Log in

CuO impregnated SBA-15; an efficient catalyst for B–V oxidation of cyclohexanone to caprolactone

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

The development of efficient, cost-effective, and environmentally friendly catalysts is pivotal in fine chemical synthesis. In this study, an impregnating approach was used to obtain copper oxide-modified SBA-15 as an efficient catalyst for the synthesis of caprolactone from cyclohexanone with molecular oxygen as an oxidant and benzaldehyde as a sacrificial agent. The influence of experimental factors such as solvents, copper loading, substrate-to-oxidant mole ratio, temperature, and reaction duration on substrate conversion and selectivity to caprolactone was also investigated. Under the optimal reaction conditions, a cyclohexanone conversion of 63% was observed with a selectivity higher than 96% after a duration of 6 h at 50 °C. Catalyst recovery could be achieved by simple filtration and reused at least four times without a significant loss in conversion and selectivity.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Scheme 2
Fig. 10

Similar content being viewed by others

References

  1. M. Renz, B. Meunier, Eur. J. Org. Chem. 1999, 737–750 (1999)

    Article  Google Scholar 

  2. G.-J. Ten Brink, I.W.C.E. Arends, R.A. Sheldon, Chem. Rev. 104, 4105 (2004)

    Article  CAS  PubMed  Google Scholar 

  3. A. Corma, L.T. Nemeth, M. Renz, S. Valencia, Nature 412, 423 (2001)

    Article  ADS  CAS  PubMed  Google Scholar 

  4. K. Matuszek, P. Zawadzki, W. Czardybon, A. Chrobok, New J. Chem. 38, 237 (2014)

    Article  CAS  Google Scholar 

  5. R. Randino, E. Cini, A.M. D’Ursi, E. Novellino, M. Rodriquez, Tetrahedron Lett. 56, 5723 (2015)

    Article  CAS  Google Scholar 

  6. S. Staudt, U.T. Bornscheuer, U. Menyes, W. Hummel, H. Gröger, Enzyme Microb. Technol. 53, 288 (2013)

    Article  CAS  PubMed  Google Scholar 

  7. H. Mallin, H. Wulf, U.T. Bornscheuer, Enzyme Microb. Technol. 53, 283 (2013)

    Article  CAS  PubMed  Google Scholar 

  8. W. Zheng, R. Tan, X. Luo, C. **ng, D. Yin, Catal. Lett. 146, 281 (2016)

    Article  CAS  Google Scholar 

  9. F. Cavani, K. Raabova, F. Bigi, C. Quarantelli, Chem. Eur. J. 16, 12962 (2010)

    Article  CAS  PubMed  Google Scholar 

  10. K. Pamin, M. Prończuk, S. Basąg, W. Kubiak, Z. Sojka, J. Połtowicz, Inorg. Chem. Commun. 59, 13 (2015)

    Article  CAS  Google Scholar 

  11. A.S. Priya, K.R.S. Devi, M.K. Mohan, S. Sugunan, J. Porous Mater. 27, 1027 (2020)

    Article  CAS  Google Scholar 

  12. D.N. Bikiaris, G.Z. Papageorgiou, D.S. Achilias, E. Pavlidou, A. Stergiou, Eur. Polym. J. 43, 2491 (2007)

    Article  CAS  Google Scholar 

  13. J. Chen, X. Zhao, G. Zhang, B. Chen, W. Cai, Chin. J. Chem. Eng. 21, 1404 (2013)

