Citation: MIAO Hai-Xia, MA Li, MA Jing-Hong, LI Dui-Chun, LI Rui-Feng. Benzylation of Naphthalene over a Mesoporous ZSM-5 Zeolite Microsphere Catalyst[J]. Acta Physico-Chimica Sinica, ;2014, 30(8): 1518-1526. doi: 10.3866/PKU.WHXB201405271 shu

Benzylation of Naphthalene over a Mesoporous ZSM-5 Zeolite Microsphere Catalyst

  • Received Date: 2 April 2014
    Available Online: 27 May 2014

    Fund Project:

  • A microspherical ZSM-5 zeolite aggregated from nanosized zeolite crystals with intra- and intercrystalline mesoporous structures (MMZ- 5) was prepared using presilanized silica as silica source. The acidic properties of this mesoporous zeolite were characterized via Fourier transform infrared spectroscopy (FTIR) in combination with pyridine (Py) and 2,6-di-tert-butylpyridine (DTBPy). Compared with conventional microporous ZSM- 5, the MMZ- 5 zeolite possessed more Lewis acid sites and many more accessible Brönsted acid sites for bulky DTBPy molecule (1.05 nm in diameter). This mesoporous zeolite thus afforded both effective active sites and reaction voids allowing the reaction of larger molecules, resulting in enhanced catalytic activity and stability of the MMZ-5 zeolite during the benzylation of naphthalene with benzyl chloride (BC) to form bulky monobenzylnaphthalenes and dibenzylnaphthalenes, during which the selectivity for monobenzylnaphthalenes was estimated to be about 79%. Moreover, the selectivity for dibenzylnaphthalenes was enhanced with increasing reaction time, owing to the consecutive reactions between monobenzylnaphthalenes and BC occurring at the effective reaction voids of the MMZ-5 zeolite. The distribution of the monobenzylnaphthalene isomers (α-BN and β-BN) was found to be independent of both reaction temperature and extent of BC conversion, the α-BN/β-BN molar ratio being about 83:17.

  • 加载中
    1. [1]

      (1) Corma, A. Chem. Rev. 1997, 97 (6), 2373. doi: 10.1021/cr960406n

    2. [2]

      (2) Perez-Ramirez, J.; Christensen, C. H.; Egeblad, K.; Christensen, C. H.; Groen, J. C. Chem. Soc. Rev. 2008, 37 (11), 2530. doi: 10.1039/b809030k

    3. [3]

      (3) Tao, Y.; Kanoh, H.; Abrams, L.; Kaneko, K. Chem. Rev. 2006, 106 (3), 896. doi: 10.1021/cr040204o

    4. [4]

      (4) Ogura, M.; Shinomiya, S. Y.; Tateno, J.; Nara, Y.; Nomura, M.; Kikuchi, E.; Matsukata, M. Appl. Catal. A 2001, 219 (1), 33.

    5. [5]

      (5) Abelló, S.; Bonilla, A.; Pérez-Ramírez, J. Appl. Catal. A 2009, 364 (1), 191.

    6. [6]

      (6) Yu, S. X.; Yang, J. H.; Chu, N. B.; Li, G.; Lu, J. M.;Wang, J. Q. Chin. J. Catal. 2009, 30 (10), 1035. [于素霞, 杨建华, 初乃波, 李刚, 鲁金明, 王金渠. 催化学报, 2009, 30 (10), 1035. ]

    7. [7]

      (7) Yang, Z. X.; Xia, Y. D.; Mokaya, R. Adv. Mater. 2004, 16 (8), 727. doi: 10.1002/adma.200306295

    8. [8]

      (8) Shetti, V. N.; Kim, J.; Srivastava, R.; Choi, M.; Ryoo, R. J. Catal. 2008, 254 (2), 296. doi: 10.1016/j.jcat.2008.01.006

    9. [9]

      (9) Choi, M.; Cho, H. S.; Srivastava, R.; Venkatesan, C.; Choi, D. H.; Ryoo, R. Nat. Mater. 2006, 5 (9), 718. doi: 10.1038/nmat1705

    10. [10]

      (10) Park, D. H.; Kim, S. S.;Wang, H.; Pinnavaia, T. J.; Papapetrou, M. C.; Lappas, A. A.; Triantafyllidis, K .S. Angew. Chem. Int. Edit. 2009, 48 (41), 7645. doi: 10.1002/anie.200901551

