Advertisement

Oxidative desulfurization of dibenzothiophene via high-shear mixing with phosphotungstic acid: the influence of calcination temperature on kinetics and catalytic activity

  • Meng-Wei Wan
  • Mark Daniel G. de Luna
  • Lucille R. Golosinda
  • Cybelle M. Futalan
  • Piaw Phatai
  • Ming-Chun LuEmail author
Original Paper
  • 8 Downloads

Abstract

The mixing-assisted oxidative desulfurization (MAOD) of model fuel was performed where the effect of calcination temperature on the catalytic activity of phosphotungstic acid (HPW) was evaluated. The MAOD system utilized tetraoctylammonium bromide as phase transfer agent (PTA) and HPW as catalyst. Calcined HPW was characterized by Fourier transform infrared spectroscopy, X-ray diffraction and scanning electron microscopy. The influence of operating conditions such as calcination temperature, reaction time and PTA:HPW molar ratio on the catalytic activity of HPW was investigated. HPW calcined at 400 °C attained the highest sulfur removal of 100.0% and rate constant of 0.1485 min−1, which is followed by HPW calcined at 300 °C (0.1328 min−1) and 200 °C (0.1192 min−1). Under all calcination temperature range studied, high coefficient of determination values (R2 ≥ 0.95), low values of root-mean-square error (RMSE ≤ 8.5157) and average relative error (ARE ≤ 6.9361) indicate that the pseudo-first-order equation correlated well with the experimental data. The oxidation rate of dibenzothiophene in a MAOD system can be arranged in the order: HPW calcined at 400 °C > 300 °C > 200 °C.

Graphic abstract

Keywords

Calcination temperature Dibenzothiophene First-order kinetics Mixing-assisted oxidative desulfurization Phosphotungstic acid 

Notes

Acknowledgements

This work was supported by the Ministry of Science and Technology, Taiwan under Grant NSC 104-2221-E-041-002 and National Research Foundation (NRF) of Korea through Ministry of Education under Grant 2016R1A6A1A03012812.