    Article  CAS  Google Scholar 

  14. T. Chen, B. Wang, Y. Li, L. Liu, S. Qiu, J. Porous Mater. 22, 949 (2015)

    Article  CAS  Google Scholar 

  15. X. Yang, Y. Jiang, Y. Li, X. Xu, D. Li, K. Lin, Microporous Mesoporous Mater. 253, 40 (2017)

    Article  CAS  Google Scholar 

  16. S. Ghosh, S.S. Acharyya, R. Singh, P. Gupta, R. Bal, Catal. Commun. 72, 33 (2015)

    Article  CAS  Google Scholar 

  17. Z. Kang, X. Zhang, H. Liu, J. Qiu, K.L. Yeung, Chem. Eng. J. 218, 425 (2013)

    Article  CAS  Google Scholar 

  18. J.P. Mehta, D.K. Parmar, H.D. Nakum, D.R. Godhani, N.C. Desai, J. Porous Mater. 23, 1507 (2016)

    Article  CAS  Google Scholar 

  19. Y.-F. Li, M.-Q. Guo, S.-F. Yin, L. Chen, Y.-B. Zhou, R.-H. Qiu, C.-T. Au, Carbon 55, 269 (2013)

    Article  CAS  Google Scholar 

  20. J. Zang, Y. Ding, L. Yan, T. Wang, Y. Lu, L. Gong, Catal. Commun. 51, 24 (2014)

    Article  ADS  CAS  Google Scholar 

  21. X. Zhang, H. Yang, G. Yang, S. Li, X. Wang, J. Ma, ACS Sustain. Chem. Eng. 6, 5868 (2018)

    Article  CAS  Google Scholar 

  22. S. Hazra, N.M.R. Martins, K. Mahmudov, F.I. Zubkov, M.F.C. Guedes Da Silva, A.J.L. Pombeiro, J. Organomet. Chem. 867, 193 (2018)

    Article  CAS  Google Scholar 

  23. E.-Y. Jeong, M.B. Ansari, S.-E. Park, ACS Catal. 1, 855 (2011)

    Article  CAS  Google Scholar 

  24. W. Zhou, Y. Chen, J. Qian, F. Sun, M. He, Q. Chen, Catal. Lett. 146, 2157 (2016)

    Article  CAS  Google Scholar 

  25. M.K. Alavijeh, M.M. Amini, Catal. Commun. 139, 105985 (2020)

    Article  CAS  Google Scholar 

  26. H. Huo, L. Wu, J. Ma, H. Yang, L. Zhang, Y. Yang, S. Li, R. Li, ChemCatChem 8, 779 (2016)

    Article  CAS  Google Scholar 

  27. W. Gao, S. Li, H. Huo, F. Li, Y. Yang, X. Li, X. Wang, Y. Tang, R. Li, Mol. Catal. 439, 108 (2017)

    Article  CAS  Google Scholar 

  28. R. Kumar, P.P. Das, A.S. Al-Fatesh, A.H. Fakeeha, J.K. Pandey, B. Chowdhury, Catal. Commun. 74, 80 (2016)

    Article  CAS  Google Scholar 

  29. K. Mandai, M. Hanata, K. Mitsudo, H. Mandai, S. Suga, H. Hashimoto, J. Takada, Tetrahedron 71, 9403 (2015)

    Article  CAS  Google Scholar 

  30. S.-Y. Chen, X.-T. Zhou, J.-X. Wang, R.-C. Luo, Q.-J. Luo, L.-J. Yu, H.-B. Ji, Mol. Catal. 438, 152 (2017)

    Article  CAS  Google Scholar 

  31. S. Chen, X. Zhou, Y. Li, R. Luo, H. Ji, Chem. Eng. J. 241, 138 (2014)

    Article  CAS  Google Scholar 

  32. C. Perego, R. Millini, Chem. Soc. Rev. 42, 3956 (2013)

    Article  CAS  PubMed  Google Scholar 

  33. A. Taguchi, F. Schüth, Microporous Mesoporous Mater. 77, 1 (2005)

    Article  CAS  Google Scholar 

  34. C. Zubieta, M.B. Sierra, M.A. Morini, P.C. Schulz, L. Albertengo, M.S. Rodríguez, Colloid Polym. Sci. 286, 377 (2008)

