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Extractive desulfurization using piperidinium based ionic liquids with Lewis acids

Yıl 2021, Cilt 8, Sayı 4, 1057 - 1088, 30.11.2021
https://doi.org/10.18596/jotcsa.963930

Öz

This work includes the preparation of ionic liquid 1,4-dimethylpiperidinium iodide [MMPip]I and its salts with ferric chloride as Lewis acid in different molar proportions [MMPip]I/nFeCl3 (n=1,2,3). The prepared compounds were diagnosed by spectroscopic and physical methods such as 1H-NMR, FT-IR, elemental analysis (CHN) and other techniques. The thermal stability of these compounds was studied to use in the extractive desulfurization process (EDS). The efficiency of these compounds in removing sulfur compounds from the petroleum model was examined using dibenzothiophene (DBT) with a concentration of 1000 ppm dissolved in the solvent of normal hexane. The results showed that the compounds used had an acceptable efficiency of up to 30% despite using medium amounts of the extracted agent relative to the oil model; these compounds have a promising future in extractive sulfur removal processes.

Kaynakça

  • 1. Corma A, Martı́nez C, Ketley G, Blair G. On the mechanism of sulfur removal during catalytic cracking. Applied Catalysis A: General. 2001 Feb;208(1–2):135–52.
  • 2. Ito E, van Veen JAR. On novel processes for removing sulphur from refinery streams. Catalysis Today. 2006 Sep;116(4):446–60.
  • 3. Mei H, Mei BW, Yen TF. A new method for obtaining ultra-low sulfur diesel fuel via ultrasound assisted oxidative desulfurization☆. Fuel. 2003 Mar;82(4):405–14.
  • 4. Xie Y, Chowdhury M, Bhavsar P, Zhou Y. An integrated modeling approach for facilitating emission estimations of alternative fueled vehicles. Transportation Research Part D: Transport and Environment. 2012 Jan;17(1):15–20.
  • 5. Armstrong JP, Hurst C, Jones RG, Licence P, Lovelock KRJ, Satterley CJ, et al. Vapourisation of ionic liquids. Phys Chem Chem Phys. 2007;9(8):982.
  • 6. Yang RT. Desulfurization of Transportation Fuels with Zeolites Under Ambient Conditions. Science. 2003 Jul 4;301(5629):79–81.
  • 7. Babich I. Science and technology of novel processes for deep desulfurization of oil refinery streams: a review⋆. Fuel. 2003 Apr;82(6):607–31.
  • 8. Agarwal P, Sharma DK. Comparative Studies on the Bio-desulfurization of Crude Oil with Other Desulfurization Techniques and Deep Desulfurization through Integrated Processes. Energy Fuels. 2010 Jan 21;24(1):518–24.
  • 9. Song Z, Zhou T, Qi Z, Sundmacher K. Systematic Method for Screening Ionic Liquids as Extraction Solvents Exemplified by an Extractive Desulfurization Process. ACS Sustainable Chem Eng. 2017 Apr 3;5(4):3382–9.
  • 10. Domańska U, Wlazło M. Effect of the cation and anion of the ionic liquid on desulfurization of model fuels. Fuel. 2014 Oct;134:114–25.
  • 11. Lu X, Yue L, Hu M, Cao Q, Xu L, Guo Y, et al. Piperazinium-Based Ionic Liquids with Lactate Anion for Extractive Desulfurization of Fuels. Energy Fuels. 2014 Mar 20;28(3):1774–80.
  • 12. Zhao H, Baker GA, Wagle DV, Ravula S, Zhang Q. Tuning Task-Specific Ionic Liquids for the Extractive Desulfurization of Liquid Fuel. ACS Sustainable Chem Eng. 2016 Sep 6;4(9):4771–80.
  • 13. Flieger J, Flieger M. Ionic Liquids Toxicity - Benefits and Threats. IJMS. 2020 Aug 29;21(17):6267.
  • 14. Zhao Y, Bostrom T. Application of ionic liquids in solar cells and batteries: a review. Current Organic Chemistry. 2015;19(6):556–66.
  • 15. Kulkarni PS, Afonso CAM. Deep desulfurization of diesel fuel using ionic liquids: current status and future challenges. Green Chem. 2010;12(7):1139.
  • 16. Holbrey JD, López-Martin I, Rothenberg G, Seddon KR, Silvero G, Zheng X. Desulfurisation of oils using ionic liquids: selection of cationic and anionic components to enhance extraction efficiency. Green Chem. 2008;10(1):87–92.
  • 17. Dharaskar SA, Wasewar KL, Varma MN, Shende DZ. Extractive Deep Desulfurization of Liquid Fuels Using Lewis-Based Ionic Liquids. Journal of Energy. 2013;2013:1–4.
