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A proficient catalytic reduction of nitroarenes and organic dyes using MOF-derived palladated nano-hydroxyapatite

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Abstract

In this study, a heterogeneous metal–organic framework catalyst was meticulously prepared and extensively employed for the reduction of nitroarenes, congo red, and methylene blue. The catalyst was synthesized using a straightforward method, resulting in the formation of nanorods with well-defined morphology. These nanorods, composed of nanorod-hydroxyapatite, served as an exceptional and heterogeneous support for the fabrication of a metal–organic framework composite. In the following, surface functionalization was carried out using asparagine and TAZ-IMI, which was prepared by combining imidazole and cyanuric chloride. To enhance the catalytic performance, Pd(OAc)2 was immobilized onto the composite, leading to the formation of a novel n-HA@SiO2–ASP–Pd–TAZ–IMI catalyst. Extensive characterization studies were conducted to confirm the successful formation and structural integrity of the catalyst. The n-HA@SiO2–ASP–Pd–TAZ–IMI catalyst exhibited remarkable catalytic activity in the reduction of nitro compounds, utilizing NaBH4 as the reducing agent, resulting in excellent yields. Notably, the catalyst demonstrated excellent recyclability, as it could be easily reused up to three times with only a slight decrease in reaction yield.

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References

  1. H.M. Altass, S.A. Ahmed, R.S. Salama, Z. Moussa, R.S. Jassas, R.I. Alsantali, M.M. Al-Rooqi, A.A. Ibrahim, M.A. Khder, M. Morad, A.I. Ahmed, A.S. Khder, Catal. Lett. 153, 876 (2023)

    Article  CAS  Google Scholar 

  2. M. Azaroon, A.R. Kiasat, Catal. Lett. 148, 745 (2018)

    Article  CAS  Google Scholar 

  3. D.K. Pattanayak, B.T. Rao, T.R.R. Mohan, J. Solgel Sci. Technol. 59, 432 (2011)

    Article  CAS  Google Scholar 

  4. B.H. Fellah, N. Josselin, D. Chappard, P. Weiss, P. Layrolle, J. Mater. Sci. Mater. Med. 18, 287 (2007)

    Article  CAS  PubMed  Google Scholar 

  5. N. Rafiee, S. Karbasi, A. Nourbakhsh, K. Amini, Adv. Proc. Mater. Eng. 15, 39 (2021)

    Google Scholar 

  6. E. Bouyer, F. Gitzhofer, M.I. Boulos, J. Mater. Sci. Mater. Med. 11, 523 (2000)

    Article  CAS  PubMed  Google Scholar 

  7. M.P. Ferraz, F.J. Monteiro, C.M. Manuel, J. Appl. Biomater. Biomech. 2, 74 (2004)

    CAS  PubMed  Google Scholar 

  8. I.L. Balasooriya, J. Chen, S.M. KoraleGedara, Y. Han, M.N. Wickramaratne, Nanomater 12, 2324 (2022)

    Article  CAS  Google Scholar 

  9. L. Huang, P. Luo, W. Pei, X. Liu, Y. Wang, J. Wang, W. Xing, J. Huang, Adv. Synth. Catal. 354, 2689 (2012)

    Article  CAS  Google Scholar 

  10. M. Shokouhimehr, S.M.-G. Yek, M. Nasrollahzadeh, A. Kim, R.S. Varma, Appl. Sci. 9, 4183 (2019)

    Article  CAS  Google Scholar 

  11. Z.N. Sisakhti, M. Malmir, M.B. Bisafar, M.M. Heravi, T. Hosseinnejad, Sci. Rep. 12, 21964 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Y. Qin, M. Hao, Z. Li, Metal–organic frameworks for photocatalysis (Elsevier, Interface Sci. Technol., 2020), 541

    Google Scholar 

  13. J.P. Ruffley, I. Goodenough, T.-Y. Luo, M. Richard, E. Borguet, N.L. Rosi, J.K. Johnson, J. Phys. Chem. C 123, 19748 (2019)

