Sulfur extraction from liquid fuels using trihexyl(tetradecyl)phosphonium tetrafluoroborate: as promising solvent

  • Swapnil Dharaskar
  • Mika Sillanpaa
  • Kiran Kumar Tadi
Research Article
  • 11 Downloads

Abstract

Sulfur extraction from fuel is essential to be done for environmental and industrial point of view. Extractive desulfurization (EDS) is one of the most promising techniques in order to achieve legislative sulfur content requirements. Among numerous extractants and solvents, ionic liquids (ILs) are more capable due to their desirable green solvent properties. This work demonstrated that trihexyl(tetradecyl)phosphonium tetrafluoroborate ([THTDP]BF4) was synthesized, characterized, and employed as extraction solvent for extraction of dibenzothiophene (DBT), thiophene, benzothiophene, and other alkyl-substituted derivatives of sulfur from liquid fuel. Molecular confirmation and purity of synthesized ([THTDP]BF4) were analyzed with FTIR, Raman, NMR, EPR, UV, TG/DSC, and XRD analyses. Also, physical properties of ([THTDP]BF4) were carried out. The effects of extraction time, temperature, sulfur compounds, ultra-sonication, and ([THTDP]BF4) recycling/regeneration on DBT removal from liquid fuel were also examined. DBT removal in n-dodecane was 92.6% using EDS with mass ratio (1:1) in 30 min at 30 °C under the mild reaction conditions. ([THTDP]BF4) could be reused up to ten cycles for sulfur extraction and regenerated for few more cycles with good DBT removal ability. Also, the sulfur extraction from real fuels and multistage extraction performance were tested. The experimental data and results provided in this article discover the remarkable understandings of tetrafluoroborate-based phosphonium ionic liquids as promising solvent for EDS.

Keywords

Trihexyl(tetradecyl)phosphonium tetrafluoroborate Ionic liquid Fuel Sulfur Extraction 

Nomenclature

([THTDP]BF4)

