Desulfurization of Dibenzothiophene from Model Oil by Aluminum Ammonium Sulfate/Urea (Alum) Ionic Liquid Analogue
Keywords:
Ionic liquid, Deep eutectic solvent, Desulfurization Dibenzothiophene, Ammonium Sulfate, UreaAbstract
Petroleum is the most important source of energy which is required to be free of sulfur. Ionic liquid analogue was used to desulfurize Model oil at several conditions including different concentration of dibenzothiophene (DBT), time of extraction, temperature and ionic liquid analogue to Model volume ratios. The cheap and easy made ionic liquid analogue is a mixture of 1:5 mole ratio of Aluminum ammonium sulfate.12H2O: Urea (Alum).The desulfurization was followed by ATR-IR, GC-MS. Aluminum salt ionic liquid analogue was found to have more than 90% removal of DBT from its mixture with decane (Model). The process in the Alum solvent was attributed to combination of an absorption and possibly oxidation of DBT through interaction of sulfur with the oxygen of sulfate group of the ionic liquid analogue when the IR bands of sulfate and hydrogen bond of ionic liquid analogue were influenced strongly by this interaction. The removal of dibenothiophene was more effective at 30 ºC and 10 min than higher temperature and longer time.
References
[1] Lobodin, V. V.; Robbins, W. K. J.; Rodgers, R. P.; “Separation and Characterization of Reactive and Non-Reactive Sulfur in Petroleum and Its Fractions”; Ene. Fuel. 29, 6177−6186, 2015.
[2] Dharaskar, S. A.; Deshmukh, S. K.; Bhuyar, K. D.; Wasewar, K. L.; “Effect of the BMIM BF4 immobilization on oxidized activated carbon in fuel desulfurization”; Green Chem. 11, 1-6, 2015.
[3] Faridbod, F.; Rashedi, H.; Ganjali, M. R.; Norouzi P.; Riahi, S.; “Application of room temperature ionic liquids in electrochemical sensors and biosensors”; INTECH, 644-658, 2011.
[4] Wishart, J. F.; “Energy applications of ionic liquids”; Ene. Environ. Sci. 2, 956, 2009.
[5] González-García, O.; Cedeño-Caero, L.; “V-Mo based catalysts for oxidative desulfurization of diesel fuel”; Catal. Today 148, 42–48, 2009.
[6] Rezvani, M. A.; Shaterian, M.; Akbarzadeh, F.; Khandan, S.; “Deep oxidative desulfurization of gasoline induced by PMoCu@MgCu2O4 - PVA composite as a high-performance heterogeneous nanocatalyst”; Chem. Eng. J. 333, 537–544, 2018.
[7] Zhao, H.; Baker, G. A.; Zhang, Q.; “Design rules of ionic liquids tasked for highly efficient fuel desulfurization by mild oxidative extraction”; Fuel 189, 334–339, 2017.
[8] Chen, L. J.; Li, F. T.; “Oxidative desulfurization of model gasoline over modified titanium silicalite’; Pet. Sci. Technol. 33, 196–202, 2015.
[9] Zhao, H.; Baker, G. A.; Zhang, Q.; “Design rules of ionic liquids tasked for highly efficient fuel desulfurization by mild oxidative extraction”; Fuel 189, 334–339, 2017.
[10] Bakar, W. A.; Ali, R.; Kadir, A.; Mokhtar, W. N.; “Effect of transition metal oxides catalysts on oxidative desulfurization of model diesel”; Fuel Proc. Technol. 101, 78–84, 2012.
[11] Subhan, S.; Rahman, A. U.; Yaseen, M.; Haroon, H. U.; Isha, M.; Sahibzada, M.; Tong, Z.; “Ultra-fast and highly efficient catalytic oxidative desulfurization of dibenzothiophene at ambient temperature over low Mn”; Feul, 23-56, 2012.
[12] Xun, S.; Zhu, W.; Chang, Y. H.; Zhang, Li. M.; Jiang, W.; Zheng, D. Y.; Li, H.; “Designing multifunctional SO3H-based polyoxometalate catalysts for oxidative desulfurization in acid deep eutectic solvents”; Chem. Eng. J. 288, 608-617, 2016.
