Skip to main content
SpringerLink
Log in

Green synthesis of novel nitrogen-rich covalent organic polymer for efficient removal of methylene blue from aqueous solutions

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

A novel nitrogen-rich covalent organic polymer was synthesized through a green synthetic approach by reacting 4,4'-diaminodiphenylsulfone and 4,4',4''-((1,3,5-triazine-2,4,6-triyl)tris(azanediyl))tribenzoic acid. The reaction was conducted under environmentally friendly conditions, utilizing tetra butyl ammonium bromide as a green solvent and triphenyl phosphite as a catalyst. The structure and morphology of the synthesized adsorbent were recognized using TGA, BET, XRD, FT-IR, EDX-Mapping, and FE-SEM analyses. Following characterization, the synthesized adsorbent was employed for the purpose of methylene blue (MB) dye removal. Multiple parameters, including pH, time duration, and initial concentration, were systematically assessed and analyzed. Based on isotherm models, Langmuir was fitted suitably to the experimental data of MB with maximum adsorption of 384.6 mg g−1 at pH 10 in 40 min. After examining the linear regression coefficients (R2), it was determined that the pseudo-second-order model provided a good fit for adsorbing MB.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Aliabadi HM, Zargoosh K, Afshari M, Dinari M, Maleki MH (2021) Synthesis of a luminescent g-C3N4–WO3–Bi2WO6/SrAl2O4:Eu2+, Dy3+ nanocomposite as a double z-scheme sunlight activable photocatalyst. New J Chem 45:4843–4853

    Article  CAS  Google Scholar 

  2. Alencar LV, Passos LM, Soares CM, Lima AS, Souza RL (2020) Efficiency method for methylene blue recovery using aqueous two-phase systems based on cholinium-ionic liquids. CTFTTE 6:13–20

    Article  Google Scholar 

  3. Ahmad A, Mohd-Setapar SH, Chuong CS, Khatoon A, Wani WA, Kumar R, Rafatullah M (2015) Recent advances in new generation dye removal technologies: novel search for approaches to reprocess wastewater. RSC Adv 5:30801–30818

    Article  CAS  Google Scholar 

  4. Sheng L, Zhang Y, Tang F, Liu S (2018) Mesoporous/microporous silica materials: preparation from natural sands and highly efficient fixed-bed adsorption of methylene blue in wastewater. Microporous Mesoporous Mater 257:9–18

    Article  CAS  Google Scholar 

  5. Pandey S, Do JY, Kim J, Kang M (2020) Fast and highly efficient removal of dye from aqueous solution using natural locust bean gum based hydrogels as adsorbent. Int J Biol Macromol 143:60–75

    Article  CAS  PubMed  Google Scholar 

  6. Fong W, Affam A, Chung W (2020) Synthesis of Ag/Fe/CAC for colour and COD removal from methylene blue dye wastewater. Int J Environ Sci Technol 17:3485–3494

    Article  CAS  Google Scholar 

  7. Pang Y, Tong Z-H, Tang L, Liu Y-N, Luo K (2018) Effect of humic acid on the degradation of methylene blue by peroxymonosulfate. Open Chem 16:401–406

    Article  CAS  Google Scholar 

  8. Sun L, Hu D, Zhang Z, Deng X (2019) Oxidative degradation of methylene blue via PDS-based advanced oxidation process using natural pyrite. Int J Environ Res Public Health 16:4773

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Rahmanian O, Maleki MH, Dinari M (2017) Ultrasonically assisted solvothermal synthesis of novel Ni/Al layered double hydroxide for capturing of Cd (II) from contaminated water. J Phys Chem Solids 110:195–201

    Article  CAS  Google Scholar 

  10. Dinari M, Shirani MA, Maleki MH, Tabatabaeian R (2020) Green cross-linked bionanocomposite of magnetic layered double hydroxide/guar gum polymer as an efficient adsorbent of Cr (VI) from aqueous solution. Carbohyd Polym 236:116070

    Article  CAS  Google Scholar 

  11. Dinari M, Maleki MH, Bagheri R (2019) Synthesis and characterization of new nitrogen-and oxygen-rich cyclohexanone–formaldehyde resin for fast Cd (II) adsorption in aqueous solution. Polym Int 68:1636–1644

    Article  CAS  Google Scholar 

  12. Fu X, Chen X, Wang J, Liu J (2011) Fabrication of carboxylic functionalized superparamagnetic mesoporous silica microspheres and their application for removal basic dye pollutants from water. Microporous Mesoporous Mater 139:8–15

    Article  CAS  Google Scholar 

  13. Ghoreishi S, Haghighi R (2003) Chemical catalytic reaction and biological oxidation for treatment of non-biodegradable textile effluent. Chem Eng J 95:163–169

    Article  CAS  Google Scholar 

  14. Santiago AA, Ibarra-Palos A, Cruz-Morales JA, Sierra JM, Abatal M, Alfonso I, Vargas J (2017) Synthesis, characterization, and heavy metal adsorption properties of sulfonated aromatic polyamides. High Perform Polym 30:591–601

