Citation: LI Xiu-ping, ZHAO Rong-xiang, GONG Xiao-jie, LI Ping. Preparation of C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ and its oxidative desulfurization performance[J]. Journal of Fuel Chemistry and Technology, ;2019, 47(10): 1187-1194. shu

Preparation of C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ and its oxidative desulfurization performance

College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun 113001, China

Corresponding author: ZHAO Rong-xiang, zylhzrx@126.com
Received Date: 23 May 2019
Revised Date: 17 August 2019

Fund Project: The project was supported by the Local Service Projects from Liaoning Education Department (L2017LFW004)the Local Service Projects from Liaoning Education Department L2017LFW004

Figures(13)

A C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ catalyst was successfully prepared by immobilizing phenylpropionic acid-zinc chloride(C₉H₁₀O₂-0.5ZnCl₂) double acid deep eutectic solvent on Al₂O₃, and analyzed by XRD, FT-IR, SEM, EDS and N₂ adsorption-desorption. The removal activity for aromatic sulfides in model oil using C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ as catalysis and H₂O₂ as oxidant and the effect of some reaction parameters such as temperature, catalyst dosage, O/S molar ratio and different sulfide types on the desulfurization activity of catalyst were investigated. The experimental results show that with the model oil of 5 mL, the catalyst dosage of 0.2 g and the O/S molar ratio of 8, at temperature of 60℃and reaction time of 180 min, the removal rate of DBT can reach to 99.2%. In addition, the catalyst can be recycled up to 6 times with a little decrease in catalytic activity for the ODS process. The catalysis-oxidation desulfurization mechanism of C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ was also explored.
- zinc chloride,
- alumina,
- oxidation desulfurization,
- deep eutectic solvents
1. [1]
  BOKARE A D, CHOI W. Bicarbonate-induced activation of H₂O₂ for metal-free oxidative desulfurization[J]. J Hazard Mater, 2016,304:313-319. doi: 10.1016/j.jhazmat.2015.10.063
2. [2]
  ANDEVARY H H, AKBARI A, OMIDKHAH M. High efficient and selective oxidative desulfurization of diesel fuel using dual-function[Omim]FeCl₄ as catalyst/extractant[J]. Fuel Process Technol, 2019,185:8-17. doi: 10.1016/j.fuproc.2018.11.014
3. [3]
  LIN Yan, WANG Fang, ZHANG Zhi-qing, YANG Jie, WEI Ying. Mechanism and application of ionic liquids in environmental friendly oil desulphurization[J]. Chem Ind Eng Prog, 2013,32(3):549-557.
4. [4]
  JI H Y, SUN J, WU P W, WU Y C, HE J, CHAO Y H, ZHU W S, LI H M. Silicotungstic acid immobilized on lamellar hexagonal boron nitride for oxidative desulfurization of fuel components[J]. Fuel, 2018,213:12-21. doi: 10.1016/j.fuel.2017.08.076
5. [5]
  LI Wen-xiu, CUI An-lei, FAN Jun-gang, SUN Xiang-le, ZHANG Zhi-gang. Synthesis of spherical activated carbon supported copper catalyst and its performance for adsorptive desulfurization[J]. J Fuel Chem Technol, 2013,41(5):613-618. doi: 10.3969/j.issn.0253-2409.2013.05.013
6. [6]
  TIAN Y, WANG G, LONG J, CUI J W, JIN W, ZENG D L. Ultra-deep oxidative desulfurization of fuel with H₂O₂ catalyzed by phosphomolybdic acid supported on silica[J]. Chin J Catal, 2016,37(12):2098-2105. doi: 10.1016/S1872-2067(16)62558-5
7. [7]
