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Functionalized MCM-41 based recyclable catalyst (MCM-41@CP@PAL@Cu) for the epoxidation of alkenes using tert-BuOOH

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Abstract

Herein, we have reported synthesis, characterization and catalytic activity of an efficient and reusable silica-based catalyst MCM-41@CP@PAL@Cu. The catalyst was prepared by the anchoring of Cu(II)-Schiff base complex on mesoporous MCM-41 grafted with -chloro group on the surface. The obtained catalyst was characterized with various analytical methods such as FT-IR, Low angle P-XRD, TGA, N2 adsorption–desorption, SEM, TEM and MPAES. The catalyst composition and chemical state of Cu metal identified using X-ray photoelectrons spectroscopy. The catalyst MCM-41@CP@PAL@Cu employed for the conversion of various alkenes to their epoxides using tert-butyl-hydroperoxide (tert-BuOOH, TBHP) oxidant and acetonitrile as a solvent. In present model reaction, the yield of epoxide obtained was 99%. The yield of 99% yield of the epoxide obtained with model reaction and. The catalyst can be reused minimum six times.

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References

  1. A.S. Sharma, V.S. Sharma, H. Kaur, R.S. Varma, Green Chem. 22, 5902–5936 (2020)

    Article  CAS  Google Scholar 

  2. R.M. Philip, S. Radhika, C.M.A. Abdulla, G. Anil Kumar, Adv. Synth. Catal. 363, 1272–1289 (2021)

    Article  CAS  Google Scholar 

  3. Y. Yang, X. Fan, H. Cao, S. Chu, X. Zhang, Q. Xu, L. Yu, Catal. Sci. Technol. 8, 5017–5023 (2018)

    Article  CAS  Google Scholar 

  4. J. Liu, R. Meng, J. Li, P. Jian, L. Wang, R. Jian, Appl. Catal. B. 254, 214–222 (2019)

    Article  CAS  Google Scholar 

  5. J. Sun, J. Hu, J. Han, G. Yuan, R. Guo, Langmuir 35, 12704–12710 (2019)

    Article  CAS  PubMed  Google Scholar 

  6. Q.-H. Xia, H.-Q. Ge, C.-P. Ye, Z.-M. Liu, K.-X. Su, Chem. Rev. 105, 1603–1662 (2005)

    Article  CAS  PubMed  Google Scholar 

  7. B. Qi, X.-H. Lu, D. Zhou, Q.-H. Xia, Z.-R. Tang, S.-Y. Fang, T. Pang, Y.-L. Dong, J. Mol. Catal. A Chem. 322, 73–79 (2010)

    Article  CAS  Google Scholar 

  8. K. Yuan, T. Song, D. Wang, Y. Zou, J. Li, X. Zhang, Z. Tang, W. Hu, Nanoscale 10, 1591–1597 (2018)

    Article  CAS  PubMed  Google Scholar 

  9. X. Chen, B. Gao, Y. Su, H. Huang, Adv. Synth. Catal. 359, 2535–2541 (2017)

    Article  CAS  Google Scholar 

  10. N.A. Grosso-Giordano, C. Schroeder, A. Okrut, A. Solovyov, C. Schottle, W. Chasse, N.A. Marinkovic, H. Koller, S.I. Zones, A. Katz, J. Am. Chem. Soc. 140, 4956–4960 (2018)

    Article  CAS  PubMed  Google Scholar 

  11. M. Masteri-Farahani, M. Modarres, Colloids Surf. A Physicochem. Eng. Asp. 529, 886–892 (2017)

    Article  CAS  Google Scholar 

  12. M. Masteri-Farahani, S. Mirshekar, Colloids Surf. A Physicochem. Eng. Asp. 538, 387–392 (2018)

    Article  CAS  Google Scholar 

  13. J. Zhang, H. Zhang, L. Liu, Z. Chen, React. Kinet. Mech. Catal. 135, 317–331 (2022)

    Article  CAS  Google Scholar 

  14. L. Hu, L. Shi, H. Hong, M. Li, Q. Bao, J. Tang, J. Ge, J. Lu, X. Cao, H. Gu, Chem. Commun. 46, 8591–8593 (2010)

    Article  CAS  Google Scholar 

  15. H. Cao, R. Qian, L. Yu, Catal. Sci. Technol. 10, 3113–3121 (2020)

    Article  CAS  Google Scholar 

  16. F.P. Ballistreri, R.M. Toscano, M.E. Amato, A. Pappalardo, C. Gangemi, S. Spidalieri, R. Puglisi, G. TrussoSfrazzetto, Catalysts 8, 129–139 (2018)

