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题名: Chirality inversion in enantioselective hydrogenation of isophorone over Pd/MgO catalysts in the presence of (S)-proline: Effect of Pd particle size
作者: Li, Shuang2;  Chen, Chunhui2;  Zhan, Ensheng2;  Liu, Shang-Bin1;  Shen, Wenjie2
通讯作者: 申文杰
关键词: Chirality inversion ;  Isophorone ;  3,3,5-Trimethylcyclohexanone (TMCH) ;  (S)-Proline ;  Enantioselective hydrogenation ;  Kinetic resolution
刊名: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
发表日期: 2009-05-01
DOI: 10.1016/j.molcata.2009.01.029
卷: 304, 期:1-2, 页:88-94
收录类别: SCI
文章类型: Article
部门归属: 5
项目归属: 501
产权排名: 1;1
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Physical
研究领域[WOS]: Chemistry
英文摘要: Enantioselective hydrogenation of isophorone in the presence of (S)-proline was examined over a series of Pd/MgO catalysts with varying Pd particle size. It was found that the Pd surfaces not only supply chemisorbed hydrogen required for the hydrogenation of isophorone but also be involve in the enantio-differentiating step. Moreover, it was observed for the first time that the configuration of the chiral product could be tuned by varying the size of Pd particle such that (R)-TMCH rather than (S)-TMCH was obtained over the Pd/MgO catalysts with large Pd particles. Two competitive reaction pathways during the enantioselective hydrogenation of isophorone were proposed depending on the size of Pd particle. One involves the enantioselective hydrogenation of the reaction intermediates formed on large Pd particle with size exceeding 10 nm leading to the excess formation of (R)-TMCH enantiomer, whereas the other invokes the primary hydrogenation of isophorone to racemic TMCH over Pd particle with size smaller than 4 nm, followed by the kinetic resolution process leaving the (S)-TMCH enantiomer in excess. (C) 2009 Elsevier B.V. All rights reserved.
关键词[WOS]: ACID ETHYL-ESTER ;  ASYMMETRIC HYDROGENATION ;  PALLADIUM CATALYSTS ;  MECHANISTIC INSIGHTS ;  METAL-SURFACES ;  MODIFIERS ;  CARBON ;  BOND
语种: 英语
原文出处: 查看原文
WOS记录号: WOS:000266213600015
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/101723
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Acad Sinica, Inst Atom & Mol Sci, Taipei 10617, Taiwan
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Recommended Citation:
Li, Shuang,Chen, Chunhui,Zhan, Ensheng,et al. Chirality inversion in enantioselective hydrogenation of isophorone over Pd/MgO catalysts in the presence of (S)-proline: Effect of Pd particle size[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL,2009,304(1-2):88-94.
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