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Development of a Silica-Organic Framework Ionic Solid Bronsted Acid Catalyst for the Synthesis of 2,4,5-trisubstituted Imidazole Derivatives

Year 2025, Volume: 12 Issue: 1, 1 - 14, 03.03.2025
https://doi.org/10.18596/jotcsa.1515088

Abstract

Heterogeneous Bronsted acid is one of the most promising compounds that can be used as a catalyst in chemical production, and that can certainly have a positive impact on the environment. This research includes the preparation of heterogeneous Bronsted acid by using rice hulls as a starting material. The prepared acid was characterized by FTIR, XRD, TGA, SEM-EDX, TEM, and elemental analysis. The FTIR results showed the presence of N-H and S=O absorption bands within the expected range in prepared Bronsted acid. The specific surface area of the catalyst determined by Brunauer-Emmett-Teller (BET) using the nitrogen adsorption method is 205.42 m2/g, and the average pore diameters are 3.69 nm, 2,4,5-Trisubstituted imidazole derivatives were prepared by reacting substituted aldehydes with benzil and ammonium acetate in the presence of a solid acid catalyst. The main advantages of this method are safe, cheap, and short reaction conditions. In addition, the prepared catalyst can be reused.

Ethical Statement

The authors affirm that they do not have any competing interests. It does not require ethics approval.

Supporting Institution

This project did not receive any funding

Thanks

The Department of Chemistry at Kerbala University's College of Science is gratefully acknowledged by the authors of the current study for providing financial assistance.

