Green Synthesis and Characterization of Cinnamylideneacetophenone Compound Using Fe3O4 Magnetic as Catalyst

Dori Fitria, Antonius Herry Cahyana, Agus Rimus Liandi

Abstract


Cinnamaldehyde is a compound found in the skin of cinnamon plants which has various bioactivity. In this study, the compound cinnamaldehyde was modified with the help of Fe3O4 which was synthesized with the help of seaweed extract as a heterogeneous catalyst. Fe3O4-MNPs are synthesized using FeCl3 and Sargassum filipendula extracts as their natural reducing agents. The catalytic ability of Fe3O4 was evaluated in the reaction between cinnamaldehyde and aromatic ketone compounds synthesized by the reflux method. Structure Analysis and elucidation of the synthesized compounds were carried out by measuring the vibrations of the functional groups by FTIR, and the determination of H and C atoms by HNMR and CNMR analysis. The FTIR, proton and carbon NMR analysis have identified that the synthesized product was cinnamylideneacetophenone by the name 1,5-diphenylpyenta-2,4-dien-1-one. The optimum conditions were obtained at a catalyst concentration of 10% w/w for five hours with a yield of 36%. The yield of this reaction was better than the reaction without a catalyst.

Keywords


green synthesis, Fe3O4-MNPs, cinnamaldehyde, Sargassum filipendula

Full Text:

PDF

References


Benelli, G. (2019). Green synthesis of nanomaterials. Nanomaterials, 9(1257), 1–3. https://doi.org/10.3390/nano11082130

Cahyana, A., Fitria, D., Ardiansah, B., & Rahayu, D. (2017). Preparation of Fe3O4/SiO2-guanidine organobase catalyst for 1,5-diphenylpenta-2,4-dien-1-one synthesis. Journal of Physics: Conference Series, 188(012026), 1–5. https://doi.org/10.1088/1742-6596/755/1/011001

Cahyana, A. H., Liandi, A. R., Yunarti, R. T., Febriantini, D., & Ardiansah, B. (2019). Green synthesis of dihydropyrimidine based on cinnamaldehyde compound under solvent-free using graphene oxide as catalyst. AIP Conference Proceedings, 2168(November). https://doi.org/10.1063/1.5132496

Chng, L. L., Erathodiyil, N., & Ying, J. Y. (2013). Nanostructured catalysts for organic transformations. Accounts of Chemical Research, 46(8), 1825–1837. https://doi.org/10.1021/ar300197s

El-Kassas, H. Y., Aly-Eldeen, M. A., & Gharib, S. M. (2016). Green synthesis of iron oxide (Fe3O4) nanoparticles using two selected brown seaweeds: Characterization and application for lead bioremediation. Acta Oceanologica Sinica, 35(8), 89–98. https://doi.org/10.1007/s13131-016-0880-3

Fierascu, R. C., Ortan, A., Avramescu, S. M., & Fierascu, I. (2019). Phyto-nanocatalysts: Green synthes is characterization, and applications. Molecules, 24(19), 1–35. https://doi.org/10.3390/molecules24193418

Jo, Y. J., Chun, J. Y., Kwon, Y. J., Min, S. G., Hong, G. P., & Choi, M. J. (2015). Physical and antimicrobial properties of trans-cinnamaldehyde nanoemulsions in water melon juice. Lwt, 60(1), 444–451. https://doi.org/10.1016/j.lwt.2014.09.041

Khalaj, M., Kamali, M., Costa, M. E. V., & Capela, I. (2020). Green synthesis of nanomaterials - A scientometric assessment. Journal of Cleaner Production, 267, 122036. https://doi.org/10.1016/j.jclepro.2020.122036

Kharisov, B. I., Dias, H. V. R., & Kharissova, O. V. (2019). Mini-review: Ferrite nanoparticles in the catalysis. Arabian Journal of Chemistry, 12(7), 1234–1246. https://doi.org/10.1016/j.arabjc.2014.10.049

Liandi, A. R., Yunarti, R. T., Nurmawan, M. F., & Cahyana, A. H. (2020). The Utilization of Fe3O4 nanocatalyst in modifying cinnamaldehyde compound to Synthesis 2-amino-4H-chromene derivative. Materials Today: Proceedings, 22, 193–198. https://doi.org/10.1016/j.matpr.2019.08.087

