Year 2024,
Volume: 11 Issue: 4, 1641 - 1650, 03.12.2024
Assim A. Sabah
,
Safaaldeen A. Sulyman
,
Ahmed A. Aldabagh
,
Arqam K. Ayoob
,
Mohammed Alsultan
,
Rowaa T. Hameed
References
- 1. Seddon KR. Ionic liquids for clean technology. J Chem Technol Biotechnol [Internet]. 1997;68(4):351–6. Available from: <URL>.
- 2. Wasserscheid P, Welton T. Ionic liquids in synthesis [Internet]. Wasserscheid P, Welton T, editors. Vol. 1, Ionic Liquids in Synthesis: Second Edition. Wiley; 2007. 1–721 p. Available from: <URL>.
- 3. Singh SK, Savoy AW. Ionic liquids synthesis and applications: An overview. J Mol Liq [Internet]. 2020 Jan 1;297:112038. Available from: <URL>.
- 4. Manahan SE. Green chemistry and the ten commandments of sustainability. ChemChar Res. 2006;
- 5. Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR, Dupont J. The use of imidazolium ionic liquids for the formation and stabilization of Ir0 and Rh0 nanoparticles: Efficient catalysts for the hydrogenation of arenes. Chem – A Eur J [Internet]. 2003 Jul 21;9(14):3263–9. Available from: <URL>.
- 6. Ren F, Wang J, Xie F, Zan K, Wang S, Wang S. Applications of ionic liquids in starch chemistry: A review. Green Chem [Internet]. 2020 Apr 6;22(7):2162–83. Available from: <URL>.
- 7. Schmidt R. [bmim]AlCl4 Ionic Liquid for Deep Desulfurization of Real Fuels. Energy & Fuels [Internet]. 2008 May 1;22(3):1774–8. Available from: <URL>.
- 8. Shiraishi Y, Hirai T. Desulfurization of vacuum gas oil based on chemical oxidation followed by liquid−liquid extraction. Energy & Fuels [Internet]. 2004 Jan 1;18(1):37–40. Available from: <URL>.
- 9. Welton T. Ionic liquids: A brief history. Biophys Rev [Internet]. 2018 Jun 26;10(3):691–706. Available from: <URL>.
- 10. Arce A, Francisco M, Soto A. Evaluation of the polysubstituted pyridinium ionic liquid [hmmpy][Ntf2] as a suitable solvent for desulfurization: Phase equilibria. J Chem Thermodyn [Internet]. 2010 Jun 1;42(6):712–8. Available from: <URL>.
- 11. Isosaari P, Srivastava V, Sillanpää M. Ionic liquid-based water treatment technologies for organic pollutants: Current status and future prospects of ionic liquid mediated technologies. Sci Total Environ [Internet]. 2019 Nov 10;690:604–19. Available from: <URL>.
- 12. Ehsan Kianfar, Sajjad Mafi. Ionic liquids: Properties, application, and synthesis. Fine Chem Eng [Internet]. 2020 Dec 31;22–31. Available from: <URL>.
- 13. Earle MJ, McCormac PB, Seddon KR. Regioselective alkylation in ionic liquids. Chem Commun [Internet]. 1998 Jan 1;1998(20):2245–6. Available from: <URL>.
- 14. Buttrus NH, Sabah AA, Taqa AA, Englert U. 3-Allyl-1-methyl-1H-benzotriazol-3-ium iodide. Acta Crystallogr Sect E Struct Reports Online [Internet]. 2012 Sep 15;68(9):o2735–o2735. Available from: <URL>.
- 15. Sabah AA. Extractive desulfurization using piperidinium based ionic liquids with Lewis acids. J Turkish Chem Soc Sect A Chem [Internet]. 2021 Nov 30;8(4):1057–88. Available from: <URL>.
- 16. Sabah A. Extractive desulfurization of model oil using 1-methyl-4-ethyl pyridinium iodide ionic liquids with some Lewis acids. Egypt J Chem [Internet]. 2021 Oct 30;65(5):147–52. Available from: <URL>.
- 17. Boche G, Andrews P, Harms K, Marsch M, Rangappa KS, Schimeczek M, et al. Crystal and electronic structure of stable nitrenium ions. A comparison with structurally related carbenes. J Am Chem Soc [Internet]. 1996 Jan 1;118(21):4925–30. Available from: <URL>.
