Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural

Haixin Guo; Alif Duereh; Yuya Hiraga; Taku M. Aida; Xinhua Qi; Richard Lee Smith

doi:10.1016/j.cej.2017.04.111

Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural

Haixin Guo, Alif Duereh, Yuya Hiraga, Taku M. Aida, Xinhua Qi, Richard Lee Smith

ENG - Research Center of Supercritical Fluid Terchnolody

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

42 Citations (Scopus)

Abstract

Hydrogen sulfate ionic liquid as co-solvent and homogeneous catalyst can promote efficient conversion of carbohydrates into 5-ethoxymethylfurfural (5-EMF). Yields of 5-EMF were as high as 77% and 43% from inulin and sucrose, respectively, in the mixed solvent system of ethanol-[BMIM][HSO₄] for 30 min reaction time at 130 °C. The ionic liquid could be perfectly recycled with a single pretreatment of activated carbon for 24 h. Based on the characterization with ¹H NMR and ATR-FTIR, the mechanism for the hydrogen sulfate ionic liquid promoted conversion of inulin into 5-EMF through stabilization of 5-hydroxymethylfurfural (5-HMF) with the C-2 hydrogen of the ionic liquid. Hydrogen sulfate ionic liquid as additive allows efficient conversion of carbohydrates into biofuels and as homogeneous catalysts, they can be easily reactivated and recycled with activated carbon treatment.

Original language	English
Pages (from-to)	287-294
Number of pages	8
Journal	Chemical Engineering Journal
Volume	323
DOIs	https://doi.org/10.1016/j.cej.2017.04.111
Publication status	Published - 2017

Keywords

Biofuel
Biomass inulin
Reaction mechanism
Reactivation
Reuse of homogeneous catalyst

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10.1016/j.cej.2017.04.111

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title = "Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural",

abstract = "Hydrogen sulfate ionic liquid as co-solvent and homogeneous catalyst can promote efficient conversion of carbohydrates into 5-ethoxymethylfurfural (5-EMF). Yields of 5-EMF were as high as 77% and 43% from inulin and sucrose, respectively, in the mixed solvent system of ethanol-[BMIM][HSO4] for 30 min reaction time at 130 °C. The ionic liquid could be perfectly recycled with a single pretreatment of activated carbon for 24 h. Based on the characterization with 1H NMR and ATR-FTIR, the mechanism for the hydrogen sulfate ionic liquid promoted conversion of inulin into 5-EMF through stabilization of 5-hydroxymethylfurfural (5-HMF) with the C-2 hydrogen of the ionic liquid. Hydrogen sulfate ionic liquid as additive allows efficient conversion of carbohydrates into biofuels and as homogeneous catalysts, they can be easily reactivated and recycled with activated carbon treatment.",

keywords = "Biofuel, Biomass inulin, Reaction mechanism, Reactivation, Reuse of homogeneous catalyst",

author = "Haixin Guo and Alif Duereh and Yuya Hiraga and Aida, {Taku M.} and Xinhua Qi and Smith, {Richard Lee}",

note = "Funding Information: The authors gratefully acknowledgement the financial supports by JSPS Grant in Aid Scientific Research (B), contract No. 25289272 (Japan). Support from the Japanese government (MEXT) for a doctoral study scholarship (Haixin Guo) is gratefully acknowledged (Japan). Publisher Copyright: {\textcopyright} 2017 Elsevier B.V.",

year = "2017",

doi = "10.1016/j.cej.2017.04.111",

language = "English",

volume = "323",

pages = "287--294",

journal = "Chemical Engineering Journal",

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T1 - Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural

AU - Guo, Haixin

AU - Duereh, Alif

AU - Hiraga, Yuya

AU - Aida, Taku M.

AU - Qi, Xinhua

AU - Smith, Richard Lee

N1 - Funding Information: The authors gratefully acknowledgement the financial supports by JSPS Grant in Aid Scientific Research (B), contract No. 25289272 (Japan). Support from the Japanese government (MEXT) for a doctoral study scholarship (Haixin Guo) is gratefully acknowledged (Japan). Publisher Copyright: © 2017 Elsevier B.V.

PY - 2017

Y1 - 2017

N2 - Hydrogen sulfate ionic liquid as co-solvent and homogeneous catalyst can promote efficient conversion of carbohydrates into 5-ethoxymethylfurfural (5-EMF). Yields of 5-EMF were as high as 77% and 43% from inulin and sucrose, respectively, in the mixed solvent system of ethanol-[BMIM][HSO4] for 30 min reaction time at 130 °C. The ionic liquid could be perfectly recycled with a single pretreatment of activated carbon for 24 h. Based on the characterization with 1H NMR and ATR-FTIR, the mechanism for the hydrogen sulfate ionic liquid promoted conversion of inulin into 5-EMF through stabilization of 5-hydroxymethylfurfural (5-HMF) with the C-2 hydrogen of the ionic liquid. Hydrogen sulfate ionic liquid as additive allows efficient conversion of carbohydrates into biofuels and as homogeneous catalysts, they can be easily reactivated and recycled with activated carbon treatment.

AB - Hydrogen sulfate ionic liquid as co-solvent and homogeneous catalyst can promote efficient conversion of carbohydrates into 5-ethoxymethylfurfural (5-EMF). Yields of 5-EMF were as high as 77% and 43% from inulin and sucrose, respectively, in the mixed solvent system of ethanol-[BMIM][HSO4] for 30 min reaction time at 130 °C. The ionic liquid could be perfectly recycled with a single pretreatment of activated carbon for 24 h. Based on the characterization with 1H NMR and ATR-FTIR, the mechanism for the hydrogen sulfate ionic liquid promoted conversion of inulin into 5-EMF through stabilization of 5-hydroxymethylfurfural (5-HMF) with the C-2 hydrogen of the ionic liquid. Hydrogen sulfate ionic liquid as additive allows efficient conversion of carbohydrates into biofuels and as homogeneous catalysts, they can be easily reactivated and recycled with activated carbon treatment.

KW - Biofuel

KW - Biomass inulin

KW - Reaction mechanism

KW - Reactivation

KW - Reuse of homogeneous catalyst

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Perfect recycle and mechanistic role of hydrogen sulfate ionic liquids as additive in ethanol for efficient conversion of carbohydrates into 5-ethoxymethylfurfural

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