    Article  CAS  Google Scholar 

  14. H. Furukawa, K.E. Cordova, M. O’Keeffe, O.M. Yaghi, Sci. 341, 1230444 (2013)

    Article  Google Scholar 

  15. F.T. Alshorifi, D.E. Tobbala, S.M. El-Bahy, M.A. Nassan, R.S. Salama, Catal. Commun. 169, 106479 (2022)

    Article  CAS  Google Scholar 

  16. S.A. Al-Thabaiti, M.M.M. Mostafa, A.I. Ahmed, R.S. Salama, Ceram. Int. 49, 5119 (2023)

    Article  CAS  Google Scholar 

  17. R.S. Salama, DUSJ. 2, 10 (2019)

    Google Scholar 

  18. R.S. Salama, S.A. El-Hakam, S.E. Samra, S.M. El-Dafrawy, A.A. Ibrahim, A.I. Ahmed, DUSJ. 6, 266 (2023)

    Google Scholar 

  19. M.A. Ghasemzadeh, M.H. Abdollahi-Basir, M. Babaei, Green Chem. Lett. 8, 40 (2015)

    Article  Google Scholar 

  20. B. Mirhosseini-Eshkevari, M.A. Ghasemzadeh, J. Safaei-Ghomi, Res. Chem. Intermed. 41, 7703 (2015)

    Article  CAS  Google Scholar 

  21. M. Ali Ghasemzadeh, B. Mirhosseini-Eshkevari, M. Hossein Abdollahi-Basir, Comb. Chem. High Throughput Screen. 19, 592 (2016)

    Article  Google Scholar 

  22. I. AbánadesLázaro, R.S. Forgan, F.G. Cirujano, Dalton Trans. 51, 8368 (2022)

    Article  Google Scholar 

  23. A. Tombesi, C. Pettinari, Inorg. 9, 81 (2021)

    Article  CAS  Google Scholar 

  24. A. Bavykina, N. Kolobov, I.S. Khan, J.A. Bau, A. Ramirez, J. Gascon, Chem. Rev. 120, 8468 (2020)

    Article  CAS  PubMed  Google Scholar 

  25. V.K. Gupta, N. Atar, M.L. Yola, Z. Üstündağ, L. Uzun, Water Res. 48, 210 (2014)

    Article  CAS  PubMed  Google Scholar 

  26. E. Kim, H.S. Jeong, B.M. Kim, Catal. Comm. 45, 25 (2014)

    Article  CAS  Google Scholar 

  27. K. Junge, B. Wendt, N. Shaikh, M. Beller, Chem. Comm. 46, 1769 (2010)

    Article  CAS  PubMed  Google Scholar 

  28. N. Ono, The Nitro Group in Organic Synthesis (John Wiley & Sons, Hoboken, 2003)

    Google Scholar 

  29. A.M. Tafesh, J. Weiguny, Chem. Rev. 96, 2035 (1996)

    Article  CAS  PubMed  Google Scholar 

  30. R.S. Downing, P.J. Kunkeler, H. Van Bekkum, Catal. Today. 37, 121 (1997)

    Article  CAS  Google Scholar 

  31. B.R. Ganapuram, M. Alle, R. Dadigala, A. Dasari, V. Maragoni, V. Guttena, Int. Nano Lett. 5, 215 (2015)

    Article  CAS  Google Scholar 

  32. H. Li, C. Cao, J. Liu, Y. Shi, R. Si, L. Gu, W. Song, Sci. China Mater. 62, 1306 (2019)

    Article  CAS  Google Scholar 

  33. S.A. Lawrence, Amines: Synthesis, Properties and Applications (Cambridge University Press, Cambridge, 2004)

    Google Scholar 

  34. S. Fountoulaki, V. Daikopoulou, P. Gkizis, I. Tamiolakis, G. Armatas, I. Lykakis, ACS Catal. 4, 3504 (2014)

    Article  CAS  Google Scholar 

  35. A.A. Kassem, H.N. Abdelhamid, D.M. Fouad, S.A. Ibrahim, J. Environ. Chem. Eng. 9, 104401 (2021)

    Article  CAS  Google Scholar 

  36. A. Hu, X. Lu, D. Cai, H. Pan, R. Jing, Q. Xia, D. Zhou, Y. Xia, Mol. Cat. 472, 27 (2019)

    CAS  Google Scholar 

  37. A. CheruvathoorPoulose, G. Zoppellaro, I. Konidakis, E. Serpetzoglou, E. Stratakis, O. Tomanec, M. Beller, A. Bakandritsos, R. Zbořil, Nat. Nanotechnol. 17, 485 (2022)

    Article  CAS  Google Scholar 

  38. S. Naghdi, M. Sajjadi, M. Nasrollahzadeh, K.Y. Rhee, S.M. Sajadi, B. Jaleh, J. Taiwan Inst. Chem. Eng. 86, 158 (2018)

