An Efficient Method for the Production of Cyclohexylamine from Cyclohexanone and Ammonia over Cu-Cr-La/γ-Al2O3
1
조회
0
다운로드
2
인용
0
참고문헌
키워드
초록
The reductive amination of cyclohexanone with ammonia over Cu-Cr-La/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.
Abstract
The reductive amination of cyclohexanone with ammonia over Cu-Cr-La/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.
참고문헌 (21)
- Fischer, A., "Continuous amination of propanediols in supercritical ammonia", Angew. Chem. Int. Edit, 38, pp.351~ (1999)
- Merla, B., "Efficient Synthesis of Diastereomerically pure 1, 3-Diamines", Synth, 10, pp.1365~ (2002)
- Pérez-Mendoza, M., "Carbon materials as catalysts for methylamines synthesis", Appl. Catal. A: Gen, 224, pp.239~ (2002)
- Hili, R., "Making carbon-nitrogen bonds in biological and chemical synthesis", Nat. Chem. Biol, 2, pp.284~ (2006)
- Kitamura, M., "Catalytic Leuckart-Wallach-Type reductive amination of ketones", J. Org. Chem, 67, pp.8685~ (2002)
- Rele, S., "Reductive amination of aliphatic carbonyls using low-valent titanium reagent: a convenient route to free primary amines", J. Chem. Res. Synopses, 6, pp.253~ (2002)
- Ramachandran, P. V., "Reductive amination using ammonia borane", Tetrahedron Lett, 51, pp.3167~ (2010)
- Chen, X. Z., "Application of alkoxide in catalytic transfer hydrogenation of unsaturated nitrogen compounds", Res. Chem. Intermediat, 38, pp.2255~ (2012)
- Park, S., "A magnetically separable gold catalyst for chemoselective reduction of nitro compounds", Org. Biomol. Chem, 11, pp.395~ (2013)
- Tauber, K., "Artificial Multi-Enzyme networks for the asymmetric amination of sec-alcohols", Chem. Eur. J, 19, pp.4030~ (2013)
- Becker, J., "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, 2000, pp.197, 229~
- Hayes, K. S., "Industrial processes for manufacturing amines", Appl. Catal. A: Gen, 221, pp.187~ (2001)
- Péter Falus, "Reductive amination of ketones: novel one-step transfer hydrogenations in batch and continuous-flow mode", Tetrahedron Lett, 52, pp.1310~ (2011)
- P. Veeraraghavan Ramachandran, "Reductive amination using ammonia borane", Tetrahedron Lett, 51, pp.3167~ (2010)
- Elizabeth, R. Burkhardt, "Reductive amination with 5-ethyl-2-methylpyridine borane", Tetrahedron Lett, 49, pp.5152~ (2008)
- Kirumakki, S. R., "Reductive amination of cyclohexanone in the presence of cyclohexanol over zeolites Hβ and HY", J. Mol. Catal. A: Chem, 321, pp.15~ (2010)
- Pingen, D., "Direct amination of secondary alcohols using ammonia", Angew. Chem. Int. Edit, 49, pp.8130~ (2010)
- Falus, P., "Reductive amination of ketones: novel one-step transfer hydrogenations in batch and continuous-flow mode", Tetrahedron Lett, 52, pp.1310~ (2011)
- Shimizu, K., "Heterogeneous Ni catalyst for direct synthesis of primary amines from alcohols and ammonia", ACS Catal, 3, pp.112~ (2013)
- Sun, M., "Reductive amination of triacetoneamine with n-butylamine over Cu-Cr-La", γ-Al2O3, 2011, pp.141, 1703~
- Sun, M., "The reductive amination of cyclohexanone with 1,6-diaminohexane over alumina B modified Cu-Cr-La", γ-Al2O3, 2012, pp.20, 58~