- 18. Barbour LJ. X-Seed — A software tool for supramolecular crystallography. J Supramol Chem [Internet]. 2001 Jul 1;1(4–6):189–91. Available from: <URL>.
- 19. Hübschle CB, Sheldrick GM, Dittrich B. ShelXle: a Qt graphical user interface for SHELXL. J Appl Crystallogr [Internet]. 2011 Dec 1;44(6):1281–4. Available from: <URL>.
- 20. Shiraishi Y, Tachibana K, Hirai T, Komasawa I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 3. Denitrogenation behavior of light oil feedstocks. Ind Eng Chem Res [Internet]. 2001 Jul 1;40(15):3390–7. Available from: <URL>.
- 21. Sabah AA, Assim YF, Ahmed AS, Alhassan OK, Huseen AS, Jasim BH, et al. Extractive desulfurization of model diesel oil by using novel indolium based ionic liquids. Int J Enhanc Res Sci Technol Eng [Internet]. 2017;6(12):32–9. Available from: <URL>.
- 22. Lee KM, Lee CK, Lin IJB. First example of interdigitated U-shape benzimidazolium ionic liquid crystals. Chem Commun [Internet]. 1997 Jan 1;(9):899–900. Available from: <URL>.
- 23. Yang Y, Zhang ZQ, Ding JM, Wang SM, Ju YC. Crystal structure of tetrapyridinecopper(II) bis(triiodide), [Cu(C5H5N)4][I3]2. Zeitschrift für Krist - New Cryst Struct [Internet]. 2011 Jan 1;226(2):185–6. Available from: <URL>.
- 24. Chen L. Crystal structure of bis(pyridin-2-yl)disulfide hydrotriiodide,[C10H9N2S2][I3]. Zeitschrift für Krist - New Cryst Struct [Internet]. 2006 Apr 1;221(1–4):443–4. Available from: <URL>.
- 25. Gutowski KE, Cocalia VA, Griffin ST, Bridges NJ, Dixon DA, Rogers RD. Interactions of 1-Methylimidazole with UO2(CH3CO2)2 and UO2(NO3)2: Structural, spectroscopic, and theoretical evidence for imidazole binding to the uranyl ion. J Am Chem Soc [Internet]. 2007 Jan 1;129(3):526–36. Available from: <URL>.
- 26. Tanaka R, Matsushita N. Crystal structure of bis(1-ethylpyridinium) dioxonium hexacyanidoferrate(II). Acta Crystallogr Sect E Crystallogr Commun [Internet]. 2017 Feb 1;73(2):219–22. Available from: <URL>.
- 27. Sabah AA. Synthesis and characterization of some transition metals complex salts of pyridinium iodide ionic liquids: Application on extractive desulfurization. J Turkish Chem Soc Sect A Chem [Internet]. 2021 Aug 31;8(3):763–74. Available from: <URL>.
- 28. Zaidan SW, Ameen AM, Sabah AA. Application on Extractive desulfurization using substituted pyrimidine ionic salt and its some transition metals complex salts. Coll Basic Educ Res J [Internet]. 2023;19(3):638–51. Available from: <URL>.
- 29. Li F tang, Liu Y, Sun Z min, Chen L ju, Zhao D shun, Liu R hong, et al. Deep extractive desulfurization of gasoline with xEt3NHCl·FeCl3 ionic liquids. Energy & Fuels [Internet]. 2010 Aug 19;24(8):4285–9. Available from: <URL>.
- 30. Ban LL, Liu P, Ma CH, Dai B. Deep extractive desulfurization of diesel fuels by FeCl3/ionic liquids. Chinese Chem Lett [Internet]. 2013 Aug 1;24(8):755–8. Available from: <URL>.
- 31. Ko NH, Lee JS, Huh ES, Lee H, Jung KD, Kim HS, et al. Extractive desulfurization using Fe-containing ionic liquids. Energy & Fuels [Internet]. 2008 May 1;22(3):1687–90. Available from: <URL>.
