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^*

^*Korresponderande författare för detta arbete

Forskningsoutput: Tidskriftsbidrag › Artikel › Vetenskaplig › Peer review

11 Citeringar (Scopus)

104 Nedladdningar (Pure)

Sammanfattning

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.

Originalspråk	Engelska
Sidor (från-till)	387-403
Antal sidor	17
Tidskrift	Organic Process Research and Development
Volym	26
Nummer	2
DOI	https://doi.org/10.1021/acs.oprd.1c00435
Status	Publicerad - 18 feb. 2022
MoE-publikationstyp	A1 Tidskriftsartikel-refererad

Finansiering

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).

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10.1021/acs.oprd.1c00435Licens: CC BY

acs.oprd.1c00435Slutlig publicerad version, 13,2 MBLicens: 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, nr. 2, s. 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.
I: Organic Process Research and Development, Vol. 26, Nr. 2, 18.02.2022, s. 387-403.

Forskningsoutput: Tidskriftsbidrag › Artikel › Vetenskaplig › 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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