Magnetic Nanoparticles Functionalized with Dendritic Polymer as a Host for Immobilization of MoO2(acac)2 and Investigation of its Catalytic Activity in the Epoxidation of Alkenes

Document Type: Research Paper

Authors

Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran

10.22036/icr.2020.233205.1063

Abstract

The new heterogeneous catalyst based on MoO2(acac)2 immobilized on superparamagnetic nanoparticle functionalized with dendrimer was synthesized. The dendrimer with amine and sulfur functional groups offer proper positions for a strong connection between MoO2(acac)2 and support. The synthesized catalyst was characterized by FT-IR spectroscopy, ICP, TGA, SEM, TEM, and XRD. This catalyst showed high activity in the epoxidation of alkene with tert-BuOOH. These reactions displayed the best performance in the present of 1,2-dichloroethan as a solvent and 0.0108 mmol of the catalyst. The use of magnetic nanoparticles (MNPs) as support facilitates the separation of the catalyst from the reaction media by simple magnetic decantation. Eventually, the catalyst can be recovered and reused without a decrease in its catalytic activity and significant Mo leaching for five times.

Keywords

1.            R. Ye, A. V. Zhukhovitskiy, C. V. Deraedt, F. D. Toste and G. A. Somorjai, Acc. Chem. Res., 2017, 50, 1894-1901.

2.            A. Ge, B. Rudshteyn, P. E. Videla, C. J. Miller, C. P. Kubiak, V. S. Batista and T. Lian, Acc. Chem. Res., 2019, 52, 1289-1300.

3.            F. J. Méndez, O. E. Franco-López, X. Bokhimi, D. A. Solís-Casados, L. Escobar-Alarcón and T. E. Klimova, Applied Catalysis B: Environmental, 2017, 219, 479-491.

4.            J.-J. Zhang, Z.-B. Wang, C. Li, L. Zhao, J. Liu, L.-M. Zhang and D.-M. Gu, J. Power Sources, 2015, 289, 63-70.

5.            B. Altava, M. I. Burguete, E. García-Verdugo and S. V. Luis, Chem. Soc. Rev., 2018, 47, 2722-2771.

6.            A. S. Crampton, M. D. Rötzer, F. F. Schweinberger, B. Yoon, U. Landman and U. Heiz, Angew. Chem. Int. Ed., 2016, 55, 8953-8957.

7.            W. Yu, X. Wu, Z. Si and D. Weng, Appl. Surf. Sci., 2013, 283, 209-214.

8.            X. Hu, Y. Lu, F. Dai, C. Liu and Y. Liu, Microporous Mesoporous Mater., 2013, 170, 36-44.

9.            Z. Gao, X. Zhang, K. Zhang and M. M. Yuen, The Journal of Physical Chemistry C, 2015, 119, 15636-15642.

10.         A. J. Neel, M. J. Hilton, M. S. Sigman and F. D. Toste, Nature, 2017, 543, 637-646.

11.         P. Puthiaraj, Y.-R. Lee, S. Zhang and W.-S. Ahn, Journal of Materials Chemistry A, 2016, 4, 16288-16311.

12.         M. N. Shaikh, M. A. Aziz, A. N. Kalanthoden, A. Helal, A. S. Hakeem and M. Bououdina, Catalysis Science & Technology, 2018, 8, 4709-4717.

13.         Q. Zhou, Z. Wan, X. Yuan and J. Luo, Appl. Organomet. Chem., 2016, 30, 215-220.

14.         L. Mohammadi, M. A. Zolifgol, M. Yarie, M. Ebrahiminia, K. P. Roberts and S. R. Hussaini, Res. Chem. Intermed., 2019, 45, 4789-4799.

15.         R. Duncan and L. Izzo, Advanced drug delivery reviews, 2005, 57, 2215-2237.

16.         A. K. Sharma, A. Gothwal, P. Kesharwani, H. Alsaab, A. K. Iyer and U. Gupta, Drug Discovery Today, 2017, 22, 314-326.

17.         H. J. Hsu, J. Bugno, S. r. Lee and S. Hong, Wiley Interdisciplinary Reviews: Nanomedicine and Nanobiotechnology, 2017, 9, e1409.

