Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder

Irina L. Simakova; Zuzana Vajglová; Päivi Mäki-Arvela; Kari Eränen; Leena Hupa; Markus Peurla; Ermei M. Mäkilä; Johan Wärnå; Dmitry Yu Murzin

doi:10.1021/acs.oprd.1c00435

Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder

Irina L. Simakova, Zuzana Vajglová, Päivi Mäki-Arvela, Kari Eränen, Leena Hupa, Markus Peurla, Ermei M. Mäkilä, Johan Wärnå, Dmitry Yu Murzin^*

^*Corresponding author for this work

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

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Abstract

One-pot continuous synthesis of menthols from citral was performed over 5 wt % Ni supported on a mesoporous aluminosilicate catalyst with sepiolite as a binder at 70 °C with a selectivity of 75% to menthols. Catalyst deactivation with time-on-stream resulted in a decrease of the conversion and selectivity to menthols at the expense of higher selectivity to isopulegols. Stereoselectivity to isopulegols and menthols only slightly changed with conversion and TOS. A kinetic model capable of describing experimental data for transformations of citral to menthol in a continuous mode was developed. It was based on a detailed reaction network and also comprised deactivation on both metal and acid sites. Numerical data fitting confirmed a good correspondence between the experimental data and calculations.

Original language	English
Pages (from-to)	387-403
Number of pages	17
Journal	Organic Process Research and Development
Volume	26
Issue number	2
DOIs	https://doi.org/10.1021/acs.oprd.1c00435
Publication status	Published - 18 Feb 2022
MoE publication type	A1 Journal article-refereed

Funding

The authors are grateful to the Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Electron microscopy samples were processed and analyzed at the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. I.L.S. is grateful for the support from the Ministry of Science and Higher Education of the Russian Federation, under the governmental order for Boreskov Institute of Catalysis (Project No. AAAA-A21-121011390055-8).

Keywords

citral
clay binder
menthol
shaped Ni catalyst
trickle-bed reactor

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10.1021/acs.oprd.1c00435Licence: CC BY

acs.oprd.1c00435Final published version, 13.2 MBLicence: CC BY

https://urn.fi/URN:NBN:fi-fe2023030329354

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Simakova, I. L., Vajglová, Z., Mäki-Arvela, P., Eränen, K., Hupa, L., Peurla, M., Mäkilä, E. M., Wärnå, J., & Murzin, D. Y. (2022). Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder. Organic Process Research and Development, 26(2), 387-403. https://doi.org/10.1021/acs.oprd.1c00435

@article{d7de264b07314d5d84ac002d42149c58,

title = "Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder",

abstract = "One-pot continuous synthesis of menthols from citral was performed over 5 wt \% Ni supported on a mesoporous aluminosilicate catalyst with sepiolite as a binder at 70 °C with a selectivity of 75\% to menthols. Catalyst deactivation with time-on-stream resulted in a decrease of the conversion and selectivity to menthols at the expense of higher selectivity to isopulegols. Stereoselectivity to isopulegols and menthols only slightly changed with conversion and TOS. A kinetic model capable of describing experimental data for transformations of citral to menthol in a continuous mode was developed. It was based on a detailed reaction network and also comprised deactivation on both metal and acid sites. Numerical data fitting confirmed a good correspondence between the experimental data and calculations.",

keywords = "citral, clay binder, menthol, shaped Ni catalyst, trickle-bed reactor",

author = "Simakova, \{Irina L.\} and Zuzana Vajglov{\'a} and P{\"a}ivi M{\"a}ki-Arvela and Kari Er{\"a}nen and Leena Hupa and Markus Peurla and M{\"a}kil{\"a}, \{Ermei M.\} and Johan W{\"a}rn{\aa} and Murzin, \{Dmitry Yu\}",

