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Overcoming acid–base copolymer neutralization using mesoporous carbon and its catalytic activity in the tandem deacetalization–Knoevenagel condensation reaction

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Abstract

Acid–base copolymer materials are of considerable interest because of their fundamental implications for acid–base bifunctional catalysis applications. However, quenching the acid and base sites of the copolymer with each other in free radical polymerizations is still challenging. Herein, we demonstrate that the polymerization of styrenesulfonic acid-co-4-vinylpyridine into the mesoporous carbon material (i.e., CMK-3) can control the chain growth polymerization and result in decreasing the interaction of the acid–base sites. The results showed that by using CMK-3, 40% of the acid and base sites of the copolymer remain in their original form while 60% of acid and base sites convert to the pyridinium and sulfonate forms. Furthermore, it is demonstrated that this material can be processed as a heterogeneous bifunctional acid–base catalyst in the tandem one-pot acid–base reaction (i.e., deacetalization–Knoevenagel condensation reaction) with a high catalytic activity in aqueous media.

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References

  1. M.G. Ciulla, S. Zimmermann, K. Kumar, Org. Biomol. Chem. 17, 3 (2019)

    Article  Google Scholar 

  2. L. Chen, X. Zhang, J. Zhou, Z. Xie, Q. Kuang, L. Zheng, Nanoscale 11, 7 (2019)

    Google Scholar 

  3. M.J. Climent, A. Corma, S. Iborra, Chem. Rev. 111, 2 (2011)

    Article  CAS  Google Scholar 

  4. G. Szőllősi, Catal. Sci. Technol. 8, 2 (2018)

    Article  Google Scholar 

  5. Z. Mortezaei, M. Zendehdel, M.A. Bodaghifard, Res. Chem. Intermed. 46, 4 (2020)

    Article  CAS  Google Scholar 

  6. Y.-M. Chung, Res. Chem. Intermed. 44, 6 (2018)

    Article  CAS  Google Scholar 

  7. R.J. Kalbasi, O. Mazaheri, Catal. Commun. 69, 5 (2015)

    Article  CAS  Google Scholar 

  8. G. Meng, S. Gao, Y. Liu, L. Zhang, C. Song, K. Huang, New J. Chem. 43, 5 (2019)

    Google Scholar 

  9. D. Wang, B. Wang, Y. Ding, H. Wu, P. Wu, Chem. Commun. 52, 87 (2016)

    Google Scholar 

  10. Y.-B. Huang, J. Liang, X.-S. Wang, R. Cao, Chem. Soc. Rev. 46, 1 (2017)

    Article  CAS  Google Scholar 

  11. A. Dhakshinamoorthy, H. Garcia, Chemsuschem 7, 9 (2014)

    Article  CAS  Google Scholar 

  12. N.A. Brunelli, K. Venkatasubbaiah, C.W. Jones, Chem. Mater. 24, 13 (2012)

    Article  CAS  Google Scholar 

  13. S. Banerjee, T. Maji, T.K. Paira, T.K. Mandal, Macromol. Rapid Commun. 34, 18 (2013)

    Article  CAS  Google Scholar 

  14. W. Jang, S. Sundar, S. Choi, Y.-G. Shul, H. Han, J. Membr. Sci. 280, 1 (2006)

    Article  CAS  Google Scholar 

  15. F.M. Fowkes, M.A. Mostafa, Ind. Eng. Chem. Prod. Res. Dev. 17, 1 (1978)

    Article  Google Scholar 

  16. X. Zhou, S.H. Goh, S.Y. Lee, K.L. Tan, Polymer 38, 21 (1997)

    Article  Google Scholar 

  17. A.K. Sahu, G. Selvarani, S.D. Bhat, S. Pitchumani, P. Sridhar, A.K. Shukla, N. Narayanan, A. Banerjee, N. Chandrakumar, J. Membr. Sci. 319, 1 (2008)