  LI S W, YANG Z, GAO R M, ZHANG G, ZHAO J S. Direct synthesis of mesoporous SRL-POM@MOF-199@MCM-41 and its highly catalytic performance for the oxidesulfurization of DBT[J]. Appl Catal B:Environ, 2018,221:574-583. doi: 10.1016/j.apcatb.2017.09.044
8. [8]
  ZHU W S, WANG C, LI H M, WU P W, XUN S H, JIANG W, CHEN Z G, ZHAO Z, LI H M. One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent[J]. Green Chem, 2015,17:2464-2472. doi: 10.1039/C4GC02425G
9. [9]
  LI S W, LI J R, GAO Y, LIANG L L, ZHANG R L, ZHAO J S. Metal modified heteropolyacid incorporated into porous materials for a highly oxidative desulfurization of DBT under molecular oxygen[J]. Fuel, 2017,197:551-561. doi: 10.1016/j.fuel.2017.02.064
10. [10]
  STANISLAUS A, MARAFI A, RANA M S. Recent advances in the science and technology of ultra low sulfur diesel (ULSD) production[J]. Catal Today, 2010,153(1/2):1-68.
11. [11]
  KANG L, LIU H G, HE H J, YANG C P. Oxidative desulfurization of dibenzothiophene using molybdenum catalyst supported on Ti-pillared montmorillonite and separation of sulfones by filtration[J]. Fuel, 2018,234:1229-1237. doi: 10.1016/j.fuel.2018.07.148
12. [12]
  YANG C P, 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. doi: 10.1016/j.seppur.2016.02.050
13. [13]
  WEI S N, HE H J, CHENG Y, YANG C P, ZENG G M, KANG L, QIAN H, ZHU C Y. Preparation, characterization, and catalytic performances of cobalt catalysts supported on KIT-6 silicas in oxidative desulfurization of dibenzothiophene[J]. Fuel, 2017,200:11-21. doi: 10.1016/j.fuel.2017.03.052
14. [14]
  CHOI A E S, ROCES S, DUGOS N, WAN M W. Oxidation by H₂O₂ of bezothiophene and dibenzothiophene over different polyoxometalate catalysts in the frame of ultrasound and mixing assisted oxidative desulfurization[J]. Fuel, 2016,180:127-136. doi: 10.1016/j.fuel.2016.04.014
15. [15]
  ABBOTT A P, ALAYSUY O, ANTUNES A P M, DOUGLAS A C, GUTHRIE-STRACHAN J, WISE W R. Processing of leather using deep eutectic solvents[J]. ACS Sustainable Chem Eng, 2015,3:1241-1247. doi: 10.1021/acssuschemeng.5b00226
16. [16]
  ABBOTT A P, BOOTHBY D, CAPPER G, DAVIES D L, RASHEED R K. Deep eutectic solvents formed between choline chloride and carboxylic acids:versatile alternatives to ionic liquids[J]. J Am Chem Soc, 2004,126(29):9142-9147. doi: 10.1021/ja048266j
17. [17]
  ZHANG Q, VIGIER K D O, ROYER S, JÉRÔME F. Deep eutectic solvents:Syntheses, properties and applications[J]. Chem Soc Rev, 2012,41(21):7108-7146. doi: 10.1039/c2cs35178a
18. [18]
  GUAJARDO N, CARLESI C, ARACENA Á. Toluene oxidation by hydrogen peroxide in deep eutectic solvents[J]. ChemCatChem, 2015,7(16):2451-2454. doi: 10.1002/cctc.201500604
19. [19]
  DAI Y, WITKAMP G J, VERPOORTE R, CHOI Y H. Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L[J]. Anal Chem, 2013,85(13):6272-6278. doi: 10.1021/ac400432p
20. [20]
  NKUKU C A, LESUER R J. Electrochemistry in deep eutectic solvents[J]. J Phys Chem B, 2007,111(46):13271-13277. doi: 10.1021/jp075794j
21. [21]
  GARCIA G, ATILHAN M, APARICIO S. Interfacial properties of deep eutectic solvents regarding to CO₂ capture[J]. J Phys Chem C, 2015,119(37):21413-21425. doi: 10.1021/acs.jpcc.5b04585
22. [22]
  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. doi: 10.1039/C5RA05746A
23. [23]
  HUO Liang-pei, ZHAO Rong-xiang, LI Xiu-ping, SHI Wei-wei. Preparation of methylimidazole hydrochloride/oxalic acid type deep eutectic solvent and its application in oxidative desulfurization of model oil[J]. J Chem Ind Eng, 2016,67(9):3972-3980.