    Article  CAS  Google Scholar 

  35. P. Kumar, V.V. Guliants, Microporous Mesoporous Mater. 132, 1 (2010)

    Article  CAS  Google Scholar 

  36. G. Wang, A.N. Otuonye, E.A. Blair, K. Denton, Z. Tao, T. Asefa, J. Solid State Chem. 182, 1649 (2009)

    Article  ADS  CAS  Google Scholar 

  37. R.R. Pawar, B.D. Kevadiya, H. Brahmbhatt, H.C. Bajaj, Int. J. Pharm. 446, 145 (2013)

    Article  CAS  PubMed  Google Scholar 

  38. V. Fathi Vavsari, G. Mohammadi Ziarani, A. Badiei, RSC Adv. 5, 91686 (2015)

    Article  ADS  CAS  Google Scholar 

  39. B. Melde, B. Johnson, P. Charles, Sensors 8, 5202 (2008)

    Article  ADS  CAS  PubMed  PubMed Central  Google Scholar 

  40. A. Walcarius, Electroanalysis 27, 1303 (2015)

    Article  CAS  Google Scholar 

  41. W.J.J. Stevens, K. Lebeau, M. Mertens, G. Van Tendeloo, P. Cool, E.F. Vansant, J. Phys. Chem. B 110, 9183 (2006)

    Article  CAS  PubMed  Google Scholar 

  42. Ş Veli, D. Levent, M. Kırali, Turk. J. Chem. 39, 683 (2015)

    Article  Google Scholar 

  43. D. Margolese, J.A. Melero, S.C. Christiansen, B.F. Chmelka, G.D. Stucky, Chem. Mater. 12, 2448 (2000)

    Article  CAS  Google Scholar 

  44. V. Chaudhary, S. Sharma, J. Porous Mater. 24, 741 (2017)

    Article  CAS  Google Scholar 

  45. S. Yuan, M. Wang, J. Liu, B. Guo, J. Environ. Manage. 254, 109787 (2020)

    Article  CAS  PubMed  Google Scholar 

  46. C. Soumini, S. Sugunan, S. Haridas, J. Porous Mater. 26, 631 (2019)

    Article  CAS  Google Scholar 

  47. G. Mohammadi Ziarani, N. Lashgari, A. Badiei, J. Mol. Catal. A Chem. 397, 166 (2015)

    Article  CAS  Google Scholar 

  48. L. Wang, L. Zhang, H. Li, Y. Ma, R. Zhang, Compos. B Eng. 156, 88 (2019)

    Article  CAS  Google Scholar 

  49. M.N. Timofeeva, S.H. Jhung, Y.K. Hwang, D.K. Kim, V.N. Panchenko, M.S. Melgunov, Yu.A. Chesalov, J.-S. Chang, Appl. Catal. A 317, 1 (2007)

    Article  CAS  Google Scholar 

  50. H. Liu, H. Wang, J. Shen, Y. Sun, Z. Liu, Appl. Catal. A 337, 138 (2008)

    Article  CAS  Google Scholar 

  51. Y.-M. Liu, Y. Cao, N. Yi, W.-L. Feng, W.-L. Dai, S.-R. Yan, H.-Y. He, K.-N. Fan, J. Catal. 224, 417 (2004)

    Article  CAS  Google Scholar 

  52. Z. El Berrichi, B. Louis, J.P. Tessonnier, O. Ersen, L. Cherif, M.J. Ledoux, C. Pham-Huu, Appl. Catal. A 316, 219 (2007)

    Article  Google Scholar 

  53. F. Rajabi, S. De, R. Luque, Catal. Lett. 145, 1566 (2015)

    Article  CAS  Google Scholar 

  54. S.E. Allen, R.R. Walvoord, R. Padilla-Salinas, M.C. Kozlowski, Chem. Rev. 113, 6234 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. W. Lu, H. Xu, Z. Shen, Org. Biomol. Chem. 15, 1261 (2017)