    11. [11]

      (11) Sun, Y. Y.; Prins, R. Appl. Catal. A 2008, 336 (1-2), 11. doi: 10.1016/j.apcata.2007.08.015

    12. [12]

      (12) Xue, Z.; Ma, J.; Zheng, J.; Zhang, T.; Kang, Y.; Li, R. Acta. Mater. 2012, 60, 5712. doi: 10.1016/j.actamat.2012.06.044

    13. [13]

      (13) Christensen, C . H.; Johannsen, K.; Schmidt, I.; Christensen, C. H. J. Am. Chem. Soc. 2003, 125 (44), 13370. doi: 10.1021/ja037063c

    14. [14]

      (14) Mokrzycki, L.; Sulikowski, B.; Olejniczak, Z. Catal. Lett. 2009, 127 (3-4), 296. doi: 10.1007/s10562-008-9678-z

    15. [15]

      (15) Bari, S. M.; Aitani, A.; Saeed, M.; Al-Khattaf, S. Top. Catal. 2010, 53, 1387. doi: 10.1007/s11244-010-9598-1

    16. [16]

      (16) Batt, D. G.; Maynard, G. D.; Petraitis, J. J.; Shaw, J. E.; Galbraith,W.; Harris, R. J. Med. Chem. 1990, 33 (1), 360. doi: 10.1021/jm00163a058

    17. [17]

      (17) Beltrame, P.; Demartin, F.; Zuretti, G. Appl. Catal. A 2002, 232 (1), 265.

    18. [18]

      (18) Yadav, G. D.; Purandare, S. A. J. Mol. Catal. A: Chem. 2007, 263 (1), 26.

    19. [19]

      (19) Bachari, K.; Cherifi, O. Appl. Catal. A 2007, 319, 259. doi: 10.1016/j.apcata.2006.12.010

    20. [20]

      (20) Bachari, K.; Millet, J. M. M.; Benaïchouba, B.; Cherifi, O.; Figueras, F. J. Catal. 2004, 221 (1), 55. doi: 10.1016/S0021-9517(03)00295-1

    21. [21]

      (21) Bhattacharya, D.; Pandey, A. K.; Singh, A. P. Stud. Surf. Sci. Catal. 1998, 113, 737. doi: 10.1016/S0167-2991(98)80353-4

    22. [22]

      (22) Thibault-Starzyk, F.; Stan, I.; Abelló, S.; Bonilla, A.; Thomas, K.; Fernandez, C.; Gilson, J. P.; Pérez-Ramírez, J. J. Catal. 2009, 264 (1), 11. doi: 10.1016/j.jcat.2009.03.006

    23. [23]

      (23) Zheng, S. R.; Heydenrych, H. R.; Jentys, A.; Lercher, J. A. J. Phys. Chem. B 2002, 106 (37), 9552. doi: 10.1021/jp014091d

    24. [24]

      (24) Wang,W. L.; Liu, B. J.; Zeng, X. J. Acta Phys. -Chim. Sin. 2008, 24 (11), 2102. [王文兰, 刘百军, 曾贤君. 物理化学学报, 2008, 24 (11), 2102.] doi: 10.3866/PKU.WHXB20081128

    25. [25]

      (25) Ordomsky, V. V.; Murzin, V. Y.; Monakhova, Y. V.; Zubavichus, Y. V.; Knyazeva, E. E.; Nesterenko, N. S.; Ivanova, I. I. Microporous Mesoporous Mat. 2007, 105, 101. doi: 10.1016/j.micromeso.2007.05.056

    26. [26]

      (26) Xue, Z.; Zhang, T.; Ma, J.; Miao, H.; Fan,W.; Zhang, Y.; Li, R. Microporous Mesoporous Mat. 2012, 151, 271. doi: 10.1016/j.micromeso.2011.10.026

    27. [27]

      (27) Serrano, D. P.; Aguado, J.; Rodriguez, J. M.; Peral, A. J. Mater. Chem. 2008, 18 (35), 4210. doi: 10.1039/b805502e

    28. [28]

      (28) Serrano, D. P.; García, R. A.; Vicente, G.; Linares, M.; Procházková, D.; ejka, J. J. Catal. 2011, 279 (2), 366. doi: 10.1016/j.jcat.2011.02.007

    29. [29]

      (29) Jin, H.; Ansari, M. B.; Park, S. E. Chem. Commun. 2011, 47 (26), 7482. doi: 10.1039/c1cc12259b

    30. [30]

      (30) Gracia, M. J.; Losada, E.; Luque, R.; Campelo, J. M.; Luna, D.; Marinas, J. M.; Romero, A. A. Appl. Catal. A 2008, 349 (1), 148.