References

  1. Bamoharram FF (2009) Vibrational spectra study of the interactions between Kegging heteropolyanions and amino acids. Molecules 14:3214–3221.  https://doi.org/10.3390/molecules14093214 CrossRefGoogle Scholar
  2. Bhutto AW, Abro R, Gao S, Abbas T, Chen X, Yu G (2016) Oxidative desulfurization of fuel oils using ionic liquids: a review. J Taiwan Inst Chem Eng 62:84–97.  https://doi.org/10.1016/j.jtice.2016.01.014 CrossRefGoogle Scholar
  3. Carter JL, Cusumano JA, Sinfelt JH (1966) Catalysis over supported metals. V. The effect of crystallite size on the catalytic activity of nickel. J Phys Chem 70:2257–2263.  https://doi.org/10.1021/j100879a029 CrossRefGoogle Scholar
  4. Choi AES, Roces S, Dugos N, Wan MW (2016) Mixing-assisted oxidative desulfurization of model sulfur compounds using polyoxometalate/H2O2 catalytic system. Sustain Environ Res 26:184–190.  https://doi.org/10.1016/j.serj.2015.11.005 CrossRefGoogle Scholar
  5. Dai Y, Qi Y, Zhao D, Zhang H (2008) An oxidative desulfurization method using ultrasound/Fenton’s reagent for obtaining low and/or ultra-low sulfur diesel fuel. Fuel Process Technol 89:927–932.  https://doi.org/10.1016/j.fuproc.2008.03.009 CrossRefGoogle Scholar
  6. de Luna MDG, Wan MW, Golosinda LR, Futalan CM, Lu MC (2017) Kinetics of mixing-assisted oxidative desulfurization of dibenzothiophene in toluene using a phosphotungstic acid/hydrogen peroxide system: effects of operating conditions. Energy Fuels 31:9923–9929.  https://doi.org/10.1021/acs.energyfuels.7b01773 CrossRefGoogle Scholar
  7. Frattini L, Isaacs MA, Parlett CM, Wilson K, Kyriakou G, Lee AF (2017) Support enhanced α-pinene isomerization over HPW/SBA-15. Appl Catal B 200:10–18.  https://doi.org/10.1016/j.apcatb.2016.06.064 CrossRefGoogle Scholar
  8. Galisteo FC, Mariscal R, Granados ML, Fierro JLG, Brettes P, Salas O (2005) Reactivation of a commercial diesel oxidation catalyst by acid washing. Environ Sci Technol 39(10):3844–3848.  https://doi.org/10.1021/es040062f CrossRefGoogle Scholar
  9. Ganiyu SA, Alhooshani K, Ali AA (2017) Single-pot synthesis of Ti-SBA-15-NiMo hydrodesulfurization catalysts: role of calcination temperature on dispersion and activity. Appl Catal B 203:428–441.  https://doi.org/10.1016/j.apcatb.2016.10.052 CrossRefGoogle Scholar
  10. Gomes FNDC, Mendes FMT, Souza MMVM (2017) Synthesis of 5-hydroxymethylfurfural from fructose catalyzed by phosphotungstic acid. Catal Today 279:296–304.  https://doi.org/10.1016/j.cattod.2016.02.018 CrossRefGoogle Scholar
  11. Hasan Z, Jeon J, Jhung SH (2012) Oxidative desulfurization of benzothiophene and thiophene with WOx/ZrO2 catalysts: effect of calcination temperature of catalysts. J Hazard Mater 205–206:216–221.  https://doi.org/10.1016/j.jhazmat.2011.12.059 CrossRefGoogle Scholar
  12. Huang D, Wang YJ, Yang LM, Luo GS (2006) Chemical oxidation of dibenzothiophene with a directly combined amphiphilic catalyst for deep desulfurization. Ind Eng Chem Res 45:1880–1885.  https://doi.org/10.1021/ie0513346 CrossRefGoogle Scholar
  13. Ivanov AV, Vasina TV, Nissenbaum VD, Kustov LM, Timofeeva MN, Houzvicka JI (2004) Isomerization of n-hexane on the Pt-promoted Keggin and Dawson tungstophosphoric heteropoly acids supported on zirconia. Appl Catal A 259:65–72.  https://doi.org/10.1016/j.apcata.2003.09.011 CrossRefGoogle Scholar
  14. Jalil PA, Al-Daous MA, Al-Arfaj AA, Al-Amer AM, Beltramini J, Barri SAI (2001) Characterization of tungstophosphoric acid supported on MCM-41 mesoporous silica using n-hexane cracking, benzene adsorption and X-ray diffraction. Appl Catal A 207:159–171.  https://doi.org/10.1016/S0926-860X(00)00670-0 CrossRefGoogle Scholar
