Oxidative Desulfurization of Model Diesel with O2 Catalyzed by Oxidative-thermoregulated Bifunctional Ionic Liquids

doi:10.6023/A14080570

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (11): 1152-1156.DOI: 10.6023/A14080570 Previous Articles Next Articles

Communication

氧化-温控双功能离子液体催化O₂氧化模拟柴油脱硫

于凤丽^a, 唐会宝^a, 柳春玉^a, 解从霞^a, 于世涛^b

a 青岛科技大学化学与分子工程学院青岛 266042;
b 青岛科技大学化工学院青岛 266042

投稿日期:2014-08-06 发布日期:2014-10-22
通讯作者: 解从霞 E-mail:xiecongxia@126.com
基金资助:
项目受国家自然科学基金(No. 21176129)、山东省优秀中青年科学家科研奖励基金(No. BS2011NJ008)和青岛市科技发展计划项目(No. 13-1-4-194-jch)资助.

Oxidative Desulfurization of Model Diesel with O₂ Catalyzed by Oxidative-thermoregulated Bifunctional Ionic Liquids

Yu Fengli^a, Tang Huibao^a, Liu Chunyu^a, Xie Congxia^a, Yu Shitao^b

a College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042;
b College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042

Received:2014-08-06 Published:2014-10-22
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21176129), the Foundation for Outstanding Young Scientist in Shandong Province (No. BS2011NJ008) and the Project of Basic Research in Qingdao City (No. 13-1-4-194-jch).

A series of ammonium oxidative-thermoregulated bifunctional ionic liquids (ILs) have been synthesized by introducing the thermoregulated structural unit (PEG chain) into ammonium cation and using heteropolyanion as catalytic oxidation group. The prepared ionic liquids have the thermoregulated solubility in toluene/n-dodecane mixed solvent. IL/toluene/n-dodecane system owns the feature of "homogeneous at high temperature, heterogeneous at low temperature". The effects of the dosage of the ionic liquid, the polymerization degree of the ionic liquid, and the volume ratio of toluene to n-dodecane on the thermoregulation of the system have been investigated. Model diesel is prepared by dissolving the model sulfur-containing compound thiophene in n-dodecane. By using the ionic liquid as catalyst, the thermoregulated IL/toluene/n-dodecane biphasic system has been used for catalytic oxidative desulfurization of model diesel with O₂ as oxidant to achieve the integration of homogeneous reaction and heterogeneous separation. So, the highly efficient catalysis and the simply separation of catalyst are achieved. The selected catalytic system is the polymerization degree of the ionic liquid n=111 and V(toluene):V(model oil)=1:1. The effects of the alkyl chain of the ionic liquid, reaction temperature, reaction time and the pressure of oxygen on the desulfurization rate have been fully investigated. The selected optimal conditions are as follows: the alkyl chain C₁₂, reaction temperature 100 ℃, reaction time 2 h, and the pressure of oxygen 2.0 MPa. Under the optimal conditions, the sulfur in model diesel nearly can be completely removed by using DMF as extraction agent. After the reaction, the catalyst can be automatically precipitated from the oil phase at the room temperature. Therefore, the recycle of the catalyst is easily realized. The recyclability of the ionic liquid catalyst is investigated. The result has showed that the catalyst exhibits very excellent recyclability. Under the above selected reaction conditions, the desulfurization rate still can reach above 95% after 11 recycles of the ionic liquid catalyst.

Key words: task-specific ionic liquids, thermoregulation, oxidative desulfurization, oxygen