    Article  CAS  Google Scholar 

  39. W. Zuo, G. Yu, Z. Dong, RSC Adv. 6, 11749 (2016)

    Article  CAS  Google Scholar 

  40. Y. Choi, H.S. Bae, E. Seo, S. Jang, K.H. Park, B.-S. Kim, J. Mater. Chem. 21, 15431 (2011)

    Article  CAS  Google Scholar 

  41. R. Dhanda, M. Kidwai, J. Mater. Chem. A. 3, 19563 (2015)

    Article  CAS  Google Scholar 

  42. Y. Jang, S. Kim, S.W. Jun, B.H. Kim, S. Hwang, I.K. Song, B.M. Kim, T. Hyeon, Chem. Commun. 47, 3601 (2011)

    Article  CAS  Google Scholar 

  43. S. Liu, Y. Guo, S. Yi, S. Yan, C. Ouyang, F. Deng, C. Li, G. Liao, Q. Li, Sep. Purif. Technol. 307, 122727 (2023)

    Article  CAS  Google Scholar 

  44. S. MusadiqAnis, S. HabibullahHashemi, A. Nasri, M. Sajjadi, M. Eslamipanah, B. Jaleh, Inorg. Chem. Commun. 141, 109489 (2022)

    Article  CAS  Google Scholar 

  45. M. Çalışkan, T. Baran, J. Organomet. Chem. 963, 122284 (2022)

    Article  Google Scholar 

  46. A.N. Chishti, Z. Ma, J. Zha, M. Ahmad, P. Wang, J. Gautam, M. Chen, L. Ni, G. Diao, Chin. Chem. Lett. 34, 108122 (2023)

    Article  CAS  Google Scholar 

  47. M. Brahmayya, D. Samsonu, Y. Murthy, B. Govindh, S. Afr, J. Chem. Eng. 25, 110 (2018)

    Google Scholar 

  48. J. Pal, C. Mondal, A.K. Sasmal, M. Ganguly, Y. Negishi, T. Pal, ACS Appl. Mater. Interfaces. 6, 9173 (2014)

    Article  CAS  PubMed  Google Scholar 

  49. S. Piña, D.M. Cedillo, C. Tamez, N. Izquierdo, J.G. Parsons, J.J. Gutierrez, Tetrahedron Lett. 55, 5468 (2014)

    Article  Google Scholar 

  50. G. Wang, S. Yuan, Z. Wu, W. Liu, H. Zhan, Y. Liang, X. Chen, B. Ma, S. Bi, Appl. Organomet. Chem. 33, e5159 (2019)

    Article  CAS  Google Scholar 

  51. S. Keshipour, S.S. Mirmasoudi, Adv. Environ. Technol. 3, 59 (2017)

    Google Scholar 

  52. V. Kandathil, B. Kulkarni, A. Siddiqa, M. Kempasiddaiah, B.S. Sasidhar, S.A. Patil, S.A. Patil, Catal. Lett. 150, 384 (2020)

    Article  CAS  Google Scholar 

  53. D. Nandi, S. Siwal, M. Choudhary, K. Mallick, Appl. Catal. 523, 31 (2016)

    Article  CAS  Google Scholar 

  54. Y. Alghamdi, S. Khan, Cellul. 27, 8827 (2020)

    Article  CAS  Google Scholar 

  55. M. Nasrollahzadeh, T. Baran, M. Sajjadi, N. Yılmaz Baran, M. Shokouhimehr, J. Mater. Sci. Mater. Electron. 31, 12856 (2020)

