Fast and Efficient Epoxidation of Olefins Catalyzed by Brominated Mn(III) Salophen Grafted onto CoFe2O3/Graphene Oxide as a Heterogeneous Catalyst

Document Type : Research Paper

Author

Department of Chemistry, Yazd University, Yazd 89195-741, Iran

Abstract

This study aims to prepare di-brominated Mn(III) Salophen, [MnSalBr], grafted onto CoFe2O3/graphene oxide (CFGO) via a covalent bond. The characterization of this heterogeneous catalyst (CFeGO@MnSalBr) was carried out by FTIR, DR UV-Vis, XRD, FESEM, EDX spectroscopy, elemental scanning mappings, thermogravimetric analysis (TGA/DTG), and nitrogen adsorption-desorption isotherm. The amount of manganese salophen loading on the CFG support was determined by inductively coupled plasma spectroscopy (ICP). At room temperature, the as-prepared catalyst was applied to oxidize olefins with H2O2 as a green oxidant. The result confirmed this catalyst's high catalytic reactivity and excellent selectivity in the epoxidation of various alkenes. The effects of different factors such as the kind of solvent and oxidant, amount of catalyst and oxidant, and reaction time were also studied. Furthermore, the GO-bound Mn salophen was reused for several runs without any noticeable activity loss or selectivity. 

Graphical Abstract

Fast and Efficient Epoxidation of Olefins Catalyzed by Brominated Mn(III) Salophen Grafted onto CoFe2O3/Graphene Oxide as a Heterogeneous Catalyst

