Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.jcat.2007.02.018
Title: A tandem cyclization and hydrogenation of (±)-citronellal to menthol over bifunctional Ni/Zr-beta and mixed Zr-beta and Ni/MCM-41
Authors: Nie, Y. 
Niah, W.
Jaenicke, S. 
Chuah, G.-K. 
Keywords: (±)-Citronellal
(±)-Menthol
Bifunctional catalyst
Diastereoselectivity
Nickel
Rhodium
Zr-beta
Issue Date: 15-May-2007
Source: Nie, Y.,Niah, W.,Jaenicke, S.,Chuah, G.-K. (2007-05-15). A tandem cyclization and hydrogenation of (±)-citronellal to menthol over bifunctional Ni/Zr-beta and mixed Zr-beta and Ni/MCM-41. Journal of Catalysis 248 (1) : 1-10. ScholarBank@NUS Repository. https://doi.org/10.1016/j.jcat.2007.02.018
Abstract: The addition of nickel to Zr-beta gave a useful bifunctional catalyst that combines a high rate of cyclization of (±)-citronellal to isopulegols over zirconium sites and subsequent hydrogenation to menthols. The diastereoselectivity to the desired (±)-menthol was 90%. A loading of 4 wt% is optimal; lower loadings led to a low rate of hydrogenation, whereas a higher nickel loading appears to block the zirconium Lewis acid sites essential for the cyclization of citronellal. A mixture of Zr-beta and Ni/MCM-41 also formed an effective bifunctional catalyst system where the selectivity toward menthols remained high even with nickel loadings up to 15 wt%. The yield of (±)-menthol over the dual-catalyst system was 86-89% with < 5 % of byproducts, citronellol and 3,7-dimethyloctanol. Besides nickel, bifunctional Rh/Zr-beta catalysts also formed menthols with selectivity > 93 %, although the diastereoselectivity to (±)-menthol was lower (85%). In comparison, a 2% Pd/Zr-beta catalyst exhibited lower activity and selectivity to menthols, forming substantial amounts of 3,7-dimethyloctanal. © 2007 Elsevier Inc. All rights reserved.
Source Title: Journal of Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/75495
ISSN: 00219517
DOI: 10.1016/j.jcat.2007.02.018
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