Citation: LIU Han-lin, LI Xiu-ping, ZHAO Rong-xiang. Preparation of DESs/SG catalyst and its performance in the oxidative desulfurization[J]. Journal of Fuel Chemistry and Technology, ;2020, 48(3): 369-377. shu

Preparation of DESs/SG catalyst and its performance in the oxidative desulfurization

1.
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, China
2.
College of Chemistry & Material Science Engineering, Liaoning Shihua University, Fushun 113001, China

Corresponding author: ZHAO Rong-xiang, zylhzrx@126.com
Received Date: 21 October 2019
Revised Date: 21 January 2020

Fund Project: The project was supported by the Mentoring Program Projects from Liaoning Natural Science Foundation (2019-ZD-0064)The project was supported by the Mentoring Program Projects from Liaoning Natural Science Foundation 2019-ZD-0064

Figures(13)

DESs/SG catalyst was prepared by supporting the proline-based deep eutectic solvent (DES) on the silica-gel (SG) matrix using a sol-gel method; the catalyst structure was characterized by FT-IR, XRD, SEM/EDS and N₂ adsorption-desorption. The results showed that the DESs were successfully incorporated into the silica-gel matrix, leading to a decrease in the surface area and pore volume, but an increase in the pore diameter. With hydrogen peroxide as oxidant, the catalytic performance of DESs/SG in the oxidative desulfurization of a model oil containing dibenzothiophene (DBT) was investigated; the effects of deep eutectic solvent loading, reaction temperature, n(H₂O₂)/n(S) ratio, catalyst amount, sulfur compound type and catalyst recycle times on the desulfurization efficiency were considered. The results indicated that under optimum desulfurization conditions, the desulfurization degrees for DBT, 4, 6-dimethyl-dibenzothiophene (4, 6-DMDBT) and benzothiophene (BT) over the DESs/SG catalyst were 97%, 96.5% and 46.4%, respectively; after recycling for 9 times, the DESs/SG catalyst still displayed a desulfurization degree of above 89.4%.
- silica gel,
- oxidation desulfurization,
- deep eutectic solvents,
- sol-gel,
- dibenzothiophene
1. [1]
  MA X, ZHOU A, SONG C. A novel method for oxidative desulfurization of liquid hydrocarbon fuels based on catalytic oxidation using molecular oxygen coupled with selective adsorption[J]. Catal Today, 2007,123(1/4):276-284.
2. [2]
  LI Xu-he, FANG Lei, YANG Hao, ZHANG Jian, LIANG Fei-xue, WANG Hai-yan, WANG Yan-juan. Preparation of g-C₃N₄ supported phosphotungstate hybrid materials and their catalytic performance in the oxidative desulfurization[J]. J Fuel Chem Technol, 2019,47(2):174-182.
3. [3]
  YU M, LI Z, JI Q, WANG S, SU D, LIN Y S. Effect of thermal oxidation of activated carbon surface on its adsorption towards dibenzothiophene[J]. Chem Eng J, 2009,148(2/3):242-247.
4. [4]
  LIU W, LI T, YU G, WANG J, ZHOU Z. One-pot oxidative desulfurization of fuels using dual-acidic deep eutectic solvents[J]. Fuel, 2020,265:116967-116981.
5. [5]
  YANG Y, LV G, DENG L, LU B, LI J, ZHANG J, SHI J Y, DU S J. Ultra-deep desulfurization of diesel fuel via selective adsorption over modified activated carbon assisted by pre-oxidation[J]. J Cleaner Prod, 2017,161:422-430.
6. [6]
  SAFA M, MOKHTARANI B, MORTAHEB H R. Deep extractive desulfurization of dibenzothiophene with imidazolium or pyridinium-based ionic liquids[J]. Chem Eng Res Des, 2016,111:323-331.
7. [7]
  JIANG B, YANG H, ZHANG L, ZHANG Y Y, SUN Y L, HUANG Y. Efficient oxidative desulfurization of diesel fuel using amide-based ionic liquids[J]. Chem Eng J, 2016,283:89-96.
8. [8]
