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Combination of polymer and halloysite chemistry for development of a novel catalytic hybrid system

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Abstract

A covalent hybrid of halloysite-poly(methyl methacrylate-co-maleic anhydride) was prepared and applied for the immobilization of Pd nanoparticles. The hybrid system, Pd@Hal-Gua-Poly, was then characterized via TEM, TGA, ICP, BET, FTIR and XRD and successfully used as a heterogeneous catalyst for promoting two main Pd-catalyzed reactions, i.e. hydrogenation of nitro-arenes and Suzuki coupling reaction under mild and eco-friendly conditions. The study of recyclability of the catalyst confirmed high recyclability and low Pd leaching of Pd@Hal-Gua-Poly. Moreover, the hot-filtration test showed the heterogeneous nature of the catalysts. Notably, the comparison of the activity of the catalyst with that of Pd@Hal and Pd@Poly confirmed the superior catalytic activity of the former, indicating that the hybridization of Hal and Poly could lead to the improvement of the catalytic activity.

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References

  1. Y. Lvov, A. Panchal, Y. Fu, R. Fakhrullin, M. Kryuchkova, S. Batasheva, A. Stavitskaya, A. Glotov, V. Vinokurov, Langmuir (2019, in press). https://doi.org/10.1021/acs.langmuir.8b04313

  2. A. Glotov, A. Stavitskaya, Y. Chudakov, E. Ivanov, W. Huang, V. Vinokurov, A. Zolotukhina, A. Maximov, E. Karakhanov, Y. Lvov, Bull. Chem. Soc. Jpn. 92, 61 (2019)

    Article  CAS  Google Scholar 

  3. V. Vinokurov, A. Glotov, Y. Chudakov, A. Stavitskaya, E. Ivanov, P. Gushchin, A. Zolotukhina, A. Maximov, E. Karakhanov, Y. Lvov, Ind. Eng. Chem. Res. 56, 14043 (2017)

    Article  CAS  Google Scholar 

  4. V. Vinokurov, A. Stavitskaya, A. Glotov, A. Ostudin, M. Sosna, P. Gushchin, Y. Darrat, Y. Lvov, J. Solid State Chem. 268, 182 (2018)

    Article  CAS  Google Scholar 

  5. S. Sadjadi, M.M. Heravi, M. Malmir, Carbohydr. Polym. 186, 25 (2018)

    Article  CAS  PubMed  Google Scholar 

  6. V.A. Vinokurov, A.V. Stavitskaya, E.V. Ivanov, P.A. Gushchin, D.V. Kozlov, A.Y. Kurenkova, P.A. Kolinko, E.A. Kozlova, Y.M. Lvov, ACS Sustain. Chem. Eng. 5, 11316 (2017)

    Article  CAS  Google Scholar 

  7. Z. Zhou, J. Ouyang, H. Yang, A. Tang, Appl. Clay Sci. 121–122, 63 (2016)

    Article  CAS  Google Scholar 

  8. G. Lazzara, G. Cavallaro, A. Panchal, R. Fakhrullin, A. Stavitskaya, V. Vinokurov, Y. Lvov, Curr. Opin. Colloid Interface Sci. 35, 42 (2018)

    Article  CAS  Google Scholar 

  9. Y. Zhang, A. Tang, H. Yang, J. Ouyang, Appl. Clay Sci. 119, 8 (2016)

    Article  CAS  Google Scholar 

  10. M. Massaro, C.G. Colletti, G. Lazzara, S. Milioto, R. Noto, S. Riela, J. Mater. Chem. A 5, 13276 (2017)

    Article  CAS  Google Scholar 

  11. Y. Liu, J. Zhang, H. Guan, Y. Zhao, J.-H. Yang, B. Zhang, Appl. Surf. Sci. 427, 106 (2018)

    Article  CAS  Google Scholar 

  12. G. Cavallaro, G. Lazzara, S. Milioto, F. Parisi, Chem. Rec. 18, 1 (2018)

    Article  CAS  Google Scholar 

  13. W. Ma, H. Wu, Y. Higaki, A. Takahara, Chem. Rec. 18, 1 (2018)

    Article  CAS  Google Scholar 

  14. M. Makaremi, P. Pasbakhsh, G. Cavallaro, G. Lazzara, Y.K. Aw, S.M. Lee, S. Milioto, A.C.S. Appl, Mater. Interfaces 9, 17476 (2017)

    Article  CAS  Google Scholar 

  15. V. Bertolino, G. Cavallaro, G. Lazzara, S. Milioto, F. Parisi, Langmuir 33, 3317 (2017)

    Article  CAS  PubMed  Google Scholar 

  16. T. Sugimura, K. Wakabayashi, H. Nakagama, M. Nagao, Cancer Sci. 95, 290 (2004)

    Article  CAS  PubMed  Google Scholar 

  17. H.U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 345, 103 (2003)

    Article  CAS  Google Scholar 

  18. M. Cargnello, V.V.T. Doan-Nguyen, T.R. Gordon, R.E. Diaz, E.A. Stach, R.J. Gorte, P. Fornasiero, C.B. Murray, Science 341, 771 (2013)

