可得到较高的分离收率(80%)和中等的对映选择性(ee=60%). 催化剂通过简单分离后可重复使用4次以上,其催化性能基本保持不变.

关键词: 4-羟基-L-脯氨酸, SBA-15分子筛, 负载型催化剂, 不对称Mannich反应, 对硝基苯甲醛

Abstract: The novel Pro/SBA-15 catalyst was prepared using SBA-15 zeolite as the support to immobilize L-proline (Pro) derivatives, which was synthesized from 4-hydroxy-L-proline. The Pro/SBA-15 catalyst was characterized byX-raydiffraction, N2 adsorption-desorption, scanning electron microscopy, and infrared spectroscopy. The catalytic performance of the catalyst was measured for asymmetric Mannich reaction. The results indicated that the mesoporous structure of SBA-15 was not affected by immobilization, however, the pore diameter, pore volume, and BET surface area were decreased. The Pro/SBA-15 catalyst had higher catalytic activity and enantioselectivity. Using 4-nitrobenzaldehyde as the reactant, the Mannich reaction product was obtained with high yield (80%) and moderate enantioselectivity (ee=60%). The supported catalyst could be easily separated from the reaction system and reused at least four times without loss of activity and enantioselectivity.

Key words: 4-hydroxy-L-proline, SBA-15 zeolite, supported catalyst, asymmetric Mannich reaction, 4-nitrobenzaldehyde