Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural

Jihye Ryu; Jae Wook Choi; Dong Jin Suh; Dong June Ahn; Young Woong Suh

doi:10.1016/j.catcom.2012.03.005

Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural

Jihye Ryu, Jae Wook Choi, Dong Jin Suh, Dong June Ahn, Young Woong Suh

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

33 Citations (Scopus)

Abstract

In the fructose dehydration to 5-hydroxymethylfurfural (HMF) in dimethyl sulfoxide, the catalytic function of 1,3-dialkylimidazolium-based ionic liquids with different counter-anions was investigated. It was found that the effects of alkyl chain length and additional alkyl group in Cl-containing ionic liquids were negligible whereas the activity of 1-butyl-3-methylimidazolium-based ionic liquids was considerably changed by varying the anion (particularly, halide ions). The latter finding was confirmed by the control experiment result that the addition of KBr or Ca(CH ₃COO) ₂ dramatically tuned the catalytic activity of 1-butyl-3-methylimidazolium chloride. From these results and the proposed reaction pathway, it was consequently believed that 1,3-dialkylimidazolium halide contained the dual catalytic function to act as both Brönsted acid and nucleophile for the fructose dehydration to HMF.

Original language	English
Pages (from-to)	11-15
Number of pages	5
Journal	Catalysis Communications
Volume	24
DOIs	https://doi.org/10.1016/j.catcom.2012.03.005
Publication status	Published - 2012 Jul 5

Bibliographical note

Funding Information:
The financial support by the Korea Ministry of Knowledge Economy (Project No. KC000622 ) is greatly appreciated. This work is also the outcome of a Manpower Development Program for Energy & Resources supported by the Ministry of Knowledge and Economy (MKE).

Keywords

Alkylimidazolium-based ionic liquid
Dehydration
Fructose
HMF
Halide

ASJC Scopus subject areas

Catalysis
General Chemistry
Process Chemistry and Technology

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10.1016/j.catcom.2012.03.005

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title = "Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural",

abstract = "In the fructose dehydration to 5-hydroxymethylfurfural (HMF) in dimethyl sulfoxide, the catalytic function of 1,3-dialkylimidazolium-based ionic liquids with different counter-anions was investigated. It was found that the effects of alkyl chain length and additional alkyl group in Cl-containing ionic liquids were negligible whereas the activity of 1-butyl-3-methylimidazolium-based ionic liquids was considerably changed by varying the anion (particularly, halide ions). The latter finding was confirmed by the control experiment result that the addition of KBr or Ca(CH 3COO) 2 dramatically tuned the catalytic activity of 1-butyl-3-methylimidazolium chloride. From these results and the proposed reaction pathway, it was consequently believed that 1,3-dialkylimidazolium halide contained the dual catalytic function to act as both Br{\"o}nsted acid and nucleophile for the fructose dehydration to HMF.",

keywords = "Alkylimidazolium-based ionic liquid, Dehydration, Fructose, HMF, Halide",

author = "Jihye Ryu and Choi, {Jae Wook} and Suh, {Dong Jin} and Ahn, {Dong June} and Suh, {Young Woong}",

note = "Funding Information: The financial support by the Korea Ministry of Knowledge Economy (Project No. KC000622 ) is greatly appreciated. This work is also the outcome of a Manpower Development Program for Energy & Resources supported by the Ministry of Knowledge and Economy (MKE).",

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doi = "10.1016/j.catcom.2012.03.005",

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AU - Ryu, Jihye

AU - Choi, Jae Wook

AU - Suh, Dong Jin

AU - Ahn, Dong June

AU - Suh, Young Woong

N1 - Funding Information: The financial support by the Korea Ministry of Knowledge Economy (Project No. KC000622 ) is greatly appreciated. This work is also the outcome of a Manpower Development Program for Energy & Resources supported by the Ministry of Knowledge and Economy (MKE).

PY - 2012/7/5

Y1 - 2012/7/5

N2 - In the fructose dehydration to 5-hydroxymethylfurfural (HMF) in dimethyl sulfoxide, the catalytic function of 1,3-dialkylimidazolium-based ionic liquids with different counter-anions was investigated. It was found that the effects of alkyl chain length and additional alkyl group in Cl-containing ionic liquids were negligible whereas the activity of 1-butyl-3-methylimidazolium-based ionic liquids was considerably changed by varying the anion (particularly, halide ions). The latter finding was confirmed by the control experiment result that the addition of KBr or Ca(CH 3COO) 2 dramatically tuned the catalytic activity of 1-butyl-3-methylimidazolium chloride. From these results and the proposed reaction pathway, it was consequently believed that 1,3-dialkylimidazolium halide contained the dual catalytic function to act as both Brönsted acid and nucleophile for the fructose dehydration to HMF.

AB - In the fructose dehydration to 5-hydroxymethylfurfural (HMF) in dimethyl sulfoxide, the catalytic function of 1,3-dialkylimidazolium-based ionic liquids with different counter-anions was investigated. It was found that the effects of alkyl chain length and additional alkyl group in Cl-containing ionic liquids were negligible whereas the activity of 1-butyl-3-methylimidazolium-based ionic liquids was considerably changed by varying the anion (particularly, halide ions). The latter finding was confirmed by the control experiment result that the addition of KBr or Ca(CH 3COO) 2 dramatically tuned the catalytic activity of 1-butyl-3-methylimidazolium chloride. From these results and the proposed reaction pathway, it was consequently believed that 1,3-dialkylimidazolium halide contained the dual catalytic function to act as both Brönsted acid and nucleophile for the fructose dehydration to HMF.

KW - Alkylimidazolium-based ionic liquid

KW - Dehydration

KW - Fructose

KW - HMF

KW - Halide

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M3 - Article

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ER -

Dual catalytic function of 1,3-dialkylimidzolium halide ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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