Catalytic hydrogenation of levulinic acid in ionic liquid mixtures using hydrogen gas in high-pressure CO2

Haixin Guo; Shida Tomoka; Richard Lee Smith

doi:10.1016/j.supflu.2020.104891

Catalytic hydrogenation of levulinic acid in ionic liquid mixtures using hydrogen gas in high-pressure CO₂

Haixin Guo, Shida Tomoka, Richard Lee Smith

ENV - Frontier Science for Advanced Environment

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

6 Citations (Scopus)

Abstract

Hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in ionic liquid (IL) mixtures with hydrogen gas in high-pressure CO₂ was studied to demonstrate tuning of product selectivity. Ethyl- or butyl- imidazolium-based cation with Cl, acetate [OAc], diethylphosphate, bis(trifluoro-methanesulfonyl)imide or tetrafluoroborate anion IL mixtures were used as the reaction phase with Pd/C, Pd/Al₂O₃ or Ru/Al₂O₃ commercial catalysts. Experiments were performed with batch reactors using (1 to 5) MPa partial pressure H₂ at nominal pressures of 8 MPa at 110 °C. GVL selectivities as high as 88% at 50% conversion were obtained in [EMIM]Cl-[EMIM][OAc] using 3 MPa partial pressure H₂ in presence of CO₂ at 4 h reaction time. Specific interactions of LA with Cl anion IL and CO₂ with [OAc] anion IL are key to the reaction mechanism. Reaction systems containing Cl anion - [OAc] anion IL mixtures with H₂ gas and CO₂ have wide application to hydrogenation of biomass-related compounds.

Original language	English
Article number	104891
Journal	Journal of Supercritical Fluids
Volume	164
DOIs	https://doi.org/10.1016/j.supflu.2020.104891
Publication status	Published - 2020 Oct 1

Keywords

Biomass
Hydrogen solubility
Hydrogenation reaction
Mixed ionic liquids
Supercritical carbon dioxide

ASJC Scopus subject areas

Chemical Engineering(all)
Condensed Matter Physics
Physical and Theoretical Chemistry

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10.1016/j.supflu.2020.104891

Cite this

@article{fb3d3b5e351e416c964e798195b8c232,

title = "Catalytic hydrogenation of levulinic acid in ionic liquid mixtures using hydrogen gas in high-pressure CO2",

abstract = "Hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in ionic liquid (IL) mixtures with hydrogen gas in high-pressure CO2 was studied to demonstrate tuning of product selectivity. Ethyl- or butyl- imidazolium-based cation with Cl, acetate [OAc], diethylphosphate, bis(trifluoro-methanesulfonyl)imide or tetrafluoroborate anion IL mixtures were used as the reaction phase with Pd/C, Pd/Al2O3 or Ru/Al2O3 commercial catalysts. Experiments were performed with batch reactors using (1 to 5) MPa partial pressure H2 at nominal pressures of 8 MPa at 110 °C. GVL selectivities as high as 88% at 50% conversion were obtained in [EMIM]Cl-[EMIM][OAc] using 3 MPa partial pressure H2 in presence of CO2 at 4 h reaction time. Specific interactions of LA with Cl anion IL and CO2 with [OAc] anion IL are key to the reaction mechanism. Reaction systems containing Cl anion - [OAc] anion IL mixtures with H2 gas and CO2 have wide application to hydrogenation of biomass-related compounds.",

keywords = "Biomass, Hydrogen solubility, Hydrogenation reaction, Mixed ionic liquids, Supercritical carbon dioxide",

author = "Haixin Guo and Shida Tomoka and Smith, {Richard Lee}",

note = "Funding Information: The authors are grateful to the financial supports from the JSPS Grant in Grant-in-Aid for Early-Career Scientists (No. 19K15347, Japan ) and the project program of Tohoku university center for gender equality promotion. Publisher Copyright: {\textcopyright} 2020 Elsevier B.V. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = oct,

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doi = "10.1016/j.supflu.2020.104891",

language = "English",

volume = "164",

journal = "Journal of Supercritical Fluids",

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TY - JOUR

T1 - Catalytic hydrogenation of levulinic acid in ionic liquid mixtures using hydrogen gas in high-pressure CO2

AU - Guo, Haixin

AU - Tomoka, Shida

AU - Smith, Richard Lee

N1 - Funding Information: The authors are grateful to the financial supports from the JSPS Grant in Grant-in-Aid for Early-Career Scientists (No. 19K15347, Japan ) and the project program of Tohoku university center for gender equality promotion. Publisher Copyright: © 2020 Elsevier B.V. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/10/1

Y1 - 2020/10/1

N2 - Hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in ionic liquid (IL) mixtures with hydrogen gas in high-pressure CO2 was studied to demonstrate tuning of product selectivity. Ethyl- or butyl- imidazolium-based cation with Cl, acetate [OAc], diethylphosphate, bis(trifluoro-methanesulfonyl)imide or tetrafluoroborate anion IL mixtures were used as the reaction phase with Pd/C, Pd/Al2O3 or Ru/Al2O3 commercial catalysts. Experiments were performed with batch reactors using (1 to 5) MPa partial pressure H2 at nominal pressures of 8 MPa at 110 °C. GVL selectivities as high as 88% at 50% conversion were obtained in [EMIM]Cl-[EMIM][OAc] using 3 MPa partial pressure H2 in presence of CO2 at 4 h reaction time. Specific interactions of LA with Cl anion IL and CO2 with [OAc] anion IL are key to the reaction mechanism. Reaction systems containing Cl anion - [OAc] anion IL mixtures with H2 gas and CO2 have wide application to hydrogenation of biomass-related compounds.

AB - Hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in ionic liquid (IL) mixtures with hydrogen gas in high-pressure CO2 was studied to demonstrate tuning of product selectivity. Ethyl- or butyl- imidazolium-based cation with Cl, acetate [OAc], diethylphosphate, bis(trifluoro-methanesulfonyl)imide or tetrafluoroborate anion IL mixtures were used as the reaction phase with Pd/C, Pd/Al2O3 or Ru/Al2O3 commercial catalysts. Experiments were performed with batch reactors using (1 to 5) MPa partial pressure H2 at nominal pressures of 8 MPa at 110 °C. GVL selectivities as high as 88% at 50% conversion were obtained in [EMIM]Cl-[EMIM][OAc] using 3 MPa partial pressure H2 in presence of CO2 at 4 h reaction time. Specific interactions of LA with Cl anion IL and CO2 with [OAc] anion IL are key to the reaction mechanism. Reaction systems containing Cl anion - [OAc] anion IL mixtures with H2 gas and CO2 have wide application to hydrogenation of biomass-related compounds.

KW - Biomass

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KW - Hydrogenation reaction

KW - Mixed ionic liquids

KW - Supercritical carbon dioxide

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