Using of Benzotriazolium Iodide Ionic Liquids for Extractive Desulfurization of Model Diesel Oil
Year 2024,
Volume: 11 Issue: 4, 1641 - 1650, 03.12.2024
Assim A. Sabah
,
Safaaldeen A. Sulyman
,
Ahmed A. Aldabagh
,
Arqam K. Ayoob
,
Mohammed Alsultan
,
Rowaa T. Hameed
Abstract
Benzotraazolium-based ionic salts have been prepared with an alkyl group (methyl and allyl), with iodine anion, the prepared compound ([diMBt]I (1), [AMBt]I (2) and [AMBt]I3 (3) structure have determined by single crystal x-ray and they used for desulfurization of sulfur from model diesel oil in order to obtain reduced sulfur fuel with more environmental friendly properties. The prepared compounds were characterized using several techniques, and their efficiency in removing sulfur from the sample oil was evaluated. The results showed that the removal efficiency was acceptable and could be improved in future research.
References
- 1. Seddon KR. Ionic liquids for clean technology. J Chem Technol Biotechnol [Internet]. 1997;68(4):351–6. Available from: <URL>.
- 2. Wasserscheid P, Welton T. Ionic liquids in synthesis [Internet]. Wasserscheid P, Welton T, editors. Vol. 1, Ionic Liquids in Synthesis: Second Edition. Wiley; 2007. 1–721 p. Available from: <URL>.
- 3. Singh SK, Savoy AW. Ionic liquids synthesis and applications: An overview. J Mol Liq [Internet]. 2020 Jan 1;297:112038. Available from: <URL>.
- 4. Manahan SE. Green chemistry and the ten commandments of sustainability. ChemChar Res. 2006;
- 5. Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR, Dupont J. The use of imidazolium ionic liquids for the formation and stabilization of Ir0 and Rh0 nanoparticles: Efficient catalysts for the hydrogenation of arenes. Chem – A Eur J [Internet]. 2003 Jul 21;9(14):3263–9. Available from: <URL>.
- 6. Ren F, Wang J, Xie F, Zan K, Wang S, Wang S. Applications of ionic liquids in starch chemistry: A review. Green Chem [Internet]. 2020 Apr 6;22(7):2162–83. Available from: <URL>.
- 7. Schmidt R. [bmim]AlCl4 Ionic Liquid for Deep Desulfurization of Real Fuels. Energy & Fuels [Internet]. 2008 May 1;22(3):1774–8. Available from: <URL>.
- 8. Shiraishi Y, Hirai T. Desulfurization of vacuum gas oil based on chemical oxidation followed by liquid−liquid extraction. Energy & Fuels [Internet]. 2004 Jan 1;18(1):37–40. Available from: <URL>.
- 9. Welton T. Ionic liquids: A brief history. Biophys Rev [Internet]. 2018 Jun 26;10(3):691–706. Available from: <URL>.
- 10. Arce A, Francisco M, Soto A. Evaluation of the polysubstituted pyridinium ionic liquid [hmmpy][Ntf2] as a suitable solvent for desulfurization: Phase equilibria. J Chem Thermodyn [Internet]. 2010 Jun 1;42(6):712–8. Available from: <URL>.
- 11. Isosaari P, Srivastava V, Sillanpää M. Ionic liquid-based water treatment technologies for organic pollutants: Current status and future prospects of ionic liquid mediated technologies. Sci Total Environ [Internet]. 2019 Nov 10;690:604–19. Available from: <URL>.
- 12. Ehsan Kianfar, Sajjad Mafi. Ionic liquids: Properties, application, and synthesis. Fine Chem Eng [Internet]. 2020 Dec 31;22–31. Available from: <URL>.
- 13. Earle MJ, McCormac PB, Seddon KR. Regioselective alkylation in ionic liquids. Chem Commun [Internet]. 1998 Jan 1;1998(20):2245–6. Available from: <URL>.
- 14. Buttrus NH, Sabah AA, Taqa AA, Englert U. 3-Allyl-1-methyl-1H-benzotriazol-3-ium iodide. Acta Crystallogr Sect E Struct Reports Online [Internet]. 2012 Sep 15;68(9):o2735–o2735. Available from: <URL>.
- 15. Sabah AA. Extractive desulfurization using piperidinium based ionic liquids with Lewis acids. J Turkish Chem Soc Sect A Chem [Internet]. 2021 Nov 30;8(4):1057–88. Available from: <URL>.
- 16. Sabah A. Extractive desulfurization of model oil using 1-methyl-4-ethyl pyridinium iodide ionic liquids with some Lewis acids. Egypt J Chem [Internet]. 2021 Oct 30;65(5):147–52. Available from: <URL>.
