A1 Refereed original research article in a scientific journal
Isomerization of verbenol oxide to a diol with paramenthane structure exhibiting anti-Parkinson activity
Authors: Alexandra Torozova, Päivi Mäki-Arvela, Narendra Kumar, Atte Aho, Annika Smeds, Markus Peurla, Rainer Sjöholm, Ivo Heinmaa, Konstantin P. Volcho, Nariman F. Salakhutdinov, Dmitry Yu. Murzin
Publication year: 2015
Journal: Reaction Kinetics, Mechanisms and Catalysis
Volume: 116
Issue: 2
First page : 299
Last page: 314
Number of pages: 16
ISSN: 1878-5190
DOI: https://doi.org/10.1007/s11144-015-0903-7
Abstract
Isomerization of verbenol oxide to (1R, 2R, 6S)-3-methyl-6-(prop-1-en-
2-yl)cyclohex-3-ene-1,2-diol, which exhibits anti-Parkinson activity, has been
investigated with large and medium pore zeolites, namely H-USY and H-ZSM-5
types of catalysts with different SiO2 to Al2O3 ratio in dimethylacetamide as a
solvent. The catalysts were characterized with nitrogen adsorption, 27Al MAS
NMR, pyridine desorption, XRD, SEM and TEM techniques. The main reaction
product was the target diol with the highest selectivity of 52 % achieved with
H-ZSM-5-23 (the last number corresponds to SiO2/Al2O3 ratio) at 49 % conversion
of verbenol oxide. The catalyst deactivation was, however, extensive with medium
pore zeolites, compared to large pore zeolites. The second highest selectivities to
diol with H-USY-80 and H-ZSM-5-80 were about 47–50 mol% at 100 and 78 % of
conversion, respectively, achieved at 140 C within 3 and 5 h. The other main
products were the corresponding cyclopentylhydroxyketone and oxetane. A reaction
mechanism was proposed.
Isomerization of verbenol oxide to (1R, 2R, 6S)-3-methyl-6-(prop-1-en-
2-yl)cyclohex-3-ene-1,2-diol, which exhibits anti-Parkinson activity, has been
investigated with large and medium pore zeolites, namely H-USY and H-ZSM-5
types of catalysts with different SiO2 to Al2O3 ratio in dimethylacetamide as a
solvent. The catalysts were characterized with nitrogen adsorption, 27Al MAS
NMR, pyridine desorption, XRD, SEM and TEM techniques. The main reaction
product was the target diol with the highest selectivity of 52 % achieved with
H-ZSM-5-23 (the last number corresponds to SiO2/Al2O3 ratio) at 49 % conversion
of verbenol oxide. The catalyst deactivation was, however, extensive with medium
pore zeolites, compared to large pore zeolites. The second highest selectivities to
diol with H-USY-80 and H-ZSM-5-80 were about 47–50 mol% at 100 and 78 % of
conversion, respectively, achieved at 140 C within 3 and 5 h. The other main
products were the corresponding cyclopentylhydroxyketone and oxetane. A reaction
mechanism was proposed.
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