    31. [31]

      (31) Chaube, V. D. Catal. Commun. 2004, 5 (6), 321. doi: 10.1016/j.catcom.2004.02.013

    32. [32]

      (32) Coq, B.; urves, V.; Figuéras, F. Appl. Catal. A 1993, 100 (1), 69. doi: 10.1016/0926-860X(93)80116-8

    33. [33]

      (33) Beltrame, P.; Zuretti, G. Appl. Catal. A 2003, 248 (1), 75.

    34. [34]

      (34) Beltrame, P.; Zuretti, G. Appl. Catal. A 2004, 268 (1), 169.


  • 加载中
    1. [1]

      Xingyang LITianju LIUYang GAODandan ZHANGYong ZHOUMeng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026

    2. [2]

      Xinyu You Xin Zhang Shican Jiang Yiru Ye Lin Gu Hexun Zhou Pandong Ma Jamal Ftouni Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265

    3. [3]

      Jie ZHAOSen LIUQikang YINXiaoqing LUZhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

    4. [4]

      Bing LIUHuang ZHANGHongliang HANChangwen HUYinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

    5. [5]

      Chuanming GUOKaiyang ZHANGYun WURui YAOQiang ZHAOJinping LIGuang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459

    6. [6]

      Yufang GAONan HOUYaning LIANGNing LIYanting ZHANGZelong LIXiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036

    7. [7]

      Wenyan Dan Weijie Li Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060

    8. [8]

      Yihao Zhao Jitian Rao Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050

    9. [9]

      Jiali CHENGuoxiang ZHAOYayu YANWanting XIAQiaohong LIJian ZHANG . Machine learning exploring the adsorption of electronic gases on zeolite molecular sieves. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 155-164. doi: 10.11862/CJIC.20240408

    10. [10]

      Guangming YINHuaiyao WANGJianhua ZHENGXinyue DONGJian LIYi'nan SUNYiming GAOBingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086

    11. [11]

      Lijun Huo Mingcun Wang Tianyi Zhao Mingjie Liu . Exploration of Undergraduate and Graduate Integrated Teaching in Polymer Chemistry with Aerospace Characteristics. University Chemistry, 2024, 39(6): 103-111. doi: 10.3866/PKU.DXHX202312059

    12. [12]

      Yuanpei ZHANGJiahong WANGJinming HUANGZhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077

    13. [13]

      Lina Guo Ruizhe Li Chuang Sun Xiaoli Luo Yiqiu Shi Hong Yuan Shuxin Ouyang Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

    14. [14]

      Zhifang SUZongjie GUANYu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290

    15. [15]

      Hongsheng Tang Yonghe Zhang Dexiang Wang Xiaohui Ning Tianlong Zhang Yan Li Hua Li . A Wonderful Journey through the Kingdom of Hazardous Chemicals. University Chemistry, 2024, 39(9): 196-202. doi: 10.12461/PKU.DXHX202403098

    16. [16]

      CCS Chemistry | 超分子活化底物自由基促进高效选择性光催化氧化

      . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.

    17. [17]

      Shiyan Cheng Yonghong Ruan Lei Gong Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

    18. [18]

      Yaping Li Sai An Aiqing Cao Shilong Li Ming Lei . The Application of Molecular Simulation Software in Structural Chemistry Education: First-Principles Calculation of NiFe Layered Double Hydroxide. University Chemistry, 2025, 40(3): 160-170. doi: 10.12461/PKU.DXHX202405185

    19. [19]

      Peng YUELiyao SHIJinglei CUIHuirong ZHANGYanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210

    20. [20]

      Yanxin Wang Hongjuan Wang Yuren Shi Yunxia Yang . Application of Python for Visualizing in Structural Chemistry Teaching. University Chemistry, 2024, 39(3): 108-117. doi: 10.3866/PKU.DXHX202306005

Metrics
  • PDF Downloads(367)
  • Abstract views(534)
  • HTML views(6)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return