Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

Irina Simakova; Päivi Mäki-Arvela; Mark Martinez-Klimov; Joseph Muller; Zuzana Vajglova; Markus Peurla; Kari Eränen; Dmitry Yu Murzin

doi:10.1016/j.apcata.2022.118586

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

Irina Simakova
, Päivi Mäki-Arvela
, Mark Martinez-Klimov
, Joseph Muller
, Zuzana Vajglova
, Markus Peurla
, Kari Eränen
, Dmitry Yu Murzin^*

^*Tämän työn vastaava kirjoittaja

Teknillisen kemian ja reaktiotekniikan laboratorio

Tutkimustuotos: Lehtiartikkeli › Artikkeli › Tieteellinen › vertaisarvioitu

9 Sitaatiot (Scopus)

194 Lataukset (Pure)

Abstrakti

One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N₂ physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

Alkuperäiskieli	Englanti
Artikkeli	118586
Julkaisu	Applied Catalysis A: General
Vuosikerta	636
DOI - pysyväislinkit	https://doi.org/10.1016/j.apcata.2022.118586
Tila	Julkaistu - 24 maalisk. 2022
OKM-julkaisutyyppi	A1 Julkaistu artikkeli, soviteltu

Rahoitus

The authors are grateful to Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Electron microscopy samples were processed and analyzed in the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. IS 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 AAAA-A21-121011390055-8).

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10.1016/j.apcata.2022.118586Lisenssi: CC BY

1-s2.0-S0926860X22001090-mainLopullinen julkaistu versio, 4,62 MBLisenssi: CC BY

https://urn.fi/URN:NBN:fi-fe2023030329372

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@article{8d26ad4f47304a97a870a686b6f49c0d,

title = "Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst",

abstract = "One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt\% Ni supported on H-Beta-38-sepiolite composite catalyst at 60{\textendash}70 °C under 10{\textendash}29 bar hydrogen pressure. A relatively high menthols yield of 53\% and 49\% and stereoselectivity to menthol of 71{\textendash}76\% and 72{\textendash}74\% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.",

keywords = "Citral hydrogenation, Continuous reactor, Extrudates, Menthol synthesis, Ni/Beta catalyst",

author = "Irina Simakova and P{\"a}ivi M{\"a}ki-Arvela and Mark Martinez-Klimov and Joseph Muller and Zuzana Vajglova and Markus Peurla and Kari Er{\"a}nen and Murzin, \{Dmitry Yu\}",

note = "Funding Information: The authors are grateful to Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Funding Information: Electron microscopy samples were processed and analyzed in the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. Funding Information: IS 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 AAAA-A21-121011390055-8). Publisher Copyright: {\textcopyright} 2022 The Authors",

year = "2022",

month = mar,

day = "24",

doi = "10.1016/j.apcata.2022.118586",

language = "English",

volume = "636",

journal = "Applied Catalysis A: General",

issn = "0926-860X",

publisher = "Elsevier",

}

TY - JOUR

T1 - Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

AU - Simakova, Irina

AU - Mäki-Arvela, Päivi

AU - Martinez-Klimov, Mark

AU - Muller, Joseph

AU - Vajglova, Zuzana

AU - Peurla, Markus

AU - Eränen, Kari

AU - Murzin, Dmitry Yu

N1 - Funding Information: The authors are grateful to Academy of Finland for funding through the project: Synthesis of spatially controlled catalysts with superior performance. Funding Information: Electron microscopy samples were processed and analyzed in the Electron Microscopy Laboratory, Institute of Biomedicine, University of Turku, which receives financial support from Biocenter Finland. Funding Information: IS 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 AAAA-A21-121011390055-8). Publisher Copyright: © 2022 The Authors

PY - 2022/3/24

Y1 - 2022/3/24

N2 - One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

AB - One-pot continuous synthesis of menthols both from citronellal and citral was investigated over 5 wt% Ni supported on H-Beta-38-sepiolite composite catalyst at 60–70 °C under 10–29 bar hydrogen pressure. A relatively high menthols yield of 53% and 49% and stereoselectivity to menthol of 71–76% and 72–74% were obtained from citronellal and citral respectively at the contact time 4.2 min, 70 °C and 20 bar. Citral conversion noticeably decreased with time-on-stream under 10 and 15 bar of hydrogen pressure accompanied by accumulation of citronellal, the primary hydrogenation product of citral, practically not affecting selectivity to menthol. A substantial amount of defuctionalization products observed during citral conversion, especially at the beginning of the reaction (ca. 1 h), indicated that all intermediates could contribute to formation of menthanes. Ni/H-Beta-38-sepiolite composite material prepared by extrusion was characterized by TEM, SEM, XPS, XRD, ICP-OES, N2 physisorption and FTIR techniques to perceive the interrelation between the physico-chemical and catalytic properties.

KW - Citral hydrogenation

KW - Continuous reactor

KW - Extrudates

KW - Menthol synthesis

KW - Ni/Beta catalyst

UR - https://www.scopus.com/pages/publications/85127051491

U2 - 10.1016/j.apcata.2022.118586

DO - 10.1016/j.apcata.2022.118586

M3 - Article

AN - SCOPUS:85127051491

SN - 0926-860X

VL - 636

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

M1 - 118586

ER -

Continuous synthesis of menthol from citronellal and citral over Ni-beta-zeolite-sepiolite composite catalyst

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