[13] Li, J. j.; Xiao, H.; Tang, X. D.; Zhou, M.; “Extractive Desulfurization of Model Oil with Protic Ionic Liquids”; Ene. Fuels 30, 5411– 5418, 2016.
[14] Safa, M.; Mokhtarani, B.; Mortaheb, H. R.; “Density and viscosity of pyridinium-based ionic liquids and their binary mixtures with water at several temperatures”; Chem. Eng. Res. Des. 111, 323–331, 2016.
[15] Yuan, J.; Xiong, J.; Wang, J.; Ding, W.; Yang, L.; Zhang, M.; Zhu, W.; Li, H.; “Phosphomolybdic acid immobilized on ionic liquid-modified hexagonal boron nitride for oxidative desulfurization of fuel”; J. Porous Mater. 23, 823-831, 2016.
[16] Chandran, D.; Khalid, M.; Walvekar, R.; Mubarak, N. M.; Dharaskar, S.; Wong, W. Y.; Gupta, T. C.; Manikyam, S., Deep eutectic solvents for extraction-desulphurization: A review, Journal of Molecular Liquids, 27, 723-831 , 2018.
[17] Wilfred, C. D.; Kiat, C. F.; Man, Z.; Bustam, M. A.; Mutalib, M. I. M.; Phak, C. Z.; “Extraction of dibenzothiophene from dodecane using ionic liquids”; Fuel Process. Technol 93, 85- 89, 2012.
[18] Gordon, C. M.; “New developments in catalysis using ionic liquids”; Appl. Catal. A.-Gen. 222, 101–117, 2001.
[19] Welton, T.; “Ionic liquids in catalysis”; Coord. Chem. Rev. 248, 2459-2477, 2004.
[20] Warrag, S. E.; Peters, C. J.; Kroon, M. C.; “Deep eutectic solvents for highly efficient separations in oil and gas industries”; Curr. Opin. Green Sustain. Chem. 5, 55–60, 2017.
[21] Kerton, F. M.; Marriott, R.; “Alternative Solvents for Green Chemistry”; Second edition, Royal Society of Chemistry, 2013.
[22] Zhu, W.; Wang, C.; Li, H.; Wu, P.; Xun, S.; Jiang, W.; Chen, Z.; Zhao, Z.; Li, H.; “One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent”; Green Chem. 17, 2464–2472, 2015.
[23] Peric, B.; Sierra, J.; Mart, E.; Cruañas, R.; Garau, M. A.; Arning, J.; Bottin-Weber, U.; Stolte, S.; “Toxicity and biodegradability of selected protic and aprotic ionic liquids"; J. Hazard. Mat. 261, 99–105, 2013.
[24] Pham, T. P. T.; Cho, C. W.; Yun, Y. S.; “Environmental fate and toxicity of ionic liquids, a review”; Water Res. 44, 352–372, 2010.
[25] Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K.; “Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids”; J. Am. Chem. Soc. 126, 9142–9147, 2004.
[26] Li, C.; Li, D.; Zou, S.; Li, Z.; Yin, J.; Wang, A.; Cui, Y.; Yao, Z.; Zhao, Q.; “Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents"; Green Chem. 15, 2793–2799, 2013.
[27] Gano, Z. S.; Mjalli, F. S.; Al-Wahaibi, T.; Al-Wahaibi, Y.; “The Novel Application of Hydrated Metal Halide (SnCl2. 2H2O)-Based Deep Eutectic Solvent for the Extractive Desulfurization of Liquid Fuels”; Int. J. Chem. Eng. Appl. 6, 367–371, 2015.
[28] Abood, H. M. A.; Abid, H. S.; “DSC and TGA measurement of room temperature ionic liquids (RTILs) containing Ammonium Alum or Aluminium Nitrate with Amide”; Al-Nahrain J. Sci. 18 (2) 56-68, 2015.
[29] Al-Qudsi, Z. N.; Abood, H. M. A.; “The Electronic Transition Behavior Cr (III), Fe (III), Fe (II) and Ni (II), Transition Metal Cations In Ammonium Alum-Urea Room Temperature Ionic Liquid”; Al-Nahrain J. Sci. 16 (3), 46 – 55, 2013.
[30] Phase, J.; Langer, B.; Schrader, V.; Bastian, E.; Jacob, J.; “Infrared spectra and force constant of urea in the gaseous”; Chem. 352, 489, 1995.
