Abstract
The reaction of piperidine with formaldehyde over γ-alumina, Na+-γ-alumina, NiAl2O4 and CuAl2O4 was studied as a model system in order to understand the mechanism and selectivity of alkylpyridine formation from piperidine and carbonyl compounds. Along with the expected 3-picoline, 2-picoline and other products were also formed. The selectivity for 3-picoline was high on γ-alumina whereas on NiAl2O4, 2-picoline was selectively formed. The formation of the different products has been rationalized and a probable mechanism for the formation of 2-picoline has been presented.
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References
H. Kashiwagi and S. Enomoto, Chem. Pharm. Bull. 30 (1982) 404.
H. Kashiwagi, Y. Fujuki and S. Enomoto, Chem. Pharm. Bull. 30 (1982) 2575.
U. Kameswari, C.S. Swamy and C.N. Pillai, in:Methylation of Pyridine over Zeolites, Stud. Surf. Sci. Catal., Vol. 84C, eds. J. Weitkamp et al. (Elsevier, Amsterdam, 1994) p. 1959.
U. Kameswari, React. Kinet. Catal. Lett. 52 (1995), in press.
F. David and W. Henry, US patent 5,013,843, May 1991.
M. Jayamani and C.N. Pillai, J. Catal. 87 (1984) 478.
M. Jayamani, S. Ananthan and C.N. Pillai, Ind. J. Chem. 28 B (1989) 131.
E.P. Burrows, R.F. Hutton and W.D. Burrows, J. Org. Chem. 27 (1962) 316.
W.D. Burrows and E.P. Burrows, J. Org. Chem. 28 (1963) 1180.
R.H. Poirier, R.D. Morin, A.M. McKim and A.E. Bearse, J. Org. Chem. 26 (1961) 4275.
H. Pines and W.O. Haag, J. Am. Chem. Soc. 82 (1960) 2471.
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Kameswari, U., Pillai, C.N. Reaction of piperidine with formaldehyde over alumina and spinel aluminates. Catal Lett 38, 53–56 (1996). https://doi.org/10.1007/BF00806899
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DOI: https://doi.org/10.1007/BF00806899