Cite this article

Yu Fengli, Tang Huibao, Liu Chunyu, Xie Congxia, Yu Shitao. Oxidative Desulfurization of Model Diesel with O₂ Catalyzed by Oxidative-thermoregulated Bifunctional Ionic Liquids[J]. Acta Chimica Sinica, 2014, 72(11): 1152-1156.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kulkarni, P. S.; Afonso, C. A. M. Green Chem. 2010, 12, 1139.
[2] Zhao, D. S.; Li, J. P.; Zhang, J.; Ren, P. B.; Ge, J. J.; Ren, T. J.; Cui, Y. Chin. J. Org. Chem. 2014, 37, 1462. (赵地顺, 李俊盼, 张娟, 任培兵, 葛京京, 任腾杰, 崔云, 有机化学, 2014, 37, 1462.)
[3] Rothlisberger, A.; Prins, R. J. Catal. 2005, 235, 229.
[4] Bej, S. K.; Maity, S. K.; Turaga, U. T. Energy Fuels 2004, 18, 1227.
[5] Liu, W. Q.; Zhou, H.; Lei, W. N.; Shang, T. M.; Zhang, Q.; Sun, K. D. Acta Chim. Sinica 2011, 69, 1622. (刘维桥, 周虎, 雷卫宁, 尚通明, 张强, 孙桂大, 化学学报, 2011, 69, 1622.)
[6] Campos-Martin, J. M.; Capel-Sanchez, M. C.; Fierro, J. L. G. Green Chem. 2004, 6, 557.
[7] Lo, W. H.; Yang, H. Y.; Wei, G. T. Green Chem. 2003, 5, 639.
[8] Zhang, W.; Xu, K.; Zhang, Q.; Liu, D. L.; Wu, S. Y.; Verpoort, F.; Song, X. M. Ind. Eng. Chem. Res. 2010, 49, 11760.
[9] Zhu, W. S.; Wu, P. W.; Yang, L.; Chang, Y. H.; Chao, Y. H.; Li, H. M.; Jiang, Y. Q.; Jiang, W.; Xun, S. H. Chem. Eng. J. 2013, 229, 250.
[10] Zhang, W.; Xu, K.; Zhang, Q.; Liu, D. L.; Wu, S. Y.; Verpoort, F.; Song, X. M. Ind. Eng. Chem. Res. 2010, 49, 11760.
[11] Jiang, W.; Zhu, W. S.; Chang, Y. H.; Li, H. M.; Chao, Y. H.; Xiong, J.; Liu, H.; Zhu, F. X. Energy Fuels 2014, 28, 2754.
[12] Xu, J. H.; Zhao, S.; Chen, W.; Wang, M.; Song, Y. F. Chem. Eur. J. 2012, 18, 4775.
[13] Lu, L.; Cheng, S. F.; Gao, J. B.; Gao, G. H.; He, M. Y. Energy Fuels 2007, 21, 383.
[14] Zhao, D. S. H.; Wang, J. L.; Zhou, E. P. Green Chem. 2007, 9, 1219.
[15] Rao, T. V.; Sain, B.; Kafola, S.; Nautiyal, B. R.; Sharma, Y. K.; Nanoti, S. M.; Garg, M. O. Energy Fuels 2007, 21, 3420.
[16] Zhou, X. R.; Li, J.; Wang, X. N.; Jin, K.; Ma, W. Fuel Process. Technol. 2009, 90, 317.
[17] Lu, H.; Zhang, Y. Y. N.; Jiang, Z. X.; Li, C. Green Chem. 2010, 12, 1954.
[18] Tang, N. F.; Zhang, Y. N.; Lin, F.; Lu, H. Y.; Jiang, Z. X.; Li, C. Chem. Commun. 2012, 48, 11647.
[19] Lü, H. Y.; Gao, J. B.; Jiang, Z. X.; Yang, Y. X.; Song, B.; Li, C. Chem. Commun. 2007, 6, 150.
[20] Tang, N. F.; Zhao, X. P.; Jiang, Z. X.; Li, C. Chin. J. Catal. 2014, 35, 1433. (唐南方, 赵小平, 蒋宗轩, 李灿, 催化学报, 2014, 35, 1433.)
[21] Hill, C. L.; Damica Gall, R. J. Mol. Catal. A: Chem. 1996, 114, 103.
[22] Wang, S. S.; Liu, W.; Wan, Q. X.; Liu, Y. Green Chem. 2009, 11, 1589.
[23] Qiao, Y. X.; Hou, Z. S.; Li, H.; Hu, Y.; Feng, B.; Wang, X. R.; Hua, L.; Huang, Q. F. Green Chem. 2009, 11, 1955.
[24] Yang, H. G.; Qi, X. F.; Wen, L.; Lu, C. X.; Cheng, G. B. Ind. Eng. Chem. Res. 2011, 50, 11440.
[25] Leng, Y.; Wang, J.; Zhu, D. R.; Ren, X. Q.; Ge, H. Q.; Shen, L. Angew. Chem., Int. Ed. 2009, 48, 168.
[26] Zhu, W. S.; Wu, P. W.; Chao, Y. H.; Li, H. M.; Zou, F.; Xun, S. H.; Zhu, F. X.; Zhao, Z. Ind. Eng. Chem. Res. 2013, 52, 17399.
[27] Huang, W. L.; Zhu, W. S.; Li, H. M.; Shi, H.; Zhu, G. P.; Liu, H.; Chen, G. Y. Ind. Eng. Chem. Res. 2010, 49, 8998.
[28] Yu, F. L.; Wang, R. Acta Chim. Sinica 2014, 72, 105. (于凤丽, 王睿, 化学学报, 2014, 72, 105.)
[29] An, Y.; Lu, L.; Li, C. M.; Cheng, S. F.; Gao, G. H. Chin. J. Catal. 2009, 30, 1222. (安莹, 陆亮, 李才猛, 程时富, 高国华, 催化学报, 2009, 30, 1222.)
[30] Yu, F. L.; Wang, Y. Y.; Liu, C. Y.; Xie, C. X.; Yu, S. T. Chem. Eng. J. 2014, 255, 372.
[31] Griee, I. D.; Hvarey, P. J.; Jenkins, I. D. Tetrahedron Lett. 1996, 37, 1087.
[32] Behr, A.; Miao, Q. J. Mol. Catal. A: Chem. 2004, 222, 127.