  JIANG W, ZHU W, LI H, WANG X, YIN S, CHANG Y H, LI H M. Temperature-responsive ionic liquid extraction and separation of the aromatic sulfur compounds[J]. Fuel, 2015,140:590-596.
9. [9]
  YIN J, WANG J, LI Z, LI D, YANG G, CUI Y N, WANG A L, LI C P. Deep desulfurization of fuels based on an oxidation/extraction process with acidic deep eutectic solvents[J]. Green Chem, 2015,17(9):4552-4559.
10. [10]
  ALI E, HADJ-KALI M K, MULYONO S, ALNASHEF I, FAKEEHA A, MJALLI F, HAYYAN A. Solubility of CO₂ in deep eutectic solvents:Experiments and modelling using the Peng-Robinson equation of state[J]. Chem Eng Res Des, 2014,92(10):1898-1906.
11. [11]
  LIU P, HAO J W, MO L P, ZHANG Z H. Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions[J]. RSC Adv, 2015,5(60):48675-48704.
12. [12]
  NKUKU C A, LESUER R J. Electrochemistry in deep eutectic solvents[J]. J Phys Chem B, 2007,111(46):13271-13277.
13. [13]
  SMEETS S, LIU L, DONG J, MCCUSKER L B. Cheminform abstract:Ionothermal synthesis and structure of a new layered zirconium phosphate[J]. Inorg Chem, 2015,46(42):7953-7958.
14. [14]
  TANG Xiao-dong, ZHANG Xiao-pu, LI Jing-jing, WANG Zhi-yu, YANG Liu, WANG Chun. Research progress of deep eutectic solvents in desulfurization of vehicle fuel[J]. Chem Ind Eng Prog, 2018,37(11):82-89.
15. [15]
  LÜ H, LI P, DENG C, REN W Z, WANG S N, LIU P, ZHANG H. Deep catalytic oxidative desulfurization (ODS) of dibenzothiophene (DBT) with oxalate-based deep eutectic solvents (DESs)[J]. Chem Commun, 2015,51(53):10703-10706.
16. [16]
  LÜ H, LI P, LIU Y, HAO L W, REN W Z, ZHU W J, DENG C L, YANG P. Synthesis of a hybrid Anderson-type polyoxometalate in deep eutectic solvents (DESs) for deep desulphurization of model diesel in ionic liquids (ILs)[J]. Chem Eng J, 2017,313:1004-1009.
17. [17]
  ZHANG Q, KARINE D O V, ROYER S, JEROME F. Deep eutectic solvents:Syntheses, properties and applications[J]. Chem Soc Rev, 2012,41(21):7108-7146.
18. [18]
  GARCÍA-GUTIÉRREZ J L, FUENTES G A, HERNÁNDEZ-TERÁN M E, MURRIETA F, NAVARRETE J, JIMÉNEZ-CRUZ F. Ultra-deep oxidative desulfurization of diesel fuel with H₂O₂ catalyzed under mild conditions by polymolybdates supported on Al₂O₃[J]. Appl Catal A:Gen, 2006,305(1):15-20.
19. [19]
  YANG C, ZHAO K, CHENG Y, ZENG G M, ZHANG M M, SHAO J J, LU L. Catalytic oxidative desulfurization of BT and DBT from n-octane using cyclohexanone peroxide and catalyst of molybdenum supported on 4A molecular sieve[J]. Sep Purif Technol, 2016,163:153-161.
20. [20]
  LI S, MOMINOU N, WANG Z, WANG L. Ultra-deep desulfurization of gasoline with CuW/TiO₂-go through photocatalytic oxidation[J]. Energy Fuels, 2016,30(2):962-967.
21. [21]
  YAN Xue-ming, SU Gao-shen, XIONG Lin. Oxidative desulfurization of diesel oil over Ag-modified mesoporous HPW/SiO₂ catalyst[J]. J Fuel Chem Technol, 2009,37(3):318-323.
22. [22]
  SELVAM T, MACHOKE A, SCHWIEGER W. Supported ionic liquids on non-porous and porous inorganic materials-A topical review[J]. Appl Catal A:Gen, 2012,445:92-101.
23. [23]
  AZIZI N, EDRISI M, ABBASI F. Mesoporous silica SBA-15 functionalized with acidic deep eutectic solvent:A highly active heterogeneous N-formylation catalyst under solvent-free conditions[J]. Appl Organomet Chem, 2018,32(1):3901-3910.
24. [24]
  AZIZI N, EDRISI M. Deep eutectic solvent immobilized on SBA-15 as a novel separable catalyst for one-pot three-component Mannich reaction[J]. Microporous Mesoporous Mater, 2017,240:130-136.
25. [25]
