10.1007/s40097-021-00417-6

Cu–curcumin/MCM-41 as an efficient catalyst for in situ conversion of carbazole to fuel oxygenates: a DOE approach

  1. Department of Chemistry, South Tehran Branch, Islamic Azad University, Tehran, 11365-4435, IR
  2. Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, 18735-136, IR

Published in Issue 13-07-2021

How to Cite

Rahmati, M. S., Fazaeli, R., Saravani, M. G., & Ghiasi, R. (2021). Cu–curcumin/MCM-41 as an efficient catalyst for in situ conversion of carbazole to fuel oxygenates: a DOE approach. Journal of Nanostructure in Chemistry, 12(3 (June 2022). https://doi.org/10.1007/s40097-021-00417-6

Abstract

Abstract In this study, the copper(II)–curcumin and copper(I)–curcumin complexes were immobilized onto the Mobil Composition of Matter No. 41 (MCM‐41) nanostructure, which have inherent advantages in the field of green chemistry and have been used as the catalyst for the removal of the carbazole (C 12 H 9 N) from the oil cut. The structures of the synthesized complexes were studied by Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), field emission scanning electron microscopy (FESEM), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), thermogravimetric analysis (TGA), Barret–Joyner–Halenda (BJH), and mapping techniques. Also, using the techniques and procedures in gas chromatography–mass spectrometry (GC–MS) were identified the products in the removal process. In this method, the use of Ultra-Violet (UV) light in the presence of a suitable solvent and perfect N -compounds removal from oil cut through advanced oxidation have led to the production of by-products that can function similarly to fuel octane number additives under an aldol condensation reaction. In this study, the performance of optimum catalyst was also compared under UV and visible light conditions.

Keywords

  • MCM-41 nanostructure,
  • Copper(II),
  • Copper(I),
  • Curcumin,
  • Advanced oxidation,
  • Carbazole,
  • Fuel oxygenates