氧化-温控双功能离子液体催化O₂氧化模拟柴油脱硫

Oxidative Desulfurization of Model Diesel with O₂ Catalyzed by Oxidative-thermoregulated Bifunctional Ionic Liquids

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ping Li, Qiyu Yang, Jing Zeng, Ran Zhang, Qiuyan Chen, Fei Yan. Effect of Fluorine Doping on the Performance of Reversible Solid Oxide Cells and Related Kinetic Studies [J]. Acta Chimica Sinica, 2024, 82(1): 36-45.
[2]	Feida Che, Xiaoming Zhao, Xin Zhang, Qi Ding, Xin Wang, Ping Li, Bo Tang. Fluorescence Imaging of Active Molecules Associated with Depression^★ [J]. Acta Chimica Sinica, 2023, 81(9): 1255-1264.
[3]	Yuan Zhang, Beining Zheng, Meichun Fu, Shouhua Feng. Research Progress in the Application of Spinel Oxides in Tumor Therapy^★ [J]. Acta Chimica Sinica, 2023, 81(8): 949-954.
[4]	Liu Lujie, Zhang Jian, Wang Liang, Xiao Fengshou. Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols^★ [J]. Acta Chimica Sinica, 2023, 81(5): 533-547.
[5]	Yuan Fangyan, Li Chao, Luo Meiming, Zeng Xiaoming. Chromium-Catalyzed Carbonyl-Carbonyl Deoxygenative Couplings of Ketones to Tetrasubstituted Olefins^★ [J]. Acta Chimica Sinica, 2023, 81(5): 456-460.
[6]	Jinjing Liu, Na Yang, Li Li, Zidong Wei. Theoretical Study on the Regulation of Oxygen Reduction Mechanism by Modulating the Spatial Structure of Active Sites on Platinum^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1478-1485.
[7]	Yao Li, Bingnian Chen, Dan Luo, Shan Lei, Li Wang. Study on the Antioxidant Properties of Polyoxometalates α-Glucosidase Inhibitors [J]. Acta Chimica Sinica, 2023, 81(10): 1318-1326.
[8]	Shuang Zhang, Chengfei Yang, Yubo Yang, Ningning Feng, Gang Yang. Electrochemical Behaviors of Li_xMO (x=0.79, 0.30, 0.08; M=Ni/Co/Mn) Recycled from Spent Li-ion Batteries as Cathodic Catalyst for Lithium-Oxygen Battery [J]. Acta Chimica Sinica, 2022, 80(9): 1269-1276.
[9]	Xiaojuan Li, Ziyu Ye, Shuhan Xie, Yongjing Wang, Yonghao Wang, Yuancai Lv, Chunxiang Lin. Study on Performance and Mechanism of Phenol Degradation through Peroxymonosulfate Activation by Nitrogen/Chlorine Co-doped Porous Carbon Materials [J]. Acta Chimica Sinica, 2022, 80(9): 1238-1249.
[10]	Zhaowei Tian, Weimin Da, Lei Wang, Yusen Yang, Min Wei. Structural Design and Research Progress of Heterogeneous Catalysts for the Preparation of Second Generation Biodiesel [J]. Acta Chimica Sinica, 2022, 80(9): 1322-1337.
[11]	Shaobing Yan, Long Jiao, Chuanxin He, Hailong Jiang. Pyrolysis of ZIF-67/Graphene Composite to Co Nanoparticles Confined in N-Doped Carbon for Efficient Electrocatalytic Oxygen Reduction [J]. Acta Chimica Sinica, 2022, 80(8): 1084-1090.
[12]	Dan Wang, Bo Feng, Xiaoxin Zhang, Yanan Liu, Yan Pei, Minghua Qiao, Baoning Zong. Nitrogen-doped Carbon Pyrolyzed from ZIF-8 for Electrocatalytic Oxygen Reduction to Hydrogen Peroxide [J]. Acta Chimica Sinica, 2022, 80(6): 772-780.
[13]	Yuanhao Geng, Xiaoqiu Lin, Yaxin Sun, Huiyu Li, Yue Qin, Congju Li. Preparation of Bimetallic Conductive Metal-organic Framework Material Ni/Co-CAT for Electrocatalytic Oxygen Reduction [J]. Acta Chimica Sinica, 2022, 80(6): 748-755.
[14]	Jinyuan Zhao, Qian Zhang, Jian Wang, Qi Zhang, Heng Li, Yaping Du. Advances in the Scavenging Materials for Reactive Oxygen Species [J]. Acta Chimica Sinica, 2022, 80(4): 570-580.
[15]	Yanran Li, Zigui Wang, Zhaohui Tang. Water Soluble IR-780 Polymer for Mitochondria-Targeted Photodynamic Therapy^※ [J]. Acta Chimica Sinica, 2022, 80(3): 291-296.

氧化-温控双功能离子液体催化O2氧化模拟柴油脱硫