References

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  • 2. Siddique R, Cachim P. Waste and supplementary cementitious materials in concrete [Internet]. Waste and Supplementary Cementitious Materials in Concrete: Characterisation, Properties and Applications. Elsevier; 2018. 621 p. Available from: <URL>.
  • 3. López-Alonso M, Martín-Morales M, Martínez-Echevarría MJ, Agrela F, Zamorano M. Residual biomasses as aggregates applied in cement-based materials. In: Waste and Byproducts in Cement-Based Materials [Internet]. Elsevier; 2021. p. 89–137. Available from: <URL>.
  • 4. Phonphuak N, Chindaprasirt P. Types of waste, properties, and durability of pore-forming waste-based fired masonry bricks. In: Eco-Efficient Masonry Bricks and Blocks [Internet]. Elsevier; 2015. p. 103–27. Available from: <URL>.
  • 5. Gnanamanickam SS. Rice and its importance to human life. In: Biological Control of Rice Diseases [Internet]. Dordrecht: Springer Netherlands; 2009. p. 1–11. Available from: <URL>.
  • 6. Sangwan S, Singh R, Gulati S, Rana S, Punia J, Malik K. Solvent-free rice husk mediated efficient approach for synthesis of novel imidazoles and their In vitro bio evaluation. Curr Res Green Sustain Chem [Internet]. 2022 Jan 1;5:100250. Available from: <URL>.
  • 7. Lima SPB de, Vasconcelos RP de, Paiva OA, Cordeiro GC, Chaves MR de M, Toledo Filho RD, et al. Production of silica gel from residual rice husk ash. Quim Nova [Internet]. 2011;34(1):71–5. Available from: <URL>.
  • 8. Ali HH, Hussein KA, Mihsen HH. Antimicrobial applications of nanosilica derived from rice grain husks. Silicon [Internet]. 2023 Aug 25;15(13):5735–45. Available from: <URL>.
  • 9. Eshghi H, Hassankhani A. One-pot efficient beckmann rearrangement of ketones catalyzed by silica sulfuric acid. J Korean Chem Soc [Internet]. 2007 Aug 20;51(4):361–4. Available from: <URL>.
  • 10. Riego JM, Sedin Z, Zaldívar J, Marziano NC, Tortato C. Sulfuric acid on silica-gel: An inexpensive catalyst for aromatic nitration. Tetrahedron Lett [Internet]. 1996 Jan 22;37(4):513–6. Available from: <URL>.
  • 11. Manna J, Roy B, Sharma P. Efficient hydrogen generation from sodium borohydride hydrolysis using silica sulfuric acid catalyst. J Power Sources [Internet]. 2015 Feb 1;275:727–33. Available from: <URL>.
  • 12. Adam F, Hello KM, Ali TH. Solvent free liquid-phase alkylation of phenol over solid sulfanilic acid catalyst. Appl Catal A Gen [Internet]. 2011 May 31;399(1–2):42–9. Available from: <URL>.
  • 13. Tolomeu HV, Fraga CAM. Imidazole: Synthesis, functionalization and physicochemical properties of a privileged structure in medicinal chemistry. Molecules [Internet]. 2023 Jan 13;28(2):838. Available from: <URL>.
  • 14. Ali HH, Mihsen HH, Hussain KA. Synthesis, characterization and antimicrobial studies of modified silica materials derived from rice husks. Bionanoscience [Internet]. 2023 Sep 28;13(3):1163–76. Available from: <URL>.
  • 15. Tariq A, Mihsen HH, Saeed SI. Organic–inorganic hybrid modified silica synthesized from rice husks straw for effective uptake of Co(II), Ni(II), and Cu(II) ions from aqueous solutions. Biomass Convers Biorefinery [Internet]. 2023 Dec 28;1:1–13. Available from: <URL>.
  • 16. Samai S, Nandi GC, Singh P, Singh MS. L-Proline: An efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. Tetrahedron [Internet]. 2009 Dec 5;65(49):10155–61. Available from: <URL>.
  • 17. Noriega-Iribe E, Díaz-Rubio L, Estolano-Cobián A, Barajas-Carrillo VW, Padrón JM, Salazar-Aranda R, et al. In vitro and In silico screening of 2,4,5-Trisubstituted imidazole derivatives as potential xanthine oxidase and acetylcholinesterase inhibitors, antioxidant, and antiproliferative agents. Appl Sci [Internet]. 2020 Apr 22;10(8):2889. Available from: <URL>.
  • 18. Ahmed NS, Hanoon HD. A green and simple method for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives using acidic ionic liquid as an effective and recyclable catalyst under ultrasound. Res Chem Intermed [Internet]. 2021 Oct 19;47(10):4083–100. Available from: <URL>.
