Abstract
A systematic study was carried out on the preparation and application of metal-loaded polypropylene-divinyl benzene resin for dibenzothiophene adsorption. Amidoxime groups over used industrial polypropylene-divinyl benzene chelating resin were regenerated through a chemical graft reaction, and the highest regeneration efficiency of about 90 % can be reached. Different metal phases (Zn, Ni, Cu, Fe, Bi, and Ag) were introduced to the regenerated resin via an incipient-wetness impregnation method to examine their desulfurization efficiency. The desulfurization efficiency of ca. 86.3 % can be gained over Zn-loaded resin (Zn-R) under optimized reaction conditions. The order of different desulfurization influencing factors was further verified according to the orthogonal experiments, that is, desulfurization temperature > metal loading content > space velocity > organic sulfur concentration. Distribution of adsorption products was analyzed, and the results reveal that the metal-modified resins can effectively remove the organic sulfur compounds in diesel oil without loss of its octane value. The desulfurization effect of metal-contained resins is primary determined by the π-complexation.
Similar content being viewed by others
References
Abd El-Ghaffar MA, Mohamed MH, Elwakeel KZ (2009) Adsorption of silver(I) on synthetic chelating polymer derived from 3-amino-1,2,4-triazole-5-thiol and glutaraldehyde. Chem Eng J 154:30–38
Abro R, Abdeltawab AA, Al-Deyab SS, Yu GR, Qazi AB, Gao SR, Chen XC (2014) A review of extractive desulfurization of fuel oils using ionic liquids. RSC Adv 4:35302–35317
Achmann S, Hagen G, Hammerle M, Malkowsky I, Kiener C, Moos R (2010) Sulfur removal from low-sulfur gasoline and diesel fuel by metal-organic frameworks. Chem Eng Technol 33:275–280
Ahmed MJK, Ahmaruzzaman M (2015) Adsorptive desulfurization of feed diesel using chemically impregnated coconut coir waste. Int J Environ Sci Technol 12:2847–2856
Alfarra A, Frackowiak E, Beguin F (2004) The HSAB concept as a means to interpret the adsorption of metal ions onto activated carbons. Appl Surf Sci 228:84–92
Asumana C, Haque MR, Yu L, Wu XY, Chen XC, Yu GR (2013) Desulfurization of real fuel oils by extraction with ionic liquids. Separ Sci Technol 48:2582–2588
Atia AA, Donia AM, Elwakeel KZ (2005) Selective separation of mercury(II) using a synthetic resin containing amine and mercaptan as chelating groups. React Funct Polym 65:267–275
Atia AA, Donia AM, EI-Nomany HH (2009) Adsorption of mercury(II) on amidoxime chelating resins with magnetic properties. J Dispers Sci Technol 30:451–458
Babich IV, Moulijn JA (2003) Science and technology of novel processes for deep desulfurization of oil refinery streams: a review. Fuel 82:607–631
Basfar AA, Mohamed KA (2011) Radiation-induced desulfurization of Arabian crude oil and straight-run diesel. Radiat Phys Chem 80:1289–1290
Bhatia S, Sharma DK (2012) Thermophilic desulfurization of dibenzothiophene and different petroleum oils by Klebsiella sp. 13T. Environ Sci Pollut Res 19:3491–3497
Dai W, Hu J, Zhou LM, Li S, Hu X, Huang H (2013) Removal of dibenzothiophene with composite adsorbent MOF-5/Cu(I). Energy Fuels 27:816–821
Egawa H, Nonaka T, Abe S, Nakayama M (1992) Recovery of uranium from seawater. x. pore structure and uranium adsorption of macroreticular chelating resin containing amidoxime groups. J Appl Polym Sci 45:837–841
Elwakeel KZ (2009) Removal of As(V) from aqueous solution using glycidyl methacrylate resin immobilized with Cu(II)-tetraethylenepentamine complex. Water Sci Technol Water Supply 9:181–190