trihexyl(tetradecyl)phosphonium tetrafluoroborate

ILs

ionic liquids

HDS

hydrodesulphurization system

EDS

extractive desulfurization system

ppm

parts per million

DBT

dibenzothiophene

TS

thiophene

BT

benzothiophene

3-MT

3-methylthiophene

4-MDBT

4-methyldibenzothiophene

4,6-DMDBT

4,6-dimethyldibenzothiophene

KN

partition coefficient

References

  1. Abro R, Abdeltawab A, Al-Deyab S, Yu G, Qazi A, Gao S (2014) A review of extractive desulfurization of fuel oils using ionic liquids. RSC Adv 4:35302–35317CrossRefGoogle Scholar
  2. Ahmad O, Mjalli F, Gujarathi A, Alwahaibi T, Al-Wahaibi Y, AlNashef I (2015a) Feasibility of phosphonium-based ionic liquids as solvents for extractive desulfurization of liquid fuels. Fluid Phase Equilib 401:102–109CrossRefGoogle Scholar
  3. Ahmad O, Mjalli F, Alwahaibi T, Al-Wahaibi Y, AlNashef I (2015b) Optimum performance of extractive desulfurization of liquid fuels using phosphonium and pyrrolidinium based ionic liquids. Ind Eng Chem Res 54:6540–6550CrossRefGoogle Scholar
  4. Alonso L, Arce A, Francisco M, Soto A (2008) (Liquid+liquid) equilibria of [C8mim][NTf2] ionic liquid with a sulfur-component and hydrocarbons. J Chem Thermodyn 40:265–270CrossRefGoogle Scholar
  5. Anantharaj R, Banerjee T (2011) COSMO-RS based predictions for the desulfurization of diesel oil using ionic liquids. Fuel Process Technol 92:39–52CrossRefGoogle Scholar
  6. Baeza P, Aguila G, Gracia F, Araya P (2008) Desulfurization by adsorption with copper supported on zirconia. Catal Commun 9:751–755CrossRefGoogle Scholar
  7. Ban L, Liu P, Ma C, Dai B (2013) Deep extractive desulfurization of diesel fuels by FeCl3/ionic liquids. Chin Chem Lett 24:755–758CrossRefGoogle Scholar
  8. Bosmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P (2001) Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun 7:2468–2469Google Scholar
  9. Bradaric C, Downard A, Kennedy C, Robertson A, Zhou Y (2003) Industrial preparation of phosphonium ionic liquids. Green Chem 5:143–152CrossRefGoogle Scholar
  10. Carnaroglio D, Gaudino E, Mantegna S, Moreira E, Vicente de Castro A, Flores E, Cravotto G (2014) Ultrasound-assisted oxidative desulfurization/denitrification of liquid fuels with solid oxidants. Energy Fuel 28:1854–1859CrossRefGoogle Scholar
  11. Chen X, Liu G, Yuan S, Asumana C, Wang W, Yu G (2012) Extractive desulfurization of fuel oils with thiazolium-based ionic liquids. Sep Sci Technol 47:819–826CrossRefGoogle Scholar
  12. Chen X, Yuan S, Abdeltawab A, Al-Deyab S, Zhang J, Yu L, Yu G (2014) Extractive desulfurization and denitrogenation of fuels using functional acidic ionic liquids. Sep Purif Technol 133:187–193CrossRefGoogle Scholar
  13. Cun Z, Feng W, Xiao-yu P, Xiao-qin L (2011) Study of extraction-oxidation desulfurization of model oil by acidic ionic liquid. J Fuel Chem Technol 39:689–693CrossRefGoogle Scholar
  14. Dharaskar S, Wasewar K, Varma M, Shende D, Tadi K, Yoo C (2014) Synthesis, characterization, and application of novel trihexyltetradecyl phosphonium bis (2,4,4-trimethylpentyl) phosphinate for extractive desulfurization of liquid fuel. Fuel Process Technol 123:1–10CrossRefGoogle Scholar
  15. Dharaskar S, Wasewar K, Varma M, Shende D, Yoo C (2016) Synthesis, characterization, and application of 1-butyl-3-methylimidazolium tetrafluorobaorate for extractive desulfurization of liquid fuels. Arb J Chem 9:578–587CrossRefGoogle Scholar
  16. Domanska U, Wlazlo M (2014) Effect of the cation and anion of the ionic liquid on desulfurization of model fuels. Fuel 134:114–125CrossRefGoogle Scholar
  17. Duarte F, Mello P, Bizzi C, Nunes M, Alencar E, Motta H, Dressler V, Flores E (2011) Sulfur removal from hydrotreated petroleum fractions using ultrasound-assisted oxidative desulfurization process. Fuel 90:2158–2164CrossRefGoogle Scholar
  18. Fallah R, Azizian S, Dwivedi A, Sillanpaa M (2015) Adsorptive desulfurization using different passivated carboan nanoparticles by PEG-200. Fuel Process Technol 130:214–223CrossRefGoogle Scholar
  19. Faridbod F, Ganjali M, Norouzi P, Riahi S, Rashedi H (2011) Application of Room Temperature Ionic Liquids in Electrochemical Sensors and Biosensors, Ionic Liquids: Applications and Perspectives, InTech, ISBN: 978-953-307-248-7.  https://doi.org/10.5772/14702
