Citation: LI Jia-hui, HU Jia, ZHAO Rong-xiang, LI Xiu-ping. Prepartion of amino acid functionalized heteropolyacid salt and its catalytic performance for oxidation desulfurization of model oil[J]. Journal of Fuel Chemistry and Technology, ;2014, 42(11): 1394-1399. shu

Prepartion of amino acid functionalized heteropolyacid salt and its catalytic performance for oxidation desulfurization of model oil

1.
1. College of Petrochemical Engineering, Liaoning University of Petroleum & Chemical Technology, Fushun 113001, China;

Corresponding author: ZHAO Rong-xiang,
Received Date: 9 May 2014
Available Online: 25 July 2014

A new amino-acid functionalized heteropoly tungstate ([Ala]₃PW) was prepared with alanine and phosphotungstic acid as raw materials. The structure of [Ala]₃PW was characterized by XRD, FT-IR. The removal of dibenzothiophene (DBT) in model oil was studied by using [Ala]₃PW as catalysts, hydrogen peroxide as oxidant and imidazolium tetrafluoroborate ([HMIM]BF₄) as the extractant. The influence of reaction temperature, the amount of catalysts, the molar ratio of O/S(H₂O₂/DBT), the amount of extractant and types of thiophene on the desulfurization efficiency were investigated. The results indicated that under the optimal reaction conditions of 10 mL model oil, 0.04 g of [Ala]₃PW, O/S(mol ratio) =6, V([HMIM]BF₄)/V(oil)=0.6, reaction temperature of 50 ℃ and reaction time of 180 min, removal of DBT was found to be 98.2%. The catalyst could be recycled 4 times without a significant decrease in activity.
- alanine,
- phosphotungstic acid,
- dibenzothiophene,
- desulfurization
1. [1]
  [1] 林燕, 王芳, 张志庆, 杨洁, 魏颖. 离子液体绿色脱硫机理及应用进展[J]. 化工进展, 2013, 32(3): 549-557.(LIN Yan, WANG Fang, ZHANG Zhi-qing, YANG Jie, WEI Ying. Mechanism and application of ionic liquids in environmental friendly oil desulphurization[J]. Chemical Industry and Engineering Progress, 2013, 32(3): 549-557.)
2. [2]
  [2] 郇维芳, 欧阳福生. FCC汽油脱硫降烯烃技术最新进展[J]. 工业催化, 2004, 12(8): 6-10.(XUN Wei-fang, OU YANG Fu-sheng. Latest advances in hydordesulfurization an olefin-reducing techniques for FCC gasoline[J]. Industrial Catalysis, 2004, 12(8): 6-10.)
3. [3]
  [3] 李文秀, 崔安磊, 范俊刚, 孙向乐, 张志刚. 载铜球形活性炭的制备及其吸附脱硫性能的研究[J]. 燃料化学学报, 2013, 41(5): 613-618.(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]. Journal of Fuel Chemistry and Technology, 2013, 41(5): 613-618.)
4. [4]
  [4] 曾丹林, 胡义, 王可苗, 王光辉. 燃料油萃取脱硫技术研究进展[J].石油炼制与化工, 2012, 43(5): 98-102.(ZENG Dan-lin, HU Yi, WANG Ke-miao, WANG Guang-hui. Research advance in desulfurization of transportation fuels by extraction process[J]. Petroleum Processing and Petrochemicals, 2012, 43(5): 98-102.)
5. [5]
  [5] LO W H, YANG H W, WEI G T. One-pot desulfurization of light oils by oxidation and soluent extraction with room temperature ionic liquids[J]. Green Chemistry, 2003, 5: 639-642.
6. [6]
  [6] ESSER J, WASSERSCHEID P, JESS A. Deep desulfurization of oil refinery streams by extraction with ionic liquids[J]. Green Chem, 2004, 3(2): 316-322.
7. [7]
  [7] ZHANG S, ZHANG Q. ZHANG Z C. Extractive desulphurization and denitrogenation of fuels using ionic liquids[J]. Ind Eng Chem Res, 2004, 43(2): 614-622.
8. [8]
  [8] 张海燕, 代跃利, 蔡蕾. 杂多酸催化剂催化氧化脱硫研究进展[J]. 化工进展, 2013, 32(4): 809-815.(ZHANG Hai-yan, DAI Yue-li, CAI Lei. Research progress of heteropoly acid catalyzed oxidative desulfurization[J]. Chemical Industry and Engineering Progree, 2013, 32(4): 809-815.)
