Abstract
A general process for the cyclization of aminoalcohols to the corresponding amines over Cu–Cr–La/γ-Al2O3 is established in a continuous fixed-bed reactor. The catalyst was characterized by XRD, XPS and NH3-TPD. The doped Cr is found to improve the copper particle dispersion. The addition of La neutralized the strong acid sites and decreased the amount of the acid sites, which facilitated the desorption of amino compounds on the surface of catalysts and inhibited the carbon deposition. Under the optimum conditions, the yields of pyrrolidine, piperidine and piperazine were 99.5, 99.5 and 98.6 %, in order, while the yields of hexahydro-1H-azepine and homopiperazine were 46.5 and 32.7 % due to the unstable seven-membered ring by the cyclization of the corresponding aminoalcohols over Cu–Cr–La/γ-Al2O3.
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Rudolf Z, Paul N, Gerhard F, Herbert D (1997) US Patent 5639886
Baiker A, Kijeriski J (1985) Catal Rev Sci Eng 27:653–697
Hammerschmidt W, Baiker A, Wokaun A, Fluhr W (1986) Appl Catal 20:305–312
Kijeński J, Niedzielski PJ, Baiker A (1989) Appl Catal 53:107–115
Poppelsdorf F, Myerly RC (1961) J Org Chem 26:131–134
Bai GY, Li Y, Yan XL, He F, Chen LG (2004) React Kinet Catal Lett 82:33–39
Bai GY, Chen LG, Li Y, Yan XL, He F, Xing P, Zeng T (2004) Appl Catal A 277:253–258
Wang HF, Chen LG, Luan DZ, Li Y, Yan XL, Zhang YC, Xing JD (2006) Kinet Catal Lett 89:201–208
Zhang YC, Bai GY, Yan XL, Li Y, Zeng T, Wang J, Wang HF, Xing JD, Luan DZ, Tang XY, Chen LG (2007) Catal Commun 8:1102–1106
Wu ZW, Wang HB, Sun M, Du XB, Chen LG, Li Y (2012) Res Chem Intermed 38:1149–1157
Yang F, Wu ZW, Ma JC, Wang HB, Li Y, Chen LG (2011) Catal Lett 141:1142–1148
Venot A, Glacet C (1971) C. R. Acad Sci Ser C 273:1266–1269
Karpeiskaya EI, Kukushkin YN, Trofimov VA, Ratner ID, Shashkin DP (1974) Russ Chem Bull 23:307–312
Yu CL, Ge QJ, Xu HY, Li WZ (2006) Appl Catal A 315:58–67
Ma D, Zhang WP, Shu YY, Liu XM, Xu YD, Bao XH (2000) Catal Lett 66:155–160
Ertl G, Knozinger H, Schuth F, Weitkamp J (1997) Handbook of heterogeneous catalysis, 2nd edn. Wiley–VCH, New York, pp 1170–1181
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Wu, Z., Yang, F., Wang, H. et al. A general process for the cyclization of aminoalcohols to the corresponding amines over Cu–Cr–La/γ-Al2O3 . Reac Kinet Mech Cat 106, 485–493 (2012). https://doi.org/10.1007/s11144-012-0447-z
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DOI: https://doi.org/10.1007/s11144-012-0447-z