Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)

Interna författare/redaktörer

Publikationens författare: 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
Publiceringsår: 2015
Tidskrift: Reaction Kinetics, Mechanisms and Catalysis
Tidskriftsakronym: Reac Kinet Mech Cat
Volym: 116
Nummer: 2
Artikelns första sida, sidnummer: 299
Artikelns sista sida, sidnummer: 314
eISSN: 1878-5204


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.

Senast uppdaterad 2020-08-08 vid 04:26