- 17. Boche G, Andrews P, Harms K, Marsch M, Rangappa KS, Schimeczek M, et al. Crystal and electronic structure of stable nitrenium ions. A comparison with structurally related carbenes. J Am Chem Soc [Internet]. 1996 Jan 1;118(21):4925–30. Available from: <URL>.
- 18. Barbour LJ. X-Seed — A software tool for supramolecular crystallography. J Supramol Chem [Internet]. 2001 Jul 1;1(4–6):189–91. Available from: <URL>.
- 19. Hübschle CB, Sheldrick GM, Dittrich B. ShelXle: a Qt graphical user interface for SHELXL. J Appl Crystallogr [Internet]. 2011 Dec 1;44(6):1281–4. Available from: <URL>.
- 20. Shiraishi Y, Tachibana K, Hirai T, Komasawa I. A novel desulfurization process for fuel oils based on the formation and subsequent precipitation of S-alkylsulfonium salts. 3. Denitrogenation behavior of light oil feedstocks. Ind Eng Chem Res [Internet]. 2001 Jul 1;40(15):3390–7. Available from: <URL>.
- 21. Sabah AA, Assim YF, Ahmed AS, Alhassan OK, Huseen AS, Jasim BH, et al. Extractive desulfurization of model diesel oil by using novel indolium based ionic liquids. Int J Enhanc Res Sci Technol Eng [Internet]. 2017;6(12):32–9. Available from: <URL>.
- 22. Lee KM, Lee CK, Lin IJB. First example of interdigitated U-shape benzimidazolium ionic liquid crystals. Chem Commun [Internet]. 1997 Jan 1;(9):899–900. Available from: <URL>.
- 23. Yang Y, Zhang ZQ, Ding JM, Wang SM, Ju YC. Crystal structure of tetrapyridinecopper(II) bis(triiodide), [Cu(C5H5N)4][I3]2. Zeitschrift für Krist - New Cryst Struct [Internet]. 2011 Jan 1;226(2):185–6. Available from: <URL>.
- 24. Chen L. Crystal structure of bis(pyridin-2-yl)disulfide hydrotriiodide,[C10H9N2S2][I3]. Zeitschrift für Krist - New Cryst Struct [Internet]. 2006 Apr 1;221(1–4):443–4. Available from: <URL>.
- 25. Gutowski KE, Cocalia VA, Griffin ST, Bridges NJ, Dixon DA, Rogers RD. Interactions of 1-Methylimidazole with UO2(CH3CO2)2 and UO2(NO3)2: Structural, spectroscopic, and theoretical evidence for imidazole binding to the uranyl ion. J Am Chem Soc [Internet]. 2007 Jan 1;129(3):526–36. Available from: <URL>.
- 26. Tanaka R, Matsushita N. Crystal structure of bis(1-ethylpyridinium) dioxonium hexacyanidoferrate(II). Acta Crystallogr Sect E Crystallogr Commun [Internet]. 2017 Feb 1;73(2):219–22. Available from: <URL>.
- 27. Sabah AA. Synthesis and characterization of some transition metals complex salts of pyridinium iodide ionic liquids: Application on extractive desulfurization. J Turkish Chem Soc Sect A Chem [Internet]. 2021 Aug 31;8(3):763–74. Available from: <URL>.
- 28. Zaidan SW, Ameen AM, Sabah AA. Application on Extractive desulfurization using substituted pyrimidine ionic salt and its some transition metals complex salts. Coll Basic Educ Res J [Internet]. 2023;19(3):638–51. Available from: <URL>.
- 29. Li F tang, Liu Y, Sun Z min, Chen L ju, Zhao D shun, Liu R hong, et al. Deep extractive desulfurization of gasoline with xEt3NHCl·FeCl3 ionic liquids. Energy & Fuels [Internet]. 2010 Aug 19;24(8):4285–9. Available from: <URL>.
- 30. Ban LL, Liu P, Ma CH, Dai B. Deep extractive desulfurization of diesel fuels by FeCl3/ionic liquids. Chinese Chem Lett [Internet]. 2013 Aug 1;24(8):755–8. Available from: <URL>.
- 31. Ko NH, Lee JS, Huh ES, Lee H, Jung KD, Kim HS, et al. Extractive desulfurization using Fe-containing ionic liquids. Energy & Fuels [Internet]. 2008 May 1;22(3):1687–90. Available from: <URL>.