    Article  Google Scholar 

  15. Higashi F, Nishi T (1986) Direct polyamidation with thionyl chloride in N-methyl-pyrrolidone. J Polym Sci Part A Polym Chem 24:701–706

    Article  CAS  Google Scholar 

  16. Dinari M, Haghighi A (2017) Synthesis and characterization of new heat-resistant polyamides bearing an s-triazine ring under green conditions. J Polym Res 24:1–9

    Article  CAS  Google Scholar 

  17. Dinari M, Fardmanesh K, Maleki MH, Asadi P (2022) Synthesis, characterization and antimicrobial properties of new L-cysteine based chiral aromatic polyamides. Polym Bull 79:11103–11117

    Article  CAS  Google Scholar 

  18. Dutta S, Gupta B, Srivastava SK, Gupta AK (2021) Recent advances on the removal of dyes from wastewater using various adsorbents: a critical review. Mater Adv 2(14):4497–4531

    Article  CAS  Google Scholar 

  19. Wang B, Zhang Q, Xiong G, Ding F, He Y, Ren B, You L, Fan X, Hardacre C, Sun Y (2019) Bakelite-type anionic microporous organic polymers with high capacity for selective adsorption of cationic dyes from water. Chem Eng J 366:404–414

    Article  CAS  Google Scholar 

  20. Zhu X, An S, Liu Y, Hu J, Liu H, Tian C, Dai S, Yang X, Wang H, Abney CW (2017) Efficient removal of organic dye pollutants using covalent organic frameworks. AIChE J 63:3470–3478

    Article  CAS  Google Scholar 

  21. Huang L, He M, Chen B, Hu B (2018) Magnetic Zr-MOFs nanocomposites for rapid removal of heavy metal ions and dyes from water. Chemosphere 199:435–444

    Article  CAS  PubMed  Google Scholar 

  22. Dinari M, Nabiyan A, Ensafi AA, Jafari-Asl M (2015) Polybenzimidazole and polybenzimidazole/MoS 2 hybrids as an active nitrogen sites: hydrogen generation application. RSC Adv 5:100996–101005

    Article  CAS  Google Scholar 

  23. Mallakpour S, Zadehnazari A (2013) The production of functionalized multiwall carbon nanotube/amino acid-based poly (amide–imide) composites containing a pendant dopamine moiety. Carbon 56:27–37

    Article  CAS  Google Scholar 

  24. Kithome M (1998) Reducing nitrogen losses during composting of poultry manure using the natural zeolite clinoptilolite. University of British Columbia

    Google Scholar 

  25. Tahir S, Rauf N (2006) Removal of a cationic dye from aqueous solutions by adsorption onto bentonite clay. Chemosphere 63:1842–1848

    Article  CAS  PubMed  Google Scholar 

  26. Haque E, Jun JW, Jhung SH (2011) Adsorptive removal of methyl orange and methylene blue from aqueous solution with a metal-organic framework material, iron terephthalate (MOF-235). J Hazard Mater 185:507–511

    Article  CAS  PubMed  Google Scholar 

  27. He Y, Xu T, Hu J, Peng C, Yang Q, Wang H, Liu H (2017) Amine functionalized 3D porous organic polymer as an effective adsorbent for removing organic dyes and solvents. RSC Adv 7:30500–30505

    Article  CAS  Google Scholar 

  28. Taşdelen B, Çifçi Dİ, Meriç S (2017) Preparation of N-isopropylacrylamide/itaconic acid/Pumice highly swollen composite hydrogels to explore their removal capacity of methylene blue. Colloids Surf A 519:245–253

    Article  Google Scholar 

  29. Ma D, Zhu B, Cao B, Wang J, Zhang J (2017) Fabrication of the novel hydrogel based on waste corn stalk for removal of methylene blue dye from aqueous solution. Appl Surf Sci 422:944–952

    Article  CAS  Google Scholar 

  30. Kuang Y, Zhang X, Zhou S (2020) Adsorption of methylene blue in water onto activated carbon by surfactant modification. Water 12:587

    Article  Google Scholar 

  31. Rahmanian O, Falsafin M, Dinari M (2020) High surface area benzimidazole based porous covalent organic framework for removal of methylene blue from aqueous solutions. Polym Int 69:712–718

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to sincerely acknowledge the cooperation and resources made available to us by the Isfahan University of Technology, IRAN and the Iranian National Science Foundation (INSF) for their financial (Grant No. 4026090) support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran

    Saed Arameshian, Mohammad Dinari & Fariba Rezaei

Authors
  1. Saed Arameshian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Dinari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fariba Rezaei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Dinari.

Ethics declarations

Conflict of interests

The authors declare no competing financial or nonfinancial interests that are directly or indirectly related to this work.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Arameshian, S., Dinari, M. & Rezaei, F. Green synthesis of novel nitrogen-rich covalent organic polymer for efficient removal of methylene blue from aqueous solutions. J Polym Res 31, 97 (2024). https://doi.org/10.1007/s10965-024-03943-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-024-03943-3

Keywords

Search

Navigation