[31] Podsiadła, D.; Ryba-Romanowski, W. S.; Czupin´ski, O.; Czapla, Z.; “Chromium doped deuterated (CH3)2NH2Al(SO4)2•6H2O crystals”; J. Molec. Struct. 555, 33–34, 2000.
[32] Isao, S.; “Infrared spectra and normal vibrations of acetamide and its analogues”; Bull. Chem. Soc. Jap. 35(8), 1962.
[33] Tang, X. D.; Zhang, Y. f.; Li, J. J.; Zhu, Y. Q.; Qing, D. Y.; Deng, Y. X.; “Deep extractive desulfurization with arenium ion deep eutectic solvents”; Ind. Eng. Chem., Res. 54, 4625–4632, 2015.
[34] Li, J. J.; Xiao, H.; Tang, X. D.; Zhou, M.; “Green carboxylic acid-based deep eutectic solvents as solvents for extractive desulfurization”; Ene. Fuels 30 , 5411–5418, 2016.
[35] Hadj-Kali, M. K. S.; Mulyono, H. F.; Hizaddin, I.; Wazeer, L.; El-Blidi, E.; Ali, M. A.; Hashim, I. M.; “Removal of thiophene from mixtures with n-heptane by selective extraction using deep eutectic solvents”; Ind. Eng. Chem. Res. 55, 8415–8423, 2016.
[36] Javadli, R. De.; Klerk, A.; “Desulfurization of heavy oil”; Appl. Petrochem. Res. 1, 3–19, 2012.
[37] Li, C.; Zhang, J.; Li, Z.; Yin, J.; Cui, Y.; Liu, Y.; Yang, G.; “Extraction desulfurization of fuels with ‘metal ions’ based deep eutectic solvents (MDESs)”; Green Chem. 18, 3789–3795, 2016.
[38] Khezeli, T.; Daneshfar, A.; “Synthesis and application of magnetic deep eutectic solvents: Novel solvents for ultrasound assisted liquid-liquid microextraction of Thiophene”; Ultrason. Sonochem. 38, 590–597, 2017.
[39] Zaid, H. F. M.; Chong, F. K.; Mutalib, M. I. A.; “Extractive deep desulfurization of diesel using choline chloride-glycerol eutectic-based ionic liquid as a green solvent”; Fuel 192, 10–17, 2017.
[40] Tang, X. L.; Shi, L.; “Study of the adsorption reactions of thiophene on Cu (I)/HY-Al2O3 by Fourier transform infrared and temperature-programmed desorption: Adsorption, desorption, and sorbent regeneration mechanisms”; Langmuir 27, 11999–12007, 2011.
[2] Dharaskar, S. A.; Deshmukh, S. K.; Bhuyar, K. D.; Wasewar, K. L.; “Effect of the BMIM BF4 immobilization on oxidized activated carbon in fuel desulfurization”; Green Chem. 11, 1-6, 2015.
[3] Faridbod, F.; Rashedi, H.; Ganjali, M. R.; Norouzi P.; Riahi, S.; “Application of room temperature ionic liquids in electrochemical sensors and biosensors”; INTECH, 644-658, 2011.
[4] Wishart, J. F.; “Energy applications of ionic liquids”; Ene. Environ. Sci. 2, 956, 2009.
[5] González-García, O.; Cedeño-Caero, L.; “V-Mo based catalysts for oxidative desulfurization of diesel fuel”; Catal. Today 148, 42–48, 2009.
[6] Rezvani, M. A.; Shaterian, M.; Akbarzadeh, F.; Khandan, S.; “Deep oxidative desulfurization of gasoline induced by PMoCu@MgCu2O4 - PVA composite as a high-performance heterogeneous nanocatalyst”; Chem. Eng. J. 333, 537–544, 2018.
[7] Zhao, H.; Baker, G. A.; Zhang, Q.; “Design rules of ionic liquids tasked for highly efficient fuel desulfurization by mild oxidative extraction”; Fuel 189, 334–339, 2017.
[8] Chen, L. J.; Li, F. T.; “Oxidative desulfurization of model gasoline over modified titanium silicalite’; Pet. Sci. Technol. 33, 196–202, 2015.
