Skip to main content
SpringerLink
Log in

The Catalytic Baeyer–Villiger Oxidation of Cyclohexanone to ε-Caprolactone over Stibium-containing Hydrotalcite

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A series of hydrotalcite-like compounds were prepared under microwave irradiation, which were used to catalyze the Baeyer–Villiger oxidation of cyclohexanone to ε-caprolactone with hydrogen peroxide as oxidant. The results show that stibium-containing hydrotalcite (Sb-HTL) has good catalytic properties in the reaction. In the Baeyer–Villiger oxidation of cyclohexanone to ε-caprolactone with H2O2 catalyzed by Sb-HTL, the effects of reaction time, reaction temperature, amount of catalyst and H2O2/cyclohexanone molar ratio are also investigated in details. It is shown the cyclohexanone conversion and ε-caprolactone selectivity can reach 79.15 and 93.84%, respectively, under the optimum reaction conditions. Furthermore, Sb-HTL can be reused for six times without obvious loss of activity and selectivity. Therefore, Sb-HTL is reusable and would be a promising catalyst for the Baeyer–Villiger oxidation using green and cheap oxidants like hydrogen peroxide instead of peroxycarboxylic acids.

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
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Baeyer A, Villiger V (1899) Ber Dtsch Che Ges 32:3625

    Article  Google Scholar 

  2. Strukul G (1998) Angew Chem Int E Engl 37:1198

    Article  Google Scholar 

  3. Ten Brink GJ, Arends IWCE, Sheldon RA (2004) Chem Rev 104:4105

    Article  CAS  Google Scholar 

  4. Jiménez-Sanchidrián C, Ruiz JR (2008) Tetrahedron 64:2011

    Article  CAS  Google Scholar 

  5. Bhaumik A, Kumar P, Kumar R (1996) Catal Lett 40:47

    Article  CAS  Google Scholar 

  6. Corma A, Nemeth LT, Renz M, Valencia S (2001) Nature 412:423

    Article  CAS  Google Scholar 

  7. Renz M, Blasco T, Corma A, Fomés V, Jensen R, Nemeth L (2002) Chem Eur J 8:4708

    Article  CAS  Google Scholar 

  8. Corma A, Navarro MT, Nemeth L, Renz M (2001) Chem Commun 21:2190

    Article  CAS  Google Scholar 

  9. Palazzi C, Pinna F, Strukul G (2000) J Mol Catal A Chem 151:245

    Article  CAS  Google Scholar 

  10. Bernini R, Mincione E, Cortese M, Saladino R, Gualandi G, Belfiore MC (2003) Tetrahedron Lett 44:4823

    Article  CAS  Google Scholar 

  11. Fischer J, Hölderich WF (1999) Appl Catal A Gen 180:435

    Article  CAS  Google Scholar 

  12. Davies LJ, McMorn P, Bethell D, Page PCB, King F, Hancok FE, Hutchings GJ (2001) J Mol Catal A Chem 165:243

    Article  CAS  Google Scholar 

  13. Corma A, Navarro MT, Renz M (2003) J Catal 219:242

    Article  CAS  Google Scholar 

  14. Nekoksova I, Zilkova N, Cejka (2005) J Stud Surf Sci Catal 158:1589

    Article  Google Scholar 

  15. Lei Z, Zhang Q, Wang R, Ma G, Jian C (2006) J Organomet Chem 691:5767

    Article  CAS  Google Scholar 

  16. Lei Z, Ma G, Jian C (2007) Catal Commun 8:305

    Article  CAS  Google Scholar 

  17. Sels BF, De Vos DE, Jacobs PA (2001) Catal Rev 43:443

    Article  CAS  Google Scholar 

  18. Pillai UR, Sahle-Demessie E (2003) J Mol Catal A Chem 191:93

    Article  CAS  Google Scholar 

  19. Jiménez-Sanchidrian C, Hidalgo JM, Llamas R, Ruiz JR (2006) Appl Catal A Gen 312:86

    Article  CAS  Google Scholar 

  20. Ruiz JR, Jiménez-Sanchidrian C, Llamas R (2006) Tetrahedron 62:11697

    Article  CAS  Google Scholar 

  21. Llamas R, Jiménez-Sanchidrian C, Ruiz JR (2007) Tetrahedron 63:1435

    Article  CAS  Google Scholar 

  22. Kaneda K, Ueno S, Imanaka T (1994) J Chem Soc Chem Commun: 797

  23. Ueno S, Ebitani K, Ookubo A, Kaneda K (1997) Appl Surf Sci 122:366

    Article  Google Scholar 

  24. Kawabata T, Fujisaki N, Shishida T, Nomura K, Sano T, Takehira K (2006) J Mol Catal A Chem 253:279

    Article  CAS  Google Scholar 

  25. Kaneda K, Yamashita T (1996) Tetrahedron Lett 37:4555

    Article  CAS  Google Scholar 

  26. Zhu KZ, Liu CB, Ye XK, Wu Y (1997) Chem J Chin Univer 18:1530

    CAS  Google Scholar 

  27. Reichle WT (1986) Solid states Ion 22:135

    Article  CAS  Google Scholar 

  28. Chen CX, Xu CH, Feng LR, Li ZJ, Suo JS, Qiu FL, Yang YC (2005) Adv Synth Catal 347:1848

    Article  CAS  Google Scholar 

  29. Zapata B, BoSch P, Fetter G, Valenzuela MA, Navarrete J, Lara VH (2001) Inter J Inorg Mater 3:23

    Article  CAS  Google Scholar 

  30. Kaneda K, Ueno S, Imanaka T (1995) J Mol Catal A Chem 102:135

    Article  CAS  Google Scholar 

  31. Kaneda K, Ueno S (1996) ACS Symp Ser 638:300

    Article  CAS  Google Scholar 

  32. Kooli F, Kosuge K, Tsunashima A (1995) J Solid State Chem 118:285

    Article  CAS  Google Scholar 

  33. Rives V, Prieto O, Dubey A, Kannan S (2003) J Catal 220:161

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The investigation was supported by Grant-in-Aid for Young Teachers from Northeast Forestry University (NO. 090-602052), and also supported by Grant-in-Aid for Young Scientists from Harbin Science and Technology Bureau (NO. 2008RFQXG012).

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin, 150040, People’s Republic of China

    Chunxia Chen, Jinsong Peng, Bin Li & Lili Wang

Authors
  1. Chunxia Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jinsong Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lili Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chunxia Chen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, C., Peng, J., Li, B. et al. The Catalytic Baeyer–Villiger Oxidation of Cyclohexanone to ε-Caprolactone over Stibium-containing Hydrotalcite. Catal Lett 131, 618–623 (2009). https://doi.org/10.1007/s10562-009-9967-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-009-9967-1

Keywords

Search

Navigation