  • 19. Hilal DA, Hanoon HD. Bronsted acidic ionic liquid catalyzed an eco-friendly and efficient procedure for synthesis of 2,4,5-trisubstituted imidazole derivatives under ultrasound irradiation and optimal conditions. Res Chem Intermed [Internet]. 2020 Feb 27;46(2):1521–38. Available from: <URL>.
  • 20. Hanoon HD, Radhi SM, Abbas SK. Simple and efficient synthesis of 2,4,5-triarylsubstituted imidazole derivatives via a multicomponent reaction using microwave irradiation. In: AIP Conference Proceedings [Internet]. American Institute of Physics Inc.; 2019. p. 020005. Available from: <URL>.
  • 21. Hello KM, Ibrahim AA, Shneine JK, Appaturi JN. Simple method for functionalization of silica with alkyl silane and organic ligands. South African J Chem Eng [Internet]. 2018 Jun 1;25:159–68. Available from: <URL>.
  • 22. Mihsen HH, Rfaish SY, Abass SK, Sobh HS. Synthesis and characterization of silica-thioamide hybrid compounds derived from rice husk ash with expected biological and catalytic activity. J Glob Pharma Technol [Internet]. 2018;10(11):590–8. Available from: <URL>.
  • 23. Saravanan S, Dubey RS. Synthesis of SiO2 nanoparticles by sol-gel method and their optical and structural properties. Rom J Inf Sci Technol [Internet]. 2020;23(1):105–12. Available from: <URL>.
  • 24. Abbas SK, Hassan ZM, Mihsen HH, Eesa MT, Attol DH. Uptake of nickel(II) ion by Silica-o-Phenylenediamine derived from rice husk ash. Silicon [Internet]. 2020 May 18;12(5):1103–10. Available from: <URL>.
  • 25. Adam F, Osman H, Hello KM. The immobilization of 3-(chloropropyl)triethoxysilane onto silica by a simple one-pot synthesis. J Colloid Interface Sci [Internet]. 2009 Mar 1;331(1):143–7. Available from: <URL>.
  • 26. Elzanati E, Abdallah H, Farg E, Ettouney RS. Enhancing the esterification conversion using pervaporation. J Eng Sci Technol [Internet]. 2018;13(4):990–1004. Available from: <URL>.
  • 27. Adam F, Hello KM, Osman H. Esterification via saccharine mediated silica solid catalyst. Appl Catal A Gen [Internet]. 2009 Aug 31;365(2):165–72. Available from: <URL>.
  • 28. Sobh HS, Mihsen HH. Synthesis of functionalized silica from rice husks containing C-I end group. Baghdad Sci J [Internet]. 2019 Dec 1;16(4):886–91. Available from: <URL>.
  • 29. Vijayalakshmi U, Vaibhav V, Chellappa M, Anjaneyulu U. Green synthesis of silica nanoparticles and its corrosion resistance behavior on mild steel. J Indian Chem Soc. 2015;92(5):675–8.
  • 30. Adam F, Andas J. Amino benzoic acid modified silica—An improved catalyst for the mono-substituted product in the benzylation of toluene with benzyl chloride. J Colloid Interface Sci [Internet]. 2007 Jul 1;311(1):135–43. Available from: <URL>.
  • 31. Esmaili S, Khazaei A, Ghorbani-Choghamarani A, Mohammadi M. Silica sulfuric acid coated on SnFe2O4 MNPs: Synthesis, characterization and catalytic applications in the synthesis of polyhydroquinolines. RSC Adv [Internet]. 2022 May 12;12(23):14397–410. Available from: <URL>.
  • 32. Permatasari N, Sucahya TN, Dani Nandiyanto AB. Review: Agricultural wastes as a source of silica material. Indones J Sci Technol [Internet]. 2016 Apr 1;1(1):82. Available from: <URL>.
  • 33. Nah HY, Parale VG, Jung HNR, Lee KY, Lim CH, Ku YS, et al. Role of oxalic acid in structural formation of sodium silicate-based silica aerogel by ambient pressure drying. J Sol-Gel Sci Technol [Internet]. 2018 Feb;85(2):302–10. Available from: <URL>.
  • 34. Guedes R, Prosdocimi F, Fernandes G, Moura L, Ribeiro H, Ortega J. Amino acids biosynthesis and nitrogen assimilation pathways: A great genomic deletion during eukaryotes evolution. BMC Genomics [Internet]. 2011 Dec 22;12(S4):S2. Available from: <URL>.
Year 2025, Volume: 12 Issue: 1, 1 - 14, 03.03.2025
https://doi.org/10.18596/jotcsa.1515088