    Article  CAS  Google Scholar 

  18. E. Gianotti, U. Diaz, A. Velty, A. Corma, Catal. Sci. Technol. 3, 10 (2013)

    Article  CAS  Google Scholar 

  19. H.-L. Wu, C.-C.M. Ma, H.-C. Kuan, C.-H. Wang, C.-Y. Chen, C.-L. Chiang, J. Polym. Sci., Part B: Polym. Phys. 44, 3 (2006)

    Google Scholar 

  20. H. Zhang, L. Xiong, Z. He, A. Zhong, T. Wang, Y. Xu, K. Huang, New J. Chem. 40, 9 (2016)

    Google Scholar 

  21. K. Wang, Z. Jia, X. Yang, L. Wang, Y. Gu, B. Tan, J. Catal. 348, 168 (2017)

    Article  CAS  Google Scholar 

  22. L. Xiong, H. Zhang, Z. He, T. Wang, Y. Xu, M. Zhou, K. Huang, New J. Chem. 42, 2 (2018)

    Google Scholar 

  23. F. Shang, J. Sun, S. Wu, H. Liu, J. Guan, Q. Kan, J. Colloid Interface Sci. 355, 1 (2011)

    Article  CAS  Google Scholar 

  24. Y.-S. Ye, W.-Y. Chen, Y.-J. Huang, M.-Y. Cheng, Y.-C. Yen, C.-C. Cheng, F.-C. Chang, J. Membr. Sci. 362, 1 (2010)

    Article  CAS  Google Scholar 

  25. W. Chen, J.A. Sauer, M. Hara, Polymer 44, 25 (2003)

    Article  Google Scholar 

  26. W. Chen, J.A. Sauer, M. Hara, Polymer 45, 21 (2004)

    Google Scholar 

  27. W. Chen, J.A. Sauer, M. Hara, Polymer 44, 24 (2003)

    Google Scholar 

  28. Q. Yang, J. Liu, J. Yang, M.P. Kapoor, S. Inagaki, C. Li, J. Catal. 228, 2 (2004)

    Google Scholar 

  29. M.M. Mostafavi, F. Movahedi, Eur. J. Inorg. Chem. 2019, 6 (2019)

    Article  CAS  Google Scholar 

  30. O. Fardmousavi, H. Faghihian, C. R. Chimie 17, 12 (2014)

    Article  CAS  Google Scholar 

  31. S. Shylesh, W.R. Thiel, ChemCatChem 3, 2 (2011)

    Article  CAS  Google Scholar 

  32. H. Veisi, A. Sedrpoushan, H. Ghazizadeh, S. Hemmati, Res. Chem. Intermed. 42, 2 (2016)

    Article  CAS  Google Scholar 

  33. C.B. Hoyt, L.-C. Lee, A.E. Cohen, M. Weck, C.W. Jones, ChemCatChem 9, 1 (2017)

    Article  CAS  Google Scholar 

  34. A. Modak, A. Bhaumik, ChemistrySelect 1, 6 (2016)

    Article  CAS  Google Scholar 

  35. T. Wang, Y. Xu, Z. He, H. Zhang, L. Xiong, M. Zhou, W. Yu, B. Shi, K. Huang, Macromol. Chem. Phys. 218, 7 (2017)

    Google Scholar 

  36. R. Goyal, B. Sarkar, N. Lucus, A. Bordoloi, ChemCatChem 6, 11 (2014)

    Article  CAS  Google Scholar 

  37. Y. Zou, X. Zhou, J. Ma, X. Yang, Y. Deng, Chem. Soc. Rev. 49, 4 (2020)

    Article  Google Scholar 

  38. N.H.M.H. Tehrani, M.S. Alivand, A. Rashidi, K.R. Shamskar, M. Samipoorgiri, M.D. Esrafili, D.M. Maklavany, M. Shafiei-Alavijeh, J. Hazard. Mater. 384, 121317 (2020)