Keywords

References

  1. J. de Vries, D. B. Janssen, Curr. Opin. Biotechnol. 2003, 14, 414-420.
  2. N. Song, J. C. Yuan, Z. P. Cai, D. Lin, X. Feng, N. Sheng, Y. B. Liu, X. B. Chen, X. Jin, D. Chen, C. H. Yang, Green Energy Environ. 2020, 5, 473-483.
  3. Mohajer, R. Tayebee, H. Goudarziafshar, J. Chem. Res., Synop. 1999, 168-169.
  4. Y. Liu, D. G. Nocera, Tetrahedron Lett. 2006, 47, 1923-1926.
  5. Tang, X. Chen, X. Pang, Y. Yang, X. Zhang, X. Jing, Biomacromolecules, 2004, 5, 965-970.
  6. Neshat, M. Kakavand, F. Osanlou, P. Mastrorilli, E. Schingaro, E. Mesto, S. Todisco, Eur. J. Inorg. Chem. 2020, 2020, 480-490.
  7. Pakvojoud, M. H. Ardakani, S. Saeednia, E. Heydari-Bafrooei, J. Sulfur Chem. 2020, 41, 561-580.
  8. R. Pour, A. Abdolmaleki, M. Dinari, J. Mater. Sci. 2019, 54, 2885-2896.
  9. Suresh, V. Prakash, E-J. Chem. 2011, 8, 1408-1416.
  10. A. Fardjahromi, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, RSC Adv. 2016, 6, 20128-20134.
  11. Karami, M. Montazerozohori, M. H. Habibi, J. Chem. Res. 2006, 2006, 490-492.
  12. Sarma, P. K. Chaurasia, S. L. Bharati, Russ. J. Gen. Chem. 2019, 89, 517-531.
  13. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, M. S. Saeedi, Appl. Catal., A, 2010, 381, 233-241.
  14. Rouco, A. M. Gonzalez-Noya, R. Pedrido, M. Maneiro, Antioxidants 2020, 9, 727-755.
  15. Ahmadi, M. Bahadori, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, Inorg. Chem. Res. 2020, 4, 51-65.
  16. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, Appl. Catal., A, 2006, 311, 43-50.
  17. Hajian, F. Jafari, J. Iran. Chem. Soc. 2019, 16, 563-570.
  18. A. Fardjahromi, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 2017, 14, 1317-1323.
  19. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, Appl. Catal., A, 2006, 313, 122-129.
  20. Torki, S. Tangestaninejad, V. Mirkhani, M. Moghadam, I. Mohammadpoor-Baltork, A. R. Khosropour, J. Inorg. Organomet. Polym. Mater. 2013, 23, 923-929.
  21. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, A. Mallekpoor-Shalamzari, Appl. Catal., A, 2007, 321, 49-57.
  22. Hajian, Z. Alghour, Chin. Chem. Lett. 2017, 28, 971-975.
  23. Masteri-Farahani, M. Karimi Alavijeh, M. -S. Hosseini, Inorg. Chem. Res. 2020, 4, 261-269.
  24. Nodzewska, A. Wadolowska, M. Watkinson, Coord. Chem. Rev. 2019, 382, 181-216.
  25. J. Chen, F. M. Mei, G. X. Li, React. Kinet. Catal. Lett. 2009, 98, 99-105.
  26. Ghazizadeh, A. Badiei, I. Sheikhshoaie, Arabian J. Chem. 2017, 10, S2491-S2498.
  27. Mirkhani, M. Moghadam, S. Tangestaninejad, S. Hajibagheri, J. Iran. Chem. Soc. 2010, 7, 641-645.
  28. Moghadam, V. Mirkhani, S. Tangestaninejad, I. Mohammadpoor-Baltork, H. Kargar, I. Sheikhshoaei, M. Hatefi, J. Iran. Chem. Soc. 2011, 8, 1019-1029.
  29. Dideikin, A. Y. Vul, Front. Phys. 2019, 6, 149-162.
  30. Farjadian, S. Abbaspour, M. A. A. Sadatlu, S. Mirkiani, A. Ghasemi, M. Hoseini-Ghahfarokhi, N. Mozaffari, M. Karimi, M. R. Hamblin, ChemistrySelect, 2020, 5, 10200-10219.
  31. Shamaila, A. K. L. Sajjad, A. Iqbal, Chem. Eng. J. 2016, 294, 458-477.
  32. Baghayeri, M. Ghanei-Motlagh, R. Tayebee, M. Fayazi, F. Narenji, Anal. Chim. Acta 2020, 1099, 60-67.
  33. Kumari, A. Shekhar, D. D. Pathak, RSC Adv. 2016, 6, 15340-15344.
  34. Rayati, E. Khodaei, S. Shokoohi, M. Jafarian, B. Elmi, A. Wojtczak, Inorg. Chim. Acta, 2017, 466, 520-528.
  35. Zarnegaryan, Z. Pahlevanneshan, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammdpoor-Baltork, J. Iran. Chem. Soc. 2019, 16, 747-756.
  36. S. Zhao, C. Bai, W. F. Zhang, Y. Li, G. L. Zhang, F. B. Zhang, X. B. Fan, Ind. Eng. Chem. Res. 2014, 53, 4232-4238.
