Abstract
Phosphonium-based ionic liquid (PIL) has been used as a catalyst and extractant. Here, the PIL, trihexyl tetradecyl phosphonium bromide ([THTDP]Br) was utilized for the S-removal of model oil (MO) and acted as the reaction-induced self-separation catalyst. The influence of oxidant to sulfur molar ratio (n(O/S)), mass ratio of model oil to ionic liquid (m(MO/IL)), sonication time, and temperature was observed to investigate the optimal conditions for the ultrasound-assisted extractive/oxidative desulfurization (UEODS) catalyzed by [THTDP]Br. A kinetic study was performed, and the reaction rate constant and half-life were calculated as the oxidation reaction was following pseudo-first-order reaction kinetics. Moreover, the oxidation reactivity and selectivity of various sulfur substrates were in the following order: DBT > BT > TH > 3-MT. The DBT removal with various initial S-content was observed to be constant, which makes it feasible for practical application. The interaction energy between [THTDP]Br and S-compounds was examined using Density Functional Theory. The sulfur removal of base oil (BO) was also examined using various desulfurization systems at DBT optimized conditions. The highest desulfurization efficiency of BO was obtained during the UEODS process, which made it industrially feasible. [THTDP]Br was regenerated and recycled six times with a slight variation in efficiency.
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References
Abro R, Abdeltawab AA, Al-Deyab SS et al (2014) A review of extractive desulfurization of fuel oils using ionic liquids. RSC Adv 4:35302–35317. https://doi.org/10.1039/c4ra03478c
Ahmad W, Ahmad I, Ishaq M, Ihsan K (2017) Adsorptive desulfurization of kerosene and diesel oil by Zn impregnated montmorollonite clay. Arab J Chem 10:S3263–S3269. https://doi.org/10.1016/j.arabjc.2013.12.025
Ahmed OU, Mjalli FS, Al-Wahaibi T et al (2016) Efficient non-catalytic oxidative and extractive desulfurization of liquid fuels using ionic liquids. RSC Adv 6:103606–103617. https://doi.org/10.1039/c6ra22032k
Akbari A, Omidkhah M, Towfighi Darian J (2015) Facilitated and selective oxidation of thiophenic sulfur compounds using MoOx/Al2O3-H2O2 system under ultrasonic irradiation. Ultrason Sonochem 23:231–237. https://doi.org/10.1016/j.ultsonch.2014.09.002
Andevary HH, Akbari A, Omidkhah M (2019) High efficient and selective oxidative desulfurization of diesel fuel using dual-function [Omim]FeCl4 as catalyst/extractant. Fuel Process Technol 185:. https://doi.org/10.1016/j.fuproc.2018.11.014
Bal DK, Bhasarkar JB (2019) Mechanistic investigation of sono–phosphotungstic acid/phase transfer agent assisted oxidative desulfurization of liquid fuel. Asia-Pacific J Chem Eng 14:1–12. https://doi.org/10.1002/apj.2271
Balinge KR, Khiratkar AG, Krishnamurthy M et al (2016) Deep-desulfurization of the petroleum diesel using the heterogeneous carboxyl functionalized poly-ionic liquid. Resour Technol 2:S105–S113. https://doi.org/10.1016/j.reffit.2016.10.005
Boniek D, Figueiredo D, Dos Santos AFB, De Resende Stoianoff MA (2015) Biodesulfurization: a mini review about the immediate search for the future technology. Clean Technol Environ Policy 17:29–37. https://doi.org/10.1007/s10098-014-0812-x
Chen X, Guan Y, Abdeltawab AA et al (2015) Using functional acidic ionic liquids as both extractant and catalyst in oxidative desulfurization of diesel fuel: an investigation of real feedstock. Fuel 146:6–12. https://doi.org/10.1016/j.fuel.2014.12.091
Dennington R, Keith T, Millam J, (2009) Gauss View. Version 5. Semichem Inc. Shawnee Mission.