note = "Funding Information: The authors are grateful to the Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Electron microscopy samples were processed and analyzed at the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. I.L.S. is grateful for the support from the Ministry of Science and Higher Education of the Russian Federation, under the governmental order for Boreskov Institute of Catalysis (Project No. AAAA-A21-121011390055-8). Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society",

year = "2022",

month = feb,

day = "18",

doi = "10.1021/acs.oprd.1c00435",

language = "English",

volume = "26",

pages = "387--403",

journal = "Organic Process Research and Development",

issn = "1083-6160",

publisher = "American Chemical Society",

number = "2",

}

Simakova, IL, Vajglová, Z, Mäki-Arvela, P , Eränen, K , Hupa, L, Peurla, M, Mäkilä, EM, Wärnå, J & Murzin, DY 2022, 'Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder', Organic Process Research and Development, vol. 26, no. 2, pp. 387-403. https://doi.org/10.1021/acs.oprd.1c00435

Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder. / Simakova, Irina L.; Vajglová, Zuzana; Mäki-Arvela, Päivi et al.
In: Organic Process Research and Development, Vol. 26, No. 2, 18.02.2022, p. 387-403.

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

TY - JOUR

T1 - Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder

AU - Simakova, Irina L.

AU - Vajglová, Zuzana

AU - Mäki-Arvela, Päivi

AU - Eränen, Kari

AU - Hupa, Leena

AU - Peurla, Markus

AU - Mäkilä, Ermei M.

AU - Wärnå, Johan

AU - Murzin, Dmitry Yu

N1 - Funding Information: The authors are grateful to the Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Electron microscopy samples were processed and analyzed at the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. I.L.S. is grateful for the support from the Ministry of Science and Higher Education of the Russian Federation, under the governmental order for Boreskov Institute of Catalysis (Project No. AAAA-A21-121011390055-8). Publisher Copyright: © 2022 The Authors. Published by American Chemical Society

PY - 2022/2/18

Y1 - 2022/2/18

N2 - One-pot continuous synthesis of menthols from citral was performed over 5 wt % Ni supported on a mesoporous aluminosilicate catalyst with sepiolite as a binder at 70 °C with a selectivity of 75% to menthols. Catalyst deactivation with time-on-stream resulted in a decrease of the conversion and selectivity to menthols at the expense of higher selectivity to isopulegols. Stereoselectivity to isopulegols and menthols only slightly changed with conversion and TOS. A kinetic model capable of describing experimental data for transformations of citral to menthol in a continuous mode was developed. It was based on a detailed reaction network and also comprised deactivation on both metal and acid sites. Numerical data fitting confirmed a good correspondence between the experimental data and calculations.

AB - One-pot continuous synthesis of menthols from citral was performed over 5 wt % Ni supported on a mesoporous aluminosilicate catalyst with sepiolite as a binder at 70 °C with a selectivity of 75% to menthols. Catalyst deactivation with time-on-stream resulted in a decrease of the conversion and selectivity to menthols at the expense of higher selectivity to isopulegols. Stereoselectivity to isopulegols and menthols only slightly changed with conversion and TOS. A kinetic model capable of describing experimental data for transformations of citral to menthol in a continuous mode was developed. It was based on a detailed reaction network and also comprised deactivation on both metal and acid sites. Numerical data fitting confirmed a good correspondence between the experimental data and calculations.

KW - citral

KW - clay binder

KW - menthol

KW - shaped Ni catalyst

KW - trickle-bed reactor

UR - https://www.scopus.com/pages/publications/85124158242

U2 - 10.1021/acs.oprd.1c00435

DO - 10.1021/acs.oprd.1c00435

M3 - Article

AN - SCOPUS:85124158242

SN - 1083-6160

VL - 26

SP - 387

EP - 403

JO - Organic Process Research and Development

JF - Organic Process Research and Development

IS - 2

ER -

Citral-to-Menthol Transformations in a Continuous Reactor over Ni/Mesoporous Aluminosilicate Extrudates Containing a Sepiolite Clay Binder

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