Activity and Selectivity Control in Reductive Amination of Butyraldehyde over Noble Metal Catalysts

作者: J Bódis , Leonardus Lefferts , TE Müller , R Pestman , JA Lercher

DOI: 10.1007/S10562-005-7431-4

关键词: Reductive aminationHydrogenolysisNoble metalOrganic chemistryChemistryAminationButylamineButyraldehydeCatalysisDibutylamine

摘要: Approaches to control selectivity and activity in the catalytic reductive amination of butyraldehyde with ammonia over carbon supported noble metal catalysts (Ru, Rh, Pd, Pt) were explored. Detailed analysis reaction network shows that Schiff base N-[butylidene]butan-1-amine is most prominent initial product and, only after nearly all had been converted N-[butylidene]butan-1-amine, amines are detected mixture. From this intermediate, good hydrogenolysis Rh) produce mostly butylamine, while less active (Pd, lead hydrogenation dibutylamine.

参考文章(25)
G. C. Bond, Catalysis By Metals ,(1962)
L. Mark′o, J. Bakos, Homogeneous reductive amination with cobalt and rhodium carbonyls as catalysts Journal of Organometallic Chemistry. ,vol. 81, pp. 411- 414 ,(1974) , 10.1016/S0022-328X(00)88210-8
Ki-Whan Chi, Chris Addicott, Atta M. Arif, Neeladri Das, Peter J. Stang, Bidentate ligands capable of variable bond angles in the self-assembly of discrete supramolecules. Journal of Organic Chemistry. ,vol. 68, pp. 9798- 9801 ,(2003) , 10.1021/JO0353785
Kenneth A. Pollart, Robert E. Miller, Ozonolysis-Reductive Amination of Olefins Journal of Organic Chemistry. ,vol. 27, pp. 2392- 2394 ,(1962) , 10.1021/JO01054A026
Silvia Gomez, Joop A. Peters, Jan C.van der Waal, Thomas Maschmeyer, High-throughput experimentation as a tool in catalyst design for the reductive amination of benzaldehyde Applied Catalysis A-general. ,vol. 254, pp. 77- 84 ,(2003) , 10.1016/S0926-860X(03)00278-3
Patrick L. Mills, Donald E. Willis, Ricky L. Fenton, An investigation of reaction pathways and reaction kinetics for the liquid-phase catalytic amination of long-chain alkenals by the use of a model compound Industrial & Engineering Chemistry Research. ,vol. 27, pp. 1120- 1131 ,(1988) , 10.1021/IE00079A006
Mikhail V. Klyuev, Mikhail L. Khidekel', Reductive amination of carbonyl compounds in the presence of cobalt and rhodium complexes Transition Metal Chemistry. ,vol. 5, pp. 134- 139 ,(1980) , 10.1007/BF01396893
Silvia Gomez, Joop A. Peters, Jan C. van der Waal, Peter J. van den Brink, Thomas Maschmeyer, The rationalization of catalyst behaviour in the reductive amination of benzaldehyde with ammonia using a simple computer model Applied Catalysis A-general. ,vol. 261, pp. 119- 125 ,(2004) , 10.1016/J.APCATA.2003.10.037
Mark J. Burk, Jose P. Martinez, John E. Feaster, Nick Cosford, Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the CN double bond Tetrahedron. ,vol. 50, pp. 4399- 4428 ,(1994) , 10.1016/S0040-4020(01)89375-3