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Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2

Received: 13 August 2017     Published: 14 August 2017
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Abstract

The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1.

Published in American Journal of Applied Chemistry (Volume 5, Issue 4)
DOI 10.11648/j.ajac.20170504.12
Page(s) 62-68
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2017. Published by Science Publishing Group

Keywords

Asymmetric Aldol Reaction, Organocatalyst, L-Histidine-Modified-Ionic-Liquid, D-Pantolactone, Cu-/SiO2, Hydrogenation

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    Jin Man-man, Wang Jin-jin, Lv Zhi-guo, Guo Zhen-mei. (2017). Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. American Journal of Applied Chemistry, 5(4), 62-68. https://doi.org/10.11648/j.ajac.20170504.12

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    ACS Style

    Jin Man-man; Wang Jin-jin; Lv Zhi-guo; Guo Zhen-mei. Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. Am. J. Appl. Chem. 2017, 5(4), 62-68. doi: 10.11648/j.ajac.20170504.12

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    AMA Style

    Jin Man-man, Wang Jin-jin, Lv Zhi-guo, Guo Zhen-mei. Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2. Am J Appl Chem. 2017;5(4):62-68. doi: 10.11648/j.ajac.20170504.12

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  • @article{10.11648/j.ajac.20170504.12,
      author = {Jin Man-man and Wang Jin-jin and Lv Zhi-guo and Guo Zhen-mei},
      title = {Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2},
      journal = {American Journal of Applied Chemistry},
      volume = {5},
      number = {4},
      pages = {62-68},
      doi = {10.11648/j.ajac.20170504.12},
      url = {https://doi.org/10.11648/j.ajac.20170504.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20170504.12},
      abstract = {The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - Synthesis of D-pantolactone via Combined a Novel Organocatalyst Catalyzed Asymmetric Aldol Reaction and Hydrogenation Catalyzed by Cu-/SiO2
    AU  - Jin Man-man
    AU  - Wang Jin-jin
    AU  - Lv Zhi-guo
    AU  - Guo Zhen-mei
    Y1  - 2017/08/14
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ajac.20170504.12
    DO  - 10.11648/j.ajac.20170504.12
    T2  - American Journal of Applied Chemistry
    JF  - American Journal of Applied Chemistry
    JO  - American Journal of Applied Chemistry
    SP  - 62
    EP  - 68
    PB  - Science Publishing Group
    SN  - 2330-8745
    UR  - https://doi.org/10.11648/j.ajac.20170504.12
    AB  - The combination of an asymmetric organocatalytic aldol reaction with a subsequent hydrogenation for the synthesis of D-pantolactone is demonstrated. This process consists of an initial aldol reaction catalyzed by a novel chiral L- histidine-modified-ionic-liquid- [EMIm] [His], which has been designed and synthesized as an efficient recoverable catalyst for the asymmetric aldol reaction with superior enantioselectivity in CH2Cl2, than L-histidine itself. [EMIm] [His] retains its activity and enantioselectivity over at least five reaction cycles, and its universal applicability has been demonstrated. Moreover optimum process of Cu-/SiO2-catalysed hydrogenation of condensation product- (D) -3- formyl -2- hydroxy -3- ethyl butyrate to obtain D-pantolactone has been established allowing the synthesis of D-pantolactone in >99% purity, 93% yield and 93% enantiomeric excesse (ee). The results show that CuO-CeO2/SiO2 exhibits better catalytic activity than CuO/SiO2 for better dispersion and larger surface area, and the best reaction conditions are as follows: 120°C, n (H2): n (isobutylaldehyde) =80:1, P (H2) =8.0 MPa, liquid airspeed: 0.6 h-1.
    VL  - 5
    IS  - 4
    ER  - 

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Author Information
  • College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, China

  • College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, China

  • College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, China

  • College of Marine Science and Biological Engineering, Qingdao University of Science and Technology, Qingdao, China

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