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An Efficient Method for the Production of Cyclohexylamine from Cyclohexanone and Ammonia over Cu-Cr-La/γ-Al2O3
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 Title & Authors
An Efficient Method for the Production of Cyclohexylamine from Cyclohexanone and Ammonia over Cu-Cr-La/γ-Al2O3
Qin, Shuanglin; Wang, Pan; Huang, Shuangping; Liu, Shuai; Wang, Gaopeng; Wang, Liping; Sun, Meng; Wang, Xiaoji;
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 Abstract
The reductive amination of cyclohexanone with ammonia over Cu-Cr-a/γ-Al2O3 was investigated. It was found that a proper solvent with high solubility of ammonia and 4Å molecular sieves for the elimination of generated water contributed to the formation of cyclohexylamine in the premixing process. In addition, the addition of ammonia in the fixedbed reactor could obviously improve the conversion of cyclohexanone to cyclohexylamine. Finally, reaction conditions including reaction temperature, hydrogen pressure and charging rate of the premix were optimized. Under the optimized conditions, cyclohexylamine was obtained in 83.06% yield.
 Keywords
Reductive amination;Cyclohexylamine;Cyclohexanone;;Premixing process;
 Language
English
 Cited by
 References
1.
Fischer, A.; Mallat, T.; Baiker, A. Continuous amination of propanediols in supercritical ammonia. Angew. Chem. Int. Edit. 1999, 38, 351. crossref(new window)

2.
Merla, B.; Risch, N. Efficient Synthesis of Diastereomerically pure 1, 3-Diamines. Synth. 2002, 10, 1365.

3.
Pérez-Mendoza, M.; Domingo-García, M.; López-Garzón, F. J. Carbon materials as catalysts for methylamines synthesis. Appl. Catal. A: Gen. 2002, 224, 239. crossref(new window)

4.
Hili, R.; Yudin, A. K. Making carbon-nitrogen bonds in biological and chemical synthesis. Nat. Chem. Biol. 2006, 2, 284. crossref(new window)

5.
Kitamura, M.; Lee, D.; Hayashi, S.; Tanaka, S.; Yoshimura, M. Catalytic Leuckart-Wallach-Type reductive amination of ketones. J. Org. Chem. 2002, 67, 8685. crossref(new window)

6.
Rele, S.; Banerji, A.; Talukdar, S. Reductive amination of aliphatic carbonyls using low-valent titanium reagent: a convenient route to free primary amines. J. Chem. Res. Synopses, 2002, 6, 253.

7.
Ramachandran, P. V.; Gagare, P. D.; Sakavuyi, K.; Clark, P. Reductive amination using ammonia borane. Tetrahedron Lett. 2010, 51, 3167. crossref(new window)

8.
Chen, X. Z.; Zhou, S. D.; Chen, Y. H.; Dong, Z. H.; Gao, Y. Y.; Qian, C.; He, C. H. Application of alkoxide in catalytic transfer hydrogenation of unsaturated nitrogen compounds. Res. Chem. Intermediat. 2012, 38, 2255. crossref(new window)

9.
Park, S.; Lee, I. S.; Park, J. A magnetically separable gold catalyst for chemoselective reduction of nitro compounds. Org. Biomol. Chem. 2013, 11, 395. crossref(new window)

10.
Tauber, K.; Fuchs, M.; Sattler, J. H.; Pitzer, J.; Pressnitz, D.; Koszelewski, D.; Faber, K.; Pfeffer, J.; Haas, T.; Kroutil, W. Artificial Multi-Enzyme networks for the asymmetric amination of sec-alcohols. Chem. Eur. J. 2013, 19, 4030. crossref(new window)

11.
Becker, J.; Niederer, J. P. M.; Keller, M.; Hölderich, W. F. Amination of cyclohexanone and cyclohexanol/cyclohexanone in the presence of ammonia and hydrogen using copper or a group VIII metal supported on a carrier as the catalyst. Appl. Catal. A: Gen. 2000, 197, 229. crossref(new window)

12.
Hayes, K. S. Industrial processes for manufacturing amines. Appl. Catal. A: Gen., 2001, 221, 187. crossref(new window)

13.
Péter Falus, Zoltán Boros, Gábor Hornyánszky, József, Ferenc Darvas, László Ürge, László Poppe, Reductive amination of ketones: novel one-step transfer hydrogenations in batch and continuous-flow mode. Tetrahedron Lett. 2011, 52, 1310. crossref(new window)

14.
P. Veeraraghavan Ramachandran, Pravin D. Gagare, Kaumba Sakavuyi, Paul Clark, Reductive amination using ammonia borane. Tetrahedron Lett. 2010, 51, 3167. crossref(new window)

15.
Elizabeth, R. Burkhardt, Brian M. Coleridge, Reductive amination with 5-ethyl-2-methylpyridine borane. Tetrahedron Lett. 2008, 49, 5152. crossref(new window)

16.
Kirumakki, S. R.; Papadaki, M.; Chary, K. V. R.; Nagaraju, N. Reductive amination of cyclohexanone in the presence of cyclohexanol over zeolites Hβ and HY. J. Mol. Catal. A: Chem. 2010, 321, 15. crossref(new window)

17.
Pingen, D.; Müller, C.; Vogt, D. Direct amination of secondary alcohols using ammonia. Angew. Chem. Int. Edit. 2010, 49, 8130. crossref(new window)

18.
Falus, P.; Boros, Z.; Hornyánszky, G.; Nagy, J.; Darvas, F.; Ürge, L.; Poppe, L. Reductive amination of ketones: novel one-step transfer hydrogenations in batch and continuous-flow mode. Tetrahedron Lett. 2011, 52, 1310. crossref(new window)

19.
Shimizu, K.; Kon, K.; Onodera, W.; Yamazaki, H.; Kondo, J. N. Heterogeneous Ni catalyst for direct synthesis of primary amines from alcohols and ammonia. ACS Catal. 2013, 3, 112. crossref(new window)

20.
Sun, M.; Du, X. B.; Wang, H. B.; Wu, Z. W.; Li, Y.; Chen, L. G. Reductive amination of triacetoneamine with n-butylamine over Cu-Cr-La/γ-Al2O3. Catal. Lett. 2011, 141, 1703. crossref(new window)

21.
Sun, M.; Du, X. B.; Kong, X. J.; Lu, L.; Li, Y.; Chen, L. G. The reductive amination of cyclohexanone with 1,6-diaminohexane over alumina B modified Cu-Cr-La/γ-Al2O3. Catal. Commun. 2012, 20, 58. crossref(new window)