Preysler polyoxometalate supported on functionalized graphene oxide nanoparticles: synthesis, identification and investigation of its catalytic activity

Subject Areas : journal of New Materials

Ali Javid ¹ (Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran)

Received: 2024-02-23 Accepted : 2024-05-27 Published : 2024-01-21

Keywords: Graphene oxide, Nanoparticle, polyoxometalate, Preysler, Oxime,

Abstract :

Abstract Introduction: In the last two decades, nanoparticles obtained from graphene oxide (GO) have been of great interest to researchers in various sciences, including chemistry. Also, the functionalization of graphene oxide can improve its functional properties. In industrial chemistry, one of the most important applications of functionalized graphene oxide is its use as a catalyst. Methods: In this project, after preparing graphene oxide nanoparticles, they were grafted by functionalized polyamine (GO-NH₂), and then by Preissler's heteropolyacid (Pr@GO-NH₂). Preysler is one of the types of polyoxometalate clusters, which has unique characteristics and is used as a Lewis acid catalyst due to having a large number of acidic protons. The structure of these new nanoparticles was investigated by spectral methods such as XRD, FTIR, SEM, TEM, EDX and TGA. Also, after preparing Pr@GO-NH₂, its catalytic activity was measured in the reaction of producing oxime from aldehyde and hydroxylamine. Findings: By using the mentioned spectral methods and comparing some spectra of Pr@GO-NH₂ with GO-NH₂ and GO, the structure of Pr@GO-NH₂ nanoparticles was identified and confirmed. Also, the preparation of oxime in the presence of these nanoparticles confirmed its high catalytic activity. Based on the obtained results, this reaction was carried out in the presence of 0.03 grams of catalyst at 50°C for 30 minutes and in the presence of water as an environmentally friendly solvent.

References:

1. E. Rubin, "Synthetic Socialism: Plastics and Dictatorship in the German Democratic Republic", The University of North Carolina Press, 2014.

2. C. Canario, S. Silvestre, A. Falcao, G. Alves, "Steroidal Oximes: Useful Compounds with Antitumor Activities", Current Medicinal Chemistry, vol. 25(6), pp.   660-686, 2018. doi.org/10.2174/09298673246661710031154003.

3. J.D. Campagna, M.C. Bond, E. Schabelman, B.D. Hayes, "The use of cephalosporins in penicillin-allergic patients: a literature review",  Journal of Emergency Medicine, vol. 42(5), pp.  612-620, 2012.

4. A.G. Smith, P.A. Tasker, D.J. White, "The structures of phenolic oximes and their complexes". Coordination Chemistry Reviews. vol. 241, pp. 61-85, 2003. doi.org/10.1016/S0010-8545(02)00310-7

5. L. Saikia, J.M. Baruah, A.J. Thakur, "A rapid, convenient, solvent less green approach for the synthesis of oximes using grindstone chemistry". Organic and Medicinal Chemistry Letters, vol. 1, pp. 12, 2011. doi.org/10.1186/2191-2858-1-12

6. H. Sharjhi, M.H. Sarvari, "A mild and versatile method for the preparation of oximes by use of calcium oxide". Journal of Chemical Research, vol. 1, pp. 24-25, 2000. doi.org/10.3184/030823400103165545

7. J.J. Guo, T.S. Jin, S.L. Zhang, T.S. Li "TiO₂/SO₄^2-: an efficient and convenient catalyst for preparation of aromatic oximes". Green Chemistry, vol. 3, pp. 193-195, 2001. doi.org/10.1039/b102067f.

8. D. Sloboda-Rozner, R. Neumann, "Aqueous biphasic catalysis with polyoxometalates: oximation of ketones and aldehydes with aqueous ammonia and hydrogen peroxide". Green Chemistry, vol. 8, pp. 679-681, 2006. doi.org/10.1039/b604837d.

9. H.M. Luo, Y.Q. Li, W.J. Zheng, "A novel ionic liquid/water biphasic system for the preparation of oximes". Chinese Chemical Letters, vol. 16(7), pp. 906-908, 2005.

10. K. Ramanjaneyulu, P. Seshagiri Rao, T. Rambabu, K. Jayarao, Ch.B.T. Sundari Devi, B. Venkateswara Rao, "Cupper supported silica promoted one-pot synthesis of aromatic oxime derivatives". Der Pharma Chemica, vol. 4(1), pp. 473-478, 2012.

11. I. Kozhevnikov, "Catalysts for fine chemical synthesis: catalysis by polyoxometalates", vol 2. Wiley, Chichester, 2002.