  15. Jiang B, Yang H, Zhang L, Zhang R, Sun Y, Huang Y (2016) Efficient oxidative desulfurization of diesel fuel using amide-based ionic liquids. Chem Eng J 283:89–96.  https://doi.org/10.1016/j.cej.2015.07.070 CrossRefGoogle Scholar
  16. Jose N, Sengupta S, Basu JK (2011) Optimization of oxidative desulfurization of thiophene using Cu/titanium silicate-1 by box-behnken design. Fuel 90:626–632.  https://doi.org/10.1016/j.fuel.2010.09.026 CrossRefGoogle Scholar
  17. Kang L, Liu H, He H, Yang C (2018) Oxidative desulfurization of dibenzothiophene using molybdenum catalyst supported on Ti-pillared montmorillonite and separation of sulfones by filtration. Fuel 234:1229–1237.  https://doi.org/10.1016/j.fuel.2018.07.148 CrossRefGoogle Scholar
  18. Karri RR, Sahu JN, Jayakumar NS (2017) Optimal isotherm parameters for phenol adsorption from aqueous solutions onto coconut shell based activated carbon: error analysis of linear and non-linear methods. J Taiwan Inst Chem Eng 80:472–487.  https://doi.org/10.1016/j.jtice.2017.08.004 CrossRefGoogle Scholar
  19. Li B, Liu Z, Liu J, Zhou Z, Gao X, Pang X, Sheng H (2011) Preparation, characterization and application in deep catalytic ODS of the mesoporous silica pillared clay incorporated with phosphotungstic acid. J Colloid Interface Sci 362:450–456.  https://doi.org/10.1016/j.jcis.2011.07.025 CrossRefGoogle Scholar
  20. Li J, Song Z, Ning P, Zhang Q, Liu X, Hao H, Huang Z (2015) Influence of calcination temperature on selective catalytic reduction of NOx with NH3 over CeO2–ZrO2–WO3 catalyst. J Rare Earths 33:726–735.  https://doi.org/10.1016/S1002-0721(14)60477-4 CrossRefGoogle Scholar
  21. Long Z, Yang C, Zeng G, Peng L, Dai C, He H (2014) Catalytic oxidative desulfurization of dibenzothiophene using catalyst of tungsten supported on resin D152. Fuel 130:19–24.  https://doi.org/10.1016/j.fuel.2014.04.005 CrossRefGoogle Scholar
  22. Lu MC, Biel LCC, Wan MW, De Leon R, Arco S (2014) The oxidative desulfurization of fuels with a transition metal catalyst: a comparative assessment of different mixing techniques. Int J Green Energy 11:833–848.  https://doi.org/10.1080/15435075.2013.830260 CrossRefGoogle Scholar
  23. Ma W, Xu Y, Ma K, Zhang H (2016) Electrospinning synthesis of H3PW12O40/TiO2 nanofiber catalytic materials and their application in ultra-deep desulfurization. Appl Catal A 526:147–154.  https://doi.org/10.1016/j.apcata.2016.08.021 CrossRefGoogle Scholar
  24. Ma T, Ding J, Shao XuW, Yun Z (2017) Dehydration of glycerol to acrolein over Wells-Dawson and Keggin type phosphotungstic acids supported on MCM-41 catalysts. Chem Eng J 36:797–806.  https://doi.org/10.1016/j.cej.2017.02.018 CrossRefGoogle Scholar
  25. Maricq MM (2007) Chemical characterization of particulate emissions from diesel engines: a review. J Aerosol Sci 38:1079–1118.  https://doi.org/10.1016/j.jaerosci.2007.08.001 CrossRefGoogle Scholar
  26. Matkovic SR, Valle GM, Gambaro LA, Briand LE (2008) Environmentally friendly synthesis of Wells-Dawson heteropolyacids: active acid sites investigation through TPSR of isopropanol. Catal Today 133–135:192–199.  https://doi.org/10.1016/j.cattod.2007.12.120 CrossRefGoogle Scholar
  27. Mei H, Mei BW, Yen TF (2003) A new method for obtaining ultra-low sulfur diesel fuel via ultrasound assisted oxidative desulfurization. Fuel 82:405–414.  https://doi.org/10.1016/S0016-2361(02)00318-6 CrossRefGoogle Scholar
  28. Misono M (2013) Heterogeneous catalysis of mixed oxides: Chapter 4. Catalysis of heteropoly compounds. Elsevier, AmsterdamGoogle Scholar
  29. Okuhara T (2003) Microporous heteropoly compounds and their shape selective catalysis. Appl Catal A 256:213–224.  https://doi.org/10.1016/S0926-860X(03)00401-0 CrossRefGoogle Scholar