    Article  CAS  PubMed  Google Scholar 

  19. G. Sevjidsuren, S. Zils, S. Kaserer, A. Wolz, F. Ettingshausen, D. Dixon, A. Schoekel, C. Roth, P. Altantsog, D. Sangaa, C. Ganzori, J. Nanomater. 2010, 1 (2010)

    Article  CAS  Google Scholar 

  20. M. Cargnello, V.V.T. Doan-Nguyen, T.R. Gordon, R.E. Diaz, E.A. Stach, R.J. Gorte, P. Fornasiero, C.B. Murray, Science 341, 771 (2013)

    Article  CAS  PubMed  Google Scholar 

  21. P.G.N. Bouchenafa-Saib, P. Verhasselt, F. Addoun, V. Dubois, Appl. Catal. A Gen. 286, 167 (2005)

    Article  CAS  Google Scholar 

  22. X. Yu, M. Wang, H. Li, Appl. Catal. A Gen. 202, 17 (2000)

    Article  CAS  Google Scholar 

  23. R. Giordano, P. Serp, P. Kalck, Y. Kihn, J. Schreiber, C. Marhic, J.-L. Duvail, Eur. J. Inorg. Chem. 2003, 610 (2003)

    Article  Google Scholar 

  24. C.-H. Li, Z.-X. Yu, K.-F. Yao, S.-F. Ji, J. Liang, J. Mol. Catal. A Chem. 226, 101 (2005)

    Article  CAS  Google Scholar 

  25. P. Sangeetha, K. Shanthi, K.S. Rama Rao, B. Viswanathan, P. Selvam, Appl. Catal. A Gen. 353, 160 (2009)

    Article  CAS  Google Scholar 

  26. N. Arora, A. Mehta, A. Mishra, S.S. Basu, App. Clay Sci. 151, 1 (2018)

    Article  CAS  Google Scholar 

  27. Y. Chen, L. Li, L. Zhang, J. Han, Colloid Polymer Sci. 296, 567 (2018)

    Article  CAS  Google Scholar 

  28. A.R. Hajipour, Z. Shirdashtzade, G. Azizi, Appl. Organomet. Chem. 28, 696 (2014)

    Article  CAS  Google Scholar 

  29. A.R. Gholap, K. Venkatesan, R. Pasricha, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Org. Chem. 70, 4869 (2005)

    Article  CAS  PubMed  Google Scholar 

  30. R. Thorwirth, A. Stolle, B. Ondruschka, Green Chem. 12, 985 (2010)

    Article  CAS  Google Scholar 

  31. M. Nasrollahzadeh, M. Maham, M.M. Tohidi, J. Mol. Catal. A 391, 83 (2014)

    Article  CAS  Google Scholar 

  32. M. Bakherad, Appl. Organomet. Chem. 27, 125 (2013)

    Article  CAS  Google Scholar 

  33. M. Bakherad, R. Doosti, M. Mirzaee, K. Jadidi, Tetrahedron 73, 3281 (2017)

    Article  CAS  Google Scholar 

  34. P.V. Rathod, V.H. Jadhav, Tetrahedron Lett. 58, 1006 (2017)

    Article  CAS  Google Scholar 

  35. M. Esmaeilpour, A. Sardarian, J. Javidi, Catal. Sci. Technol. 6, 4005 (2016)

    CAS  Google Scholar 

  36. M. Nasrollahzadeh, S.M. Sajadi, M. Maham, A. Ehsani, RSC Adv. 5, 2562 (2015)

    Article  CAS  Google Scholar 

  37. R. Zhou, W. Wang, Z.-J. Jiang, H.-Y. Fu, X.-L. Zheng, C.-C. Zhang, H. Chen, R.-X. Li, Catal. Sci. Technol. 4, 746 (2014)