  20. Ferreira A, Freire M, Ribeiro J, Lopes F, Crespo J, Coutinho J (2014) Ionic liquids for thiols desulfurization: experimental liquid-liquid equilibrium and COSMO-RS description. Fuel 128:314–329CrossRefGoogle Scholar
  21. Freire M, Carvalho P, Gardas R, Luis M, Santos B, Marrucho I, Countinho J (2008) Solubility of water in tetradecyltrihexylphosphonium-based ionic liquids. J Chem Eng Data 53:2378–2382CrossRefGoogle Scholar
  22. Gao H, Guo C, Xing J, Liu H (2012) Deep desulfurization of diesel oil with extraction using pyridinium-based ionic liquids. Sep Sci Technol 47:325–330CrossRefGoogle Scholar
  23. Hansmeier A, Meindersma G, de haan A (2011) Desulfurization and denitrogenation of gasoline and diesel fuels by means of ionic liquids. Green Chem 13:1907–1913CrossRefGoogle Scholar
  24. Holding A, Heikkil M, Kilpelinen I, King A (2014) Amphiphilic and phase-separable ionic liquids for biomass processing. ChemSusChem 1:1–14Google Scholar
  25. Huang W, Zhu W, Li H, Shi H, Zhu G, Liu H, Chen G (2010) Heteropolyanion-based ionic liquid for deep desulfurization of fuels in ionic liquids. Ind Eng Chem Res 49:8998–9003CrossRefGoogle Scholar
  26. Ibrahim M, Hayyan M, Hashim M, Hayyan A (2017) The role of ionic liquids in desulfurization of fuels: a review. Renew Sustain Energy Rev 76:1534–1549CrossRefGoogle Scholar
  27. Kianpour E, Azizian S (2014) Polyethylene glycol as green solvent for effective extractive desulfurization of liquid fuel at ambient conditions. Fuel 137:36–40CrossRefGoogle Scholar
  28. Kianpour E, Azizian S, Yarie M, Zolfigol M, Bayat M (2016) A task-specific phosphonium ionic liquid as an efficient extractant for green desulfurization of liquid fuel: an experimental and computational study. Chem Eng J 295:500–508CrossRefGoogle Scholar
  29. Kulkarni P, Afonso C (2010) Deep desulfurization of diesel fuel using ionic liquids: current status and future challenges. Green Chem 12:1139–1149CrossRefGoogle Scholar
  30. Li M, Zhou Z, Zhang F, Chai W, Zhang L, Ren Z (2016) Deep oxidative extractive desulfurization of fuels using benzyl based ionic liquids. AICHE J 62:4023–4034CrossRefGoogle Scholar
  31. Liu W, Etschmann B, Brugger J, Spiccia L, Foran G, Mclnnes B (2006) UV-Vis spectrophotometric and XAFS studies of ferric chloride complexes in hypersaline LiCl solutions at 25–90 C. Chem Geol 231:326–349CrossRefGoogle Scholar
  32. Liu X, Zhou G, Zhang S, Yu G (2010) Molecular simulations of phosphonium based ionic liquid. Mol Simul 36:79–86CrossRefGoogle Scholar
  33. Liu X, Afsal W, Prausnitz J (2013) Solubility’s of small hydrocarbons in tetrabutylphosphonium bis(2,4,4-trimethylpentyl) phosphinate and in 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Ind Eng Chem Res 52:14975–14978CrossRefGoogle Scholar
  34. Lu H, Deng C, Ren W, Yang X (2014a) Oxidative desulfurization of model diesel using [(C4H9)4N]6Mo7O24 as a catalyst in ionic liquids. Fuel Process Technol 119:87–91CrossRefGoogle Scholar
  35. Lu X, Yue L, Hu M, Cao Q, Xu L, Guo Y, Hu S, Fang W (2014b) Piperazinium-based ionic liquids with lactate anion for extractive desulfurization of fuels. Energy Fuel 28:1774–1780CrossRefGoogle Scholar
  36. Maldonado A, Yang F, Qi G, Yang R (2005) Desulfurization of transportation fuels by π-complexation sorbents. Appl Catal B 56:111–126CrossRefGoogle Scholar
  37. Manic M, Macedo E, Visak V (2012) Trihexyltetradecylphosphonium bromide: liquid density, surface tension and solubility of carbon dioxide. Fluid Phase Equilib 324:8–12CrossRefGoogle Scholar
  38. Marcelis M (2002) Anaerobic biodesulfurization of thiophenes. University of Wageningen, WageningenGoogle Scholar
  39. McNulty J, Nair J, Cheekoori S, Larichev V, Capretta A, Robertson A (2006) Scope and mechanistic insights into the use of tetradecyl(trihexyl)phosphonium bistriflimide: a remarkably selective ionic liquid solvent for substitution reactions. Chem Eur J 12:9314–9322CrossRefGoogle Scholar