12. C. Louis, W. Baker, Diana C. Glick, "Present General Status of Understanding of Heteropoly Electrolytes and a Tracing of Some Major Highlights in the History of Their Elucidation". Chemical Reviews, vol. 98, pp. 3-49, 1998. doi.org/10.1021/cr960392l

13. A. Javid, A. Khojastehnezhad, H. Eshghi, F. Moeinpour, F.F. Bamoharram, J. Ebrahimi, "Synthesis of Pyranopyrazoles using a Magnetically Separable Modified Preyssler Heteropoly Acid". Organic Preparations and Procedures International, vol. 48, pp. 377-384, 2016. doi.org/10.1080/00304948.2016.1206424

14. O. Neogi, "Preyssler Polyoxometalate an Overview". International Journal of Innovative Science and Research Technology, vol. 8, pp. 142-160, 2023.

15. J. Ahmad, "Lipid Nanoparticles Based Cosmetics with Potential Application in Alleviating Skin Disorders" Cosmetics, vol. 8, pp. 84, 2021. doi.org/10.3390/cosmetics8030084

16. Y. Dang, J. Guan, "Nanoparticle-based drug delivery systems for cancer therapy". Smart Materials in Medicine, vol. 1, pp. 10-19, 2020. doi.org/10.1016/j.smaim.2020.04.001

17. R.F. do Nascimento, V. de Oliveira, P.B.A. Fechine, "Nanomaterials and Nanotechnology", Springer, 2021.

18. N. Sadeghpour, M. Vadi, N. Bagheri, "Efficient Removal of Omeprazole from Water Samples by Utilizing of Carbon Nanotubes as Powerful nanoadsorbent and Comprising with Graphite: Kinetic and Thermodynamic studies", Journal of New Materials, vol. 12 (46), pp. 1-18, 2022. doi.org/10.30495/jnm.2022.28354.1925

19. B.C. Brodie, "On the Atomic Weight of Graphite". Philosophical transactions of the Royal Society of London, vol. 149, pp. 249-259, 1859. doi.org/10.1098/rstl.1859.0013

20. G. Gonçalves, M. Vila, M.T. Portoles, M. Vallet-Regi, J. Gracio, "Nano‐graphene oxide: a potential multifunctional platform for cancer therapy". Advanced Healthcare Materials, vol. 2, pp. 1072-1090, 2013. doi.org/10.1002/adhm.201300023

21. H.M. Ali, "Analysis of heat pipe-aided graphene-oxide based nanoparticle-enhanced phase change material heat sink for passive cooling of electronic components". Journal of Thermal Analysis and Calorimetry, vol. 146, pp. 277-286, 2021. doi.org/10.1007/s10973-020-09946-8

22. Y. Yang, R. Zhang, X. Zhang, Z. Chen, "Effects of Graphene Oxide on Plant Growth: A Review". Plants, vol. 11(21), pp.  2826-2838, 2022. https:/doi.org/10.3390/plants11212826

23. L. Liu, Q. Ma, J. Cao, Y. Gao, S. Han, Y. Liang, T. Zhang, Y. Song, Y. Sun, "Recent progress of graphene oxide-based multifunctional nanomaterials for cancer treatment". Cancer Nanotechnology. Vol. 12, pp. 18-49, 2021. doi.org/10.1186/s12645-021-00087-7

24. A. Al-Nayili, M. Albdiry, "AuPd bimetallic nanoparticles supported on reduced graphene oxide nanosheets as catalysts for hydrogen generation from formic acid under ambient temperature". New Journal of Chemistry, vol. 45, pp. 10040, 2021. doi.org/10.1039/D1NJ01658J

25. E.M. Abd El-Monaem, M. Abd El-Latif, A.S. Eltaweil, G.M. El-Subruiti, "Cobalt Nanoparticles Supported on Reduced Amine-Functionalized Graphene Oxide for Catalytic Reduction of Nitroanilines and Organic Dyes". Nano, vol. 16, pp. 2150039, 2021. doi.org/10.1142/S1793292021500399

26. A. Rahman, S. Zulfiqar, A.U. Haq, I.A. Alsafari, U.Y. Qazi, M.F. Warsi, M. Shahid, "Cd-Gd-doped nickel spinel ferrite nanoparticles and their nanocomposites with reduced graphene oxide for catalysis and antibacterial activity studies". Ceramics International, vol. 47, pp. 9513-9521, 2021. doi.org/10.1016/j.ceramint.2020.12.085

