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Selective etherification of beta-citronellene catalyzed by zeolite beta

(2015) GREEN CHEMISTRY. 17(5). p.2840-2845
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Abstract
The etherification of beta-citronellene with bioalcohols over zeolite beta was performed in a continuous flow liquid phase reactor. At 80 degrees C, the catalyst exhibits 50% beta-citronellene conversion with a high selectivity for the etherification reaction. High chemoselectivity (90%) at the beta-double bond of beta-citronellene was observed, while beta-citronellene isomers were formed as minor products. In order to rationalize the observed chemoselectivity, the relative stabilities of the protonated reaction intermediates were estimated using theoretical calculations. The zeolite beta catalyst exhibits high stability as well as low coke formation. Considering the industrial importance of terpene ethers as sophisticated solvents, fragrance or flavor additives, a novel and environmentally friendly synthesis is presented as an alternative to homogeneous catalysis using strong Bronsted or Lewis acids in solution.
Keywords
AUGMENTED-WAVE METHOD, INITIO MOLECULAR-DYNAMICS, TIRE PYROLYSIS OIL, LIMONENE ETHERS, HYDROALKOXYLATION, TRANSITION, CONVERSION, MTBE

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MLA
Radhakrishnan, S et al. “Selective Etherification of Beta-citronellene Catalyzed by Zeolite Beta.” GREEN CHEMISTRY 17.5 (2015): 2840–2845. Print.
APA
Radhakrishnan, S., Purino, M., Alexopoulos, K., Taulelle, F., Reyniers, M.-F., Marin, G., & Martens, J. (2015). Selective etherification of beta-citronellene catalyzed by zeolite beta. GREEN CHEMISTRY, 17(5), 2840–2845.
Chicago author-date
Radhakrishnan, S, Martin Purino, Konstantinos Alexopoulos, F Taulelle, Marie-Françoise Reyniers, Guy Marin, and JA Martens. 2015. “Selective Etherification of Beta-citronellene Catalyzed by Zeolite Beta.” Green Chemistry 17 (5): 2840–2845.
Chicago author-date (all authors)
Radhakrishnan, S, Martin Purino, Konstantinos Alexopoulos, F Taulelle, Marie-Françoise Reyniers, Guy Marin, and JA Martens. 2015. “Selective Etherification of Beta-citronellene Catalyzed by Zeolite Beta.” Green Chemistry 17 (5): 2840–2845.
Vancouver
1.
Radhakrishnan S, Purino M, Alexopoulos K, Taulelle F, Reyniers M-F, Marin G, et al. Selective etherification of beta-citronellene catalyzed by zeolite beta. GREEN CHEMISTRY. 2015;17(5):2840–5.
IEEE
[1]
S. Radhakrishnan et al., “Selective etherification of beta-citronellene catalyzed by zeolite beta,” GREEN CHEMISTRY, vol. 17, no. 5, pp. 2840–2845, 2015.
@article{6880617,
  abstract     = {The etherification of beta-citronellene with bioalcohols over zeolite beta was performed in a continuous flow liquid phase reactor. At 80 degrees C, the catalyst exhibits 50% beta-citronellene conversion with a high selectivity for the etherification reaction. High chemoselectivity (90%) at the beta-double bond of beta-citronellene was observed, while beta-citronellene isomers were formed as minor products. In order to rationalize the observed chemoselectivity, the relative stabilities of the protonated reaction intermediates were estimated using theoretical calculations. The zeolite beta catalyst exhibits high stability as well as low coke formation. Considering the industrial importance of terpene ethers as sophisticated solvents, fragrance or flavor additives, a novel and environmentally friendly synthesis is presented as an alternative to homogeneous catalysis using strong Bronsted or Lewis acids in solution.},
  author       = {Radhakrishnan, S and Purino, Martin and Alexopoulos, Konstantinos and Taulelle, F and Reyniers, Marie-Françoise and Marin, Guy and Martens, JA},
  issn         = {1463-9262},
  journal      = {GREEN CHEMISTRY},
  keywords     = {AUGMENTED-WAVE METHOD,INITIO MOLECULAR-DYNAMICS,TIRE PYROLYSIS OIL,LIMONENE ETHERS,HYDROALKOXYLATION,TRANSITION,CONVERSION,MTBE},
  language     = {eng},
  number       = {5},
  pages        = {2840--2845},
  title        = {Selective etherification of beta-citronellene catalyzed by zeolite beta},
  url          = {http://dx.doi.org/10.1039/C5GC00361J},
  volume       = {17},
  year         = {2015},
}

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