    Article  CAS  Google Scholar 

  56. N. Sabaghnia, M. Janmohammadi, M. Dalili, Z. Karimi, S. Rostamnia, Environ. Sci. Pollut. Res. 26, 11719 (2019)

    Article  CAS  Google Scholar 

  57. M. Naz, A. Rafiq, M. Ikram, A. Haider, S.O.A. Ahmad, J. Haider, S. Naz, J. Mater. Sci. 56, 15572 (2021)

    Article  CAS  Google Scholar 

  58. Z. Amiri, M. Malmir, T. Hosseinnejad, K. Kafshdarzadeh, M.M. Heravi, Mol. Catal. 524, 112319 (2022)

    Article  CAS  Google Scholar 

  59. S. Sadjadi, M.M. Heravi, M. Malmir, Res. Chem. Intermed. 43, 6701 (2017)

    Article  CAS  Google Scholar 

  60. M.M. Heravi, R. Malakooti, K. Kafshdarzadeh, Z. Amiri, V. Zadsirjan, H. Atashin, Res. Chem. Intermed. 48, 203 (2022)

    Article  CAS  Google Scholar 

  61. M.M. Heravi, Z. Kheilkordi, V. Zadsirjan, M. Heydari, M. Malmir, J. Organomet. Chem. 861, 17 (2018)

    Article  CAS  Google Scholar 

  62. S. Sadjadi, G. Lazzara, M. Malmir, M.M. Heravi, J. Catal. 366, 245 (2018)

    Article  CAS  Google Scholar 

  63. M. Malmir, M.M. Heravi, Z. Amiri, K. Kafshdarzadeh, Sci. Rep. 11, 22409 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  64. S. Sadjadi, M. Malmir, G. Lazzara, G. Cavallaro, M.M. Heravi, Sci. Rep. 10, 2039 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  65. Z. Yekke-Ghasemi, M.M. Heravi, M. Malmir, G. Jahani, M.B. Bisafar, M. Mirzaei, Inorg. Chem. Commun. 140, 109456 (2022)

    Article  CAS  Google Scholar 

  66. S. Sadjadi, M.M. Heravi, L. Mohammadi, M. Malmir, ChemistrySelect 4, 7300–7307 (2019)

    Article  CAS  Google Scholar 

  67. M.B. Bisafar, M. Malmir, M.M. Heravi, J. Chem. Technol. Biotechnol. (2023)

  68. S. Sadjadi, M. Malmir, M.M. Heravi, Appl. Organomet. Chem. 32, e4413 (2018)

    Article  Google Scholar 

  69. G. Muralithran, S. Ramesh, Ceram. Int. 26, 221 (2000)

    Article  CAS  Google Scholar 

  70. T.K.H. Ta, M.-T. Trinh, N.V. Long, T.T.M. Nguyen, T.L.T. Nguyen, T.L. Thuoc, B.T. Phan, D. Mott, S. Maenosono, H. Tran-Van, Colloids Surf. A Physicochem. Eng. Asp. 504, 376 (2016)

    Article  CAS  Google Scholar 

  71. J. Mondal, A. Modak, A. Dutta, S. Basu, S.N. Jha, D. Bhattacharyya, A. Bhaumik, Chem. Commun. 48, 8000 (2012)

    Article  CAS  Google Scholar 

  72. X.-Y. Sun, G. Gao, D. Yan, C. Feng, Appl. Surf. Sci. 405, 52 (2017)

    Article  CAS  Google Scholar 

  73. J. Li, H. Gao, L. Tan, Y. Luan, M. Yang, Eur. J. Inorg. Chem. 2016, 4906 (2016)

    Article  CAS  Google Scholar 

  74. S.A. Manafi, B. Yazdani, M.R. Rahimiopour, S.K. Sadrnezhaad, M.H. Amin, M. Razavi, Biomed. Mater. 3, 025002 (2008)

    Article  CAS  PubMed  Google Scholar 

  75. F.U. Khan, S. Mehmood, S. Liu, W. Xu, M.N. Shah, X. Zhao, J. Ma, Y. Yang, X. Pan, Front. Chem. 9, 742488 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  76. K.M. Elsabawy, Z.O. Owidah, A.M. Fallatah, J. Mol. Struct. 1245, 130912 (2021)

    Article  CAS  Google Scholar 

  77. Y. Dong, T. Hu, M. Pudukudy, H. Su, L. Jiang, S. Shan, Q. Jia, Mater. Chem. Phys. 251, 123060 (2020)

    Article  CAS  Google Scholar 

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Acknowledgements

All authors appreciate the Alzahra University for its financial support.

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ZK contributed to experimental work and preparing the draft manuscript. MM contributed to methodology, supervision, designing project, writing the manuscript and finalizing the revised file. MMH contributed to financial support and reviewing the manuscript.

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Correspondence to Majid M. Heravi.

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Kefayati, Z., Malmir, M. & Heravi, M.M. A proficient catalytic reduction of nitroarenes and organic dyes using MOF-derived palladated nano-hydroxyapatite. Res Chem Intermed 50, 127–146 (2024). https://doi.org/10.1007/s11164-023-05139-8

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