Abstract
In the current study, a new catalytic system based on Fe3O4 nanoparticles immobilized on zeolite-SO3H (Fe3O4@zeolite-SO3H) is introduced. In the first stage, zeolite@SO3H was synthesized from the reaction of zeolite-NaY with chlorosulfonic acid to produce zeolo sulfuric acid. Then, Fe3O4@zeolite-SO3H was prepared via immobilizing magnetic nanoparticles on the surface of functionalized zeolite-NaY as a support. Fe3O4@zeolite-SO3H as a multifunctional nanoplatform system was recognized by FT-IR, FE-SEM, XRD, EDS, BET, and VSM techniques. This nanocomposite demonstrated high activity in the catalytic synthesis of perimidine derivatives under solvent-free conditions. Combining the advantages of solid acids based nanocomposites and magnetic separation, this method provides an efficient and much improved modification of the general synthesis of perimidines. Recycling experiments confirmed the good stability of the nanocatalyst for six times and its constant activity.
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C. Hou, Z. Tai, L. Zhao, Y. Zhai, Y. Hou, Y. Fan, F.J. Wang, H. Lio, J. Mater. Chem. A. 7, 13460 (2019)
H. Sun, Z. Yang, Y. Pu, W. Dou, C. Wang, W. Wang, X. Hao, S. Chen, Q. Shao, M. Dong, S. Wu, T. Ding, Z. Guo, J. Colloid Interf. Sci. 547, 40 (2019)
B. Lin, Z. Lin, S. Chen, M. Yu, W. Li, Q. Gao, M. Dong, Q. Shao, S. Wu, T. Ding, Z. Guo, Dalton Trans. 48, 8279 (2019)
G. Zhu, X. Cui, Y. Zhang, S. Chen, M. Dong, H. Liu, Q. Shao, T. Ding, S. Wu, Z. Guo, Polymer 172, 415 (2019)
C. Wang, V. Murugadoss, J. Kong, Z. He, X. Mai, Q. Shao, Y. Chen, L. Guo, C. Liu, S. Angaiah, Z. Guo, Carbon 140, 696 (2018)
X. Gong, Y. Liu, Y. Wang, Z. Xie, Q. Dong, M. Dong, H. Liu, Q. Shao, N. Lu, V. Murugadoss, T. Ding, Z. Guo, Polymer 168, 131 (2019)
Z. Lin, B. Line, Z. Wang, S. Chen, C. Wang, M. Dong, Q. Gao, Q. Shao, T. Ding, H. Liu, Z. Gao, Chemcatchem. 11, 2217 (2019)
N. Wu, D. Xu, Z. Wang, F. Wang, J. Liu, W. Liu, Q. Shao, H. Liu, Q. Gao, Z. Guo, Carbon 145, 433 (2019)
K. Li, Z. Wang, Q. Wang, Q. Shao, V. Murugadoss, S. Wu, W. Liu, J. Liu, Q. Gao, Z. Gao, Dalton Trans. 48, 5193 (2019)
X.L. Luo, F. Pei, W. Wang, H.M. Qian, K.K. Miao, Z. Pan, Y.S. Chen, G.D. Feng, Micropor. Mesopor. Mater. 262, 148 (2018)
Z. Shi, C. Wu, Y. Wu, H. Liu, G. Xu, J. Deng, H. Gu, H. Liu, J. Zhang, A. Umar, Y. Ma, Z. Guo, Sci. Adv. Mater. 11, 699 (2019)
Z. Shi, C. Jia, D. Wang, J. Deng, G. Xu, C. Wu, M. Dong, Z. Gau, Int. J. Biol. Macromol. 133, 964 (2019)
H. Gu, X. Xu, J. Cai, S. Wei, H. Wei, H. Liu, D.P. Yong, Q. Shao, S. Wu, T. Diang, Z. Gau, Chem. Commun. 53, 11802 (2017)
G. Perot, M. Guisnet, J. Mol. Catal. 61, 173 (1990)
C.G.S. Lima, N.M. Moreira, M.W. Paixão, A.G. Corrêa, Curr. Opin. Green. Sustain. Chem. 15, 7 (2019)
Z. Shi, C. Wu, Y. Gu, Y. Liang, G. Xu, H. Liu, J. Zhang, H. Hou, J. Zhang, Z. Guo, Sci. Adv. Mater. 11, 1198 (2019)
A.R. Massah, R. Javad Kalbasi, A. Shafiei, Monatsh. Chem. 143, 643 (2012)
R. Estevez, I. Iglesias, D. Luna, F.M. Bautista, Molecules 22, 2206 (2017)
H. Nur, G.L. Kee, H. Hamdan, T.M.I. Mahlia, J. Efendi, H.S.C. Metselaar, Int. J. Hydrogen Energy 37, 12513 (2012)
