Citation: ZHANG Juan, HU Yan-hui, CHENG Lin-yan, REN Teng-jie, LI Jun-pan, ZHAO Di-shun. Synthesis of binuclear metal phthalocyanine and its catalytic performance in the oxidative desulfurization of dibenzothiophene[J]. Journal of Fuel Chemistry and Technology, ;2014, 42(12): 1493-1499. shu

Synthesis of binuclear metal phthalocyanine and its catalytic performance in the oxidative desulfurization of dibenzothiophene

1.
1. College of Chemistry and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, China;

Corresponding author: ZHANG Juan,
Received Date: 29 May 2014
Available Online: 4 September 2014
Fund Project: 国家自然科学基金(21106032) (21106032) 国家级大学生创新创业计划项目(201310082019) (201310082019) 河北科技大学博士科研启动基金(000172)。 (000172)

Binuclear cobalt phthalocyanine was synthesized by microwave method and characterized by infrared spectroscopy, UV-visible spectroscopy and thermogravimetry; its catalytic performance in the oxidative desulfurization of dibenzothiophene (DBT) was investigated. The results showed that the binuclear cobalt phthalocyanine exhibits the highest activity among five catalysts; over it, with the catalyst amount of 0.01 g(cat)/5 mL and air flow rate of 80 mL/min, the sulfur removal rate reaches 97.17% after reaction at 40 ℃ for 1 h. The product of DBT oxidation is DBTO₂, as verified by the FT-IR and mass spectrometry. The catalytic performance in the oxidation of aromatics and olefins was also investigated, which illustrates that current process using binuclear cobalt phthalocyanine as the catalyst has little influence on the quality of the oil product. Moreover, the catalyst can be reused for 5 times without significant decrease of its oxidation activity.
- binuclear cobalt phthalocyanine,
- dibenzothiophene,
- catalytic oxidation,
- desulfurization
1. [1]
  [1] 高庆毓, 高跃. 浅谈汽车尾气污染与治理[J]. 中国产经, 2013, 5: 42-43. (GAO Qing-yu, GAO Yue. The automobile exhaust pollution and control[J]. Industry of China, 2013, 5: 42-43.)
2. [2]
  [2] 赵地顺, 张娟, 孙增涛, 王佳蕾. 活性炭负载TiO₂光催化氧化二苯并噻吩的研究[J]. 燃料化学学报, 2008, 36(3): 322-325. (ZHAO Di-shun, ZHANG Juan, SUN Zeng-tao, WANG Jia-lei Study on photocatalytic oxidation of dibenzothiophene by activated carbon supported TiO₂[J]. Journal of FuelChemistry and Technology, 2008, 36(3): 322-325.)
3. [3]
  [3] JABBARNEZHAD P, HAGHIGHI M, TAGHAVINEZHAD P. Sonochemical synthesis of NiMo/Al₂O₃-ZrO₂ nanocatalyst: Effect of sonication and zirconia loading on catalytic properties and performance in hydrodesulfurization reaction[J]. Fuel Process Technol, 2014, 126: 392-401.
4. [4]
  [4] WANG H, WU Y, LIU Z W, HE L, YAO Z Y, ZHAO W Y. Deposition of WO₃ on Al₂O₃ via a microwave hydrothermal method to prepare highly dispersed W/Al₂O₃ hydrodesulfurization catalyst[J]. Fuel, 2014, 136: 185-193.
5. [5]
  [5] 裴玉同, 罗勇, 吴向阳, 李建龙, 宋家龙. 改性NaY分子筛吸附脱硫性能的研究[J]. 高校化学工程学报, 2012, 25(6): 1078-1083. (PEI Yu-tong, LUO Yong, WU Xiang-yang, LI Jian-long, SONG Jia-long. Performance of Adsorptive Desulfurization over Modified NaY Zeolite[J]. Journal of Chemical Engineering of Chinese Universities, 2012, 25(6): 1078-1083.)
6. [6]
  [6] 张傑, 黄崇品, 陈标华, 李英霞, 乔聪震. 用离子液体萃取脱除汽油中的硫化物[J]. 燃料化学学报, 2005, 33(4): 431-434. (ZHANG Jie, HUANG Chong-pin, CHEN Biao-hua, LI Ying-xia, QIAO Cong-zhen. Extractive desulfurization from gasoline by [Cu₂Cl₃\[J]. Journal of Fuel Chemistry and Technology, 2005, 33(4): 431-434.)