Desai K, Bhatt S, Dharaskar S et al (2020) Butyl triphenyl phosphonium bromide as an effective catalyst for ultrasound assisted oxidative desulfurization process. Mater Today Proc. https://doi.org/10.1016/j.matpr.2019.12.308
Desai K, Dharaskar S (2021a) Triphenyl methyl phosphonium tosylate as an efficient phase transfer catalyst for ultrasound-assisted oxidative desulfurization of liquid fuel. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-021-12391-1
Desai K, Dharaskar S (2021b) Ultrasound-assisted oxidative desulfurization of fuel using butyl triphenyl phosphonium chloride as a promising catalyst. Mater Today Proc 2–6. https://doi.org/10.1016/j.matpr.2021.11.353
Desai K, Dharaskar S, Pandya J, Shinde S (2021) Ultrasound-assisted extractive / oxidative desulfurization of oil using environmentally benign trihexyl tetradecyl phosphonium chloride. Environ Technol Innov 24:
Devi R (2015) Ionic liquids-useful reaction green solvents for the future (a review). 2:26–29
Dharaskar S, Desai K, Tadi KK, Sillanpää M (2021) Synthesis, characterization and application of trihexyl (tetradecyl) phosphonium bromide as a promising solvent for sulfur extraction from liquid fuels. Ind Eng Chem Res. https://doi.org/10.1021/acs.iecr.1c02169
Dharaskar S, Sillanpaa M (2018a) Synthesis, characterization, and application of trihexyl(tetradecyl)phosphonium chloride as promising solvent for extractive desulfurization of liquid fuel. Chem Eng Res Des 133:388–397. https://doi.org/10.1016/j.cherd.2018.03.016
Dharaskar S, Sillanpaa M, Tadi KK (2018) Sulfur extraction from liquid fuels using trihexyl(tetradecyl)phosphonium tetrafluoroborate: as promising solvent. Environ Sci Pollut Res 25:17156–17167. https://doi.org/10.1007/s11356-018-1789-5
Dharaskar SA, Sillanpaa M (2018b) Trihexyl(tetradecyl)phosphonium hexafluorophosphate as an promising extractant for extractive desulfurization from liquid fuels. Sep Sci Technol 53:2044–2054. https://doi.org/10.1080/01496395.2018.1443133
Dharaskar SA, Wasewar KL, Varma MN et al (2014) Synthesis, characterization, and application of novel trihexyl tetradecyl phosphonium bis (2,4,4-trimethylpentyl) phosphinate for extractive desulfurization of liquid fuel. Fuel Process Technol 123:1–10. https://doi.org/10.1016/j.fuproc.2014.02.001
Duarte FA, Mello PDA, Bizzi CA et al (2011) Sulfur removal from hydrotreated petroleum fractions using ultrasound-assisted oxidative desulfurization process. Fuel 90:2158–2164. https://doi.org/10.1016/j.fuel.2011.01.030
Francisco M, Arce A, Soto A (2010) Ionic liquids on desulfurization of fuel oils. Fluid Phase Equilib 294:39–48. https://doi.org/10.1016/j.fluid.2009.12.020
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich A, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz, JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA, Peralta Jr J E, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ, (2016) Gaussian 09. Revision A.02., Gaussian Inc., Wallingford CT.
Ge J, Zhou Y, Yang Y, Xue M (2011) Catalytic oxidative desulfurization of gasoline using ionic liquid emulsion system. Ind Eng Chem Res 50:13686–13692. https://doi.org/10.1021/ie201325e
Glendening ED, Reed AE, Carpenter JE, Weinhold F (2003) NBO Version 3.1, Gaussian Inc. Pittsburgh.
Guo YF, Gao CY, Yang KG et al (2019) Mild and deep oxidative extraction desulfurization using dual-function imidazolium peroxydisulfate ionic liquid. Energy Fuels 33:10728–10733. https://doi.org/10.1021/acs.energyfuels.9b02603
Hao L, Sun L, Su T, et al (2019) Polyoxometalate-based ionic liquid catalyst with unprecedented activity and selectivity for oxidative desulfurization of diesel in [Omim]BF4. Chem Eng J 358: https://doi.org/10.1016/j.cej.2018.10.006
Hassan M, Hayyan M, Ali M, Hayyan A (2016) The role of ionic liquids in desulfurization of fuels : a review. Renew Sustain Energy Rev 0–1. https://doi.org/10.1016/j.rser.2016.11.194
Humphrey W, Dalke A, Schulten K (1996) VMD : visual molecular dynamics. 7855:33–38
Ja M, Leila S, Khosravi-nikou MR (2018) Ultrasonics - sonochemistry ultrasound-assisted oxidative desulfurization and denitrogenation of liquid hydrocarbon fuels : a critical review. Ultrason - Sonochemistry 40:955–968. https://doi.org/10.1016/j.ultsonch.2017.09.002
Jian-long W, Zhao DS, Zhou EP, Dong Z (2007) Desulfurization of gasoline by extraction with N-alkyl-pyridinium-based ionic liquids. Ranliao Huaxue Xuebao/Journal Fuel Chem Technol 35:293–296. https://doi.org/10.1016/S1872-5813(07)60022-X
