Skip to main content
SpringerLink
Log in

Supported ionic-liquid layer on polystyrene–TEMPO resin: a highly efficient catalyst for selective oxidation of activated alcohols with molecular oxygen

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

We report a facile, efficient procedure for selective oxidation of activated alcohols by use of a novel supported ionic-liquid catalyst produced by coating polystyrene–TEMPO resin with the ionic liquid [bmim]PF6 and CuCl2. The oxidation affords aldehydes or ketones in excellent yield and with high selectivity. It is worthy of note that the supported ionic-liquid layer substantially enhances catalytic activity, and the catalyst can easily be recycled.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Tojo G, Fernández M (2006) Oxidation of alcohols to aldehydes and ketones: a guide to current common practice. Springer, New York

    Google Scholar 

  2. Wang XR, Yang HM, Feng B, Hou ZS, Hu Y, Qiao YX, Li H, Zhao XG (2009) Catal Lett 132:34

    Article  CAS  Google Scholar 

  3. Wang H, Deng S-X, Shen Z-R, Wang J-G, Ding D-T, Chen T-H (2009) Green Chem 11:1499

    Article  CAS  Google Scholar 

  4. Bawaked S, He Q, Dummer NF, Carley AF, Knight DW, Bethell D, Kiely CJ, Hutchings GJ (2011) Catal Sci Technol 1:747

    Article  Google Scholar 

  5. Choudhary VR, Dumbre DK (2009) Catal Commun 10:1738

    Article  CAS  Google Scholar 

  6. Enache DI, Knight DW, Hutchings GJ (2005) Catal Lett 103:43

    Article  CAS  Google Scholar 

  7. Choudhary VR, Dumbre DK, Narkhede VS, Jana SK (2003) Catal Lett 86:229

    Article  CAS  Google Scholar 

  8. Yu H, Zhang Y, Fu XB, Peng F, Wang HJ, Yang J (2009) Catal Commun 10:1752

    Article  CAS  Google Scholar 

  9. Hosokawa S, Hayashi Y, Imamura S, Wada K, Inoue M (2009) Catal Lett 129:394

    Article  CAS  Google Scholar 

  10. Liu L, Ma J, Xia J, Li L, Li C, Zhang X, Gong J, Tong Z (2011) Catal Commun 12:323

    Article  CAS  Google Scholar 

  11. Geisslmeier D, Jary WG, Falk H (2005) Monatsh Chem 136:1591

    Article  Google Scholar 

  12. Hanson SK, Wu RL, Silks LA (2011) Org Lett 13:1908

    Article  CAS  Google Scholar 

  13. Chen YT, Chen W, Tang QH, Guo Z, Yang YH, Su FB (2011) Catal Lett 141:149

    Article  CAS  Google Scholar 

  14. Karimi B, Farhangi E (2011) Chem Eur J 17:6056

    Article  CAS  Google Scholar 

  15. Bolm C, Fey T (1999) Chem Commun 1795

  16. Karimi B, Badreh E (2011) Org Biomol Chem 9:4194

    Article  CAS  Google Scholar 

  17. Matsumoto K, Iwata T, Suenaga M, Okudomi M, Nogawa M, Nakano M, Sugahara A, Bannai Y, Baba K (2010) Heterocycles 81:2539

