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http://dx.doi.org/10.5012/jkcs.2015.59.6.493

An Efficient Method for the Production of Cyclohexylamine from Cyclohexanone and Ammonia over Cu-Cr-La/γ-Al2O3  

Qin, Shuanglin (School of Pharmacy, Jiangxi Science and Technology Normal University)
Wang, Pan (First Teaching Hospital of Tianjin University of Traditional Chinese Medicine)
Huang, Shuangping (School of Pharmacy, Jiangxi Science and Technology Normal University)
Liu, Shuai (School of Pharmacy, Jiangxi Science and Technology Normal University)
Wang, Gaopeng (School of Pharmacy, Jiangxi Science and Technology Normal University)
Wang, Liping (School of Pharmacy, Jiangxi Science and Technology Normal University)
Sun, Meng (School of Pharmacy, Jiangxi Science and Technology Normal University)
Wang, Xiaoji (School of Pharmacy, Jiangxi Science and Technology Normal University)
Publication Information
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; $Cu-Cr-La/{\gamma}-Al_2O_3$; Premixing process;
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1 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.
2 Kitamura, M.; Lee, D.; Hayashi, S.; Tanaka, S.; Yoshimura, M. Catalytic Leuckart-Wallach-Type reductive amination of ketones. J. Org. Chem. 2002, 67, 8685.   DOI
3 Hili, R.; Yudin, A. K. Making carbon-nitrogen bonds in biological and chemical synthesis. Nat. Chem. Biol. 2006, 2, 284.   DOI
4 Pérez-Mendoza, M.; Domingo-García, M.; López-Garzón, F. J. Carbon materials as catalysts for methylamines synthesis. Appl. Catal. A: Gen. 2002, 224, 239.   DOI
5 Merla, B.; Risch, N. Efficient Synthesis of Diastereomerically pure 1, 3-Diamines. Synth. 2002, 10, 1365.
6 Fischer, A.; Mallat, T.; Baiker, A. Continuous amination of propanediols in supercritical ammonia. Angew. Chem. Int. Edit. 1999, 38, 351.   DOI
7 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.   DOI
8 Ramachandran, P. V.; Gagare, P. D.; Sakavuyi, K.; Clark, P. Reductive amination using ammonia borane. Tetrahedron Lett. 2010, 51, 3167.   DOI
9 P. Veeraraghavan Ramachandran, Pravin D. Gagare, Kaumba Sakavuyi, Paul Clark, Reductive amination using ammonia borane. Tetrahedron Lett. 2010, 51, 3167.   DOI
10 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.   DOI
11 Hayes, K. S. Industrial processes for manufacturing amines. Appl. Catal. A: Gen., 2001, 221, 187.   DOI
12 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.   DOI
13 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.   DOI
14 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.   DOI
15 Park, S.; Lee, I. S.; Park, J. A magnetically separable gold catalyst for chemoselective reduction of nitro compounds. Org. Biomol. Chem. 2013, 11, 395.   DOI
16 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.   DOI
17 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.   DOI
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.   DOI
19 Pingen, D.; Müller, C.; Vogt, D. Direct amination of secondary alcohols using ammonia. Angew. Chem. Int. Edit. 2010, 49, 8130.   DOI
20 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.   DOI
21 Elizabeth, R. Burkhardt, Brian M. Coleridge, Reductive amination with 5-ethyl-2-methylpyridine borane. Tetrahedron Lett. 2008, 49, 5152.   DOI