References

  1. Cho and Lee (2014) Effects of nitrogen compounds, aromatics, and aprotic solvents on the oxidative desulfurization (ODS) of light cycle oil over Ti-SBA-15 catalyst (pp. 35-42) https://doi.org/10.1016/j.apcatb.2013.08.017
  2. Ahmed et al. (2013) Effect of catalyst deactivation on vacuum residue hydrocracking 22(3) (pp. 367-372) https://doi.org/10.1016/j.ejpe.2013.10.006
  3. Medel et al. (2019) Evaluating the electrochemical and photoelectrochemical production of hydroxyl radical during electrocoagulation process (pp. 59-67) https://doi.org/10.1016/j.seppur.2018.05.021
  4. Zhang et al. (2017) Extraction and mechanism for the separation of neutral N-compounds from coal tar by ionic liquids (pp. 27-35) https://doi.org/10.1016/j.fuel.2016.12.095
  5. Khoshkarvandani et al. (2021) Mesoporous MCM-41 modified with Cu (II) for indole removal: a Taguchi design 10(1) (pp. 1-8) https://doi.org/10.5267/j.ccl.2020.4.002
  6. Palomeque-Santiago et al. (2018) Deep oxidative desulfurization with simultaneous oxidative denitrogenation of diesel fuel and straight run gas oil (pp. 326-337) https://doi.org/10.1016/j.apcatb.2018.04.079
  7. Laredo et al. (2016) Comparison of the metal–organic framework MIL-101 (Cr) versus four commercial adsorbents for nitrogen compounds removal in diesel feedstocks (pp. 284-291) https://doi.org/10.1016/j.fuel.2016.04.038
  8. Vandani et al. (2021) Preparation of Ni/CuO/MCM-41 for indole oxidation: optimization by DOE (pp. 1-11)
  9. Meng et al. (2021) Electrospun nanofibers of Pd-doped α-Bi2O3 for enhancing photocatalytic denitrification of fuel oil under visible light https://doi.org/10.1016/j.mssp.2020.105359
  10. Albinati et al. (1985) Reactions of cyclopalladated benzylidene-aniline Schiff's base complexes selective synthesis of 2′-substituted Schiff's base derivatives and the X-ray crystal structure of the dimer [Pd (μ-OAc) (5′-OCH3 C6H3 CH NC6H4-4-CH3)]2 68(7) (pp. 2046-2061) https://doi.org/10.1002/hlca.19850680730
  11. Mondol et al. (2021) A remarkable adsorbent for removal of nitrogenous compounds from fuel: a metal–organic framework functionalized both on metal and ligand https://doi.org/10.1016/j.cej.2020.126491
  12. Van de Voorde et al. (2014) Adsorptive separation on metal–organic frameworks in the liquid phase 43(16) (pp. 5766-5788) https://doi.org/10.1039/C4CS00006D
  13. Asumana et al. (2011) Extractive denitrogenation of fuel oils with dicyanamide-based ionic liquids 13(11) (pp. 3300-3305) https://doi.org/10.1039/c1gc15747g
  14. Nikoorazm et al. (2016) Immobilization of a vanadium complex onto functionalized nanoporous MCM-41 and its application as a catalyst for the solvent-free chemoselective oxidation of sulfide to sulfoxide 30(4) (pp. 236-241) https://doi.org/10.1002/aoc.3422
  15. Kalyani and Gurunathan (2020) Composites of π-stacking materials with low-dimensional metal oxide nanoblends for photocatalytic hydrogen production 10(2) (pp. 169-177) https://doi.org/10.1007/s40097-020-00339-9
  16. Hasanzadeh et al. (2013) Mesoporous silica (MCM-41)-Fe2O3 as a novel magnetic nanosensor for determination of trace amounts of amino acids (pp. 52-59) https://doi.org/10.1016/j.colsurfb.2013.02.015
  17. Jae et al. (2011) Investigation into the shape selectivity of zeolite catalysts for biomass conversion 279(2) (pp. 257-268) https://doi.org/10.1016/j.jcat.2011.01.019
  18. Li et al. (2020) Hierarchical mesoporous ZSM-5 supported nickel catalyst for the catalytic hydrodeoxygenation of anisole to cyclohexane https://doi.org/10.1016/j.mcat.2019.110642
  19. Nikoorazm and Jabbari (2017) Synthesis and characterization of M-5NSA-MCM-41, (M = Cr, Fe) as reusable catalysts for the selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols into disulfides in the presence of H2O2 24(2) (pp. 477-486) https://doi.org/10.1007/s10934-016-0283-z
  20. Wen et al. (2014) Recent advances in silver-based heterogeneous catalysts for green chemistry processes (pp. 730-741) https://doi.org/10.1016/j.apcatb.2014.06.016
  21. Nikoorazm et al. (2020) Two Schiff-base complexes of copper and zirconium oxide supported on mesoporous MCM-41 as an organic–inorganic hybrid catalysts in the chemo and homoselective oxidation of sulfides and synthesis of tetrazoles (pp. 1-19)
  22. Salavati-Niasari et al. (2006) Alumina-supported Mn (II), Co (II), Ni (II) and Cu (II) N, N-bis (salicylidene)-2, 2-dimethylpropane-1, 3-diamine complexes: synthesis, characterization and catalytic oxidation of cyclohexene with tert-butylhydroperoxide and hydrogen peroxide 7(12) (pp. 955-962) https://doi.org/10.1016/j.catcom.2006.04.005
  23. Antony et al. (2018) Ethoxysilane appended M (II) complexes and their SiO2/MCM-41 supported forms as catalysts for efficient oxidation of secondary alcohols (pp. 173-182) https://doi.org/10.1016/j.ica.2017.09.024
  24. Taebnia et al. (2016) Curcumin-loaded amine-functionalized mesoporous silica nanoparticles inhibit α-synuclein fibrillation and reduce its cytotoxicity-associated effects 32(50) (pp. 13394-13402) https://doi.org/10.1021/acs.langmuir.6b02935
  25. Moradi et al. (2020) Removal of heavy metal ions using a new high performance nanofiltration membrane modified with curcumin boehmite nanoparticles https://doi.org/10.1016/j.cej.2020.124546