  30. Otsuki S, Nonaka T, Takashima N, Qian W, Ishihara A, Imai T, Kabe T (2000) Oxidative desulfurization of light gas oils and vacuum gas oil by oxidation and solvent extraction. Energy Fuels 14:1232–1239.  https://doi.org/10.1021/ef000096i CrossRefGoogle Scholar
  31. Pizzio LR, Cáceres CV, Blanco MN (1998) Acid catalysts prepared by impregnation of tungstophosphoric acid solutions on different supports. Appl Catal A 167:283–294.  https://doi.org/10.1016/S0926-860X(97)00328-1 CrossRefGoogle Scholar
  32. Qui J, Wang G, Zeng D, Tang Y, Wang M, Li Y (2009) Oxidative desulfurization of diesel fuel using amphiphilic quaternary ammonium phosphomolybdate catalysts. Fuel Process Technol 90:1538–1542.  https://doi.org/10.1016/j.fuproc.2009.08.001 CrossRefGoogle Scholar
  33. Ramirez-Verduzco LF, Torres-Garcia E, Gomez-Quintana R, Gonzalez-Pena V, Murrieta-Guevara F (2004) Desulfurization of diesel by oxidation/extraction scheme: influence of the extraction solvent. Catal Today 98:289–294.  https://doi.org/10.1016/j.cattod.2004.07.042 CrossRefGoogle Scholar
  34. Ribeiro SO, Julião D, Cunha-Silva L, Domingues VF, Valença R, Ribeiro JC, de Castro B, Balula SS (2016) Catalytic oxidative/extractive desulfurization of model and untreated diesel using hybrid based zinc-substituted polyoxometalates. Fuel 166:268–275.  https://doi.org/10.1016/j.fuel.2015.10.095 CrossRefGoogle Scholar
  35. Sachdeva TO, Pant KK (2010) Deep desulfurization of of diesel via peroxide oxidation using phosphotungstic acid as phase transfer catalyst. Fuel Process Technol 91:1133–1138.  https://doi.org/10.1016/j.fuproc.2010.03.027 CrossRefGoogle Scholar
  36. Shen W, Li X, Lu X, Guo W, Zhou S, Wan Y (2018) Experimental study and isotherm models of water vapor adsorption in shale rocks. J Nat Gas Sci Eng 52:484–491.  https://doi.org/10.1016/j.jngse.2018.02.002 CrossRefGoogle Scholar
  37. Shiraishi Y, Tachibana K, Hirai T, Komasawa I (2002) Desulfurization and denitrogenation process for light oils based on chemical oxidation followed by liquid–liquid extraction. Ind Eng Chem Res 41:4362–4375.  https://doi.org/10.1021/ie010618x CrossRefGoogle Scholar
  38. Song C, Ma X (2003) New design approaches to ultra-clean diesel fuels by deep desulfurization and deep dearomatization. Appl Catal B 41:207–238.  https://doi.org/10.1016/S0926-3373(02)00212-6 CrossRefGoogle Scholar
  39. Stanislaus A, Marafi A, Rana MS (2010) Recent advances in the science and technology of ultra low sulfur diesel (ULSD) production. Catal Today 153:1–68.  https://doi.org/10.1016/j.cattod.2010.05.011 CrossRefGoogle Scholar
  40. Tang L, Luo G, Zhu M, Kang L, Dai B (2013) Preparation, characterization and catalytic performance of HPW-TUD-1 catalyst on oxidative desulfurization. J Ind Eng Chem 19:620–626.  https://doi.org/10.1016/j.jiec.2012.09.015 CrossRefGoogle Scholar
  41. Timofeeva MN (2003) Acid catalysis by heteropoly acids. Appl Catal A 256:19–35.  https://doi.org/10.1016/S0926-860X(03)00386-7 CrossRefGoogle Scholar
  42. Udayakumar S, Ajaikumar S, Pandurangan A (2006) A protocol on yields to synthesize commercial imperative bisphenols using HPA and supported HPA: effective condensation over solid acid catalysts. Appl Catal A 302:86–95.  https://doi.org/10.1016/j.apcata.2005.12.026 CrossRefGoogle Scholar
  43. Wan S, Yang G (2015) Recent advances in polyoxometalate-catalyzed reactions. Chem Rev 115:4893–4962.  https://doi.org/10.1021/cr500390v CrossRefGoogle Scholar
  44. Wan MW, Yen TF (2007) Enhance efficiency of tetraoctylammonium fluoride applied to ultrasound-assisted oxidative desulfurization (UAOD) process. Appl Catal A 319:237–245.  https://doi.org/10.1016/j.apcata.2006.12.008 CrossRefGoogle Scholar
