Catalytic production of hydroxymethylfurfural from sucrose using 1-methyl-3-octylimidazolium chloride ionic liquid

被引:41
作者
Chun, Jae-An [1 ]
Lee, Jin-Woo [1 ]
Yi, Young-Byung [1 ]
Hong, Seong-Sig [2 ]
Chung, Chung-Han [1 ]
机构
[1] Dong A Univ, Dept Biotechnol, Pusan 604714, South Korea
[2] Natl Inst Hort & Herbal Sci, RDA, Suwon 441853, South Korea
关键词
Hydroxymethylfurfural; Ionic Liquid; Metal Chloride Catalyst; Sucrose Hydrolysis; FRUCTOSE; BIOMASS; HYDROLYSIS; TRANSFORMATION; TEMPERATURE; DEHYDRATION; CHEMICALS; FUELS;
D O I
10.1007/s11814-010-0167-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hydroxymethylfurfural (HMF) is an important chemical intermediate, but it has not been widely used because of low yields and high production costs. Sucrose is available at lower costs than other sugars and thus could be a biomass-derived abundant source for HMF production. In this study, a catalytic process for efficiently producing HMF from sucrose was scrutinized using 1-methyl-3-octylimidazolium chloride ([MOIM]Cl) as a reaction solvent, and HCl and metal chlorides (CrCl2 and Zncl(2)) as a catalyst. The rate of sucrose hydrolysis was relatively much faster in the reactions with HCl than without it. The hydrolysis of sucrose to fructose and glucose was affected by its reaction time. The mixed solvent of 50% [MOIM]Cl and 50% sucrose solution with HCl was more effective in HMF synthesis than single solvent alone. The addition of ZnCl2 and CrCl2 increased HMF yields by approximately 1.2-1.8-fold and its higher yield was found in the latter. The highest yield (82.0 +/- 3.9 wt%) in HMF production was achieved in the reaction mixture containing 5 g [MOIM]Cl and 5 mL of 20% sucrose solution with 0.5M HCl plus CrCl2 at 30 min reaction time. However, 0.3 M HCl was more effective for the HMF productivity than 0.5 M HCl.
引用
收藏
页码:930 / 935
页数:6
相关论文
共 25 条
[1]   Zinc chloride mediated degradation of cellulose at 200 °C and identification of the products [J].
Amarasekara, Ananda S. ;
Ebede, Chidinma C. .
BIORESOURCE TECHNOLOGY, 2009, 100 (21) :5301-5304
[2]   KINETIC-STUDIES OF THE REACTIONS OF KETOSES AND ALDOSES IN WATER AT HIGH-TEMPERATURE .1. MECHANISM OF FORMATION OF 5-(HYDROXYMETHYL)-2-FURALDEHYDE FROM D-FRUCTOSE AND SUCROSE [J].
ANTAL, MJ ;
MOK, WSL ;
RICHARDS, GN .
CARBOHYDRATE RESEARCH, 1990, 199 (01) :91-109
[3]   Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals [J].
Binder, Joseph B. ;
Raines, Ronald T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1979-1985
[4]   Chemical routes for the transformation of biomass into chemicals [J].
Corma, Avelino ;
Iborra, Sara ;
Velty, Alexandra .
CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502
[5]   IMIDAZOLE CATALYSIS OF SUCROSE HYDROLYSIS [J].
FARR, GW ;
HEITZ, JR .
JOURNAL OF DENTAL RESEARCH, 1974, 53 (03) :516-519
[6]  
Fort DA, 2007, GREEN CHEM, V9, P63, DOI 10.1039/B607614A
[7]   Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates [J].
Huber, GW ;
Chheda, JN ;
Barrett, CJ ;
Dumesic, JA .
SCIENCE, 2005, 308 (5727) :1446-1450
[8]   Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation [J].
Huddleston, JG ;
Visser, AE ;
Reichert, WM ;
Willauer, HD ;
Broker, GA ;
Rogers, RD .
GREEN CHEMISTRY, 2001, 3 (04) :156-164
[9]   Thermal stabilities of di-alkylimidazolium chloride ionic liquids [J].
Kamavaram, V. ;
Reddy, Ramana G. .
INTERNATIONAL JOURNAL OF THERMAL SCIENCES, 2008, 47 (06) :773-777
[10]   The hydrolysis of sucrose by hydrochloric acid in the presence of alkali and alkaline earth chlorides [J].
Kautz, CF ;
Robinson, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1928, 50 :1022-1030