  26. Fard et al. (2019) Oxidation of carbazole by shape-controllable Cu2O on MWW catalysis 125(9) https://doi.org/10.1007/s00339-019-2918-9
  27. Lima et al. (2019) Concurrent desulfurization and denitrogenation of fuels using deep eutectic solvents 7(13) (pp. 11341-11349) https://doi.org/10.1021/acssuschemeng.9b00877
  28. Zarrinabadi et al. (2018) Environmental effects of enhancement of mechanical and hydrophobic properties of polyester fabrics using silica/kaolinite/silver nanocomposite: a facile technique for synthesis and RSM optimization 12(2) (pp. 437-450)
  29. Sahne et al. (2016) Extraction of bioactive compound curcumin from turmeric (Curcuma longa L.) via different routes: a comparative study 13(3) (pp. 173-180)
  30. Nikoorazm et al. (2015) Oxo-vanadium (IV) Schiff base complex supported on modified MCM-41: a reusable and efficient catalyst for the oxidation of sulfides and oxidative S–S coupling of thiols 29(5) (pp. 328-333) https://doi.org/10.1002/aoc.3295
  31. AbouAitah et al. (2016) pH-controlled release system for curcumin based on functionalized dendritic mesoporous silica nanoparticles 7(1)
  32. Mohammadnezhad et al. (2017) A novel porous nanocomposite of aminated silica MCM-41 and nylon-6: Isotherm, kinetic, and thermodynamic studies on adsorption of Cu (II) and Cd (II) 134(40) https://doi.org/10.1002/app.45383
  33. Keefer and Andrews (1958) The equilibration of iodobenzene dichlorides with their components in nitromethane 80(20) (pp. 5350-5355) https://doi.org/10.1021/ja01553a008
  34. Mohamed et al. (2020) The photocatalytic performance of silica fume based Co3O4/MCM-41 green nanocomposite for instantaneous degradation of Omethoate pesticide under visible light https://doi.org/10.1016/j.jphotochem.2020.112434
  35. Ambrogi et al. (2012) MCM-41 for furosemide dissolution improvement 147(1) (pp. 343-349) https://doi.org/10.1016/j.micromeso.2011.07.007
  36. Speakman, S.A.: Introduction to x-ray powder diffraction data analysis. Cent. Mater. Sci. Eng. MIT (2013)
  37. Ghorbani-Choghamarani et al. (2015) Anchoring of Pd (II) complex in functionalized MCM-41 as an efficient and recoverable novel nano catalyst in C–C, C–O and C–N coupling reactions using Ph 3 SnCl 5(42) (pp. 33212-33220) https://doi.org/10.1039/C5RA01934F
  38. Ghorbani-Choghamarani et al. (2019) Covalent immobilization of Co complex on the surface of SBA-15: green, novel and efficient catalyst for the oxidation of sulfides and synthesis of polyhydroquinoline derivatives in green condition (pp. 25-35) https://doi.org/10.1016/j.poly.2018.10.054
  39. Moradi et al. (2020) Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents https://doi.org/10.1016/j.poly.2019.114169
  40. Khanmoradi et al. (2017) Anchoring of Cu (II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides 31(9) https://doi.org/10.1002/aoc.3693
  41. Martin et al. (2017) Zinc and Chromium elimination from complex aqueous matrices using a unique aminopropyl-modified MCM-41 sorbent: temperature, kinetics and selectivity studies 5(1) (pp. 1210-1218) https://doi.org/10.1016/j.jece.2017.02.003
  42. Bollu et al. (2016) Curcumin-loaded silica-based mesoporous materials: Synthesis, characterization and cytotoxic properties against cancer cells (pp. 393-410) https://doi.org/10.1016/j.msec.2016.03.011
  43. Kim et al. (2015) pH-and glutathione-responsive release of curcumin from mesoporous silica nanoparticles coated using tannic acid–Fe (iii) complex 5(110) (pp. 90550-90558) https://doi.org/10.1039/C5RA16004A
  44. Barrientos et al. (2013) Group additivity in soot formation for the example of C-5 oxygenated hydrocarbon fuels 160(8) (pp. 1484-1498) https://doi.org/10.1016/j.combustflame.2013.02.024
  45. Borders (1972) ACS Publications
  46. Klzilkilic et al. (1980) The photolysis of tetrahydrofuran and of some of its methyl derivatives at 185 nm 58(24) (pp. 2819-2826) https://doi.org/10.1139/v80-452
  47. Chakraborty (1993) Chemistry and biology of carbazole alkaloids (pp. 257-364) Academic Press
  48. Kamani et al. (2020) Synthesis of CuO/MCM-41 photocatalyst nanocomposite, mechanistic study and optimization of quinoline oxidative degradation without auxiliary oxidant using response surface methodology 8(1) (pp. 175-202)
  49. Saadi et al. (2015) Monolayer and multilayer adsorption isotherm models for sorption from aqueous media 32(5) (pp. 787-799) https://doi.org/10.1007/s11814-015-0053-7
  50. Ebrahimi-Gatkash et al. (2017) Amino-functionalized mesoporous MCM-41 silica as an efficient adsorbent for water treatment: batch and fixed-bed column adsorption of the nitrate anion 7(4) (pp. 1887-1901) https://doi.org/10.1007/s13201-015-0364-1
  51. Fard and Fazaeli (2018) Optimization of operating parameters in photocatalytic activity of visible light active Ag/TiO2 nanoparticles 92(13) (pp. 2835-2846) https://doi.org/10.1134/S0036024418130071
  52. Kamani et al. (2020) PROMOTION OF catalytic properties of vanillin loaded MCM-41 by Cu (I) and Cu (II) for enhanced removal of quinoline contaminats 65(2) (pp. 4833-4841) https://doi.org/10.4067/S0717-97072020000204833