Citation: NA Yin-Na, LIU Min, SONG Chun-Shan, GUO Xin-Wen. Effect of Water on Biphenyl Methylation over Modified HZSM-5[J]. Acta Physico-Chimica Sinica, ;2013, 29(05): 1073-1079. doi: 10.3866/PKU.WHXB201303082 shu

Effect of Water on Biphenyl Methylation over Modified HZSM-5

NA Yin-Na ¹ ,
LIU Min ^1, ,
SONG Chun-Shan ^1,2 ,
GUO Xin-Wen ^1,

1.
1 State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, Liaoning Province, P. R. China;
2 EMS Energy Institute, Department of Energy and Mineral Engineering, Pennsylvania State University, University Park, PA 16802, USA

Received Date: 25 December 2012
Available Online: 8 March 2013
Fund Project: 新世纪优秀人才(NCET-04-0268) (NCET-04-0268)

Nanosized HZSM-5 (n(SiO₂)/n(Al₂O₃)=26) samples were hydrothermally treated with and without subsequent HNO₃ leaching. The performance of the samples for the alkylation of biphenyl (BP) with methanol to 4-methylbiphenyl (4-MBP) under fixed-bed down-flow conditions was investigated. Characterization was conducted by the adsorption of pyridine using Fourier transform infrared (FTIR) spectroscopy and thermogravimetric (TG) analysis. The effect of water on the catalytic performance of modified HZSM-5 was investigated. Both hydrothermal and combined hydrothermal-HNO₃ treatments improved catalytic stability, with the latter exhibiting better stability. Without the addition of water, BP conversion behavior resembled an open down parabolic vs reaction time over modified HZSM-5. However, this change disappeared upon the addition of water to the reaction system. Both catalytic stability and selectivity of 4-MBP were improved upon the addition of water. BP conversion after 30 h on stream was 8.6%, and the selectivity of 4-MBP was as high as about 60%. Elevating the reaction temperature to 500℃ in the presence of water led to increased BP conversion with time on stream up to 30 h, and the selectivity was stable at ~58%. The activity and stability of HZSM-5 were improved, and para selectivity was enhanced with the addition of water.
- Nano HZSM-5,
- Biphenyl,
- 4-Methybiphenyl,
- Hydrothermal treatment,
- Water
1. [1]
  
