Citation: ZHUO Zuoxi, LIN Longfei, DENG Xiujuan, WANG Yuning, LIU Yueming. Fixed-bed process of liquid-phase ammoximation of cyclohexanone over titanosilicates[J]. Chinese Journal of Catalysis, ;2013, 34(3): 604-611. doi: 10.3724/SP.J.1088.2013.20939 shu

Fixed-bed process of liquid-phase ammoximation of cyclohexanone over titanosilicates

1.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, EastChinaNormalUniversity, Shanghai 200062, China

Corresponding author: LIU Yueming,
Received Date: 30 September 2012
Available Online: 30 October 2012
Fund Project: 国家自然科学基金(20973064) (20973064) 国家科技支撑计划(2012BAE05B02) (2012BAE05B02) 上海市科委基础研究重点项目(12JC14030600) (12JC14030600) 上海市重点学科建设项目基金(B409). (B409)

Liquid-phase ammoximation of cyclohexanone to the corresponding oxime was conducted in a fixed-bed reactor over titanium silicalite (TS-1), which was proved to be a feasible and universal process. The primary rules of ammoximation were explored in the fixed-bed reactor system.The initial results indicated that the utilization of H₂O₂ was enhanced obviously through this mode, which is attributed to successful hydroxylamine generation and smooth contact with ketones. Further investigations of H₂O₂ reaction behavior showed that the proper weight hourly space velocity of H₂O₂ and the concentrations of ammonia and ketone both play a key role in highly efficient utilization of H₂O₂. The cyclohexanone and H₂O₂ conversion, cyclohexanone-oxime selectivity, and H₂O₂ efficiency reached 18.7%, 94.7%, 99.5%, and 98.7%, respectively, under the optimum reaction conditions of temperature of 333 K, ammonia concentration higher than 2%, cyclohexanone/H₂O₂ molar ratio of 5, and WHSV (H₂O₂)of 0.083h^-¹ with 85% t-BuOH as solvent.
- cyclohexanone,
- ammoximation,
- titanium silicalite,
- fixed bed,
- hydrogen peroxide
1. [1]
  1 Roffa P, Moretti E, Padovan M, De Alberti G. US Patent 4745221. 1988
2. [2]
  2 Thangaraj A, Sivasanker S, Ratnasamy P. J Catal,1991, 131: 394
3. [3]
  3 ReddyJ S, Sivasanker S, Ratnasamy P. J Mol Catal, 1991, 69: 383
4. [4]
  4 TvarlžkováZ, Habersberger K, Zˇilkova N, Jírł P. Appl CatalA, 1991, 79: 105
5. [5]
  5 ZecchinaA, Spoto G, Bordiga S, Geobaldo F, Petrini G,Leofanti G,Padovan M, Mantegazza M, Roffa P.Stud Surf Sci Catal, 1993, 75: 719
6. [6]
  6 ZecchinaA, Bordiga S, Lamberti C,Ricchiardi G, LambertiC, Ricchiardi G, Scarano D, Petrini G, Leofanti G, Mantegazza M. Catal Today, 1996, 32: 97
7. [7]
  7 Dal Pozzo L, Fornasari G, Monti T. Catal Commun, 2002, 3: 369
8. [8]
  8 CesanaA, Mantegazza M A, Pastori M. J Mol Catal A,1997, 117: 367
9. [9]
  9 Mantegazza M A, Cesana A, Pastori M. Top Catal, 1996, 3: 327
10. [10]
  10 PetriniG, Cesana A, De Alberti G, Genoni F, Padovan M, Paparatto G, Roffia P.StudSurfSciCatal, 1991, 68: 761
11. [11]
  11 Liu N, Guo H Ch, Wang X Sh, Chen L X, Chen Y Y.Chin J Catal(刘娜,郭洪臣,王祥生,陈黎行,陈永英.催化学报), 2003, 24: 441
12. [12]
  12 Zhan X J, Wang Y, Yang L B, Xin F. Chin J Catal(张向京,王燕,杨立斌,辛峰. 催化学报), 2006, 27: 427
13. [13]
  13 Sun B. Petrol Process Petrochem(孙斌.石油炼制与化工), 2005, 36(11): 54
14. [14]
  14 Fu S B, Wang H B, Xu F H, Zhu Z H (傅送保,王洪波,徐风华,朱泽华). CN Patent 1 324 684A.2001
15. [15]
  15 RoffiaP, Leofanti G, Cesana A, Mantegazza M, Padovan M, Petrini G, Tonti S, Gervasutti P.StudSurf Sci Catal, 1990, 55: 43
16. [16]
  16 Li P,Lu G Zh, Luo Y, Dia Y N. Acta Chim Sin(李平, 卢冠忠, 罗勇, 代亚男.化学学报), 2000, 58: 204
17. [17]