Elwakeel KZ (2014) Removal of arsenate from aqueous media by magnetic chitosan resin immobilized with molybdate oxoanions. Int J Environ Sci Technol 11:1051–1062
Fallah RN, Azizian S, Reggers D, Schreurs S, Carleer R, Yperman J (2012) Selective desulfurization of model diesel fuel by carbon nanoparticles as adsorbent. Ind Eng Chem Res 51:14419–14427
Hernández-Maldonado AJ, Yang RT (2004a) Desulfurization of diesel fuels by adsorption via π-complexation with vapor-phase exchanged Cu(I)-Y zeolites. J Am Chem Soc 126:992–993
Hernández-Maldonado AJ, Yang RT (2004b) Desulfurization of diesel fuels via π-complexation with nickel (II)-exchanged X- and Y-zeolites. Ind Eng Chem Res 43:1081–1089
Khan IM, Ahmad A (2013) Synthesis, spectroscopic characterization and structural studies of a new proton transfer (H-bonded) complex of o-phenylenediamine with L-tartaric acid. J Mol Struct 1050:122–127
Kong Y, Lin LG, Wang G, Qu HM, Yang JR, Wang YF, Shi DS (2006) Pervaporation performance of crosslinked polyethylene glycol membranes for deep desulfurization of FCC gasoline. J Membrane Sci 280:651–658
Kulkarni PS, Afonso CAM (2010) Deep desulfurization of diesel fuel using ionic liquids: current status and future challenges. Green Chem 12:1139–1149
Li B, Xu D, Jiang ZY, Zhang XF, Liu WP, Dong X (2008) Pervaporation performance of PDMS-Ni2+ Y zeolite hybrid membranes in the desulfurization of gasoline. J Membrane Sci 322:293–301
Lutfor MR, Silong S, Zin WZ, Ab Rahman MZ, Ahmad M, Haron J (2000) Preparation and characterization of poly (amidoxime) chelating resin from polyacrylonitrile grafted sago starch. Eur Polym J 36:2105–2113
Ma XL, Sun L, Song CS (2002) A new approach to deep desulfurization of gasoline, diesel fuel and jet fuel by selective adsorption for ultra-clean fuels and for fuel cell applications. Catal Today 77:107–116
Mohammed J, Nasri NS, Zaini MAA, Hamza UD, Ani FN (2015) Adsorption of benzene and toluene onto KOH activated coconut shell based carbon treated with NH3. Int Biodeterior Biodegrad 102:245–255
Munch AS, Katzsch F, Weber E, Mertens FORL (2013) Synthesis, spectroscopic characterization and structural investigation of a new symmetrically trisubstituted benzene derivative: 3,3′,3″-(Benzene-1,3,5-triyl)tripropiolic acid. J Mol Struct 1043:103–108
Nejad NF, Shams E, Amini MK, Bennett JC (2013) Sythesis of magnetic mesoporous carbon and its application for adsorption of dibenzothiophene. Fuel Process Technol 106:376–384
Nejad NF, Shams E, Amini MK (2015) Synthesis of magnetic ordered mesoporous carbon (Fe-OMC) adsorbent and its evaluation for fuel desulfurization. J Magn Magn Mater 309:1–7
Nilchi A, Rafiee R, Babalou AA (2008) Adsorption behavior of metal ions by amidoxime chelating resins. Macromol Symp 274:101–108
Peralta D, Chaplais G, Simon-Masseron A, Barthelet K, Pirngruber GD (2012) Metal-organic framework materials for desulfurization by adsorption. Energy Fuels 26:4953–4960
Qin YC, Mo ZS, Yu WG, Dong SW, Duan LH, Gao XH, Song LJ (2014) Adsorption behaviors of thiophene, benzene, and cyclohexene on FAU zeolites: comparison of CeY obtained by liquid-, and solid-state ion exchange. Appl Surf Sci 292:5–15
Rahaman MSA, Ismail AF, Mustafa A (2007) A review of heat treatment on polyacrylonitrile fiber. Polym Degrad Stabil 92:1421–1432
Saeed K, Haider S, Oh TJ, Park SY (2008) Preparation of amidoxime-modified polyacrylonitrile (PAN-oxime) nanofibers and their applications to metal ions adsorption. J Membrane Sci 322:400–405