  • 18. Ko NH, Lee JS, Huh ES, Lee H, Jung KD, Kim HS, et al. Extractive Desulfurization Using Fe-Containing Ionic Liquids. Energy Fuels. 2008 May 1;22(3):1687–90.
  • 19. Bösmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P. Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun. 2001 Nov 22;(23):2494–5.
  • 20. Zhang L, Wang J, Sun Y, Jiang B, Yang H. Deep oxidative desulfurization of fuels by superbase-derived Lewis acidic ionic liquids. Chemical Engineering Journal. 2017 Nov;328:445–53.
  • 21. Zhang M, Zhu W, Xun S, Li H, Gu Q, Zhao Z, et al. Deep oxidative desulfurization of dibenzothiophene with POM-based hybrid materials in ionic liquids. Chemical Engineering Journal. 2013 Mar;220:328–36.
  • 22. Buttrus NH, Sabah AA, Taqa AA, Englert U. 3-Allyl-1-methyl-1 H -benzotriazol-3-ium iodide. Acta Crystallogr E Struct Rep Online. 2012 Sep 15;68(9):o2735–o2735.
  • 23. Singh SK, Savoy AW. Ionic liquids synthesis and applications: An overview. Journal of Molecular Liquids. 2020 Jan;297:112038.
  • 24. Brown LC, Hogg JM, Swadźba-Kwaśny M. Lewis Acidic Ionic Liquids. In: Kirchner B, Perlt E, editors. Ionic Liquids II [Internet]. Cham: Springer International Publishing; 2017 [cited 2021 Sep 20]. p. 185–224. (Topics in Current Chemistry Collections). <URL>
  • 25. Zeng S, Liu L, Shang D, Feng J, Dong H, Xu Q, et al. Efficient and reversible absorption of ammonia by cobalt ionic liquids through Lewis acid–base and cooperative hydrogen bond interactions. Green Chem. 2018;20(9):2075–83.
  • 26. Mohammed EH, Ameen AM, Sabah AA, Mustafa TS, Sulyman SAA, Younus NG. Synthesis and Characterization of Mn (II), Fe (III), Co (II), Ni (II), and Cu (II) 1, 3-Dimethylbenzotrizolium Salt Complexes and Their Uses for Decreasing of Sulfur in Diesel Oil. Indian Journal of Heterocyclic Chemistry. 2020;30(04):565–70.
  • 27. Kore R, Kelley Steven P, Aduri P, Rogers RD. Mixed metal double salt ionic liquids comprised of [HN222]2 [ZnCl4] and AlCl3 provide tunable Lewis acid catalysts related to the ionic environment. Dalton Trans. 2018;47(23):7795–803.
  • 28. Fainleib A, Grigoryeva O, Starostenko O, Vashchuk A, Rogalsky S, Grande D. Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters. Express Polymer Letters. 2016;10(9):722.
  • 29. Chen X, Guo H, Abdeltawab AA, Guan Y, Al-Deyab SS, Yu G, et al. Brønsted–Lewis Acidic Ionic Liquids and Application in Oxidative Desulfurization of Diesel Fuel. Energy Fuels. 2015 May 21;29(5):2998–3003.
  • 30. Chan JW, Taylor DS, Zwerdling T, Lane SM, Ihara K, Huser T. Micro-Raman Spectroscopy Detects Individual Neoplastic and Normal Hematopoietic Cells. Biophysical Journal. 2006 Jan;90(2):648–56.
  • 31. Montanino M, Carewska M, Alessandrini F, Passerini S, Appetecchi GB. The role of the cation aliphatic side chain length in piperidinium bis(trifluoromethansulfonyl)imide ionic liquids. Electrochimica Acta. 2011 Dec;57:153–9.
  • 32. Salminen J, Papaiconomou N, Kumar RA, Lee J-M, Kerr J, Newman J, et al. Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids. Fluid Phase Equilibria. 2007 Dec;261(1–2):421–6.
  • 33. Sabah AA. Synthesis and Characterization of Some Transition Metals Complex Salts of Pyridinium Iodide Ionic Liquids: Application on Extractive Desulfurization. Journal of the Turkish Chemical Society Section A: Chemistry. 2021 Jul 23;8(3):763–74.
  • 34. Song Z, Zhou T, Zhang J, Cheng H, Chen L, Qi Z. Screening of ionic liquids for solvent-sensitive extraction–with deep desulfurization as an example. Chemical Engineering Science. 2015 Jun;129:69–77.
  • 35. Wang S, Li P, Hao L, Deng C, Ren W, Lü H. Oxidative Desulfurization of Model Diesel Using a Fenton-Like Catalyst in the Ionic Liquid [Dmim]BF 4. Chem Eng Technol. 2017 Mar;40(3):555–60.
  • 36. Wang Q, Lei L, Zhu J, Yang B, Li Z. Deep Desulfurization of Fuels by Extraction with 4-Dimethylaminopyridinium-Based Ionic Liquids. Energy Fuels. 2013 Aug 15;27(8):4617–23.
  • 37. Ren Z, Zhou Z, Li M, Zhang F, Wei L, Liu W. Deep Desulfurization of Fuels Using Imidazole Anion-Based Ionic Liquids. ACS Sustainable Chem Eng. 2019 Jan 22;7(2):1890–900.

