Carbon letters

  • Volume 27
  • /
  • Pages.42-49
  • /
  • 2018
  • /
  • 1976-4251(pISSN)
  • /
  • 2233-4998(eISSN)
Korean Carbon Society (한국탄소학회)
권호 표지
DOI QR코드

DOI QR Code

Surface modification of graphene oxide by citric acid and its application as a heterogeneous nanocatalyst in organic condensation reaction

  • Maleki, Ali (Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology) ;
  • Hajizadeh, Zoleikha (Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology) ;
  • Abbasi, Hamid (Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology)
  • Received : 2017.12.25
  • Accepted : 2018.02.19
  • Published : 2018.07.31
Download PDF
⟨ Previous Next ⟩

Abstract

A citric acid functionalized graphene oxide nanocomposite was successfully synthesized and the structure and morphology of the nanocatalyst were comprehensively characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, X-ray diffraction patterns, atomic force microscopy images, scanning electron microscopy images, transmission electron microscopy images, and thermogravimetric analysis. The application of this nanocatalyst was exemplified in an important condensation reaction to give imidazole derivatives in high yields and short reaction times at room temperature. The catalyst shows high catalytic activity and could be reused after simple work up and easy purification for at least six cycles without significant loss of activity, which indicates efficient immobilizing of citrate groups on the surface of graphene oxide sheets.