Abstract

References

  • 1. Oluseun Adejumo I, Adebukola Adebiyi O. Agricultural solid wastes: Causes, effects, and effective management. In: Strategies of Sustainable Solid Waste Management [Internet]. IntechOpen; 2021. Available from: <URL>.
  • 2. Siddique R, Cachim P. Waste and supplementary cementitious materials in concrete [Internet]. Waste and Supplementary Cementitious Materials in Concrete: Characterisation, Properties and Applications. Elsevier; 2018. 621 p. Available from: <URL>.
  • 3. López-Alonso M, Martín-Morales M, Martínez-Echevarría MJ, Agrela F, Zamorano M. Residual biomasses as aggregates applied in cement-based materials. In: Waste and Byproducts in Cement-Based Materials [Internet]. Elsevier; 2021. p. 89–137. Available from: <URL>.
  • 4. Phonphuak N, Chindaprasirt P. Types of waste, properties, and durability of pore-forming waste-based fired masonry bricks. In: Eco-Efficient Masonry Bricks and Blocks [Internet]. Elsevier; 2015. p. 103–27. Available from: <URL>.
  • 5. Gnanamanickam SS. Rice and its importance to human life. In: Biological Control of Rice Diseases [Internet]. Dordrecht: Springer Netherlands; 2009. p. 1–11. Available from: <URL>.
  • 6. Sangwan S, Singh R, Gulati S, Rana S, Punia J, Malik K. Solvent-free rice husk mediated efficient approach for synthesis of novel imidazoles and their In vitro bio evaluation. Curr Res Green Sustain Chem [Internet]. 2022 Jan 1;5:100250. Available from: <URL>.
  • 7. Lima SPB de, Vasconcelos RP de, Paiva OA, Cordeiro GC, Chaves MR de M, Toledo Filho RD, et al. Production of silica gel from residual rice husk ash. Quim Nova [Internet]. 2011;34(1):71–5. Available from: <URL>.
  • 8. Ali HH, Hussein KA, Mihsen HH. Antimicrobial applications of nanosilica derived from rice grain husks. Silicon [Internet]. 2023 Aug 25;15(13):5735–45. Available from: <URL>.
  • 9. Eshghi H, Hassankhani A. One-pot efficient beckmann rearrangement of ketones catalyzed by silica sulfuric acid. J Korean Chem Soc [Internet]. 2007 Aug 20;51(4):361–4. Available from: <URL>.
  • 10. Riego JM, Sedin Z, Zaldívar J, Marziano NC, Tortato C. Sulfuric acid on silica-gel: An inexpensive catalyst for aromatic nitration. Tetrahedron Lett [Internet]. 1996 Jan 22;37(4):513–6. Available from: <URL>.
  • 11. Manna J, Roy B, Sharma P. Efficient hydrogen generation from sodium borohydride hydrolysis using silica sulfuric acid catalyst. J Power Sources [Internet]. 2015 Feb 1;275:727–33. Available from: <URL>.
  • 12. Adam F, Hello KM, Ali TH. Solvent free liquid-phase alkylation of phenol over solid sulfanilic acid catalyst. Appl Catal A Gen [Internet]. 2011 May 31;399(1–2):42–9. Available from: <URL>.
  • 13. Tolomeu HV, Fraga CAM. Imidazole: Synthesis, functionalization and physicochemical properties of a privileged structure in medicinal chemistry. Molecules [Internet]. 2023 Jan 13;28(2):838. Available from: <URL>.
  • 14. Ali HH, Mihsen HH, Hussain KA. Synthesis, characterization and antimicrobial studies of modified silica materials derived from rice husks. Bionanoscience [Internet]. 2023 Sep 28;13(3):1163–76. Available from: <URL>.
  • 15. Tariq A, Mihsen HH, Saeed SI. Organic–inorganic hybrid modified silica synthesized from rice husks straw for effective uptake of Co(II), Ni(II), and Cu(II) ions from aqueous solutions. Biomass Convers Biorefinery [Internet]. 2023 Dec 28;1:1–13. Available from: <URL>.
  • 16. Samai S, Nandi GC, Singh P, Singh MS. L-Proline: An efficient catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles. Tetrahedron [Internet]. 2009 Dec 5;65(49):10155–61. Available from: <URL>.
  • 17. Noriega-Iribe E, Díaz-Rubio L, Estolano-Cobián A, Barajas-Carrillo VW, Padrón JM, Salazar-Aranda R, et al. In vitro and In silico screening of 2,4,5-Trisubstituted imidazole derivatives as potential xanthine oxidase and acetylcholinesterase inhibitors, antioxidant, and antiproliferative agents. Appl Sci [Internet]. 2020 Apr 22;10(8):2889. Available from: <URL>.
  • 18. Ahmed NS, Hanoon HD. A green and simple method for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives using acidic ionic liquid as an effective and recyclable catalyst under ultrasound. Res Chem Intermed [Internet]. 2021 Oct 19;47(10):4083–100. Available from: <URL>.