    Article  Google Scholar 

  17. J. Lu, L. Liang, M. Weck, J. Mol. Catal. A Chem. 417, 122–125 (2016)

    Article  CAS  Google Scholar 

  18. J. Liu, T. Chen, P. Jian, L. Wang, X. Yan, J. Colloid Interf. Sci. 526, 295–301 (2018)

    Article  CAS  Google Scholar 

  19. N. Masunga, G.S. Tito, R. Meijboom, Appl. Catal. A 552, 154–167 (2018)

    Article  CAS  Google Scholar 

  20. L. Wu, X. Wang, B. Li, Appl. Surf. Sci. 591, e153158 (2022)

    Article  Google Scholar 

  21. J. Liu, W. Wang, P. Jian, L. Wang, X. Yan, J. Colloid Interf. Sci. 614, 102–109 (2022)

    Article  CAS  Google Scholar 

  22. M.S. Batra, R. Dwivedi, R. Prasad, ChemistrySelect 4, 11636–11673 (2019)

    Article  CAS  Google Scholar 

  23. M.A. Andrade, L. Martins, Molecules 26, 1680–1718 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. G. Wen, Q. Gu, Y. Liu, R. Schlogl, C. Wang, Z. Tian, D.S. Su, Angewandte Chemie Int. Edn. 57, 16898–16902 (2018)

    Article  CAS  Google Scholar 

  25. H. Zakeri, S. Rayati, G. Zarei, Appl. Organomet. Chem. 32, e4593 (2018)

    Article  Google Scholar 

  26. G. Zhang, Y. Shi, Y. Wei, Q. Zhang, Y. Zhang, K. Cai, S. Xiu, Inorg. Chem. Commun. 91, 81–84 (2018)

    Article  CAS  Google Scholar 

  27. A.R. Antonangelo, C.G. Bezzu, N.B. McKeown, S. Nakagaki, J. Catal. 369, 133–142 (2019)

    Article  CAS  Google Scholar 

  28. M. Saltarelli, E.H. de Faria, K.J. Ciuffi, E.J. Nassar, R. Trujillano, V. Rives, M.A. Vicente, Mol. Catal. 462, 114–125 (2019)