    Article  CAS  Google Scholar 

  18. Pozzi G, Cavazzini M, Quici S, Benaglia M, Dell’Anna G (2004) Org Lett 6:441

    Article  CAS  Google Scholar 

  19. Weik S, Nicholson G, Jung G, Rademann J (2001) Angew Chem Int Ed 40:1436

    Article  CAS  Google Scholar 

  20. Brunel D, Fajula F, Nagy JB, Deroide B, Verhoef MJ, Veum L, Peters JA, van Bekkum H (2001) Appl Catal A Gen 213:73

    Article  CAS  Google Scholar 

  21. Dijksman A, Arends I, Sheldon RA (2001) Synlett 102

  22. Tundo P, Perosa A (2007) Chem Soc Rev 36:532

    Article  CAS  Google Scholar 

  23. Gu YL, Li GX (2009) Adv Synth Catal 351:817

    Article  CAS  Google Scholar 

  24. Collis AEC, Horvath IT (2011) Catal Sci Technol 1:912

    Article  CAS  Google Scholar 

  25. Gu Y, Ogawa C, Kobayashi J, Mori Y, Kobayashi S (2006) Angew Chem Int Edit 45:7217

    Article  CAS  Google Scholar 

  26. Kernchen U, Etzold B, Korth W, Jess A (2007) Chem Eng Technol 30:985

    Article  CAS  Google Scholar 

  27. Arras J, Steffan M, Shayeghi Y, Ruppert D, Claus P (2009) Green Chem 11:716

    Article  CAS  Google Scholar 

  28. Moucel R, Perrigaud K, Goupil JM, Madec PJ, Marinel S, Guibal E, Gaumont AC, Dez I (2010) Adv Synth Catal 352:433

    Article  CAS  Google Scholar 

  29. Sobota M, Happel M, Amende M, Paape N, Wasserscheid P, Laurin M, Libuda J (2011) Adv Mater 23:2617

    Article  CAS  Google Scholar 

  30. Rodriguez-Perez L, Pradel C, Serp P, Gomez M, Teuma E (2011) ChemCatChem 3:749

    Article  CAS  Google Scholar 

  31. Liu L, Ji LY, Wei YY (2008) Catal Commun 9:1379

    Article  Google Scholar 

  32. Liu L, Ji L-Y, Wei Y-Y (2008) Monatsh Chem 139:901

    Article  CAS  Google Scholar 

  33. Liu L, Ma JJ, Ji LY, Wei YY (2008) J Mol Catal A Chem 291:1

    Article  CAS  Google Scholar 

  34. Yue C, Fang D, Liu L, Yi T-F (2011) J Mol Liq 163:99

    Article  CAS  Google Scholar 

  35. Liu L, Ma JJ, Sun Z, Zhang JP, Huang JJ, Li SZ, Tong ZW (2011) Can J Chem 89:68

    Article  CAS  Google Scholar 

  36. Pouchert CJ (1985) The Aldrich library of FT-IR spectra. Aldrich Chemical Co, Milwaukee

    Google Scholar 

  37. Pouchert CJ (1993) The Aldrich library of 13C and 1H FT-NMR spectra. Aldrich Chemical Co, Milwaukee

    Google Scholar 

Download references

Acknowledgments

The authors are grateful for the support from the National Natural Science Foundation of China (50873042, 21001048), the Natural Science Fund of Jiangsu Province (BK2011399), the Key University Science Research Project of Jiangsu Province (11KJA430008), and the Jiangsu Marine Resource Development Research Institute Foundation (JSIMR10D03).

Author information

Authors and Affiliations

  1. Jiangsu Marine Resource Development Research Institute, Lianyungang, 222005, China

    Lin Liu, Tianlin Zhang, Juanjuan Ma & Dongen Zhang

  2. Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, 222005, China

    Lin Liu, Dong Liu, Zhiwei Xia, Jiulin Gao, Tianlin Zhang, Juanjuan Ma, Dongen Zhang & Zhiwei Tong

  3. SORST, Japan Science and Technology Agency (JST), Kawaguchi-shi, Saitama, Japan

    Zhiwei Tong

Authors
  1. Lin Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dong Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhiwei Xia
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jiulin Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tianlin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Juanjuan Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dongen Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Zhiwei Tong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Lin Liu or Zhiwei Tong.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, L., Liu, D., Xia, Z. et al. Supported ionic-liquid layer on polystyrene–TEMPO resin: a highly efficient catalyst for selective oxidation of activated alcohols with molecular oxygen. Monatsh Chem 144, 251–254 (2013). https://doi.org/10.1007/s00706-012-0780-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-012-0780-y

Keywords

Search

Navigation