[9] Zhao, H.; Baker, G. A.; Zhang, Q.; “Design rules of ionic liquids tasked for highly efficient fuel desulfurization by mild oxidative extraction”; Fuel 189, 334–339, 2017.
[10] Bakar, W. A.; Ali, R.; Kadir, A.; Mokhtar, W. N.; “Effect of transition metal oxides catalysts on oxidative desulfurization of model diesel”; Fuel Proc. Technol. 101, 78–84, 2012.
[11] Subhan, S.; Rahman, A. U.; Yaseen, M.; Haroon, H. U.; Isha, M.; Sahibzada, M.; Tong, Z.; “Ultra-fast and highly efficient catalytic oxidative desulfurization of dibenzothiophene at ambient temperature over low Mn”; Feul, 23-56, 2012.
[12] Xun, S.; Zhu, W.; Chang, Y. H.; Zhang, Li. M.; Jiang, W.; Zheng, D. Y.; Li, H.; “Designing multifunctional SO3H-based polyoxometalate catalysts for oxidative desulfurization in acid deep eutectic solvents”; Chem. Eng. J. 288, 608-617, 2016.
[13] Li, J. j.; Xiao, H.; Tang, X. D.; Zhou, M.; “Extractive Desulfurization of Model Oil with Protic Ionic Liquids”; Ene. Fuels 30, 5411– 5418, 2016.
[14] Safa, M.; Mokhtarani, B.; Mortaheb, H. R.; “Density and viscosity of pyridinium-based ionic liquids and their binary mixtures with water at several temperatures”; Chem. Eng. Res. Des. 111, 323–331, 2016.
[15] Yuan, J.; Xiong, J.; Wang, J.; Ding, W.; Yang, L.; Zhang, M.; Zhu, W.; Li, H.; “Phosphomolybdic acid immobilized on ionic liquid-modified hexagonal boron nitride for oxidative desulfurization of fuel”; J. Porous Mater. 23, 823-831, 2016.
[16] Chandran, D.; Khalid, M.; Walvekar, R.; Mubarak, N. M.; Dharaskar, S.; Wong, W. Y.; Gupta, T. C.; Manikyam, S., Deep eutectic solvents for extraction-desulphurization: A review, Journal of Molecular Liquids, 27, 723-831 , 2018.
[17] Wilfred, C. D.; Kiat, C. F.; Man, Z.; Bustam, M. A.; Mutalib, M. I. M.; Phak, C. Z.; “Extraction of dibenzothiophene from dodecane using ionic liquids”; Fuel Process. Technol 93, 85- 89, 2012.
[18] Gordon, C. M.; “New developments in catalysis using ionic liquids”; Appl. Catal. A.-Gen. 222, 101–117, 2001.
[19] Welton, T.; “Ionic liquids in catalysis”; Coord. Chem. Rev. 248, 2459-2477, 2004.
[20] Warrag, S. E.; Peters, C. J.; Kroon, M. C.; “Deep eutectic solvents for highly efficient separations in oil and gas industries”; Curr. Opin. Green Sustain. Chem. 5, 55–60, 2017.
[21] Kerton, F. M.; Marriott, R.; “Alternative Solvents for Green Chemistry”; Second edition, Royal Society of Chemistry, 2013.
[22] Zhu, W.; Wang, C.; Li, H.; Wu, P.; Xun, S.; Jiang, W.; Chen, Z.; Zhao, Z.; Li, H.; “One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent”; Green Chem. 17, 2464–2472, 2015.
[23] Peric, B.; Sierra, J.; Mart, E.; Cruañas, R.; Garau, M. A.; Arning, J.; Bottin-Weber, U.; Stolte, S.; “Toxicity and biodegradability of selected protic and aprotic ionic liquids"; J. Hazard. Mat. 261, 99–105, 2013.
[24] Pham, T. P. T.; Cho, C. W.; Yun, Y. S.; “Environmental fate and toxicity of ionic liquids, a review”; Water Res. 44, 352–372, 2010.
[25] Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K.; “Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids”; J. Am. Chem. Soc. 126, 9142–9147, 2004.
[26] Li, C.; Li, D.; Zou, S.; Li, Z.; Yin, J.; Wang, A.; Cui, Y.; Yao, Z.; Zhao, Q.; “Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents"; Green Chem. 15, 2793–2799, 2013.