7. [7]
  [7] 戴咏川, 亓玉台, 赵德智, 张会成. 柴油在超声波/Cu²⁺/H₂O₂中的氧化脱硫[J]. 燃料化学学报, 2007, 35(2): 188-191. (DAI Yong-chuan, QI Yu-tai ZHAO De-zhi, ZHANG Hui-cheng. Ultrasound oxidative desulfurization of diesel oil with copper ion and hydrogen peroxide[J]. Journal of Fuel Chemistry and Technology, 2007, 35(2): 188-191.)
8. [8]
  [8] CHAMACK M, MAHJOUB A R, AGHAYAN H. Cesium salts of tungsten-substituted molybdophosphoric acid immobilized onto platelet mesoporous silica: Efficient catalysts for oxidative desulfurization of dibenzothiophene[J]. Chem Eng J, 2014, 255: 686-694.
9. [9]
  [9] GARCÍA-GUTIÉRREZ J L, LAREDO G C, GARCÍA-GUTIÉRREZ P, JIMNEZ-CRUZ F. Oxidative desulfurization of diesel using promising heterogeneous tungsten catalysts and hydrogen peroxide[J]. Fuel, 2014, 138: 118-125.
10. [10]
  [10] MURATA S, MURATA K, KIDENA K, NOMURA M. A novel oxidative desulfurization system for diesel fuels with molecular oxygen in the presence of cobalt catalysts and aldehydes[J]. Energy Fuel, 2004, 18(l): 116-121.
11. [11]
  [11] HUANG Z, BAO H, YAO Y, LU W, CHEN W. Novel green activation processes and mechanism of peroxymonosulfate based on supported cobalt phthalocyanine catalyst[J]. Appl Catal B: Environ, 2014, 154: 36-43.
12. [12]
  [12] GHASEMI M, DAUD W R W, RAHIMNEJAD M, REZAYI M, FATEMI A, JAFARI Y, SOMALU M R, MANZOUR A. Copper-phthalocyanine and nickel nanoparticles as novel cathode catalysts in microbial fuel cells[J]. Int J Hydrogen Energy, 2013, 38(22): 9533-9540.
13. [13]
  [13] 许恒哲, 乐园, 陈建峰. 超细酞菁蓝微粒的制备及其电泳性能的研究[J]. 高校化学工程学报, 2009, 23(4): 639-643. (XU Heng-zhe, LE Yuan, CHEN Jian-feng. Preparation of phthalocyanine blue nanocrystals and their electrophoretic Properties[J]. Journal of Chemical Engineering of Chinese Universities, 2009, 23(4): 639-643.)
14. [14]
  [14] 冯海霞, 张智慧, 朱志昂, 严诗楷, 王传忠. 金属酞菁催化巯基乙醇氧化的研究[J]. 燃料化学学报, 1998, 26(6): 516-520. (FENG Hai-xia, ZHANG Zhi-hui, ZHU Zhi-ang, YAN Shi-kai, WANG Chuan-zhong. Study on catalyzed oxidation of 2-mercaptoehanol by metallophthalocyanine[J]. Journal of Fuel Chemistry and Technology, 1998, 26(6): 516-520.)
15. [15]
  [15] ZHOU X R, LI J, WANG X N, JIN K, MA W. Oxidative desulfurization of dibenzothiophene based on molecular oxygen and iron phthalocyanine[J]. Fuel Process Technol, 2009, 90(2): 317-323.
16. [16]
  [16] 赵地顺, 任红威, 马四国, 刘翠微. 催化裂化汽油的相转移催化氧化脱硫反应研究[J]. 化学学报, 2006, 64(20): 2086-2090. (ZHAO Di-shun, REN Hong-wei, MA Si-guo, LIU Cui-wei. Study of oxidative desulfurization of fluid catalytic cracking gasoline by phase transfer catalysis [J]. Acta Chimi Sinica, 2006, 64(20): 2086-2090.)
17. [17]
  [17] ZHANG J, LI J, REN T, HU Y, GE J, ZHAO D. Oxidative desulfurization of dibenzothiophene based on air and cobalt phthalocyanine in ionic liquid[J]. RSC Adv, 2014, 4(7): 3206-3210.
18. [18]
  [18] ILIEV V, MIHAYLOVA A, BILYARSKA L P. Oxidationof phenols in aqueous solution, catalyzed by mononuclear and polynuclear metal phthalocya, nine complexes[J]. J Mol Catal A: Chem, 2002, 184(1/2): 121-130.
19. [19]
  [19] YANG J, VAN D, MARK M R. Synthesis of binuclear phthalocyanines sharing a benzene or naphthalene ring[J]. Tetrahedron lett, 1993, 34(33): 5223-5226.