  40. Min G, Yim T, Lee H, Huh D, Lee E, Mun J, Oh S, Kim Y (2006) Synthesis and Properties of Ionic Liquids: Imidazolium Tetrafluoroborates with Unsaturated Side Chains. Bull Korean Chem Soc 27:847–852Google Scholar
  41. Moghadam F, Azizian S, Kianpour E, Yarie M, Bayat M, Zolfigol M (2017a) Green fuel through green route by using a task-specific and neutral phosphonium ionic liquid: a joint experimental and theoretical study. Chem Eng J 309:480–488CrossRefGoogle Scholar
  42. Moghadam F, Azizian S, Bayat M, Yarie M, Kianpour E, Zolfigol M (2017b) Extractive desulfurization of liquid fuel by using a green, neutral and task specific phosphonium ionic liquid with glyceryl moiety: a joint experimental and computational study. Fuel 208:214–222CrossRefGoogle Scholar
  43. Nejad N, Soolari E, Adibi M, Beigi A, Torkestani S (2013) Imidazolium-based alkylsulfate ionic liquids and removal of sulfur content from model of gasoline. Pet Sci Technol 31:472–480CrossRefGoogle Scholar
  44. Otsuki S, Nonaka T, Takashima N, Qian W, Ishihara A, Imai T, Kabe T (2000) Oxidative desulfurization of light gas oil and vacuum gas oil by oxidation and solvent extraction. Energy Fuel 14:1232–1239CrossRefGoogle Scholar
  45. Pawelec B, Mariscal R, Fierro J, Greenwood A, Vasudevan A (2001) Carbon-supported tungsten and nickel catalysts for hydrodesulfurization and hydrogenation reactions. Appl Catal A 206:295–307CrossRefGoogle Scholar
  46. Raj J, Magaret S, Matheswaran M, Kallidanthiyil L, Wilfred C, Mutalib M (2017) Extractive desulfurization of model fuel oil using ester functionalized imidazolium ionic liquids. Sep Purification Technol online 22th August 2017Google Scholar
  47. Stojanovic A, Morgenbesser C, Kogelnig D, Krachler R, Keppler B (2011) Quaternary ammonium and phosphonium ionic liquids in chemical and environmental engineering In: Kokorin A (ed) Ionic liquids: theory, properties, new approaches, pp 657–680Google Scholar
  48. Sun X, Jin Z, Yang L, Hao J, Zu Y, Wang W, Liu W (2013) Ultrasonic-assisted extraction of procyanidins using ionic liquid solution from Larixgmelinii bark. J Chem 1:1–9Google Scholar
  49. Thompson L, Doraiswamy L (1999) Sonochemistry: science and engineering. Ind Eng Chem Res 38:1215–1249CrossRefGoogle Scholar
  50. Varma N, Ramalingam A, Banerjee T (2011) Experiments, correlations and COSMO-RS predictions for the extraction of benzothiophene from n-hexane using imidazolium-based ionic liquids. Chem Eng J 166:30–39CrossRefGoogle Scholar
  51. Wang Q, Lei L, Zhu J, Yang B, Li Z (2013) Deep desulfurization of fuels by extraction with 4-dimethylaminopyridinium-based ionic liquids. Energy Fuel 27:4617–4623CrossRefGoogle Scholar
  52. Wasewar K (2013) Multistage extractive desulfurization of liquid fuel by ionic liquids. J Mech Eng 3:10–15Google Scholar
  53. Wolff M, Alexander K, Belder G (2000) Uses of quaternary phosphonium compounds in phase transfer catalysis. Chim Oggi 18:29–32Google Scholar
  54. Wu Z, Ondruschka B (2010) Ultrasound-assisted oxidative desulphurization of liquid fuels and its industrial application. Ultrason Sonochem 17:1027–1032CrossRefGoogle Scholar
  55. Zhang S, Zhang Z (2002) Novel properties of ionic liquids in selective sulfur removal from fuels at room temperature. Green Chem 4:376–379CrossRefGoogle Scholar
  56. Zhang S, Zhang Q, Zhang Z (2004) Extractive desulfurization and denitrogenation of fuels using ionic liquids. Ind Eng Chem Res 43:614–622CrossRefGoogle Scholar
  57. Zhu W, Zhang J, Li H, Chao Y, Jiang W, Yin S, Liu H (2012) Fenton-like ionic liquids/H2O2 system: one-pot extraction combined with oxidation desulfurization of fuel. RSC Adv 2:658–664CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Swapnil Dharaskar
    • 1
    • 2
  • Mika Sillanpaa
    • 1
    • 3
  • Kiran Kumar Tadi
    • 4
  1. 1.Laboratory of Green Chemistry, LUT Savo Sustainable TechnologiesLappeenranta University of TechnologyMikkeliFinland
  2. 2.Department of Chemical Engineering, School of TechnologyPandit Deendayal PetroleumGandhinagarIndia
  3. 3.Department of Civil and Environmental EngineeringFlorida International UniversityMiamiUSA
  4. 4.Institute of ChemistryHebrew University of JerusalemJerusalemIsrael

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