Yıl 2021, Cilt 8, Sayı 4, 1057 - 1088, 30.11.2021
https://doi.org/10.18596/jotcsa.963930

Öz

Kaynakça

  • 1. Corma A, Martı́nez C, Ketley G, Blair G. On the mechanism of sulfur removal during catalytic cracking. Applied Catalysis A: General. 2001 Feb;208(1–2):135–52.
  • 2. Ito E, van Veen JAR. On novel processes for removing sulphur from refinery streams. Catalysis Today. 2006 Sep;116(4):446–60.
  • 3. Mei H, Mei BW, Yen TF. A new method for obtaining ultra-low sulfur diesel fuel via ultrasound assisted oxidative desulfurization☆. Fuel. 2003 Mar;82(4):405–14.
  • 4. Xie Y, Chowdhury M, Bhavsar P, Zhou Y. An integrated modeling approach for facilitating emission estimations of alternative fueled vehicles. Transportation Research Part D: Transport and Environment. 2012 Jan;17(1):15–20.
  • 5. Armstrong JP, Hurst C, Jones RG, Licence P, Lovelock KRJ, Satterley CJ, et al. Vapourisation of ionic liquids. Phys Chem Chem Phys. 2007;9(8):982.
  • 6. Yang RT. Desulfurization of Transportation Fuels with Zeolites Under Ambient Conditions. Science. 2003 Jul 4;301(5629):79–81.
  • 7. Babich I. Science and technology of novel processes for deep desulfurization of oil refinery streams: a review⋆. Fuel. 2003 Apr;82(6):607–31.
  • 8. Agarwal P, Sharma DK. Comparative Studies on the Bio-desulfurization of Crude Oil with Other Desulfurization Techniques and Deep Desulfurization through Integrated Processes. Energy Fuels. 2010 Jan 21;24(1):518–24.
  • 9. Song Z, Zhou T, Qi Z, Sundmacher K. Systematic Method for Screening Ionic Liquids as Extraction Solvents Exemplified by an Extractive Desulfurization Process. ACS Sustainable Chem Eng. 2017 Apr 3;5(4):3382–9.
  • 10. Domańska U, Wlazło M. Effect of the cation and anion of the ionic liquid on desulfurization of model fuels. Fuel. 2014 Oct;134:114–25.
  • 11. Lu X, Yue L, Hu M, Cao Q, Xu L, Guo Y, et al. Piperazinium-Based Ionic Liquids with Lactate Anion for Extractive Desulfurization of Fuels. Energy Fuels. 2014 Mar 20;28(3):1774–80.
  • 12. Zhao H, Baker GA, Wagle DV, Ravula S, Zhang Q. Tuning Task-Specific Ionic Liquids for the Extractive Desulfurization of Liquid Fuel. ACS Sustainable Chem Eng. 2016 Sep 6;4(9):4771–80.
  • 13. Flieger J, Flieger M. Ionic Liquids Toxicity - Benefits and Threats. IJMS. 2020 Aug 29;21(17):6267.
  • 14. Zhao Y, Bostrom T. Application of ionic liquids in solar cells and batteries: a review. Current Organic Chemistry. 2015;19(6):556–66.
  • 15. Kulkarni PS, Afonso CAM. Deep desulfurization of diesel fuel using ionic liquids: current status and future challenges. Green Chem. 2010;12(7):1139.