  37. Qian, P. Liu, S. Shao, M. J. Wang, X. Zhan, S. X. Gao, Chem. Eng. J. 2019, 360, 54-63.
  38. Q. Lv, C. Y. Chen, B. Q. Lu, J. L. Li, Y. X. Yang, C. M. Chen, T. S. Deng, Y. L. Zhu, X. L. Hou, RSC Adv. 2016, 6, 101277-101282.
  39. Verma, M. Aila, S. Kaul, S. L. Jain, RSC Adv. 2014, 4, 30598-30604.
  40. L. Su, S. J. Wu, Z. F. Li, Q. S. Huo, J. Q. Guan, Q. B. Kan, Appl. Organomet. Chem. 2015, 29, 462-467.
  41. Bagherzadeh, H. Karimi, M. Amini, J. Coord. Chem. 2017, 70, 2986-2998.
  42. Allahresani, Iran. Chem. Commun. 2018, 6, 180-191.
  43. S. Wu, D. H. Lan, N. A. Y. Tan, R. Wang, C. T. Au, B. Yi, J. Chem. Soc. Pak. 2021, 43, 57-66.
  44. Vangroenou, P. F. Bongers, A. L. Stuyts, Mater. Sci. Eng. 1969, 3, 317-392.
  45. P. Dalawai, S. Kumar, M. A. S. Aly, M. Z. H. Khan, R. M. Xing, P. N. Vasambekar, S. H. Liu, J. Mater. Sci.: Mater. Electron. 2019, 30, 7752-7779.
  46. K. Kefeni, B. B. Mamba, Sustainable Mater. Technol. 2020, 23, 140-158.
  47. Y. Srinivasan, K. M. Paknikar, D. Bodas, V. Gajbhiye, Nanomedicine 2018, 13, 1221-1238.
  48. Maleki, F. Taheri, R. Tayebee, F. Adibian, Org. Prep. Proced. Int. 2021, 53, 284-290.
  49. Song, W. Ran, F. Wei, Water Sci. Technol. 2017, 75, 397-405.
  50. Y. Zhao, D`. -G. Lee, C. -W. Kim, H. -G. Cha, Y. -H. Kim, Y. -S. Kang, Bull. Korean Chem. Soc. 2006, 27, 237-242.
  51. Kooti, M. Afshari, Catal. Lett. 2012, 142, 319-325.
  52. Saffar-Teluri, RSC Adv. 2015, 5, 70577-70585.
  53. F. Zhou, Z. J. Wan, X. F. Yuan, J. Luo, Appl. Organomet. Chem. 2016, 30, 215-220.
  54. W. Chen, D. H. Ding, C. Liu, H. Cai, Y. Qu, S. J. Yang, Y. Gao, T. M. Cai, Chem. Eng. J. 2018, 334, 273-284.
  55. Tabit, O. Amadine, Y. Essamlali, K. Danoun, A. Rhihil, M. Zahouily, RSC Adv. 2018, 8, 1351-1360
  56. Abbasi, H. Hosseini-Monfared, S. M. Hosseini, New J. Chem. 2017, 41, 9866-9874.
  57. Abbasi, H. Hosseini-Monfared, S. M. Hosseini, Appl. Organomet. Chem. 2017, 31, 10.
  58. Hajian, A. Ehsanikhah, Chem. Phys. Lett. 2018, 691, 146-154.
  59. Hajian, S. Tangestaninejad, M. Moghadam, V. Mirkhani, A. R. Khosropour, Comptes Rendus Chimie 2012, 15, 975-979.
  60. Hajian, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 2016, 13, 1061-1067.
  61. Hajian, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A. R. Khosropour, J. Coord. Chem. 2011, 64, 4134-4144.
  62. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, R. Hajian, Inorg. Chem. Commun. 2010, 13, 1501-1503.
  63. Tayebee, J. Chem. Sci. 2006, 118, 429-433.
  64. Jacobsen, L. Cavallo, Organometallics 2006, 25, 177-183.
  65. C. Marcano, D. V. Kosynkin, J. M. Berlin, A. Sinitskii, Z. Sun, A. Slesarev, L. B. Alemany, W. Lu, J. M. Tour, ACS Nano 2010, 4, 4806-4814.
  66. Maaz, A. Mumtaz, S. Hasanain, A. Ceylan, J. Magn. Magn. Mater. 2007, 308, 289-295.
  67. Chen, A. Martell, Inorg. Chem. 1987, 26, 1026-1030.
  68. Rana, J. Philip, B. Raj, Mater. Chem. Phys. 2010, 124, 264-269.
  69. Parhizkar, M. H. Habibi, J. Water Environ. Nanotechnol. 2019, 4, 17-30.
  70. Garcia, V. Moreno, S. X. Delgado, A. E. Ramirez, L. A. Vargas, M. A. Vicente, A. Gil, L. A. Galeano, J. Mol. Catal. A: Chem. 2016, 416, 10-19.
  71. Lane, M. Vogt, V. J. DeRose, K. Burgess, J. Am. Chem. Soc. 2002, 124, 11946-11954.
Inorganic Chemistry Research
Volume 6, Issue 1
Spring and Summer; Special Issue: In Memory of Prof. Mehdi Rashidi
2022
Pages 1-9

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History

  • Receive Date: 04 November 2021
  • Revise Date: 17 December 2021
  • Accept Date: 17 December 2021

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