27. K. Ganesan, V.K. Jothi, A. Natarajan, A. Rajaram, S. Ravichandran, "Green synthesis of Copper oxide nanoparticles decorated with graphene oxide for anticancer activity and catalytic applications". Arabian Journal of Chemistry, vol. 13, pp. 6802-6814, 2020. doi.org/10.1016/j.arabjc.2020.06.033

28. B. Jain, A. Hashmi, S. Sanwaria, A.K. Singh, M.A.B.H. Susan, A. Singh, "Zinc oxide nanoparticle incorporated on graphene oxide: an efficient and stable photocatalyst for water treatment through the Fenton process". Advanced Composites and Hybrid Materials, vol. 3, pp. 231-242, 2020. doi.org/10.1007/s42114-020-00153-5

29. W. Yang, G. Chata, Y. Zhang, Y. Peng, J. En Lu, N. Wang, R. Mercado, J. Li, S. Chen, "Graphene oxide-supported zinc cobalt oxides as effective cathode catalysts for microbial fuel cell: High catalytic activity and inhibition of biofilm formation". Nano Energy, vol. 57, pp. 811-819, 2019. doi.org/10.1016/j.nanoen.2018.12.089

30. A. Khodadadi Dizaji, H.R. Mortaheb, B. Mokhtarani, "Extractive-Catalytic Oxidative Desulfurization with Graphene Oxide-Based Heteropolyacid Catalysts: Investigation of Affective Parameters and Kinetic Modeling". Catalysis Letters, vol. 149, pp. 259, 2019. doi.org/10.1007/s10562-018-2595-x

31. D. Zhao, X. Gao, C. Wu, R. Xie, S. Feng, C. Chen, "Facile preparation of amino functionalized graphene oxide decorated with Fe3O4 nanoparticles for the adsorption of Cr(VI)". Applied Surface Science, vol. 384, pp. 1-9, 2016. doi.org/10.1016/j.apsusc.2016.05.022

32. J.N. Jebaranjitham, C. Mageshwari, R. Saravanan, N. Mu, "Fabrication of amine functionalized graphene oxide – AgNPs nanocomposite with improved dispersibility for reduction of 4-nitrophenol". Composites Part B: Engineering, vol. 171, pp. 302-309, 2019. doi.org/10.1016/j.compositesb.2019.05.018

33. V.B. Saptal, M.V. Spatal, R.S. Mane, T. Sasaki, B.M. Bhanage, "Amine-Functionalized Graphene Oxide-Stabilized Pd Nanoparticles (Pd@APGO): A Novel and Efficient Catalyst for the Suzuki and Carbonylative Suzuki–Miyaura Coupling Reactions". ACS Omega, vol. 4, pp. 643-649, 2019. doi.org/10.1021/acsomega.8b03023

34. A. Javid, A. Khojastehnezhad, A. Pombeiro, "Preparation, Characterization, and Application of Preyssler Heteropoly Acid Immobilized on Magnetic Nanoparticles as a Green and Recoverable Catalyst for the Synthesis of Imidazoles". Russian Journal of General Chemistry, vol. 87, pp. 3000-3005, 2017. doi.org/10.1134/S1070363217120453

35. A. Khojastehnezhad, M. Bakavoli, A. Javid, M.M. Khakzad Siuki, M. Shahidzadeh, "Synthesis, characterization, and investigation of catalytic activity of copper(II) porphyrin graphene oxide for azide-alkyne cycloaddition". Research on Chemical Intermediates, vol. 45, pp. 4473-4485, 2019. https:/dx.doi.org/10.1007/s11164-019-03843-y

36. A. Khojastehnezhad, F. Moeinpour, A. Javid, "NiFe2O4 @ SiO2–PPA Nanoparticle: A Green Nanocatalyst for the Synthesis of β-Acetamido Ketones." Polycyclic Aromatic Compounds, vol. 39, pp. 404, 2019. doi.org/10.1080/10406638.2017.1335218

37. B. Paulchamy, G. Arthi, B.D. Lignesh, "A Simple Approach to Stepwise Synthesis of Graphene Oxide Nanomaterial". Jornal of Nanomedicine and Nanotechnology, vol. 6, pp. 1, 2015. doi.org/10.4172/2157-7439.1000253

38. H. Kim, R. Namgung, K. Singha, W.J. Kim, "Graphene Oxide–Polyethylenimine Nanoconstruct as a Gene Delivery Vector and Bioimaging Tool". Bioconjugate chemistry, vol. 22, pp. 2558-2567, 2011. doi.org/10.1021/bc200397j