9. [9]
  [9] 安莹, 陆亮, 李才猛, 程时富, 高国华. 磷钼杂多酸离子液体催化氧化脱硫[J]. 催化学报, 2009, 30(12): 1222-1226.(AN Ying, LU Liang, LI Cai-meng, CHENG Shi-fu, GAO Guo-hua. Oxidative desulfurization catalyzed by molybdophosphate-based ionic liquid[J]. Chinese Journal of Catalysis, 2009, 30(12): 1222-1226.)
10. [10]
  [10] HUANG W L, ZHU W S, LI H M, SHI H, ZHU G P, LIU H, CHEN G Y.Heteropolyanion-based ionic liquids for deep desulfurization of fuelsin ionic liquids[J]. Ind Eng Chem Res, 2010, 49(19): 8998-9003.
11. [11]
  [11] RICKERT P G, ANTONIO M R, FIRESTONE M A, KUBATKO K A, SZREDER T, WISHART J F, DIETZ M L. Tetraalkylphosphonium polyoxometalate ionic liquids: Novel, organic-inorganic hybrid materials[J]. J Phys Chem B, 2007, 111(18): 4685-4692.
12. [12]
  [12] 刘静, 黄小文, 赵小平, 刘秀梅, 颜佩芳, 王畅, 高艳安.氨基酸功能化杂多酸盐的制备及其在无溶剂条件下催化正十二醇与乙酸酯化反应性能[J].石油学报(石油加工), 2013, 29(3): 383-384.(LIU Jing, HUANG Xiao-wen, ZHAO Xiao-ping, LIU Xiu-meng, YAN Pei-fang, WANG Chang, GAO Yan-an. Preparation of amino acid funcionalized heteropolyacid salt and its catalytic performance for solvent-free esterification of dodecanol with acetic acid[J]. Acta petrolei sinica (Petroleum Processing Section), 2013, 29(3): 383-384.)
13. [13]
  [13] LU L, CHENG S F, GAO J B, GAO G H, HE M Y. Deep oxidative desulfurization of fuels catalyzed by ionic liquid in the presence of H₂O₂[J]. Energy Fuels, 2007, 21(1): 383-384.
14. [14]
  [14] 刘日嘉, 王睿. 氨基化中空SiO₂杂多化合物复合型催化剂的合成、表征及催化燃油深度脱硫性能[J]. 高等学校化学学报, 2013, 34(12): 2814-2820.(LIU Ri-jia, WANG Rui. Synthesis, characterization and catalytic fuel ultra-deep desulfurization of hollow amino-SiO₂ supported heteropoly compound catalyst[J]. Chemical Journal of Chinese Universities, 2013, 34(12): 2814-2819.)
15. [15]
  [15] 李宇慧, 冯丽娟, 王景刚, 周旋, 程斌斌, 王晓燕, 李春虎. MoO₃/介孔Al₂O₃催化氧化脱除模拟油中的硫[J]. 高等学校化学学报, 2011, 32(3): 778-782.(LI Yu-hui, FENG Li-juan, WANG Jing-gang, ZHOU Xuan, CHENG Bin-bin,WANG Xiao-yan, LI Chu-hu. Catalytic oxidative desulfurization of model oil by MoO₃/mesoporous Al₂O₃[J]. Chemical Journal of Chinese Universities, 2011, 32(3): 778-782.)
16. [16]
  [16] LUIS C C, HILDA G B, ADRIANA F C, HECTOR D. G G, ROGELIO C G. Oxidative desulfurization of synthetic diesel using supported catalysts: Part III. Support effect on vanadium-based catalysts[J]. Catal Today, 2008, 133-135: 244-254.
17. [17]
  [17] 张薇, 丁永萍, 宫摇敬, 宋溪明. 羧基功能化离子液体催化二苯并噻吩氧化脱硫[J]. 燃料化学学报, 2012, 5(40): 628-632.(ZHANG Wei, DING Yong-ping, GONG Yao-jing, SONG Xi-ming. Oxidative desulfurization of dibenzothiophene catalysed by carboxyl-functionalized ionic liquid cmmim BF₄[J]. Journal of Fuel Chemistry and Technology, 2012, 5(40): 628-632.)
18. [18]
  [18] 李佳慧, 胡嘉, 赵荣祥, 乔海燕, 李秀萍. 氯化胆碱/草酸型低共熔溶剂氧化脱除模拟油硫化物[J]. 燃料化学学报, 2014, 42(7): 870-876.(LI Jia-hui, HU Jia, ZHAO Rong-xiang, QIAO Hai-yan, LI Xiu-ping. Oxidative desulfurization of model oil with choline chloride/oxalic acid as a eutectic solvent[J]. Journal of Fuel Chemistry and Technology, 2014, 42(7): 870-876.)
19. [19]
  [19] CATHERINE A, GENEVIEVE C, NICOLE P, JEAN-MARIE B, RENE T, FRANCOISE C, CATHERINE H, HENRY L. Reinvestigation of epoxidation using tungsten-based precursors and hydrogen peroxide in a biphase medium[J]. Inorg Chem, 1991, 30(23): 4409-4415.
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