  • 19. Hilal DA, Hanoon HD. Bronsted acidic ionic liquid catalyzed an eco-friendly and efficient procedure for synthesis of 2,4,5-trisubstituted imidazole derivatives under ultrasound irradiation and optimal conditions. Res Chem Intermed [Internet]. 2020 Feb 27;46(2):1521–38. Available from: <URL>.
  • 20. Hanoon HD, Radhi SM, Abbas SK. Simple and efficient synthesis of 2,4,5-triarylsubstituted imidazole derivatives via a multicomponent reaction using microwave irradiation. In: AIP Conference Proceedings [Internet]. American Institute of Physics Inc.; 2019. p. 020005. Available from: <URL>.
  • 21. Hello KM, Ibrahim AA, Shneine JK, Appaturi JN. Simple method for functionalization of silica with alkyl silane and organic ligands. South African J Chem Eng [Internet]. 2018 Jun 1;25:159–68. Available from: <URL>.
  • 22. Mihsen HH, Rfaish SY, Abass SK, Sobh HS. Synthesis and characterization of silica-thioamide hybrid compounds derived from rice husk ash with expected biological and catalytic activity. J Glob Pharma Technol [Internet]. 2018;10(11):590–8. Available from: <URL>.
  • 23. Saravanan S, Dubey RS. Synthesis of SiO2 nanoparticles by sol-gel method and their optical and structural properties. Rom J Inf Sci Technol [Internet]. 2020;23(1):105–12. Available from: <URL>.
  • 24. Abbas SK, Hassan ZM, Mihsen HH, Eesa MT, Attol DH. Uptake of nickel(II) ion by Silica-o-Phenylenediamine derived from rice husk ash. Silicon [Internet]. 2020 May 18;12(5):1103–10. Available from: <URL>.
  • 25. Adam F, Osman H, Hello KM. The immobilization of 3-(chloropropyl)triethoxysilane onto silica by a simple one-pot synthesis. J Colloid Interface Sci [Internet]. 2009 Mar 1;331(1):143–7. Available from: <URL>.
  • 26. Elzanati E, Abdallah H, Farg E, Ettouney RS. Enhancing the esterification conversion using pervaporation. J Eng Sci Technol [Internet]. 2018;13(4):990–1004. Available from: <URL>.
  • 27. Adam F, Hello KM, Osman H. Esterification via saccharine mediated silica solid catalyst. Appl Catal A Gen [Internet]. 2009 Aug 31;365(2):165–72. Available from: <URL>.
  • 28. Sobh HS, Mihsen HH. Synthesis of functionalized silica from rice husks containing C-I end group. Baghdad Sci J [Internet]. 2019 Dec 1;16(4):886–91. Available from: <URL>.
  • 29. Vijayalakshmi U, Vaibhav V, Chellappa M, Anjaneyulu U. Green synthesis of silica nanoparticles and its corrosion resistance behavior on mild steel. J Indian Chem Soc. 2015;92(5):675–8.
  • 30. Adam F, Andas J. Amino benzoic acid modified silica—An improved catalyst for the mono-substituted product in the benzylation of toluene with benzyl chloride. J Colloid Interface Sci [Internet]. 2007 Jul 1;311(1):135–43. Available from: <URL>.
  • 31. Esmaili S, Khazaei A, Ghorbani-Choghamarani A, Mohammadi M. Silica sulfuric acid coated on SnFe2O4 MNPs: Synthesis, characterization and catalytic applications in the synthesis of polyhydroquinolines. RSC Adv [Internet]. 2022 May 12;12(23):14397–410. Available from: <URL>.
  • 32. Permatasari N, Sucahya TN, Dani Nandiyanto AB. Review: Agricultural wastes as a source of silica material. Indones J Sci Technol [Internet]. 2016 Apr 1;1(1):82. Available from: <URL>.
  • 33. Nah HY, Parale VG, Jung HNR, Lee KY, Lim CH, Ku YS, et al. Role of oxalic acid in structural formation of sodium silicate-based silica aerogel by ambient pressure drying. J Sol-Gel Sci Technol [Internet]. 2018 Feb;85(2):302–10. Available from: <URL>.
  • 34. Guedes R, Prosdocimi F, Fernandes G, Moura L, Ribeiro H, Ortega J. Amino acids biosynthesis and nitrogen assimilation pathways: A great genomic deletion during eukaryotes evolution. BMC Genomics [Internet]. 2011 Dec 22;12(S4):S2. Available from: <URL>.
There are 34 citations in total.

Details

Primary Language English
Subjects Organic Chemical Synthesis, Organic Chemistry (Other)
Journal Section RESEARCH ARTICLES
Authors

Noor Abbas Alshook 0009-0008-0051-5609

Haitham Dalol Hanoon 0000-0001-8108-4477

Hayder Hamied Mihsen 0000-0003-0205-2835

Publication Date March 3, 2025
Submission Date July 12, 2024
Acceptance Date December 19, 2024
Published in Issue Year 2025 Volume: 12 Issue: 1

Cite

Vancouver Alshook NA, Hanoon HD, Mihsen HH. Development of a Silica-Organic Framework Ionic Solid Bronsted Acid Catalyst for the Synthesis of 2,4,5-trisubstituted Imidazole Derivatives. JOTCSA. 2025;12(1):1-14.