18.         A.-M. Caminade, Chem. Soc. Rev., 2016, 45, 5174-5186.

19.         C. Deraedt, R. Ye, W. T. Ralston, F. D. Toste and G. A. Somorjai, J. Am. Chem. Soc., 2017, 139, 18084-18092.

20.         A.-M. Caminade, A. Ouali, R. Laurent and J.-P. Majoral, in Effects of Nanoconfinement on Catalysis, Springer, 2017, pp. 173-207.

21.         K. Yamamoto and T. Imaoka, Bull. Chem. Soc. Jpn., 2006, 79, 511-526.

22.         V. Balzani, P. Ceroni, A. Juris, M. Venturi, S. Campagna, F. Puntoriero and S. Serroni, Coord. Chem. Rev., 2001, 219, 545-572.

23.         H. G. Cheng, C. Wu, H. Chen, R. Chen, G. Qian, Z. Geng, Q. Wei, Y. Xia, J. Zhang and Y. Zhang, Angew. Chem. Int. Ed., 2018, 57, 3444-3448.

24.         S. Liu, N. Suematsu, K. Maruoka and S. Shirakawa, Green Chemistry, 2016, 18, 4611-4615.

25.         C. Miao, B. Wang, Y. Wang, C. Xia, Y.-M. Lee, W. Nam and W. Sun, J. Am. Chem. Soc., 2016, 138, 936-943.

26.         E. P. Talsi, T. V. Rybalova and K. P. Bryliakov, J. Mol. Catal. A: Chem., 2016, 421, 131-137.

27.         H. M. Hassan, M. A. Betiha, E. El-Sharkawy, R. F. Elshaarawy, N. El-Assy, A. A. Essawy, A. Tolba and A. M. Rabie, Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2020, 124520.

28.         R. V. Ottenbacher, E. P. Talsi and K. P. Bryliakov, Catal. Today, 2016, 278, 30-39.

29.         A. Bezaatpour, S. Khatami and M. Amiri, RSC advances, 2016, 6, 27452-27459.

30.         J. Wang, M. Yang, W. Dong, Z. Jin, J. Tang, S. Fan, Y. Lu and G. Wang, Catalysis Science & Technology, 2016, 6, 161-168.

31.         B. Shi, H. Yu, S. Gao, L. Zhang, Y. Liu and K. Huang, Microporous Mesoporous Mater., 2020, 294, 109890.

32.         J. Zhang, Y. Zhao, A. Li, H. Ye, Q. Shang, X. Shi and Y. Shen, J. Porous Mater., 2019, 26, 869-880.

33.         A. Lazar, W. Thiel and A. Singh, Metal-Organofunctionalized SBA-15 catalysts for fine chemical syntheses, 2018, 4, 50.

34.         R. Mbeleck, K. Ambroziak, B. Saha and D. C. Sherrington, React. Funct. Polym., 2007, 67, 1448-1457.

35.         A. Landarani-Isfahani, M. Moghadam, S. Mohammadi, M. Royvaran, N. Moshtael-Arani, S. Rezaei, S. Tangestaninejad, V. Mirkhani and I. Mohammadpoor-Baltork, Langmuir, 2017, 33, 8503-8515.

36.         A. L. Isfahani, I. Mohammadpoor‐Baltork, V. Mirkhani, A. R. Khosropour, M. Moghadam, S. Tangestaninejad and R. Kia, Adv. Synth. Catal., 2013, 355, 957-972.

37.         G. J. Chen, J. W. McDonald and W. Newton, Inorg. Chem., 1976, 15, 2612-2615.

38.         D. Kim, Y. Zhang, W. Voit, K. Rao and M. Muhammed, J. Magn. Magn. Mater., 2001, 225, 30-36.

39.         G. Blotny, Tetrahedron, 2006, 62, 9507-9522.

40.         X. Guo, F. Mao, W. Wang, Y. Yang and Z. Bai, ACS applied materials & interfaces, 2015, 7, 14983-14991.

41.         B. Asadi, I. Mohammadpoor-Baltork, S. Tangestaninejad, M. Moghadam, V. Mirkhani and A. Landarani-Isfahani, New J. Chem., 2016, 40, 6171-6184.

42.         Y. Liu, S. Ma, H. Zuo, J. Li, X. Shi and M. Zhao, Ceram. Int., 2016, 42, 16499-16504.


Volume 4, Issue 1
Summer and Autumn 2020
Pages 51-65
  • Receive Date: 30 May 2020
  • Revise Date: 03 July 2020
  • Accept Date: 03 July 2020