Citation: YANG Fang, XU Xiang-Sheng, GU Hui-Zi, CHEN Ao-Ang, YAN Xin-Huan. Heterogeneously Catalyzed One-Pot Synthesis of N-alkyl anilines from Nitroaromatics by Assembled Pt₃Sn/Al₂O₃ Catalyst[J]. Acta Physico-Chimica Sinica doi: 10.3866/PKU.WHXB201206201 shu

Heterogeneously Catalyzed One-Pot Synthesis of N-alkyl anilines from Nitroaromatics by Assembled Pt₃Sn/Al₂O₃ Catalyst

1.
State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, P. R. China

Received Date: 6 April 2012
Available Online: 20 June 2012
Fund Project: 国家自然科学基金(21076197) (21076197) 浙江省自然科学基金(Y4090440) (Y4090440)浙江省钱江人才项目(2010R10038)资助 (2010R10038)

N-alkyl anilines were obtained from nitroaromatics by a one-pot method using assembled Pt₃Sn/Al₂O₃ catalyst for heterogeneous in situ hydrogenation in a continuous-flow fixed-bed reactor. At the optimum reaction conditions (503 K, liquid hourly space velocity (LHSV) of 7.5 h^-1, 5% (volume fraction) water, 1% (mass fraction) Pt₃Sn/Al₂O₃ catalyst), nitrobenzene conversion was 100%, with a total N-ethyl and N,N-diethyl aniline yield of 98.2%. Moreover, the Pt₃Sn/Al₂O₃ catalyst had a great conjoint effect for all in situ hydrogenation reactions for N-alkylation. High yields of N-alkylation products were obtained in aliphatic alcohol/water systems for 14 selected nitroaromatics.
- N-alkylation,
- In situ liquid hydrogenation,
- Nitroaromatic,
- N-alkyl aniline,
- Pt-Sn bimetallic catalyst
1. [1]
  