24. [24]
  SHAH D, GAPEYENKO D, URAKPAYEV A, TORKMAHALLEH M. Molecular dynamics simulations on extractive desulfurization of fuels by tetrabutylammonium chloride based Deep Eutectic Solvents[J]. J Mol Liq, 2019,274:254-260. doi: 10.1016/j.molliq.2018.10.131
25. [25]
  HAO L, SU T, HAO D, DENG C L, REN W Z, LÜ H Y. Oxidative desulfurization of diesel fuel with caprolactam-based acidic deep eutectic solvents:Tailoring the reactivity of DESs by adjusting the composition[J]. Chin J Catal, 2018,39(9):1552-1559. doi: 10.1016/S1872-2067(18)63091-8
26. [26]
  MAO C F, ZHAO R X, LI X P. Phenylpropanoic acid-based DESs as efficient extractants and catalysts for the removal of sulfur compounds from oil[J]. Fuel, 2017,189:400-407. doi: 10.1016/j.fuel.2016.10.113
27. [27]
  MAO C F, ZHAO R X, LI X P. Propionic acid-based deep eutectic solvents:Synthesis and ultra-deep oxidative desulfurization activity[J]. RSC Adv, 2017,7(67):42590-42596. doi: 10.1039/C7RA05687G
28. [28]
  LIU Z M, WANG J W, KANG M Q, YIN N, WANG X H, TAN Y S, ZHU Y L. Synthesis of glycerol carbonate by transesterification of glycerol and dimethyl carbonate over KF/γ-Al₂O₃ catalyst[J]. J Braz Chem Soc, 2014,25(1):152-160.
29. [29]
  AKBARI A, OMIDKHAH M, DARIAN J T. Investigation of process variables and intensification effects of ultrasound applied in oxidative desulfurization of model diesel over MoO₃/Al₂O₃ catalyst[J]. Ultrason Sonochem, 2014,21(2):692-705.
30. [30]
  ZHAO D, WANG J, ZHOU E. Oxidative desulfurization of diesel fuel using a Brønsted acid room temperature ionic liquid in the presence of H₂O₂[J]. Green Chem, 2007,9(11):1219-1222. doi: 10.1039/b706574d
31. [31]
  AL-SHAHRANI F, XIAO T, LLEWELLYN S A, BARRI S, JIANG Z, SHI H H, MARTINIE G, L H GREEN M. Desulfurization of diesel via the H₂O₂ oxidation of aromatic sulfides to sulfones using a tungstate catalyst[J]. Appl Catal B:Environ, 2007,73(3/4):311-316.
32. [32]
  JIANG X, LI H M, ZHU W, HE L N, SHU H M, LU J D. Deep desulfurization of fuels catalyzed by surfactant-type decatungstates using H₂O₂ as oxidant[J]. Fuel, 2009,88(3):431-436. doi: 10.1016/j.fuel.2008.11.010
33. [33]
  XIE D, HE Q H, SU Y Y, WANF T W, XU R F, HU B J. Oxidative desulfurization of dibenzothiophene catalyzed by peroxotungstate on functionalized MCM-41 materials using hydrogen peroxide as oxidant[J]. Chin J Catal, 2015,36(8):1205-1213. doi: 10.1016/S1872-2067(15)60897-X
34. [34]
  DAI B L, WU P W, ZHU W S, CHAO YH, SUN J, XIONG J, JIANG W, LI H M. Heterogenization of homogenous oxidative desulfurization reaction on graphene-like boron nitride with a peroxomolybdate ionic liquid[J]. RSC Adv, 2016,6(1):140-147. doi: 10.1039/C5RA23272D
35. [35]
  ZHANG Wei, DING Yong-ping, GONG Yao-jing, SONG Xi-ming. Oxidative desulfurization of dibenzothiophene catalyzed by carboxyl-functionalized ionic liquid[J]. J Fuel Chem Technol, 2012,40(5):628-632.
36. [36]
  HAO L W, WANG M R, SHAN W J, 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. doi: 10.1016/j.jhazmat.2017.06.050
37. [37]
  XIANG Xiao-yan, LIN Jin-qin. Progress of extractive desulfurization technology with ionic liquids[J]. Chem Ind Eng Prog, 2007,26(12):1681-1685. doi: 10.3321/j.issn:1000-6613.2007.12.003
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Preparation of C₉H₁₀O₂-0.5ZnCl₂/Al₂O₃ and its oxidative desulfurization performance