  17 Gao H X, Shu Z B, Cao J, Zhang Y X, Lu W K, Chen Q L. Chin J Catal(高焕新, 舒祖斌, 曹静, 张玉贤, 卢文奎, 陈庆龄.催化学报), 1998, 19: 329
18. [18]
  18 Fang X Q, Wang Y N, Deng X J, Wu H H, Wu P, Liu Y M, He M Y. Chin J Catal(方向青, 王钰宁, 邓秀娟, 吴海虹, 吴鹏, 刘月明, 何鸣元. 催化学报), 2011, 32: 333
19. [19]
  19 Deng X J, Shen L, Zhang Sh, Liu Y M. Chin J Catal(邓秀娟, 申璐, 张硕, 刘月明. 催化学报), 2011, 32: 1550
20. [20]
  20 Zhang Sh, Deng X J, Shen L, Liu Y M. Chin J Catal(张硕, 邓秀娟, 申璐, 刘月明. 催化学报), 2012, 33: 723
21. [21]
  21 Taramasso M, Perego G, Notari B. US Patent 4 410 501.1983
22. [22]
  22 Wu P, Tatsumi T, Komatsu T, Yashima T. J Phys Chem B, 2001, 105: 2897
23. [23]
  23 Clerici M G, Bellussi G, Romano U. J Catal, 1991, 129: 159
24. [24]
  24 MantegazzaM A, Leofanti G, Petrini G, Padovan M, Zecchina A, Bordiga S. StudSurfSciCatal, 1994, 82: 541
25. [25]
  25 ClericiM G, IngallinaP. J Catal, 1993, 140: 71
26. [26]
  26 Wu P, Komatsu T, Yashima T. J Catal, 1997, 168: 400
27. [27]
  27 Yao M K, Yang J X, Zhao S, Liu Y M, Wu H H, Wu P.Chin J Catal(姚明恺, 杨俊霞, 赵松, 刘月明, 吴海虹,吴鹏.催化学报), 2008, 29: 1271
28. [28]
  28 RatnasamyP,Srinivas D, Knoezinger H.Adv Catal,2004, 48: 1
29. [29]
  29 Mantegazza M A, Petrini G, Cesana A. EP Patent 0564040A2.1993
30. [30]
  30 Li Y X, Wu W, Min E Z, Sun B.Petrol Process Petrochem (李永祥, 吴巍, 闵恩泽, 孙斌.石油炼制与化工), 2002, 33: 41
31. [31]
  31 Yang J X, Yao M K, Zhao S, Liu Y M, Wu P, He M Y. Chin J Catal(杨俊霞, 姚明恺, 赵松, 刘月明, 吴鹏, 何鸣元.催化学报), 2010, 31: 95
1. [1]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
2. [2]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
3. [3]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
4. [4]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
5. [5]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
6. [6]
  Pei Li , Yuenan Zheng , Zhankai Liu , An-Hui Lu . Boron-Containing MFI Zeolite: Microstructure Control and Its Performance of Propane Oxidative Dehydrogenation. Acta Physico-Chimica Sinica, 2025, 41(4): 100034-. doi: 10.3866/PKU.WHXB202406012
7. [7]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng 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
8. [8]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
9. [9]
  Jiali CHEN , Guoxiang ZHAO , Yayu YAN , Wanting XIA , Qiaohong LI , Jian 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]
  Yiping HUANG , Liqin TANG , Yufan JI , Cheng CHEN , Shuangtao LI , Jingjing HUANG , Xuechao GAO , Xuehong GU . Hollow fiber NaA zeolite membrane for deep dehydration of ethanol solvent by vapor permeation. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 225-234. doi: 10.11862/CJIC.20240224
11. [11]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
12. [12]
  Shanghua Li , Malin Li , Xiwen Chi , Xin Yin , Zhaodi Luo , Jihong Yu . 基于高离子迁移动力学的取向ZnQ分子筛保护层实现高稳定水系锌金属负极的构筑. Acta Physico-Chimica Sinica, 2025, 41(1): 2309003-. doi: 10.3866/PKU.WHXB202309003
13. [13]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
14. [14]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
15. [15]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
16. [16]
  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
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  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
19. [19]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
20. [20]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(359)
HTML views(12)

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