  HAO L, WANG M, SHAN W, DENG C L, REN W Z, SHI Z Z, LÜ H Y. L-proline-based deep eutectic solvents (DESs) for deep catalytic oxidative desulfurization (ODS) of diesel[J]. J Hazard Mater, 2017,339:216-222.
26. [26]
  ZHAO R, LI X, SU J, GAO X H. Preparation of WO₃/g-C₃N₄ composites and their application in oxidative desulfurization[J]. Appl Surf Sci, 2016,392:810-816.
27. [27]
  PIRZADA T, SHAH S S. Water-resistant poly (vinyl alcohol)-silica hybrids through sol-gel processing[J]. Chem Eng Technol, 2014,37(4):620-626.
28. [28]
  MATOS M C, ILHARCO L M, ALMEIDA R M. The evolution of TEOS to silica gel and glass by vibrational spectroscopy[J]. J Non-Cryst Solids, 1992,147:232-237.
29. [29]
  WU Y, LI Z, XIA C. Silica-gel-supported dual acidic ionic liquids as efficient catalysts for the synthesis of polyoxymethylene dimethyl ethers[J]. Ind Eng Chem Res, 2016,55(7):1859-1865.
30. [30]
  AZIZI N, EDRISI M, ABBASI F. Mesoporous silica SBA-15 functionalized with acidic deep eutectic solvent:A highly active heterogeneous N-formylation catalyst under solvent-free conditions[J]. Appl Organomet Chem, 2018,32(1):3901-3910.
31. [31]
  SAFA M, MOKHTARANI B, MORTAHEB H R, HEIDAR K T, SHARIFI A, MIRZAEI M. Oxidative desulfurization of diesel fuel using a Brønsted acidic ionic liquid supported on silica gel[J]. Energy Fuels, 2017,31(9):10196-10205.
32. [32]
  WEI J, ZHU W, LI H, WANG X, YIN S, CHANGY H, LI H M. Temperature-responsive ionic liquid extraction and separation of the aromatic sulfur compounds[J]. Fuel, 2015,140:590-596.
33. [33]
  YANG W X, GUO G, MEI Z, YU Y H. Deep oxidative desulfurization of model fuels catalysed by immobilized ionic liquid on MIL-100(Fe)[J]. RSC Adv, 2019,9(38):21804-21809.
34. [34]
  YANG C, ZHAO K, CHENG Y, ZENG G M, ZHANG M M, SHAO J J. Catalytic oxidative desulfurization of BT and DBT from n-octane using cyclohexanone peroxide and catalyst of molybdenum supported on 4A molecular sieve[J]. Sep Purif Technol, 2016,163:153-161.
35. [35]
  YU Feng-li, WANG Rui. Study on oxidative desulfurization catalyzed by organic-inorganic heteropoiyacids as phase transfer catalyst[J]. Acta Chim Sin, 2014,72(1):105-113.
36. [36]
  MAO C, ZHAO R, LI X. Phenylpropanoic acid-based DESs as efficient extractants and catalysts for the removal of sulfur compounds from oil[J]. Fuel, 2017,189:400-407.
37. [37]
  SHI C, WANG W, LIU N, XUEYAN XU, WANG D H, ZHANG M H, SUN P C, CHEN T H. Low temperature oxidative desulfurization with hierarchically mesoporous titaniumsilicate Ti-SBA-2 single crystals[J]. Chem Commun, 2015,51(57):11500-11503.
38. [38]
  VIDAL L, RIEKKOLA M L, CANALS A. Ionic liquid-modified materials for solid-phase extraction and separation:A review[J]. Anal Chim Acta, 2012,715:0-41.
39. [39]
  ZHANG B Y, JIANG Z X, LI J, ZHANG Y, LIN F, LIU Y, LI C. Catalytic oxidation of thiophene and its derivatives via dual activation for ultra-deep desulfurization of fuels[J]. J Catal, 2012,287(3):5-12.
40. [40]
  WANG S, LI P, HAO L, DENG C L, REN W Z, LÜ H Y. Oxidative desulfurization of model diesel using a fenton-like catalyst in the ionic liquid[Dmim]BF₄[J]. Chem Eng Technol, 2017, 40(3): 555-560.
41. [41]
  MAGGI R, PISCOPO C G, SARTORI G, STORAROB L, MORETTI E. Supported sulfonic acids:Metal-free catalysts for the oxidation of hydroquinones to benzoquinones with hydrogen peroxide[J]. Appl Catal A:Gen, 2012,411(2):146-152.
42. [42]
  LI N, YUAN G, ZHANG X, YU Z J, SHI L, SUN Q. Oxidation of styrene to benzaldehyde by p-toluenesulfonic acid using hydrogen peroxide in the presence of activated carbon[J]. Chin J Catal, 2015,36(5):721-727.
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