  45. Wan MW, Biel LCC, Lu MC, de Leon R, Arco S (2012) Ultrasound-assisted oxidative desulfurization (UAOD) using phosphotungstic acid: effect of process parameters on sulfur removal. Desalin Water Treat 47:96–104.  https://doi.org/10.1080/19443994.2012.696802 CrossRefGoogle Scholar
  46. Wang Z, Navarrete J (2012) Keggin structure and surface acidity of 12-phosphotungstic acid grafted Zr-MCM-48 mesoporous molecular sieves. World J Nano Sci Eng 2:134–141.  https://doi.org/10.4236/wjnse.2012.23017 CrossRefGoogle Scholar
  47. Wang B, Zhu J, Ma H (2009) Desulfurization from thiophene by SO4−2/ZrO2 catalytic oxidation at room temperature and atmospheric pressure. J Hazard Mater 164:256–264.  https://doi.org/10.1016/j.jhazmat.2008.08.003 CrossRefGoogle Scholar
  48. Wei S, He H, Cheng Y, Yang C, Zeng G, Kang L, Qian H, Zhu C (2017) Preparation, characterization, and catalytic performances of cobalt catalysts supported on KIT-6 silicas in oxidative desulfurization of dibenzothiophene. Fuel 200:11–21.  https://doi.org/10.1016/j.fuel.2017.03.052 CrossRefGoogle Scholar
  49. Wu S, Zhang L, Wang X, Zou W, Cao Y, Sun J, Tang C, Gao F, Deng Y, Dong L (2015) Synthesis, characterization and catalytic performance of FeMnTiOx mixed oxides catalyst prepared by a CTAB-assisted process for mid-low temperature NH3-SCR. Appl Catal A 505:235–242.  https://doi.org/10.1016/j.apcata.2015.08.009 CrossRefGoogle Scholar
  50. Yan XM, Lei JH, Liu D, Wu YC, Liu W (2007) Synthesis and catalytic properties of mesoporous phosphotungstic acid/SiO2 in a self-generated acidic environment by evaporation-induced self-assembly. Mater Res Bull 42:1905–1913.  https://doi.org/10.1016/j.materresbull.2006.12.013 CrossRefGoogle Scholar
  51. Yan XM, Mei P, Lei J, Mi Y, Xiong L, Guo L (2009) Synthesis and characterization of mesoporous phosphotungstic acid/TiO2 nanocomposite as a novel oxidative desulfurization catalyst. J Mol Catal A Chem 304:52–57.  https://doi.org/10.1016/j.molcata.2009.01.023 CrossRefGoogle Scholar
  52. Yang C, Zhao K, Cheng Y, Zeng G, Zhang M, Shao J, Lu L (2016) Catalytic oxidative desulfurization of BT and DBT from n-octane using cyclohexanone peroxide and catalyst of molybdenum supported on 4A molecular sieve. Sep Purif Technol 163:153–161.  https://doi.org/10.1016/j.seppur.2016.02.050 CrossRefGoogle Scholar
  53. Zeng X, Xiao X, Li Y, Chen J, Wang H (2017) Deep desulfurization of liquid fuels with molecular oxygen through graphene photocatalytic oxidation. Appl Catal B 209:98–109.  https://doi.org/10.1016/j.apcatb.2017.02.077 CrossRefGoogle Scholar
  54. Zeng X, Xiao X, Chen J, Wang H (2018) Electron-hole interactions in choline-phosphotungstic acid boosting molecular oxygen activation for fuel desulfurization. Appl Catal B 10:10.  https://doi.org/10.1016/j.apcatb.2018.09.038 Google Scholar
  55. Zhou XR, Gai HT, Wang J, Zang SS, Yang JZ, Zhang SF (2009) Oxidation of benzothiophenes using tert-amyl hydroperoxide. Chin J Chem Eng 17:189–194.  https://doi.org/10.1016/S1004-9541(08)60192-5 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Environmental Resources ManagementChia-Nan University of Pharmacy and ScienceTainanTaiwan
  2. 2.Department of Chemical EngineeringUniversity of the PhilippinesDiliman, Quezon CityPhilippines
  3. 3.Environmental Engineering Program, National Graduate School of EngineeringUniversity of the PhilippinesDiliman, Quezon CityPhilippines
  4. 4.National Research, Center for Disaster-Free and Safe Ocean CityBusanRepublic of Korea
  5. 5.Department of Chemistry, Faculty of ScienceUdon Thani Rajabhat UniversityUdon ThaniThailand

Personalised recommendations