    Article  CAS  Google Scholar 

  39. M.J. Nasab, A.R. Kiasat, Microporous Mesoporous Mater. 223, 10 (2016)

    Article  CAS  Google Scholar 

  40. R.J. Kalbasi, S. Mansouri, O. Mazaheri, Res. Chem. Intermed. 44, 5 (2018)

    Google Scholar 

  41. R.J. Kalbasi, N. Mosaddegh, A. Abbaspourrad, Appl. Catal. A Gen. 423–424, 78 (2012)

    Article  CAS  Google Scholar 

  42. J. He, K. Ma, J. Jin, Z. Dong, J. Wang, R. Li, Microporous Mesoporous Mater. 121, 1 (2009)

    Article  CAS  Google Scholar 

  43. R.J. Kalbasi, O. Mazaheri, New J. Chem. 40, 11 (2016)

    Article  CAS  Google Scholar 

  44. W. Su, X. Lu, F. Sheng, Y. Sun, C. Liu, G. He, J. Liu, X. Wang, J. Chem. Eng. Data 63, 12 (2018)

    Google Scholar 

  45. C.-C. Hwang, Z. Jin, W. Lu, Z. Sun, L.B. Alemany, J.R. Lomeda, J.M. Tour, ACS Appl. Mater. Interfaces. 3, 12 (2011)

    Google Scholar 

  46. R.J. Kalbasi, P. Parishani, O. Mazaheri, J. Cluster Sci. 29, 4 (2018)

    Google Scholar 

  47. C. Li, J. Yang, P. Wang, J. Liu, Q. Yang, Microporous Mesoporous Mater. 123, 1 (2009)

    Article  CAS  Google Scholar 

  48. M.S. Alivand, M. Najmi, N.H.M.H. Tehrani, A. Kamali, O. Tavakoli, A. Rashidi, M.D. Esrafili, E. Ghasemy, O. Mazaheri, Chem. Eng. J. 374, 274 (2019)

    Article  CAS  Google Scholar 

  49. N.H.M.H. Tehrani, M.S. Alivand, D.M. Maklavany, A. Rashidi, M. Samipoorgiri, A. Seif, Z. Yousefian, Chem. Eng. J. 358, 1126 (2019)

    Article  CAS  Google Scholar 

  50. F. Zamani, S.M. Hosseini, S. Kianpour, Solid State Sci. 26, 139 (2013)

    Article  CAS  Google Scholar 

  51. M.R. Benzigar, S.N. Talapaneni, S. Joseph, K. Ramadass, G. Singh, J. Scaranto, U. Ravon, K. Al-Bahily, A. Vinu, Chem. Soc. Rev. 47, 8 (2018)