Keywords

References

  1. Maleki A, Hajizadeh Z, Firouzi-Haji R. Eco-friendly functionalization of magnetic halloysite nanotube with $SO_3H$ for synthesis of dihydropyrimidinones. Micropor Mesopor Mater, 259, 46 (2018). https://doi.org/10.1016/j.micromeso.2017.09.034.
  2. Maleki A, Ghassemi M, Firouzi-Haji R. Green multicomponent synthesis of four different classes of six-membered N-containing and O-containing heterocycles catalyzed by an efficient chitosanbased magnetic bionanocomposite. Pure Appl Chem, 90, 387 (2018). https://doi.org/10.1515/pac-2017-0702.
  3. Maleki A, Firouzi-Haji R, Hajizadeh Z, Magnetic guanidinylated chitosan nanobiocomposite: A green catalyst for the synthesis of 1,4-dihydropyridinesInt. J Biol Macromol, 116, 320 (2018). https://doi.org/10.1016/j.ijbiomac.2018.05.035
  4. Mahesh R, Dhar AK, Tara Sasank TVNV, Thirunavukkarasu S, Devadoss T. Citric acid: an efficient and green catalyst for rapid one pot synthesis of quinoxaline derivatives at room temperature. Chin Chem Lett, 22, 389 (2011). https://doi.org/10.1016/j.cclet.2010.11.002.
  5. Chen JP, Wu S, Chong KH. Surface modification of a granular activated carbon by citric acid for enhancement of copper adsorption. Carbon, 41, 1979 (2003). https://doi.org/10.1016/s0008-6223(03)00197-0.
  6. Namvari M, Namazi H. Synthesis of magnetic citric-acid-functionalized graphene oxide and its application in the removal of methylene blue from contaminated water. Polym Int, 63, 1881 (2014). https://doi.org/10.1002/pi.4769.
  7. Ghonchepour E, Nakisa A, Heydari A. Citric acid coated magnetite nanoparticles: an efficient and reusable green catalyst for rapid acetylation of alcohols and phenols. Org Chem Res, 12, 96 (2016).
  8. Huang J, Ding S, Xiao W, Peng Y, Deng S, Zhang N. 3-Aminopropyl-triethoxysilane functionalized graphene oxide: a highly efficient and recyclable catalyst for Knoevenagel condensation. Catalysis Lett, 145, 1000 (2014). https://doi.org/10.1007/s10562-014-1461-8.
  9. Maleki A, Paydar R. Bionanostructure-catalyzed one-pot threecomponent synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives under solvent-free conditions. React Funct Polym, 109, 120 (2016). https://doi.org/10.1016/j.reactfunctpolym.2016.10.013.
  10. Pant B, Park M, Jang RS, Choi WC, Kim HY, Park SJ. Synthesis, characterization, and antibacterial performance of Ag-modified graphene oxide reinforced electrospun polyurethane nanofibers. Carbon Lett, 23, 17 (2017). https://doi.org/10.5714/CL.2017.23.017.
  11. Park J, Song C, Sun Q, Jung Y, Kim S. Catalytic activity and controllable deposition of platinum nanoparticles on ionic polymer-functionalized graphene as catalysts for direct methanol fuel cells. Carbon Lett, 16, 260 (2015). https://doi.org/10.5714/cl.2015.16.4.260.
  12. Shelke KF, Sapkal SB, Kakade GK, Shingate BB, Shingare MS. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot synthesis of 2,4,5-triarylimidazoles under microwave irradiation. Green Chem Lett Rev, 3, 27 (2010). https://doi.org/10.1080/17518250903505246.
  13. Maleki B, Shirvan HK, Taimazi F, Akbarzadeh E. Sulfuric acid immobilized on silica gel as highly efficient and heterogeneous catalyst for the one-pot synthesis of 2,4,5-triaryl-1H-imidazoles. Int J Org Chem, 2, 93 (2012). https://doi.org/10.4236/ijoc.2012.21015.
  14. Wang XC, Gong HP, Quan ZJ, Li L, Ye HL. PEG-400 as an efficient reaction medium for the synthesis of 2,4,5-triaryl-1H-imidazoles and 1,2,4,5-tetraaryl-1H-imidazoles. Chin Chem Lett, 20, 44 (2009). https://doi.org/10.1016/j.cclet.2008.10.005.
  15. Maleki A, Paydar R. Graphene oxide-chitosan bionanocomposite: a highly efficient nanocatalyst for the one-pot three-component synthesis of trisubstituted imidazoles under solvent-free conditions. RSC Adv, 5, 33177 (2015). https://doi.org/10.1039/c5ra03355a.
  16. Heravi MM, Sadjadi S, Oskooie HA, Hekmatshoar R, Bamoharram FF. The one-pot synthesis of 2,4,5-triaryl-imidazoles using heteropolyacids as heterogeneous and recyclable catalysts. J Chin Chem Soc, 55, 1199 (2008). https://doi.org/10.1002/jccs.200800178.
  17. Hummers WS, Offeman RE. Preparation of graphitic oxide. J Am Chem Soc, 80, 1339 (1958). https://doi.org/10.1021/ja01539a017.
  18. Yao Y, Miao S, Liu S, Ma LP, Sun H, Wang S. Synthesis, characterization, and adsorption properties of magnetic $Fe_3O_4$@graphene nanocomposite. Chem Eng J, 184, 326 (2012). https://doi.org/10.1016/j.cej.2011.12.017.
  19. Yang Q, Pan X, Clarke K, Li K. Covalent functionalization of graphene with polysaccharides. Ind Eng Chem Res, 51, 310 (2011). https://doi.org/10.1021/ie201391e.
  20. Paredes JI, Villar-Rodil S, Martinez-Alonso A, Tascon JMD. Graphene oxide dispersions in organic solvents. Langmuir, 24, 10560 (2008). https://doi.org/10.1021/la801744a.
  21. Hanawalt JD, Rinn HW, Frevel LK. Chemical analysis by X-ray diffraction. Ind Eng Chem Anal Ed, 10, 457 (1938). https://doi.org/10.1021/ac50125a001.
  22. Hsiao MC, Ma CCM, Chiang JC, Ho KK, Chou TY, Xie X, Tsai CH, Chang LH, Hsieh CK. Thermally conductive and electrically insulating epoxy nanocomposites with thermally reduced graphene oxide–silica hybrid nanosheets. Nanoscale, 5, 5863 (2013). https://doi.org/10.1039/c3nr01471a.
  23. Heravi MM, Tajbakhsh M, Ahmadi AN, Mohajerani B. Zeolites. Efficient and eco-friendly catalysts for the synthesis of benzimidazoles. Monatsh Chem, 137, 175 (2005). https://doi.org/10.1007/s00706-005-0407-7.
  24. Shirini F, Abedini M, Seddighi M, Arbosara FS. Preparation, characterization, and application of 1,1′-disulfo-[2,2′-bipyridine]-1,1′-diium chloride ionic liquid as an efficient catalyst for the synthesis of benzimidazole derivatives. Res Chem Intermed, 41, 7683 (2014). https://doi.org/10.1007/s11164-014-1852-x.
  25. Mobinikhaledi A, Zendehdel M, Goudarzi F, Rezanejade Bardajee G. Nano-Ni(II)/Y zeolite catalyzed synthesis of 2-aryl- and 2-alkyl benzimidazoles under solvent-free conditions. Synth React Inorg Met Org Nano Met Chem, 46, 1526 (2016). https://doi.org/10.1080/15533174.2015.1137020.
  26. Ghafuri H, Esmaili E, Talebi M. $Fe_3O_4@SiO_2$/collagen: an efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives. C R Chim, 19, 942 (2016). https://doi.org/10.1016/j.crci.2016.05.003.
  27. Bahrami K, Khodaei MM, Nejati A. Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles. Green Chem, 12, 1237 (2010). https://doi.org/10.1039/c000047g.
  28. Eshghi H, Rahimizadeh M, Shiri A, Sedaghat P. One-pot synthesis of benzimidazoles and benzothiazoles in the presence of $Fe(HSO_4)_3$ as a new and efficient oxidant. Bull Korean Chem Soc, 33, 515 (2012). https://doi.org/10.5012/bkcs.2012.33.2.515.
  29. Lakshman S. Gadekar, Balasaheb R. Arbad, Machhindra K. Lande. Eco-friendly synthesis of benzimidazole derivatives using solid acid scolecite catalyst. Chin Chem Lett, 21, 1053 (2010). https://doi.org/10.1016/j.cclet.2010.03.038.
  30. Ravi O, Shaikh A, Upare A, Singarapu KK, Bathula SR. Benzimidazoles from aryl alkyl ketones and 2-amino anilines by an iodine catalyzed oxidative C(CO)-C(alkyl) bond cleavage. J Org Chem, 82, 4422 (2017). https://doi.org/10.1021/acs.joc.7b00165.
  31. Naeimi H, Alishahi N. A simple, mild and efficient one-pot synthesis of 2-substituted benzimidazoles in the presence of $H_2O_2/HCl$ under microwave irradiation. J Chin Chem Soc, 59, 1001 (2012). https://doi.org/10.1002/jccs.201100591.
  32. Mobinikhaledi A, Zendehdel M, Goudarzi F, Bardajee GR. Nano-Ni(II)/Y zeolite catalyzed synthesis of 2-aryl- and 2-alkyl benzimidazoles under solvent-free conditions. Synth React Inorg Met Org Nano Met Chem, 46, 1526 (2016). https://doi.org/10.1080/15533174.2015.1137020.
  33. Feizpour F, Jafarpour M, Rezaeifard A. A tandem aerobic photocatalytic synthesis of benzimidazoles by cobalt ascorbic acid complex coated on $TiO_2$ nanoparticles under visible light. Catal Lett, 148, 30 (2017). https://doi.org/10.1007/s10562-017-2232-0.