Catalytic conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural and levulinic and formic acids in gamma-valerolactone as a green solvent

Chemistry

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https://doi.org/10.1021/cs401160y
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Keywords

carbohydrates, 5-(hydroxymethyl)furfural, levulinic acid, formic acid, gamma-valerolactone, sulfuric acid, isotopic labeling, HETEROGENEOUS CATALYSTS, TRANSPORTATION FUELS, BIOMASS, CELLULOSE, DEHYDRATION, LIQUID, HYDROGENATION, DECOMPOSITION, CHEMICALS, EFFICIENT

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Catalytic conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural and levulinic and formic acids in gamma-valerolactone as a green solvent. / Qi, Long; Mui, Yiu Fung; Lo, See Wing et al.
In: ACS Catalysis, Vol. 4, No. 5, 05.2014, p. 1470-1477.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Bibtex

@article{ac14012e410248d489ae47e9a7284550,

title = "Catalytic conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural and levulinic and formic acids in gamma-valerolactone as a green solvent",

abstract = "The conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural (HMF) and levulinic acid (LA)/formic acid (FA) was investigated in detail using sulfuric acid as the catalyst and gamma-valerolactone (GVL) as a green solvent. The H2SO4/GVL/H2O system can be tuned to produce either HMF or LA/FA by changing the acid concentration and thus allowing selective switching between the products. Although the best yields of HMF were around 75%, the LA/FA yields ranged from 50% to 70%, depending on the structure of the carbohydrates and the reaction parameters, including temperature, acid, and carbohydrate concentrations. While the conversion of fructose is much faster than glucose, sucrose behaves like a 1:1 mixture of fructose and glucose, indicating facile hydrolysis of the glycosidic bond in sucrose. The mechanism of the conversion of glucose to HMF or LA/FA in GVL involves three intermediates: 1,6-anhydro-beta-D-glucofuranose, 1,6-anhydro-beta-D-glucopyranose, and levoglucosenone.",

keywords = "carbohydrates, 5-(hydroxymethyl)furfural, levulinic acid, formic acid, gamma-valerolactone, sulfuric acid, isotopic labeling, HETEROGENEOUS CATALYSTS, TRANSPORTATION FUELS, BIOMASS, CELLULOSE, DEHYDRATION, LIQUID, HYDROGENATION, DECOMPOSITION, CHEMICALS, EFFICIENT",

author = "Long Qi and Mui, {Yiu Fung} and Lo, {See Wing} and Lui, {Matthew Y.} and Akien, {Geoffrey R.} and Horvath, {Istvan T.}",

year = "2014",

month = may,

doi = "10.1021/cs401160y",

language = "English",

volume = "4",

pages = "1470--1477",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "5",

}

RIS

TY - JOUR

T1 - Catalytic conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural and levulinic and formic acids in gamma-valerolactone as a green solvent

AU - Qi, Long

AU - Mui, Yiu Fung

AU - Lo, See Wing

AU - Lui, Matthew Y.

AU - Akien, Geoffrey R.

AU - Horvath, Istvan T.

PY - 2014/5

Y1 - 2014/5

N2 - The conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural (HMF) and levulinic acid (LA)/formic acid (FA) was investigated in detail using sulfuric acid as the catalyst and gamma-valerolactone (GVL) as a green solvent. The H2SO4/GVL/H2O system can be tuned to produce either HMF or LA/FA by changing the acid concentration and thus allowing selective switching between the products. Although the best yields of HMF were around 75%, the LA/FA yields ranged from 50% to 70%, depending on the structure of the carbohydrates and the reaction parameters, including temperature, acid, and carbohydrate concentrations. While the conversion of fructose is much faster than glucose, sucrose behaves like a 1:1 mixture of fructose and glucose, indicating facile hydrolysis of the glycosidic bond in sucrose. The mechanism of the conversion of glucose to HMF or LA/FA in GVL involves three intermediates: 1,6-anhydro-beta-D-glucofuranose, 1,6-anhydro-beta-D-glucopyranose, and levoglucosenone.

AB - The conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural (HMF) and levulinic acid (LA)/formic acid (FA) was investigated in detail using sulfuric acid as the catalyst and gamma-valerolactone (GVL) as a green solvent. The H2SO4/GVL/H2O system can be tuned to produce either HMF or LA/FA by changing the acid concentration and thus allowing selective switching between the products. Although the best yields of HMF were around 75%, the LA/FA yields ranged from 50% to 70%, depending on the structure of the carbohydrates and the reaction parameters, including temperature, acid, and carbohydrate concentrations. While the conversion of fructose is much faster than glucose, sucrose behaves like a 1:1 mixture of fructose and glucose, indicating facile hydrolysis of the glycosidic bond in sucrose. The mechanism of the conversion of glucose to HMF or LA/FA in GVL involves three intermediates: 1,6-anhydro-beta-D-glucofuranose, 1,6-anhydro-beta-D-glucopyranose, and levoglucosenone.

KW - carbohydrates

KW - 5-(hydroxymethyl)furfural

KW - levulinic acid

KW - formic acid

KW - gamma-valerolactone

KW - sulfuric acid

KW - isotopic labeling

KW - HETEROGENEOUS CATALYSTS

KW - TRANSPORTATION FUELS

KW - BIOMASS

KW - CELLULOSE

KW - DEHYDRATION

KW - LIQUID

KW - HYDROGENATION

KW - DECOMPOSITION

KW - CHEMICALS

KW - EFFICIENT

U2 - 10.1021/cs401160y

DO - 10.1021/cs401160y

M3 - Journal article

VL - 4

SP - 1470

EP - 1477

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 5

ER -

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