20. [20]
  [20] 杨欣雨. 溴代酞菁配合物的合成及其对锂/亚硫酰氯电池催化性能的研究[D]. 西安: 西北大学, 2009. (YANG Xin-yu. Synthesis of brominated phthalocyanine complexes and their study of lithium / thionyl chloride batteries catalytic properties[D]. Xi-An: Northwest University, 2009.)
21. [21]
  [21] SHIRAI H, HANABUSA K, KITAMURA M, MASUDA E, HIRABARU O, HOJO N. Synthesis and properties of metal complexes[J]. Makromol Chem, 1984, 185: 2537-2542.
22. [22]
  [22] 胡晓明. 双核酞菁铁电催化性能研究[D]. 北京: 北京工业大学, 2012. (HU Xiao-ming. Study of electric catalytic properties of biunclear iron pthalocyanine[D]. Beijing: Beijing University of Technology, 2012.)
23. [23]
  [23] 陈文兴, 姚玉元, 吕素芳, 陈海相, 胡智文, 余志成. 平面双核金属酞菁衍生物的催化氧化性能[J]. 化工学报, 2004, 55(6): 924-928. (CHEN Wen-xing, YAO Yu-yuan, LV Su-fang, CHEN Xiang-hai, HU Zhi-wen, YU Zhi-cheng. Catalytic oxidation activity of planar binuclear metal-phthalocyanine derivatives[J]. Journal of Chemical Industry and Engineering, 2004, 55(6): 924-928.)
24. [24]
  [24] LI B T, ZHOU X X, WANG X J. Hybrid binuclear-cobalt-phthalocyanine as oxygen reduction reaction catalyst in single chamber microbial fuel cells[J]. J Power sources, 2014, 272: 320-327.
25. [25]
  [25] 陈文兴, 魏莉莉, 汪进前, 姚玉元, 吕慎水, 陈世良. 平面双核铜酞菁催化氧化硫醇[J]. 中国科学: B辑, 2006, 36(4): 299-303. (CHEN Wen-xing, WEI Li-li, WANG Qian-jin, YAO Yu-yuan, LV Shen-shui, CHEN Shi-liang. Planar binuclear copper phthalocyanine catalyzed oxidation of thiols[J]. Science in China: Series B, 2006, 36(4): 299-303.)
1. [1]
  Yongmei Liu , Lisen Sun , Zhen Huang , Tao Tu . Curriculum-Based Ideological and Political Design for the Experiment of Methanol Oxidation to Formaldehyde Catalyzed by Electrolytic Silver. University Chemistry, 2024, 39(2): 67-71. doi: 10.3866/PKU.DXHX202308020
2. [2]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
3. [3]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
4. [4]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
5. [5]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
6. [6]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
7. [7]
  Wang Wang , Yucheng Liu , Shengli Chen . Use of NiFe Layered Double Hydroxide as Electrocatalyst in Oxygen Evolution Reaction: Catalytic Mechanisms, Electrode Design, and Durability. Acta Physico-Chimica Sinica, 2024, 40(2): 2303059-0. doi: 10.3866/PKU.WHXB202303059
8. [8]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
9. [9]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
10. [10]
  Jianan Hong , Chenyu Xu , Yan Liu , Changqi Li , Menglin Wang , Yanwei Zhang . Decoding the interfacial competition between hydrogen evolution and CO₂ reduction via edge-active-site modulation in photothermal catalysis. Acta Physico-Chimica Sinica, 2025, 41(9): 100099-0. doi: 10.1016/j.actphy.2025.100099
11. [11]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
12. [12]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
13. [13]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
14. [14]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
15. [15]
  Huafeng SHI . Construction of MnCoNi layered double hydroxide@Co-Ni-S amorphous hollow polyhedron composite with excellent electrocatalytic oxygen evolution performance. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1380-1386. doi: 10.11862/CJIC.20240378
16. [16]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
17. [17]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
18. [18]
  Ye Wang , Ruixiang Ge , Xiang Liu , Jing Li , Haohong Duan . An Anion Leaching Strategy towards Metal Oxyhydroxides Synthesis for Electrocatalytic Oxidation of Glycerol. Acta Physico-Chimica Sinica, 2024, 40(7): 2307019-0. doi: 10.3866/PKU.WHXB202307019
19. [19]
  Liu Lin , Zemin Sun , Huatian Chen , Lian Zhao , Mingyue Sun , Yitao Yang , Zhensheng Liao , Xinyu Wu , Xinxin Li , Cheng Tang . Recent Advances in Electrocatalytic Two-Electron Water Oxidation for Green H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(4): 2305019-0. doi: 10.3866/PKU.WHXB202305019
20. [20]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(433)
HTML views(33)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142