[27] Gano, Z. S.; Mjalli, F. S.; Al-Wahaibi, T.; Al-Wahaibi, Y.; “The Novel Application of Hydrated Metal Halide (SnCl2. 2H2O)-Based Deep Eutectic Solvent for the Extractive Desulfurization of Liquid Fuels”; Int. J. Chem. Eng. Appl. 6, 367–371, 2015.
[28] Abood, H. M. A.; Abid, H. S.; “DSC and TGA measurement of room temperature ionic liquids (RTILs) containing Ammonium Alum or Aluminium Nitrate with Amide”; Al-Nahrain J. Sci. 18 (2) 56-68, 2015.
[29] Al-Qudsi, Z. N.; Abood, H. M. A.; “The Electronic Transition Behavior Cr (III), Fe (III), Fe (II) and Ni (II), Transition Metal Cations In Ammonium Alum-Urea Room Temperature Ionic Liquid”; Al-Nahrain J. Sci. 16 (3), 46 – 55, 2013.
[30] Phase, J.; Langer, B.; Schrader, V.; Bastian, E.; Jacob, J.; “Infrared spectra and force constant of urea in the gaseous”; Chem. 352, 489, 1995.
[31] Podsiadła, D.; Ryba-Romanowski, W. S.; Czupin´ski, O.; Czapla, Z.; “Chromium doped deuterated (CH3)2NH2Al(SO4)2•6H2O crystals”; J. Molec. Struct. 555, 33–34, 2000.
[32] Isao, S.; “Infrared spectra and normal vibrations of acetamide and its analogues”; Bull. Chem. Soc. Jap. 35(8), 1962.
[33] Tang, X. D.; Zhang, Y. f.; Li, J. J.; Zhu, Y. Q.; Qing, D. Y.; Deng, Y. X.; “Deep extractive desulfurization with arenium ion deep eutectic solvents”; Ind. Eng. Chem., Res. 54, 4625–4632, 2015.
[34] Li, J. J.; Xiao, H.; Tang, X. D.; Zhou, M.; “Green carboxylic acid-based deep eutectic solvents as solvents for extractive desulfurization”; Ene. Fuels 30 , 5411–5418, 2016.
[35] Hadj-Kali, M. K. S.; Mulyono, H. F.; Hizaddin, I.; Wazeer, L.; El-Blidi, E.; Ali, M. A.; Hashim, I. M.; “Removal of thiophene from mixtures with n-heptane by selective extraction using deep eutectic solvents”; Ind. Eng. Chem. Res. 55, 8415–8423, 2016.
[36] Javadli, R. De.; Klerk, A.; “Desulfurization of heavy oil”; Appl. Petrochem. Res. 1, 3–19, 2012.
[37] Li, C.; Zhang, J.; Li, Z.; Yin, J.; Cui, Y.; Liu, Y.; Yang, G.; “Extraction desulfurization of fuels with ‘metal ions’ based deep eutectic solvents (MDESs)”; Green Chem. 18, 3789–3795, 2016.
[38] Khezeli, T.; Daneshfar, A.; “Synthesis and application of magnetic deep eutectic solvents: Novel solvents for ultrasound assisted liquid-liquid microextraction of Thiophene”; Ultrason. Sonochem. 38, 590–597, 2017.
[39] Zaid, H. F. M.; Chong, F. K.; Mutalib, M. I. A.; “Extractive deep desulfurization of diesel using choline chloride-glycerol eutectic-based ionic liquid as a green solvent”; Fuel 192, 10–17, 2017.
[40] Tang, X. L.; Shi, L.; “Study of the adsorption reactions of thiophene on Cu (I)/HY-Al2O3 by Fourier transform infrared and temperature-programmed desorption: Adsorption, desorption, and sorbent regeneration mechanisms”; Langmuir 27, 11999–12007, 2011.
Downloads
Published
2020-06-04
Issue
Section
Articles
How to Cite
(1)
Desulfurization of Dibenzothiophene from Model Oil by Aluminum Ammonium Sulfate Urea (Alum) Ionic Liquid Analogue. ANJS 2020, 23 (2), 8-17.
.jpg)