  • 16. Holbrey JD, López-Martin I, Rothenberg G, Seddon KR, Silvero G, Zheng X. Desulfurisation of oils using ionic liquids: selection of cationic and anionic components to enhance extraction efficiency. Green Chem. 2008;10(1):87–92.
  • 17. Dharaskar SA, Wasewar KL, Varma MN, Shende DZ. Extractive Deep Desulfurization of Liquid Fuels Using Lewis-Based Ionic Liquids. Journal of Energy. 2013;2013:1–4.
  • 18. Ko NH, Lee JS, Huh ES, Lee H, Jung KD, Kim HS, et al. Extractive Desulfurization Using Fe-Containing Ionic Liquids. Energy Fuels. 2008 May 1;22(3):1687–90.
  • 19. Bösmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P. Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun. 2001 Nov 22;(23):2494–5.
  • 20. Zhang L, Wang J, Sun Y, Jiang B, Yang H. Deep oxidative desulfurization of fuels by superbase-derived Lewis acidic ionic liquids. Chemical Engineering Journal. 2017 Nov;328:445–53.
  • 21. Zhang M, Zhu W, Xun S, Li H, Gu Q, Zhao Z, et al. Deep oxidative desulfurization of dibenzothiophene with POM-based hybrid materials in ionic liquids. Chemical Engineering Journal. 2013 Mar;220:328–36.
  • 22. Buttrus NH, Sabah AA, Taqa AA, Englert U. 3-Allyl-1-methyl-1 H -benzotriazol-3-ium iodide. Acta Crystallogr E Struct Rep Online. 2012 Sep 15;68(9):o2735–o2735.
  • 23. Singh SK, Savoy AW. Ionic liquids synthesis and applications: An overview. Journal of Molecular Liquids. 2020 Jan;297:112038.
  • 24. Brown LC, Hogg JM, Swadźba-Kwaśny M. Lewis Acidic Ionic Liquids. In: Kirchner B, Perlt E, editors. Ionic Liquids II [Internet]. Cham: Springer International Publishing; 2017 [cited 2021 Sep 20]. p. 185–224. (Topics in Current Chemistry Collections). <URL>
  • 25. Zeng S, Liu L, Shang D, Feng J, Dong H, Xu Q, et al. Efficient and reversible absorption of ammonia by cobalt ionic liquids through Lewis acid–base and cooperative hydrogen bond interactions. Green Chem. 2018;20(9):2075–83.
  • 26. Mohammed EH, Ameen AM, Sabah AA, Mustafa TS, Sulyman SAA, Younus NG. Synthesis and Characterization of Mn (II), Fe (III), Co (II), Ni (II), and Cu (II) 1, 3-Dimethylbenzotrizolium Salt Complexes and Their Uses for Decreasing of Sulfur in Diesel Oil. Indian Journal of Heterocyclic Chemistry. 2020;30(04):565–70.
  • 27. Kore R, Kelley Steven P, Aduri P, Rogers RD. Mixed metal double salt ionic liquids comprised of [HN222]2 [ZnCl4] and AlCl3 provide tunable Lewis acid catalysts related to the ionic environment. Dalton Trans. 2018;47(23):7795–803.
  • 28. Fainleib A, Grigoryeva O, Starostenko O, Vashchuk A, Rogalsky S, Grande D. Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters. Express Polymer Letters. 2016;10(9):722.