  (1) Xia, J. H.; Zhang, X.; Matyjaszewski, K. ACS Symp. Ser. 2000,760, 207. doi: 10.1021/bk-2000-0760.ch013
2. [2]
  (2) Clardy, J. M.; Fischbach, A.;Walsh, C. T. Nat. Biotechnol.2006, 24, 1541. doi: 10.1038/nbt1266
3. [3]
  (3) Oku, T.; Arita, Y.; Tsuneki, H.; Ikariya, T. J. Am. Chem. Soc.2004, 126, 7368. doi: 10.1021/ja048557s
4. [4]
  (4) Salvatore, R. N.; Nagle, A. S.; Jung, K.W. J. Org. Chem. 2002,67, 674. doi: 10.1021/jo010643c
5. [5]
  (5) Basu, B.; Paul, S.; Nanda, A. K. Green Chem. 2009, 11, 1115.doi: 10.1039/b905878h
6. [6]
  (6) Tripathi, R. P.; Verma, S. S.; Pandey, J.; Tiwari, V. K. Curr. Org. Chem. 2008, 10, 1093.
7. [7]
  (7) Byun, E.; Hong, B.; De Castro, K. A.; Lim, M.; Rhee, H. J. Org. Chem. 2007, 72, 9815. doi: 10.1021/jo701503q
8. [8]
  (8) Abdel-Magid, A. F.; Mehrman, S. J. Org. Process Res. Dev.2006, 10, 971. doi: 10.1021/op0601013
9. [9]
  (9) Shimizu, K.; Shimura, K.; Ohshima, K.; Tamura, M.; Satsuma,A. Green Chem. 2011, 13, 3096. doi: 10.1039/c1gc15835j
10. [10]
  (10) Xu, C.; Xiao, Z.; Zhou, B.;Wang, Y.; Huang, P. Chem. Commun. 2010, 46, 7834. doi: 10.1039/c0cc01487g
11. [11]
  (11) Yamaguchi, K.; He, J.; Oishi, T.; Mizuno, N. Chem. Eur. J.2010, 16, 7199.
12. [12]
  (12) Hamid, M. H. S.; Allen, A. C. L.; Lamb, G.W.; Maxwell, A. C.;Maytum, H. C.;Waston, A. J. A.;Williams, J. M. J. J. Am. Chem. Soc. 2009, 131, 1766. doi: 10.1021/ja807323a
13. [13]
  (13) He, L.; Lou, X.; Ni, J.; Liu, Y.; Cao, Y.; He, H.; Fan, K. Chem. Eur. J. 2010, 16, 13965. doi: 10.1002/chem.201001848
14. [14]
  (14) Kawahara, R.; Fujita, K.; Yamaguchi, R. Adv. Synth. Catal.2011, 353, 1161. doi: 10.1002/adsc.201000962
15. [15]
  (15) Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.;Williams, J. M. J. Chem. Commun. 2010, 46, 1541. doi: 10.1039/b923083a
16. [16]
  (16) Ruano, J. L. G.; Parra, A.; Aleman, J.; Yuste, F.; Mastranzo, V.M. Chem. Commun. 2009, 404.
17. [17]
  (17) Zhu, A.; Li, L.;Wang, J.; Zhuo, K. Green Chem. 2011, 13, 1244.doi: 10.1039/c0gc00763c
18. [18]
  (18) Enthaler, S. Catal. Lett. 2011, 141, 55. doi: 10.1007/s10562-010-0463-4
19. [19]
  (19) Peng, Q.; Zhang, Y.; Shi, F.; Deng, Y. Q. Chem. Commun. 2011,47, 6476. doi: 10.1039/c1cc11057h
20. [20]
  (20) Pandarus, V.; Ciriminna, R.; Beland, F.; Pagliaro, M. Catal. Sci. Technol. 2011, 1, 1616. doi: 10.1039/c1cy00097g
21. [21]
  (21) Lee, C. C.; Liu, S. T. Chem. Commun. 2011, 47, 6981. doi: 10.1039/c1cc11609f
22. [22]
  (22) Xiang, Y. Z.; Li, X. N.; Lu, C.; Ma, L.; Zhang, Q. Alpplied Catal. A: Gen. 2010, 375, 289. doi: 10.1016/j.apcata.2010.01.004
23. [23]
  (23) Feng, C.; Liu, Y.; Peng, S.; Shuai, Q.; Deng, G.; Li, C. Org. Lett.2010, 12, 4888. doi: 10.1021/ol1020527
24. [24]
  (24) Bea, J.W.; Cho, Y. J.; Lee, S. H.; Yoon, C. M.; Yoon, C. M.Chem. Commun. 2000, 1857.
25. [25]
  (25) Reddy, R. C.; Vijeender, K., Bhusan, B. P.; Madhavi, P. P.;Chandrasekhar, S. Tetrahedron Lett. 2007, 48, 2765. doi: 10.1016/j.tetlet.2007.02.050
26. [26]
  (26) Ely, T. O.; Pan, C.; Amiens, C.; Chaudret, B.; Dassenoy, F.;Lecante, P.; Casanove, M. J.; Mosset, A.; Respaud, M.; Broto, J.M. J. Phys. Chem. B 2000, 104, 695. doi: 10.1021/jp9924427
27. [27]
  (27) Mao, J. Z.; Yan, X. H.; Gu, H. Z.; Jiang, L. C. Chin. J. Catal.2009, 30, 182. [毛建忠, 严新焕, 顾辉子, 江玲超. 催化学报,2009, 30, 182.] doi: 10.1016/S1872-2067(08)60095-9
28. [28]
  (28) Zhou, L.; Gu, H. Z.; Yan, X. H. Catal. Lett. 2009, 132, 16. doi: 10.1007/s10562-009-0036-6
29. [29]
  (29) Riguetto, B. A.; Damyanova, S.; luliev, G.; Marques, C. M.P.; Petrov, L.; Bueno, J. M. C. J. Phys. Chem. B 2004, 108, 5349.
30. [30]
  (30) Navarro, R. M.; Álvarez-Galván, M. C.; Sánchez-Sánchez, M.C.; Rosa, F.; Fierro, J. L. G. Appl. Catal. B: Environ. 2005, 55,229. doi: 10.1016/j.apcatb.2004.09.002
31. [31]
  (31) Merlen, E.; Beccat, P.; Bertolini, J. C.; Delichère, P.; Zanier, N.;Didillon, B. J. Catal. 1996, 159, 178. doi: 10.1006/jcat.1996.0077
32. [32]
  (32) Dupont, C.; Delbecq, F.; Loffreda, D.; Jugnet, Y. J. Catal. 2011,278, 239. doi: 10.1016/j.jcat.2010.12.012
33. [33]
  (33) Narayanan, S.; Deshpande, K. Appl. Catal. A 1996, 135, 125.doi: 10.1016/0926-860X(95)00220-0
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Heterogeneously Catalyzed One-Pot Synthesis of N-alkyl anilines from Nitroaromatics by Assembled Pt3Sn/Al2O3 Catalyst

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通讯作者: 陈斌, bchen63@163.com

Heterogeneously Catalyzed One-Pot Synthesis of N-alkyl anilines from Nitroaromatics by Assembled Pt₃Sn/Al₂O₃ Catalyst