N. Krathumkhet, K. Vongjitpimol, T. Chuesutham, S. Changkhamchom, K. Phasuksom, A. Sirivat, K. Wattanakul, Solid State Ion. 319, 278 (2018)
H. Liu, S. Peng, L. Shu, T. Chen, T. Bao, R.L. Frost, Chemosphere 91, 1539 (2013)
A. Gaffer, A.A. Al Kahlawy, D. Aman, Egypt. J. Petrol. 26, 995 (2017)
A. Mesdaghinia, A. Azari, R. Nabizadeh Nodehi, K. Yaghmaeian, A.K. Bharti, S. Agarwal, V.K. Gupta, K. Sharafi, J. Mol. Liq. 233, 378 (2017)
D. Lin, X. Feng, Y. Wu, B. Ding, T. Lu, Y. Liu, X. Chen, D.C. Yang, Appl. Surf. Sci. 456, 140 (2018)
P. Abasian, M. Radmansouri, M. Habibi Jouybari, M. Vaez Ghasemi, A. Mohammadi, M. Irani, F. Sharifian Jazi, Int. J. Biol. Macromol. 121, 398 (2019)
S.V.H.S. Bhaskaruni, S. Maddila, K.K. Gangu, S.B. Jonnalagadda, Arab. J. Chem. (2017)
C.V.T. Vo, J.W. Bode, J. Org. Chem. 79, 2809 (2014)
V. Paragamian, M.B. Baker, B.M. Puma, J. Reale, J. Heterocycl. Chem. 5, 591 (1968)
T.A. Farghaly, M.A. Abdallah, Z.A. Muhammad, Res. Chem. Intermed. 41, 3937 (2015)
F.A. Bassyouni, S.M. Abu-Bakr, K.H. Hegab, W. El-Eraky, A.A.E. Beih, M.E.A. Rehim, Res. Chem. Intermed. 38, 1527 (2012)
M. Kalhor, N. Khodaparast, Res. Chem. Intermed. 41, 3235 (2015)
M. Kalhor, F. Rezaee-Baroonaghi, A. Dadras, Z. Zarnegar, Appl Organometal Chem. 33, e4784 (2019)
J.J. Vanden-Eynde, F. Delfosse, A. Mayence, Y.V. Haverbeke, Tetrahedron 51, 5813 (1995)
V.A. Ozeryanskii, E.A. Filatova, V.I. Sorokin, A.F. Pozharskii, Russ. Chem. Bull. 50, 846 (2001)
M. Kalhor, Org. Chem. Res. 1, 59 (2015)
M. Kalhor, S. Banibairami, S.A. Mirshokraie, Green Chem. Lett. Rev. 11, 334 (2018)
J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)
F. Rouquerol, J. Rouquerol, K.S.W. Sing, Adsorption by Powder and Porous Solids (Academic Press, San Diego, 1999), p. 1
M.M. Khakzad-Siuki, M. Bakavoli, H. Eshghi, Appl. Orgmet. Chem. 32, e4290 (2018)
M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2017)
O. Maloshitskaya, J. Sinkkonen, V.V. Ovcharenko, K.N. Zelenin, K. Pihlaja, Tetrahedron 60, 6913 (2004)
F.K. Behbahani, F.M. Golchin, J. Taibah. Univ. Sci. 11, 85 (2017)
A. Mobinikhaledi, N. Foroughifar, Turk. J. Chem. 33, 555 (2009)
C.K. Wu, T.J. Teau-Jiuan Liou, H.Y. Wei, P.S. Tsai, D.Y. Yang, Tetrahedron 70, 8219 (2014)
A. Farrokhi, K. Keivan Ghodrati, I. Yavari, Catal. Commun. 63, 41 (2015)
K.M. Salih, H.J. Azeez, Res. Pharm. Biotechnol. 51, 1 (2014)
A. Mobinikhaledi, P. Steel, Synth. React. Inorg. Metal-Org. Nano-Met. Chem. 39, 133 (2009)
A. Bamoniri, B.B.F. Mirjalili, S. Saleh, RSC Adv. 8, 6178 (2018)
A. Mobinikhaledi, F. Sasani, A. Hamta, S.M. Shariatzadeh, Bulg. Chem. Commun. 45, 353 (2013)
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We are thankful to the Payame Noor University for the partial support of this work.
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Kalhor, M., Zarnegar, Z., Janghorban, F. et al. Fe3O4@zeolite-SO3H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of perimidines. Res Chem Intermed 46, 821–836 (2020). https://doi.org/10.1007/s11164-019-03992-0
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DOI: https://doi.org/10.1007/s11164-019-03992-0