Mahdavi, M., Ahmad, M. Bin, Haron, M. J., Namvar, F., Nadi, B., Ab Rahman, M. Z., & Amin, J. (2013). Synthesis, surface modification and characterisation of biocompatible magnetic iron oxide nanoparticles for biomedical applications. Molecules, 18(7), 7533–7548. https://doi.org/10.3390/molecules18077533

Mahdavian, A. R., & Mirrahimi, M. A. S. (2010). Efficient separation of heavy metal cations by anchoring polyacrylic acid on superparamagnetic magnetite nanoparticles through surface modification. Chemical Engineering Journal, 159(1–3), 264–271. https://doi.org/10.1016/j.cej.2010.02.041

Mahmoud, M. E., Abdou, A. E. H., & Nabil, G. M. (2015). Facile microwave-assisted fabrication of nano-zirconium silicate-functionalized-3-aminopropyltrimethoxysilane as a novel adsorbent for superior removal of divalent ions. Journal of Industrial and Engineering Chemistry, 32, 365–372. https://doi.org/10.1016/j.jiec.2015.09.005

Nasir Baig, R. B., Nadagouda, M. N., & Varma, R. S. (2015). Magnetically retrievable catalysts for asymmetric synthesis. Coordination Chemistry Reviews, 287, 137–156. https://doi.org/10.1016/j.ccr.2014.12.017

Rajendaran, K., Muthuramalingam, R., & Ayyadurai, S. (2019). Green synthesis of Ag-Mo/CuO nanoparticles using Azadirachta indica leaf extracts to study its solar photocatalytic and antimicrobial activities. Materials Science in Semiconductor Processing, 91(September 2018), 230–238. https://doi.org/10.1016/j.mssp.2018.11.021

Sadjadi, S., Malmir, M., & Heravi, M. M. (2017). A green approach to the synthesis of Ag doped nano magnetic γ-Fe2O3@SiO2-CD core-shell hollow spheres as an efficient and heterogeneous catalyst for ultrasonic-assisted A3 and KA2 coupling reactions. RSC Advances, 7(58), 36807–36818. https://doi.org/10.1039/c7ra04635a

Salem, D. M. S. A., Ismail, M. M., & Aly-Eldeen, M. A. (2019). Biogenic synthesis and antimicrobial potency of iron oxide (Fe3O4) nanoparticles using algae harvested from the Mediterranean Sea, Egypt. Egyptian Journal of Aquatic Research, 45(3), 197–204. https://doi.org/10.1016/j.ejar.2019.07.002

Wang, H., Yuan, H., Li, S., Li, Z., & Jiang, M. (2016). Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids. Bioorganic and Medicinal Chemistry Letters, 26(3), 809–813. https://doi.org/10.1016/j.bmcl.2015.12.089

Yen, T. B., & Chang, S. T. (2008). Synergistic effects of cinnamaldehyde in combination with eugenol against wood decay fungi. Bioresource Technology, 99(1), 232–236. https://doi.org/10.1016/j.biortech.2006.11.022

Yew, Y. P., Shameli, K., Miyake, M., Kuwano, N., Bt Ahmad Khairudin, N. B., Bt Mohamad, S. E., & Lee, K. X. (2016). Green Synthesis of Magnetite (Fe3O4) Nanoparticles Using Seaweed (Kappaphycus alvarezii) Extract. Nanoscale Research Letters, 11(1). https://doi.org/10.1186/s11671-016-1498-2




DOI: http://dx.doi.org/10.30870/educhemia.v6i2.10412

Refbacks

  • There are currently no refbacks.


Copyright (c) 2022 dori fitria

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

EduChemia Indexed by:

   

                                                                                                                                                                                                                                                 More Indecxing...                                                         

Creative Commons License

EduChemia: Jurnal Kimia dan Pendidikan is licensed under a Creative Commons Attribution 4.0 International License

________________________________________________________

EduChemia: Jurnal Kimia dan Pendidikan ISSN 2502-4779 (print) | ISSN 2502-4787 (online)
Published by Department of Chemistry Education - Universitas Sultan Ageng Tirtayasa
Address : Jl. Ciwaru Raya No. 25, Sempu, Kota Serang, Banten 42117, Indonesia
Email  : [email protected]