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

doi:10.3724/SP.J.1088.2013.20939

Abstract

Abstract:

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.

Key words: cyclohexanone, ammoximation, titanium silicalite, fixed bed, hydrogen peroxide

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.

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References

1 Roffa P, Moretti E, Padovan M, De Alberti G. US Patent 4745221. 1988

2 Thangaraj A, Sivasanker S, Ratnasamy P. J Catal,1991, 131: 394

3 ReddyJ S, Sivasanker S, Ratnasamy P. J Mol Catal, 1991, 69: 383

4 Tvarl?kováZ, Habersberger K, Zˇilkova N, Jír? P. Appl CatalA, 1991, 79: 105

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 ZecchinaA, Bordiga S, Lamberti C,Ricchiardi G, LambertiC, Ricchiardi G, Scarano D, Petrini G, Leofanti G, Mantegazza M. Catal Today, 1996, 32: 97

7 Dal Pozzo L, Fornasari G, Monti T. Catal Commun, 2002, 3: 369

8 CesanaA, Mantegazza M A, Pastori M. J Mol Catal A,1997, 117: 367

9 Mantegazza M A, Cesana A, Pastori M. Top Catal, 1996, 3: 327

10 PetriniG, Cesana A, De Alberti G, Genoni F, Padovan M, Paparatto G, Roffia P.StudSurfSciCatal, 1991, 68: 761

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 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 Sun B. Petrol Process Petrochem(孙斌.石油炼制与化工), 2005, 36(11): 54

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 RoffiaP, Leofanti G, Cesana A, Mantegazza M, Padovan M, Petrini G, Tonti S, Gervasutti P.StudSurf Sci Catal, 1990, 55: 43

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 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 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 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 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 Taramasso M, Perego G, Notari B. US Patent 4 410 501.1983

22 Wu P, Tatsumi T, Komatsu T, Yashima T. J Phys Chem B, 2001, 105: 2897

23 Clerici M G, Bellussi G, Romano U. J Catal, 1991, 129: 159

24 MantegazzaM A, Leofanti G, Petrini G, Padovan M, Zecchina A, Bordiga S. StudSurfSciCatal, 1994, 82: 541

25 ClericiM G, IngallinaP. J Catal, 1993, 140: 71

26 Wu P, Komatsu T, Yashima T. J Catal, 1997, 168: 400

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 RatnasamyP,Srinivas D, Knoezinger H.Adv Catal,2004, 48: 1

29 Mantegazza M A, Petrini G, Cesana A. EP Patent 0564040A2.1993

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 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

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