    Article  CAS  PubMed  Google Scholar 

  56. F. Lin, M. Si, Y. Lu, K. Tang, Mater. Lett. 335, 133825 (2023)

    Article  CAS  Google Scholar 

  57. X. Su, D.J. Fox, D.T. Blackwell, K. Tanaka, D.R. Spring, Chem. Commun. (2006). https://doi.org/10.1039/b610218b

    Article  Google Scholar 

  58. A.E. Wendlandt, A.M. Suess, S.S. Stahl, Angew. Chem. Int. Ed. 50, 11062 (2011)

    Article  CAS  Google Scholar 

  59. V. Chaudhary, Chin. J. Chem. Eng. 26, 1300 (2018)

    Article  CAS  Google Scholar 

  60. T. Deng, G. Xu, Y. Fu, Chin. J. Catal. 41, 404 (2020)

    Article  CAS  Google Scholar 

  61. C.K.P. Neeli, A. Narani, R.K. Marella, K.S. Rama Rao, D.R. Burri, Catal. Commun. 39, 5 (2013)

    Article  CAS  Google Scholar 

  62. F.-W. Chang, M.-S. Kuo, M.-T. Tsay, M.-C. Hsieh, Appl. Catal. A 247, 309 (2003)

    Article  CAS  Google Scholar 

  63. P. Munnik, P.E. De Jongh, K.P. De Jong, Chem. Rev. 115, 6687 (2015)

    Article  CAS  PubMed  Google Scholar 

  64. M. Campanati, G. Fornasari, A. Vaccari, Catal. Today 77, 299 (2003)

    Article  CAS  Google Scholar 

  65. V. Şimşek, Arab. J. Sci. Eng. 44, 5301 (2019)

    Article  Google Scholar 

  66. D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279, 548 (1998)

    Article  ADS  CAS  PubMed  Google Scholar 

  67. R. Arun, M.P. Athira, S.N. Remello, S. Haridas, React. Kinet. Mech. Catal. 136, 2277 (2023)

    Article  CAS  Google Scholar 

  68. S. Wang, W. Guo, H. Wang, L. Zhu, S. Yin, K. Qiu, New J. Chem. 38, 2792 (2014)

    Article  CAS  Google Scholar 

  69. G. Luo, S. Yan, M. Qiao, K. Fan, Appl. Catal. A 332, 79 (2007)

    Article  CAS  Google Scholar 

  70. K. Miao, X. Luo, W. Wang, J. Guo, S. Guo, F. Cao, Y. Hu, P. Chang, G. Feng, Microporous Mesoporous Mater. 289, 109640 (2019)

    Article  CAS  Google Scholar 

  71. S. Balci, Int. J. Chem. React. Eng. (2019). https://doi.org/10.1515/ijcre-2018-0167

    Article  Google Scholar 

  72. J. Mu, Y. He, Y. Wang, Talanta 148, 22 (2016)

    Article  CAS  PubMed  Google Scholar 

  73. L. Wang, A. Kong, B. Chen, H. Ding, Y. Shan, M. He, J. Mol. Catal. A: Chem. 230, 143 (2005)

    Article  CAS  Google Scholar 

  74. X. Guo, A. Yin, W.-L. Dai, K. Fan, Catal. Lett. 132, 22 (2009)

    Article  CAS  Google Scholar 

  75. Z. **a, H. Liu, H. Lu, Z. Zhang, Y. Chen, Catal. Lett. 147, 1295 (2017)

    Article  Google Scholar 

  76. H.-Y. Lan, X.-T. Zhou, H.-B. Ji, Tetrahedron 69, 4241 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful for providing fellowship to Athira.M.P. The financial support from UGC SAP, DST- PURSE, RUSA 2.0 and SMNRI, CUSAT for general facility creation is acknowledged. The analytical service provided by STIC, CUSAT is also acknowledged.

Author information

Authors and Affiliations

Authors

Contributions

The first author is AMP: She planned the scheme, worked on it, and then wrote the manuscript. AR: contributed to the characterization of the synthesized samples. The works corresponding author, SH: assisted in its creation and wrote the manuscript.

Corresponding author

Correspondence to Suja Haridas.

Ethics declarations

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 740 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Athira, M.P., Arun, R. & Haridas, S. CuO impregnated SBA-15; an efficient catalyst for B–V oxidation of cyclohexanone to caprolactone. J Porous Mater 31, 305–316 (2024). https://doi.org/10.1007/s10934-023-01514-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-023-01514-3

Keywords

Navigation