    Article  CAS  Google Scholar 

  29. X. Chen, J. Wang, Y. Yu, H. Chen, X. Wu, S. Gao, Catal. Lett. 152, 3807–3813 (2022)

    Article  CAS  Google Scholar 

  30. M. Samani, M.H. Ardakani, M. Sabet, Res. Chem. Intermed. 48, 1481–1494 (2022)

    Article  CAS  Google Scholar 

  31. R. Hajian, E. Bahrami, Catal. Lett. 152, 2445–2456 (2022)

    Article  CAS  Google Scholar 

  32. X. Song, D. Hu, X. Yang, H. Zhang, W. Zhang, J. Li, M. Jia, J. Yu, ACS Sustain. Chem. Eng. 7, 3624–3631 (2019)

    Article  CAS  Google Scholar 

  33. Z.A. ALOthman, Materials 5, 2874–2902 (2012)

    Article  CAS  PubMed Central  Google Scholar 

  34. S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, K. Ghani, Catal. Commun. 10, 853–858 (2009)

    Article  CAS  Google Scholar 

  35. S. Xiang, Y. Zhang, Q. Xin, C. Li, Chem. Commun. 22, 2696–2697 (2002)

    Article  Google Scholar 

  36. S. Jana, B. Dutta, R. Bera, S. Koner, Langmuir 23, 2492–2496 (2007)

    Article  CAS  PubMed  Google Scholar 

  37. J.M.R. Gallo, I.S. Paulino, U. Schuchardt, Appl. Catal. A 266, 223–227 (2004)

    Article  CAS  Google Scholar 

  38. S. Sharma, U.P. Singh, Inorg. Chem. Commun. 139, 109359–109366 (2022)

    Article  CAS  Google Scholar 

  39. S. Sharma, U.P. Singh, Results in Chem. 3, 100189–100196 (2021)

    Article  CAS  Google Scholar 

  40. S. Sharma, U.P. Singh, A.P. Singh, Polyhedron 199, 115102–115113 (2021)

    Article  CAS  Google Scholar 

  41. U.P. Singh, S. Sharma, A. Malik, J. Coord. Chem. 75, 1–13 (2022)

    Article  Google Scholar 

  42. L.A. Juarez, A.M. Costero, M. Parra, P. Gavina, S. Gil, F. Sancenon, R. Martinez-Manez, Chem. Comm. 53, 585–588 (2017)

    Article  Google Scholar 

  43. A. Malik, U.P. Singh, ChemistrySelect. 7, e202200794 (2022)

    Article  CAS  Google Scholar 

  44. L. Lihong, G.J. Clarkson, D.J. Evans, M.R. Lees, S.S. Turner, P. Scott, Chem. Comm. 47, 12646–12648 (2011)

    Article  Google Scholar 

  45. J.F. Malone, C.M. Murray, G.M. Dolan, R. Docherty, A.J. Lavery, Chem. Mater. 9, 2983–2989 (1997)

    Article  CAS  Google Scholar 

  46. R.K. Khaled, M.A. Wahba, M.D. Badry, M.F. Zawrah, E.A. Heikal, J. Mater. Sci. 57, 4504–4527 (2022)

    Article  CAS  Google Scholar 

  47. V. Morales, M.N. Idso, M. Balabasquer, B. Chmelka, R.A. Garcia-Munoz, J. Phys. Chem. 120, 16887–16898 (2016)

    CAS  Google Scholar 

  48. S. Zheng, L. Gao, J. Guo. Mater. Chem. Phys. 71, 174–178 (2001)

    Article  CAS  Google Scholar 

  49. M. Niakan, Z. Asadi, S. Zare, ChemistrySelect 5, 40–48 (2020)

    Article  CAS  Google Scholar 

  50. A. Sakthivel, J. Zhao, G. Raudaschl-Sieber, M. Hanzlik, A.S.T. Chiang, F.E. Kuhn, Appl. Catal. A: Gen. 281, 267–283 (2005)

    Article  CAS  Google Scholar 

  51. S. Rayati, S. Zakavi, M. Koliaei, A. Wojtczak, A. Kozakiewicz, Inorg. Chem. Commun. 13, 203–207 (2010)

    Article  CAS  Google Scholar 

  52. S. Ray, S. Jana, A. Jana, S. Konar, K. Das, S. Chatterjee, R.J. Butcher, S.K. Kar, Polyhedron 46, 74–80 (2012)

    Article  CAS  Google Scholar 

  53. Q. Zhao, C. Bai, W. Zhang, Y. Li, G. Zhang, F. Zhang, X. Fan, Ind. Eng. Chem. Res. 53, 4232 (2014)

    Article  CAS  Google Scholar 

  54. M. Nandi, P. Roy, H. Uyamac, A. Bhaumik, Dalton Trans. 40, 12510–12518 (2011)

    Article  CAS  PubMed  Google Scholar 

  55. P. Roy, M. Nandi, M. Manassero, M. Ricco, M. Mazzani, A. Bhaumik, P. Banerjee, Dalton Trans. 43, 9543–9554 (2009)

    Article  Google Scholar 

  56. R. Bera, C. Adhikary, S. Ianelli, S. Chaudhuri, S. Koner, Polyhedron 29, 2166–2170 (2010)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the BRNS, Grant No. 37018 (DAE), Mumbai, India for financial assistance. Arti Malik is thankful to CSIR for fellowship.

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  1. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India

    Arti Malik & Udai P. Singh

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Arti Malik and Udai P. Singh wrote the main manuscript text and prepared the figures. Udai P. Singh reviewed the manuscript

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Malik, A., Singh, U.P. Functionalized MCM-41 based recyclable catalyst (MCM-41@CP@PAL@Cu) for the epoxidation of alkenes using tert-BuOOH. J Porous Mater 30, 2011–2021 (2023). https://doi.org/10.1007/s10934-023-01475-7

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