  (1) Song, C.; Schobert, H. H. Fuel Process. Technol. 1993, 34 (2),157. doi: 10.1016/0378-3820(93)90098-O
2. [2]
  (2) Song, C. S. CATTECH 2002, 6 (2), 64.
3. [3]
  (3) Brechtelsbauer, C.; Emig, G. Appl. Catal. A-Gen. 1997, 161 (1-2), 79. doi: 10.1016/S0926-860X(96)00382-1
4. [4]
  (4) Horikawa, Y.; Bulgarevich, D. S.; Uchino, Y.; Shichijo, Y.;Sako, T. In. Eng. Chem. Res. 2005, 44, 2917. doi: 10.1021/ie0493661
5. [5]
  (5) Yoshiteru, H.; Yuki, U.; Yasuji, S. J. Jpn. Petrol. Inst. 2004, 47 (2), 136. doi: 10.1627/jpi.47.136
6. [6]
  (6) Guo, X.W.;Wang, X. S.; Shen, J. P.; Song, C. S. Catal. Today2004, 93-95, 411.
7. [7]
  (7) Guo, X.W.; Shen, J. P.; Sun, L.; Song, C. S.;Wang, X. S. Appl.Catal. A-Gen. 2004, 261 (2), 183. doi: 10.1016/j.apcata.2003.11.001
8. [8]
  (8) Guo, X.W.; Shen, J. P.; Sun, L.; Song, C. S.;Wang, X. S. Catal.Lett. 2003, 87 (3-4), 159.
9. [9]
  (9) Guo, X.W.; Shen, J. P.; Sun, L.; Song, C. S.;Wang, X. S. Catal.Lett. 2003, 87 (1-2), 25.
10. [10]
  (10) Dubuis, S.; Doepper, R.; Renken, A. Methylation of Biphenylover Zeolite H-ZSM-5 in Gas Phase with Methanol in PresenceofWater: Effect of the Catalyst Impregnation by TetraethylOrthosilicate. In Reaction Kinetics and the Development ofCatalytic Processes, Proceedings of the InternationalSymposium, Brugge, Belgium, April 19-21, 1999; Froment, G.F.,Waugh, K. C., Eds.; Elsevier: Amsterdam, 1999; pp 359-366.
11. [11]
  (11) Sugi, Y.; Tawada, S.; Sugimura, T. Appl. Catal. A-Gen. 1999,189 (2), 251. doi: 10.1016/S0926-860X(99)00282-3
12. [12]
  (12) Yamamura, M.; Chaki, K.;Wakatsuki, T.; Okado, H.; Fujimoto,K. Zeolites 1994, 14 (8), 643. doi: 10.1016/0144-2449(94)90121-X
13. [13]
  (13) Sugimoto, M.; Katsuno, H.; Takatsu, K.; Kawata, N. Zeolites1987, 7 (6), 503. doi: 10.1016/0144-2449(87)90087-X
14. [14]
  (14) Herrmann, C.; Haas, J.; Fetting, F. Appl. Catal. 1987, 35 (2),299. doi: 10.1016/S0166-9834(00)82868-7
15. [15]
  (15) Olson, D. H.; Kokotailo, G. T.; Lawton, S. L.; Meier,W. M.J. Phys. Chem. 1981, 85, 2238. doi: 10.1021/j150615a020
16. [16]
  (16) Ding, C. H. Preparation and Catalytic Properties of Catalysts forShape-Selective Alkylation of Toluene with Methanol. Ph. D.Dissertation, Dalian University of Technology, Dalian, 2007.[丁春华. 甲苯/甲醇选择烷基化催化剂的研制和催化性能研究[D]. 大连: 大连理工大学, 2007.]
17. [17]
  (17) Wang, X. Q.;Wang, X. S.; Guo, X.W. Ultrafine Particles 5 MRType Zeolite. CN Patent 1240193A, 2000-01-05. [王学勤,王祥生, 郭新闻. 超细颗粒五元环型沸石: 中国, CN 1240193A[P], 2000-01-05.]
18. [18]
  (18) Olah, G. A.; Lapierre, J. C. J. Org. Chem. 1966, 31, 1271.
19. [19]
  (19) Ding, C.;Wang, X.; Guo, X.; Zhang, S. Catal. Commun. 2008, 9 (4), 487. doi: 10.1016/j.catcom.2007.07.013
20. [20]
  (20) Zhang, C.; Guo, X.W.; Song, C. S.; Zhao, S. Q.;Wang, X. S.Catal. Today 2010, 149 (1-2), 196. doi: 10.1016/j.cattod.2009.04.015
21. [21]
  (21) Zhao, L.;Wang, H. B.; Liu, M.; Guo, X.W.;Wang, X. S.; Song,C. S.; Liu, H. M. Chem. Eng. Sci. 2008, 63, 5298. doi: 10.1016/j.ces.2008.07.018
22. [22]
  (22) Lucas, A.; Canizares, P.; Durán, A. Appl. Catal. A-Gen. 1997,154 (1-2), 221.
23. [23]
  (23) Schmitz, A. D.; Song, C. S. Catal. Lett. 1996, 40 (1-2), 59. doi: 10.1007/BF00807458
24. [24]
  (24) Song, C. S. C. R. Acad. Sci. Paris, Série IIc, Chimie Chemistry2000, 3 (6), 477.
25. [25]
  (25) Lefrancois, M.; Malbois, G. J. Catal. 1971, 20 (3), 350. doi: 10.1016/0021-9517(71)90097-2
26. [26]
  (26) Cannings, F. R. J. Phys. Chem. 1968, 72 (13), 4691. doi: 10.1021/j100859a058
27. [27]
  (27) Sauer, J. Science 1996, 271, 774. doi: 10.1126/science.271.5250.774
28. [28]
  (28) Wang, G. R. Catalyst and Catalytic Action, 1st ed.; DalianUniversity of Technology Press: Dalian, 2000; pp 115-116.[王桂茹. 催化剂与催化作用. 第一版. 大连: 大连理工大学出版社, 2000: 115-116.]
1. [1]
  Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
2. [2]
  Yuena Yang , Xufang Hu , Yushan Liu , Yaya Kuang , Jian Ling , Qiue Cao , Chuanhua Zhou . The Realm of Smart Hydrogels. University Chemistry, 2024, 39(5): 172-183. doi: 10.3866/PKU.DXHX202310125
3. [3]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
4. [4]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
5. [5]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
6. [6]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
7. [7]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
8. [8]
  Qiang Zhou , Pingping Zhu , Wei Shao , Wanqun Hu , Xuan Lei , Haiyang Yang . Innovative Experimental Teaching Design for 3D Printing High-Strength Hydrogel Experiments. University Chemistry, 2024, 39(6): 264-270. doi: 10.3866/PKU.DXHX202310064
9. [9]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
10. [10]
  Qingyang Cui , Feng Yu , Zirun Wang , Bangkun Jin , Wanqun Hu , Wan Li . From Jelly to Soft Matter: Preparation and Properties-Exploring of Different Kinds of Hydrogels. University Chemistry, 2024, 39(9): 338-348. doi: 10.3866/PKU.DXHX202309046
11. [11]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
12. [12]
  Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
13. [13]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
14. [14]
  Hongyun Liu , Jiarun Li , Xinyi Li , Zhe Liu , Jiaxuan Li , Cong Xiao . Course Ideological and Political Design of a Comprehensive Chemistry Experiment: Constructing a Visual Molecular Logic System Based on Intelligent Hydrogel Film Electrodes. University Chemistry, 2024, 39(2): 227-233. doi: 10.3866/PKU.DXHX202309070
15. [15]
  Yanling Luo , Xuejie Qi , Rui Shen , Xuling Peng , Xiaoyan Han . Design and Implementation of Ideological and Political Education in the Physical Chemistry Course at Traditional Chinese Medicine Universities: A Case Study of the Phase Diagram of Water. University Chemistry, 2024, 39(11): 9-14. doi: 10.3866/PKU.DXHX202402003
16. [16]
  Lijuan Liu , Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060
17. [17]
  Kun Xu , Xinxin Song , Zhilei Yin , Jian Yang , Qisheng Song . Comprehensive Experimental Design of Preferential Orientation of Zinc Metal by Heat Treatment for Enhanced Electrochemical Performance. University Chemistry, 2024, 39(4): 192-197. doi: 10.3866/PKU.DXHX202309050
18. [18]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
19. [19]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
20. [20]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

Get Citation

PDF

XML

Metrics

PDF Downloads(677)
Abstract views(921)
HTML views(2)

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