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Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity. / Torozova, Alexandra; Mäki-Arvela, Päivi; Kumar, Narendra et al.

In: Reaction Kinetics, Mechanisms and Catalysis, Vol. 116, No. 2, 24.07.2015.

Research output: Contribution to journal › Article › peer-review

Harvard

Torozova, A, Mäki-Arvela, P, Kumar, N, Aho, A, Smeds, A, Peurla, M, Sjöholm, R, Heinmaa, I, Volcho, KP, Salakhutdinov, NF & Murzin, DY 2015, 'Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity', Reaction Kinetics, Mechanisms and Catalysis, vol. 116, no. 2. https://doi.org/10.1007/s11144-015-0903-7

APA

Torozova, A., Mäki-Arvela, P., Kumar, N., Aho, A., Smeds, A., Peurla, M., Sjöholm, R., Heinmaa, I., Volcho, K. P., Salakhutdinov, N. F., & Murzin, D. Y. (2015). Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity. Reaction Kinetics, Mechanisms and Catalysis, 116(2). https://doi.org/10.1007/s11144-015-0903-7

Vancouver

Torozova A, Mäki-Arvela P, Kumar N, Aho A, Smeds A, Peurla M et al. Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity. Reaction Kinetics, Mechanisms and Catalysis. 2015 Jul 24;116(2). doi: 10.1007/s11144-015-0903-7

Author

Torozova, Alexandra ; Mäki-Arvela, Päivi ; Kumar, Narendra et al. / Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity. In: Reaction Kinetics, Mechanisms and Catalysis. 2015 ; Vol. 116, No. 2.

BibTeX

@article{f8d2a78248a84726aaf13db4d520e0a2,
title = "Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity",
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.",
keywords = "Cyclopentylhydroxyketone, Isomerization, Oxetane, Para-menthane, Verbenol oxide, Zeolite",
author = "Alexandra Torozova and P{\"a}ivi M{\"a}ki-Arvela and Narendra Kumar and Atte Aho and Annika Smeds and Markus Peurla and Rainer Sj{\"o}holm and Ivo Heinmaa and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.} and Murzin, {Dmitry Yu}",
year = "2015",
month = jul,
day = "24",
doi = "10.1007/s11144-015-0903-7",
language = "English",
volume = "116",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
issn = "1878-5190",
publisher = "Springer Netherlands",
number = "2",

}

RIS

TY - JOUR

T1 - Isomerization of verbenol oxide to a diol with para-menthane structure exhibiting anti-Parkinson activity

AU - Torozova, Alexandra

AU - Mäki-Arvela, Päivi

AU - Kumar, Narendra

AU - Aho, Atte

AU - Smeds, Annika

AU - Peurla, Markus

AU - Sjöholm, Rainer

AU - Heinmaa, Ivo

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

AU - Murzin, Dmitry Yu

PY - 2015/7/24

Y1 - 2015/7/24

N2 - 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.

AB - 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.

KW - Cyclopentylhydroxyketone

KW - Isomerization

KW - Oxetane

KW - Para-menthane

KW - Verbenol oxide

KW - Zeolite

UR - http://www.scopus.com/inward/record.url?scp=84937922962&partnerID=8YFLogxK

U2 - 10.1007/s11144-015-0903-7

DO - 10.1007/s11144-015-0903-7

M3 - Article

AN - SCOPUS:84937922962

VL - 116

JO - Reaction Kinetics, Mechanisms and Catalysis

JF - Reaction Kinetics, Mechanisms and Catalysis

SN - 1878-5190

IS - 2

ER -

ID: 9561159