    CAS  Google Scholar 

  38. M. Nasrollahzadeh, M. Khalaj, A. Ehsani, Tetrahedron Lett. 55, 5298 (2014)

    Article  CAS  Google Scholar 

  39. M. Shunmughanathan, P. Puthiaraj, K. Pitchumani, Chem. Catal. Chem. 7, 666 (2015)

    CAS  Google Scholar 

  40. A.S. Roya, J. Mondal, B. Banerjee, P. Mondal, A. Bhaumik, S. Manirul Islam, Appl. Catal. A 469, 320 (2014)

    Article  CAS  Google Scholar 

  41. N. Bahri-Laleh, S. Sadjad, A. Poater, J. Colloid Interface Sci. 531, 421 (2018)

    Article  CAS  PubMed  Google Scholar 

  42. S. Sadjadi, G. Lazzara, M. Malmir, M.M. Heravi, J. Catal. 633, 245 (2018)

    Article  CAS  Google Scholar 

  43. S. Sadjadi, M. Malmir, M.M. Heravi, F. Ghoreyshi Kahangi, Int. J. Biol. Macromol. 118, 1903 (2018)

    Article  CAS  PubMed  Google Scholar 

  44. S. Sadjadi, M. Atai, Appl. Clay Sci. 153, 78 (2018)

    Article  CAS  Google Scholar 

  45. S. Sadjadi, M.M. Heravi, M. Raja, Carbohydr. Polym. 185, 48 (2018)

    Article  CAS  PubMed  Google Scholar 

  46. S. Bordeepong, D. Bhongsuwan, T. Pungrassami, T. Bhongsuwan, T. Songklanakarin, J. Sci. Technol. 33, 599 (2011)

    CAS  Google Scholar 

  47. L. Zatta, J.E.F. da Costa Gardolinski, F. Wypych, Appl. Clay Sci. 51, 165 (2011)

    Article  CAS  Google Scholar 

  48. P. Yuan, D. Tan, F. Annabi-Bergaya, Appl. Clay Sci. 112–113, 75 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. P. Yuan, P.D. Southon, Z. Liu, M.E.R. Green, J.M. Hook, S.J. Antill, C.J. Kepert, J. Phys. Chem. C 112, 15742 (2008)

    Article  CAS  Google Scholar 

  51. S. Dehghani, S. Sadjadi, N. Bahri-Laleh, M. Nekoomanesh-Haghighi, A. Poater, Appl. Organomet. Chem. 3(5), e4891 (2019). https://doi.org/10.1002/aoc.4891

    Article  CAS  Google Scholar 

  52. N.M. Patil, M.A. Bhosale, B.M. Bhanage, RSC Adv. 5, 86529 (2015)

    Article  CAS  Google Scholar 

  53. M. Guo, H. Li, Y. Ren, X. Ren, Q. Yang, C. Li, ACS Catal. 8, 6476 (2018)

    Article  CAS  Google Scholar 

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

    Google Scholar 

  55. S. Agrahari, S. Lande, V. Balachandran, G. Kalpana, R. Jasra, J. Nanosci. Curr. Res. 2, 2572 (2017)

    Article  Google Scholar 

  56. O. Verho, K.P. Gustafson, A. Nagendiran, C.W. Tai, J.E. Bäckvall, ChemCatChem 6, 3153 (2014)

    Article  CAS  Google Scholar 

  57. S. Doherty, J. Knight, T. Backhouse, A. Bradford, F. Saunders, R. Bourne, T. Chamberlain, R. Stones, A. Clayton, K. Lovelock, Catal. Sci. Technol. 8, 1454 (2018)

    Article  CAS  Google Scholar 

  58. Y.-S. Feng, J.-J. Ma, Y.-M. Kang, H.-J. Xu, Tetrahedron 70, 6100 (2014)

    Article  CAS  Google Scholar 

  59. M. Nasrollahzadeh, S.M. Sajadi, A. Rostami-Vartooni, M. Alizadeh, M. Bagherzadeh, J. Colloid Interface Sci. 466, 360 (2016)

    Article  CAS  PubMed  Google Scholar 

  60. R. Sharma, Y. Monga, A. Puri, J. Mol. Catal. A Chem. 393, 84 (2014)

    Article  CAS  Google Scholar 

  61. G. Singh, S. Rani, A. Arora, H. Duggal, D. Mehta, Mol. Catal. 431, 15 (2017)

    Article  CAS  Google Scholar 

  62. Z. Duan, G. Ma, W. Zhang, Bull. Korean Chem. Soc. 33, 4003 (2012)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors appreciate partial financial supports from Iran Polymer and Petrochemical Institute and Alzahra University. MMH is also thankful to Iran National Science Foundation for the Individual given grant.

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Authors and Affiliations

  1. Gas Conversion Department, Faculty of Petrochemicals, Iran Polymer and Petrochemicals Institute, PO Box 14975-112, Tehran, Iran

    Samahe Sadjadi

  2. Department of Chemistry, School of Science, Alzahra University, PO Box 1993891176, Vanak, Tehran, Iran

    Masoumeh Malmir, Nargess Pourmohammad & Majid M. Heravi

  3. Department of Polymer Processing, Iran Polymer and Petrochemical Institute, Tehran, Iran

    Shervin Ahmadi

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  1. Samahe Sadjadi
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  2. Masoumeh Malmir
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Correspondence to Samahe Sadjadi, Shervin Ahmadi or Majid M. Heravi.

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Sadjadi, S., Malmir, M., Pourmohammad, N. et al. Combination of polymer and halloysite chemistry for development of a novel catalytic hybrid system. Res Chem Intermed 45, 4349–4366 (2019). https://doi.org/10.1007/s11164-019-03835-y

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