  • 29. Chen X, Guo H, Abdeltawab AA, Guan Y, Al-Deyab SS, Yu G, et al. Brønsted–Lewis Acidic Ionic Liquids and Application in Oxidative Desulfurization of Diesel Fuel. Energy Fuels. 2015 May 21;29(5):2998–3003.
  • 30. Chan JW, Taylor DS, Zwerdling T, Lane SM, Ihara K, Huser T. Micro-Raman Spectroscopy Detects Individual Neoplastic and Normal Hematopoietic Cells. Biophysical Journal. 2006 Jan;90(2):648–56.
  • 31. Montanino M, Carewska M, Alessandrini F, Passerini S, Appetecchi GB. The role of the cation aliphatic side chain length in piperidinium bis(trifluoromethansulfonyl)imide ionic liquids. Electrochimica Acta. 2011 Dec;57:153–9.
  • 32. Salminen J, Papaiconomou N, Kumar RA, Lee J-M, Kerr J, Newman J, et al. Physicochemical properties and toxicities of hydrophobic piperidinium and pyrrolidinium ionic liquids. Fluid Phase Equilibria. 2007 Dec;261(1–2):421–6.
  • 33. Sabah AA. Synthesis and Characterization of Some Transition Metals Complex Salts of Pyridinium Iodide Ionic Liquids: Application on Extractive Desulfurization. Journal of the Turkish Chemical Society Section A: Chemistry. 2021 Jul 23;8(3):763–74.
  • 34. Song Z, Zhou T, Zhang J, Cheng H, Chen L, Qi Z. Screening of ionic liquids for solvent-sensitive extraction–with deep desulfurization as an example. Chemical Engineering Science. 2015 Jun;129:69–77.
  • 35. Wang S, Li P, Hao L, Deng C, Ren W, Lü H. Oxidative Desulfurization of Model Diesel Using a Fenton-Like Catalyst in the Ionic Liquid [Dmim]BF 4. Chem Eng Technol. 2017 Mar;40(3):555–60.
  • 36. Wang Q, Lei L, Zhu J, Yang B, Li Z. Deep Desulfurization of Fuels by Extraction with 4-Dimethylaminopyridinium-Based Ionic Liquids. Energy Fuels. 2013 Aug 15;27(8):4617–23.
  • 37. Ren Z, Zhou Z, Li M, Zhang F, Wei L, Liu W. Deep Desulfurization of Fuels Using Imidazole Anion-Based Ionic Liquids. ACS Sustainable Chem Eng. 2019 Jan 22;7(2):1890–900.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya, Uygulamalı
Bölüm Makaleler
Yazarlar

Assim A. SABAH (Sorumlu Yazar)
College of Basic Education
0000-0001-9985-496X
Iraq

Destekleyen Kurum Mosul University
Proje Numarası Non
Teşekkür The author is grateful to the University of Mosul for their support of scientific research and the Department of Chemistry at the University of Liverpool for helping to carry out some of the required research measurements.
Yayımlanma Tarihi 30 Kasım 2021
Başvuru Tarihi 7 Temmuz 2021
Kabul Tarihi 20 Eylül 2021
Yayınlandığı Sayı Yıl 2021, Cilt 8, Sayı 4

Kaynak Göster

Vancouver Sabah A. A. Extractive desulfurization using piperidinium based ionic liquids with Lewis acids. Journal of the Turkish Chemical Society Section A: Chemistry. 2021; 8(4): 1057-1088.
J. Turk. Chem. Soc., Sect. A: Chem.