Jiang W, Dong L, Li H et al (2019) Magnetic supported ionic liquid catalysts with tunable pore volume for enhanced deep oxidative desulfurization. J Mol Liq 274:293–299. https://doi.org/10.1016/j.molliq.2018.10.069
Johnson ER, Keinan S, Mori-sa P, et al (2010) Revealing noncovalent interactions. 6498–6506
Khan NA, Jhung SH (2015) Scandium-triflate/metal-organic frameworks: remarkable adsorbents for desulfurization and denitrogenation. Inorg Chem 54:11498–11504. https://doi.org/10.1021/acs.inorgchem.5b02118
Khodaei B, Amin M, Shahrokh S (2016) Rapid oxidation of dibenzothiophene in model fuel under ultrasound irradiation. Monatshefte Für Chemie - Chem Mon. https://doi.org/10.1007/s00706-016-1801-z
Khodaei B, Rahimi M, Sobati MA et al (2018) Effect of operating pressure on the performance of ultrasound-assisted oxidative desulfurization (UAOD) using a horn type sonicator: experimental investigation and CFD simulation. Chem Eng Process - Process Intensif 132:75–88. https://doi.org/10.1016/j.cep.2018.08.006
Kim IK, Huang CP, Chiu PC (2001) Sonochemical decomposition of dibenzothiophene in aqueous solution. Water Res 35:4370–4378. https://doi.org/10.1016/S0043-1354(01)00176-2
Królikowski M (2019) Liquid–liquid extraction of sulfur compounds from heptane with tricyanomethanide based ionic liquids. J Chem Thermodyn 131:460–470. https://doi.org/10.1016/j.jct.2018.10.009
Li A, Song H, Meng H, et al (2020) Ultrafast desulfurization of diesel oil with ionic liquid based PMoO catalysts and recyclable NaClO oxidant. Chem Eng J 380: https://doi.org/10.1016/j.cej.2019.122453
Li F, Zhang Z, Feng J et al (2007) Biodesulfurization of DBT in tetradecane and crude oil by a facultative thermophilic bacterium Mycobacterium goodii X7B. J Biotechnol 127:222–228. https://doi.org/10.1016/j.jbiotec.2006.07.002
Li J, Hu B, Hu C (2013) Deep desulfurization of fuels by heteropolyanion-based ionic liquid. Bull Korean Chem Soc 34:225–230. https://doi.org/10.5012/bkcs.2013.34.1.225
Lu T, Chen F (2011). Multiwfn : a Multifunctional Wavefunction Analyzer. https://doi.org/10.1002/jcc.22885
Margeta D, Sertić-Bionda K, Foglar L (2016) Ultrasound assisted oxidative desulfurization of model diesel fuel. Appl Acoust 103:202–206. https://doi.org/10.1016/j.apacoust.2015.07.004
Misra P, Badoga S, Chenna A, et al (2017) Denitrogenation and desulfurization of model diesel fuel using functionalized polymer: charge transfer complex formation and adsorption isotherm study
Moghadam FR, Azizian S, Bayat M et al (2017) 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 208:214–222. https://doi.org/10.1016/j.fuel.2017.07.025
Nie Y, Dong Y, Gao H et al (2016) Regulating sulfur removal efficiency of fuels by Lewis acidity of ionic liquids. Sci China Chem 59:526–531. https://doi.org/10.1007/s11426-016-5563-6
Nie Y, Yuan X (2011) Theoretical study on interaction between ionic liquids and aromatic sulfur compounds. J Theor Comput Chem 10:31–40. https://doi.org/10.1142/S0219633611006268
Quyen NDV, Tuyen TN, Khieu DQ et al (2019) Oxidation of dibenzothiophene using the heterogeneous catalyst of tungsten-based carbon nanotubes. Green Process Synth 8:68–77. https://doi.org/10.1515/gps-2017-0189
Ren Z, Zhou Z, Li M et al (2019) Deep desulfurization of fuels using imidazole anion-based ionic liquids. ACS Sustain Chem Eng 7:1890–1900. https://doi.org/10.1021/acssuschemeng.8b03566
Safa M, Mokhtarani B, Mortaheb HR, Tabar Heidar K (2016) Oxidative desulfurization of model diesel using ionic liquid 1-octyl-3-methylimidazolium hydrogen sulfate: an investigation of the ultrasonic irradiation effect on performance. Energy Fuels 30:10909–10916. https://doi.org/10.1021/acs.energyfuels.6b01708
Samokhvalov A, Tatarchuk BJ (2010) Review of experimental characterization of active sites and determination of molecular mechanisms of adsorption, desorption and regeneration of the deep and ultradeep desulfurization sorbents for liquid fuels. Catal Rev - Sci Eng 52:381–410. https://doi.org/10.1080/01614940.2010.498749
Shamseddini A, Mowla D, Esmaeilzadeh F (2019) Continuous treatment of petroleum products in a tailor-made flow-through sonoreactor. J Pet Sci Eng 173: https://doi.org/10.1016/j.petrol.2018.10.068
Simon S, Duran M, Dannenberg JJ, Duran M (1996) How does basis set superposition error change the potential surfaces for hydrogenbonded dimers ? How does basis set superposition error change the potential surfaces. 11024: https://doi.org/10.1063/1.472902