    Article  Google Scholar 

  52. G. Pang, P. Nie, C. Yuan, L. Shen, X. Zhang, H. Li, C. Zhang, J. Mater. Chem. A 2, 48 (2014)

    Article  CAS  Google Scholar 

  53. G. Chandrasekar, W.-J. Son, W.-S. Ahn, J. Porous Mater. 16, 5 (2009)

    Google Scholar 

  54. S. Sarkar, A.K. SenGupta, J.E. Greenleaf, M. El-Moselhy, Ind. Eng. Chem. Res. 50, 21 (2011)

    Google Scholar 

  55. Z. Sun, Y. Wang, Z. Zhang, F. Zhu, P. Zhao, G. Li, F. Shao, J. Rui, Res. Chem. Intermed. 45, 5 (2019)

    Google Scholar 

  56. L. Wu, Y. Long, J. Ma, G. Lu, Res. Chem. Intermed. 45, 7 (2019)

    Google Scholar 

  57. Y. Hu, J. Zhang, H. Huo, Z. Wang, X. Xu, Y. Yang, K. Lin, R. Fan, Catal. Sci. Technol. 10, 2 (2020)

    Article  Google Scholar 

  58. R.J. Kalbasi, N. Mesgarsaravi, R. Gharibi, Appl. Organomet. Chem. 33, 4 (2019)

    Google Scholar 

  59. R.J. Kalbasi, A. Khojastegi, Catal. Lett. 148, 3 (2018)

    Google Scholar 

  60. X. Wang, L. Zhang, Z. Guo, Y. Shi, Y. Zhou, J. Wang, Appl. Surf. Sci. 478, 3837 (2019)

    Google Scholar 

  61. S.B. Kamble, C.V. Rode, ChemCatChem 8, 16 (2016)

    Article  CAS  Google Scholar 

  62. R.J. Kalbasi, N. Mosaddegh, J. Solid State Chem. 184, 11 (2011)

    Google Scholar 

  63. S. Mishra, A. Rawal, L. Nebhani, Microporous Mesoporous Mater. 294, 109898 (2020)

    Article  CAS  Google Scholar 

  64. K. Motokura, M. Tada, Y. Iwasawa, J. Am. Chem. Soc. 131, 23 (2009)

    Article  CAS  Google Scholar 

  65. F. Shang, J. Sun, S. Wu, Y. Yang, Q. Kan, J. Guan, Microporous Mesoporous Mater. 134, 1 (2010)

    Article  CAS  Google Scholar 

  66. F. Shang, J. Sun, H. Liu, C. Wang, J. Guan, Q. Kan, Mater. Res. Bull. 47, 3 (2012)

    Article  CAS  Google Scholar 

  67. T. Toyao, M. Fujiwaki, Y. Horiuchi, M. Matsuoka, RSC Adv. 3, 44 (2013)

    Article  CAS  Google Scholar 

  68. L. Xu, C.-G. Li, K. Zhang, P. Wu, ACS Catal. 4, 9 (2014)

    Article  CAS  Google Scholar 

  69. Y.-R. Lee, X.H. Do, S.S. Hwang, K.-Y. Baek, Catal. Today (2019). https://doi.org/10.1016/j.cattod.2019.06.076

  70. Z. Sun, X. Yang, X. Huang, M. Zhang, G. Bian, Y. Qi, X. Yang, W. Zhang, New J. Chem. 43, 42 (2019)

    Google Scholar 

  71. M.-L. Gao, M.-H. Qi, L. Liu, Z.-B. Han, Chem. Commun. 55, 45 (2019)

    Google Scholar 

  72. S. Mistry, A. Sarkar, S. Natarajan, Cryst. Growth Des. 19, 2 (2019)

    Article  CAS  Google Scholar 

  73. T. Toyao, M.J. Styles, T. Yago, M.M. Sadiq, R. Riccò, K. Suzuki, Y. Horiuchi, M. Takahashi, M. Matsuoka, P. Falcaro, CrystEngComm 19, 29 (2017)

    Article  Google Scholar 

  74. Y. Sheng, X. Wang, Z. Xing, X. Chen, X. Zou, X. Lu, ACS Sustain. Chem. Eng. 7, 9 (2019)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Kharazmi University, Tehran, Iran

    Roozbeh Javad Kalbasi

  2. Department of Chemistry, Shahreza Branch, Islamic Azad University, Isfahan, 311-86145, Iran

    Fatemeh Rahmati

  3. School of Agriculture and Food, Faculty of Veterinary and Agricultural Sciences, The University of Melbourne, Parkville, VIC, 3010, Australia

    Omid Mazaheri

  4. Department of Chemical Engineering, The University of Melbourne, Parkville, VIC, 3010, Australia

    Omid Mazaheri

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  1. Roozbeh Javad Kalbasi
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In the supporting information, the experimental methods including the instruments and the characterization, the catalyst preparation, and the general procedure for the deacetalization–Knoevenagel condensation reaction are provided. (DOCX 20 kb)

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Javad Kalbasi, R., Rahmati, F. & Mazaheri, O. Overcoming acid–base copolymer neutralization using mesoporous carbon and its catalytic activity in the tandem deacetalization–Knoevenagel condensation reaction. Res Chem Intermed 46, 3413–3430 (2020). https://doi.org/10.1007/s11164-020-04153-4

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