Sarda KK, Bhandari A, Pant KK, Jain S (2012) Deep desulfurization of diesel fuel by selective adsorption over Ni/Al2O3 and Ni/ZSM-5 extrudates. Fuel 92:86–91
Sentorun-Shalaby C, Saha SK, Ma XL, Song CS (2011) Mesoporous-molecular-sieve-supported nickel sorbents for adsorptive desulfurization of commercial ultra-low-sulfur diesel fuel. Appl Catal B Environ 101:718–726
Shavandi M, Sadeghizadeh M, Zomorodipour A, Khajeh K (2009) Biodesulfurization of dibenzothiophene by recombinant Gordonia alkanivorans RIPI90A. Bioresour Technol 100:475–479
Srivastava VC (2012) An evaluation of desulfurization technologies for sulfur removal from liquid fuels. RSC Adv 2:759–783
Tamanai A, Beck S, Pucci A (2013) Mid-infrared characterization of thiophene-based thin polymer films. Displays 34:399–405
Tian FP, Wu WC, Jiang ZX, Liang CH, Yang YX, Ying PL, Sun XP, Cai TX, Li C (2006) The study of thiophene adsorption onto La(III)-exchanged zeolite NaY by FT-IR spectroscopy. J Colloid Interface Sci 301:395–401
Wang Y, Ma XJ, Li YF, Li XL, Yang LQ, He Y (2012a) Preparation of a novel chelating resin containing amidoxime–guanidine group and its recovery properties for silver ions in aqueous solution. Chem Eng J 209:394–400
Wang LF, Sun BD, Yang FH, Yang RT (2012b) Effects of aromatics on desulfurization of liquid fuel by pi-complexation and carbon adsorbents. Chem Eng Sci 73(2012):208–217
Wang R, Wan JB, Li YH, Sun HW (2014) An insight into effect of methanol on catalytic behavior of Amberlyst 35 resins for alkylation desulfurization of fluid catalytic cracking gasoline. Fuel 115:609–617
Woodward S (2002) HSAB matching and mismatching in selective catalysis and synthesis. Tetrahedron 58:1017–1050
Xiao J, Song CS, Ma XL, Li Z (2012) Effects of aromatics, diesel additives, nitrogen compounds, and moisture on adsorptive desulfurization of diesel fuel over activated carbon. Ind Eng Chem Res 51:3436–3443
Yu GR, Zhao JJ, Song DD, Asumana C, Zhang XY, Chen XC (2014) Deep oxidative desulfurization of diesel fuels by acidic ionic liquids. Ind Eng Chem Res 50:11690–11697
Zhu WS, Wu PW, Yang L, Chang YH, Chao YH, Li HM, Zou F, Xun SH, Zhu FX, Zhao Z (2013a) A novel reaction-controlled foam-type polyoxometalate catalyst for deep oxidative desulfurization of fuels. Ind Eng Chem Res 52:17399–17406
Zhu WS, Wu PW, Yang L, Chang YH, Chao YH, Li HM, Jiang YQ, Xun SH (2013b) Pyridinium-based temperature-responsive magnetic ionic liquid for oxidative desulfurization of fuels. Chem Eng J 229:250–256
Acknowledgments
Financial supports of the National Key Research and Development Program (2016YFC0204201), the National Natural Science Foundation of China (21477095, 21677114), the Industrial Research Project of Science and Technology of Shaanxi Province (2016GY-243), the Postdoctoral Science Foundation of China (2014M550498), the Postdoctoral Science Foundation of Shaanxi Province, and the Natural Science Basic Research Plan in Shaanxi Province of China (2015JM2047). The authors are also grateful to the reviewers and the editor for their helpful comments.
Author information
Authors and Affiliations
Corresponding author
Additional information
Editorial responsibility: M. Abbaspour.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
He, C., Xu, B., Chen, S. et al. Facile regeneration and modification of industrial used chelating resin for fuel oil desulfurization. Int. J. Environ. Sci. Technol. 14, 165–176 (2017). https://doi.org/10.1007/s13762-016-1135-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13762-016-1135-8