Wan MW, Yen TF (2007) Enhance efficiency of tetraoctylammonium fluoride applied to ultrasound-assisted oxidative desulfurization (UAOD) process. Appl Catal A Gen 319:237–245. https://doi.org/10.1016/j.apcata.2006.12.008
Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis
Xu J, Liu X, Song C et al (2019) Biodesulfurization of high sulfur coal from Shanxi: optimization of the desulfurization parameters of three kinds of bacteria. Energy Sources, Part A Recover Util Environ Eff 00:1–19. https://doi.org/10.1080/15567036.2019.1675821
Xun S, Jiang W, Guo T et al (2019) Magnetic mesoporous nanospheres supported phosphomolybdate-based ionic liquid for aerobic oxidative desulfurization of fuel. J Colloid Interface Sci 534:239–247. https://doi.org/10.1016/j.jcis.2018.08.115
Yi Z, Ma X, Song J et al (2019) Investigations in enhancement biodesulfurization of model compounds by ultrasound pre-oxidation. Ultrason Sonochem 54:110–120. https://doi.org/10.1016/j.ultsonch.2019.02.009
Zagajski Kučan K, Rogošić M (2019) Purification of motor fuels by means of extraction using deep eutectic solvent based on choline chloride and glycerol. J Chem Technol Biotechnol 94:1282–1293. https://doi.org/10.1002/jctb.5885
Zeelani GG, Pal SL (2016) A review on desulfurization techniques of liquid fuels. Int J Sci Res 5:2413–2419. https://doi.org/10.21275/v5i5.nov164036
Zhang L, Wang J, Sun Y et al (2017) Deep oxidative desulfurization of fuels by superbase-derived Lewis acidic ionic liquids. Chem Eng J 328:445–453. https://doi.org/10.1016/j.cej.2017.07.060
Zhang M, Liu J, Li H et al (2020) Tuning the electrophilicity of vanadium-substituted polyoxometalate based ionic liquids for high-efficiency aerobic oxidative desulfurization. Appl Catal B Environ 271:118936. https://doi.org/10.1016/j.apcatb.2020.118936
Zhao D, Sun Z, Li F et al (2008) Oxidative desulfurization of thiophene catalyzed by (C4H9)4NBr·2C6H11NO coordinated ionic liquid. Energy Fuels 22:3065–3069. https://doi.org/10.1021/ef800162w
Zhao D, Wang Y, Duan E, Zhang J (2010) Oxidation desulfurization of fuel using pyridinium-based ionic liquids as phase-transfer catalysts. Fuel Process Technol 91:1803–1806. https://doi.org/10.1016/j.fuproc.2010.08.001
Zhu W, Wu P, Yang L et al (2013) Pyridinium-based temperature-responsive magnetic ionic liquid for oxidative desulfurization of fuels. Chem Eng J 229:250–256. https://doi.org/10.1016/j.cej.2013.05.115
Zhu W, Zhu G, Li H et al (2011) Oxidative desulfurization of fuel catalyzed by metal-based surfactant-type ionic liquids. J Mol Catal A Chem 347:8–14. https://doi.org/10.1016/j.molcata.2011.07.002
Zolotareva D, Zazybin A, Rafikova K, Dembitsky VM (2019) Ionic liquids assisted desulfurization and denitrogenation of fuels. 57: https://doi.org/10.1002/vjch.201900008
Acknowledgements
We thank the Office of the Research and Sponsored Programs (ORSP), Pandit Deendayal Energy University (PDEU), Gandhinagar, Gujarat, India, for financial support and Centre for Biofuels and Bioenergy Studies (CBBS) for the support provided to carry out the experimental work.
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The authors are grateful for the financial supports from the Office of the Research and Sponsored Programs (ORSP), Pandit Deendayal Energy University (PDEU), Gandhinagar, Gujarat, India.
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Conception and design of the study: Komal Desai, Swapnil Dharaskar.
Acquisition of data: Komal Desai, Swapnil Dharaskar.
Analysis and/or interpretation of data: Komal Desai, Swapnil Dhar Askar, Jalaja Pandya, Satyam Shinde.
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Manuscript preparation: Komal Desai, Swapnil Dharaskar, Jalaja Pandya, Satyam Shinde, Thummalapalli Gupta.
Critical revision of the manuscript: Komal Desai, Swapnil Dharaskar, Jalaja Pandya, Satyam Shinde, Thummalapalli Gupta.
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Desai, K., Dharaskar, S., Pandya, J. et al. Trihexyl tetradecyl phosphonium bromide as an effective catalyst/extractant in ultrasound-assisted extractive/oxidative desulfurization. Environ Sci Pollut Res 29, 49770–49783 (2022). https://doi.org/10.1007/s11356-022-19310-y
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DOI: https://doi.org/10.1007/s11356-022-19310-y