Preparation of 5-HMF from sucrose catalyzed in DMF-[BMIm]Cl mixed solvent

doi:10.16085/j.issn.1000-6613.2015.01.023

Chemical Industry and Engineering Progree ›› 2015, Vol. 34 ›› Issue (1): 133-137.DOI: 10.16085/j.issn.1000-6613.2015.01.023

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Preparation of 5-HMF from sucrose catalyzed in DMF-[BMIm]Cl mixed solvent

HAN Yingxin¹, YANG Zhonglian¹, CHEN Mingqiang¹, ZHANG Ye¹, LIU Shaomin²

1 School of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, Anhui, China;
2 School of Earth Science and Environmental Engineering, Anhui University of Science and Technology, Huainan 232001, Anhui, China

Received:2014-07-03 Revised:2014-08-25 Online:2015-01-05 Published:2015-01-05

蔗糖在DMF-[BMIm]Cl溶剂中催化制备5-HMF

韩迎新¹, 杨忠连¹, 陈明强¹, 张晔¹, 刘少敏²

1 安徽理工大学化学工程学院, 安徽淮南 232001;
2 安徽理工大学地球与环境学院, 安徽淮南 232001

通讯作者: 陈明强,教授,博士生导师,主要从事能源转化与生物质能利用领域的研究与教学工作。E-mail mqchen@aust.edu.cn。
作者简介:韩迎新(1992-),女,硕士研究生,主要从事生物质能源转化的研究。E-mail 415045948@qq.com。
基金资助:
国家自然科学基金(21376007)、国家科技支撑计划(2014BAD02B03)及安徽省高校自然科学基金(KJ2013Z074)项目。

Abstract

Abstract: A series of experiments were used to study the conversion of sucrose into 5-hydroxymethylfurfural(5-HMF) in DMF-ionic liquid ([BMIm]CI) mixed solvent. UV-vis spectrophotometer was used for the quantitative analysis and the yield of 5-HMF calculation. The catalytic efficiencies of the eight metal chlorides (CrCl₃·6H₂O, AlCl₃·6H₂O, SnCl₄·5H₂O, FeCl₃, CoCl₂·6H₂O, ZnCl₂, CuCl₂·2H₂O, CaCl₂) were studied. The results show that catalytic efficiency of AlCl₃·6H₂O is the highest. Different reaction conditions, such as time, temperature, quality ratio of DMF-[BMIm]Cl mixed solvent and catalyst dosage were investigated. The optimal condition for the highest 5-HMF yield, 63.4%, is determined as follows:0.5mmol sucrose as reactants, 0.4mmol AlCl₃·6H₂O as catalyst, reaction time 2h, reaction temperature 120℃ in 5g quality ratio of 85:15 DMF-[BMIm]Cl mixed solvent. Research indicates that DMF-[BMIm]Cl mixed solvent system has certain promoting effect to the conversion of sucrose into 5-HMF, as catalyst AlCl₃·6H₂O can get higher 5-HMF yield in the solvent system.

Key words: 5-hydroxymethylfurfural, biomass, N,N-dimethyl formamide, [BMIm]Cl, hydrolysis, catalysis

摘要： 研究了在N,N-二甲基甲酰胺(DMF)-离子液体[BMIm]Cl混合溶剂中将蔗糖高效转化为5-羟甲基糠醛(5-HMF)的反应。运用紫外-可见分光光度计对水解液中5-HMF进行定量分析并计算其收率。考察了CrCl₃·6H₂O、AlCl₃·6H₂O、SnCl₄·5H₂O、FeCl₃、CoCl₂·6H₂O、ZnCl₂、CuCl₂·2H₂O、CaCl₂ 8种催化剂对反应的催化效果,结果表明AlCl₃·6H₂O催化效果最为明显。以AlCl₃·6H₂O为催化剂研究了不同反应条件如时间、温度、溶剂中DMF-[BMIm]Cl质量比、催化剂AlCl₃·6H₂O的用量对5-HMF收率的影响,得到的最佳条件为以0.5mmol蔗糖为反应物,0.4mmol AlCl₃·6H₂O为催化剂,反应时间2h,反应温度120℃,5g质量比为85:15的DMF-[BMIm]Cl混合溶剂,此条件下5-HMF收率最高可达63.4%。研究表明,DMF-[BMIm]Cl混合溶剂体系对蔗糖转化为5-HMF有一定的促进效果,在此溶剂体系中以AlCl₃·6H₂O为催化剂时可以得到较高的5-HMF产率。

关键词: 5-羟甲基糠醛, 生物质, N,N-二甲基甲酰胺, [BMIm]Cl, 水解, 催化

CLC Number:

TK6
TQ281

HAN Yingxin, YANG Zhonglian, CHEN Mingqiang, ZHANG Ye, LIU Shaomin. Preparation of 5-HMF from sucrose catalyzed in DMF-[BMIm]Cl mixed solvent[J]. Chemical Industry and Engineering Progree, 2015, 34(1): 133-137.

韩迎新, 杨忠连, 陈明强, 张晔, 刘少敏. 蔗糖在DMF-[BMIm]Cl溶剂中催化制备5-HMF[J]. 化工进展, 2015, 34(1): 133-137.

References

[1] Berndes G,Hoogwijk M,van den Broek R. The contribution of biomass in the future global energy supply:A review of 17 studies[J]. Biomass and Bioenergy,2003,25(1):1-28.

[2] Rofiqul Islam M,Rabiul Islam M,Rafiqul Alam Beg M. Renewable energy resources and technologies practice in Bangladesh[J] . Renewable and Sustainable Energy Reviews,2008, 12(2) : 299-343.

[3] Xiao S,Liu B,Wang Y,et al. Efficient conversion of cellulose into biofuel precursor 5-hydroxymethylfurfural in dimethyl sulfoxide-ionic liquid mixtures[J]. Bioresource Technology,2014,151:361-366.

[4] Binder J B,Raines R T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals[J]. Journal of the American Chemical Society,2009,131(5):1979-1985.

[5] 王军,张春鹏,欧阳平凯. 5-羟甲基糠醛制备及应用的研究进展[J]. 化工进展,2008,27(5):702-707.

[6] Ogasawara Y, Itagaki S,Yamaguchi K,et al. Saccharification of natural lignocellulose biomass and polysaccharides by highly negatively charged heteropolyacids in concentrated aqueous solution[J]. Chem. Sus. Chem.,2011,4(4):519-525.

[7] Moreau C,Durand R,Aliès F,et al. Hydrolysis of sucrose in the presence of H-form zeolites[J]. Industrial Crops and Products,2000,11(2):237-242.

[8] Zhao H,Holladay J E,Brown H,et al. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfur-fural[J]. Science, 2007,316(5831):1597-1600.

[9] Hu S,Zhang Z,Song J,et al. Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl₄ in an ionic liquid[J]. Green Chemistry,2009,11(11):1746-1749.

[10] Román-Leshkov Y,Moliner M,Labinger J A,et al. Mechanism of glucose isomerization using a solid Lewis acid catalyst in water[J]. An-gewandte Chemie International Edition,2010,49(47):8954- 8957.

[11] Pagán-Torres Y J,Wang T,Gallo J M R,et al. Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Brønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent[J]. ACS Catalysis,2012,2(6):930-934.

[12] Lai L,Zhang Y. The effect of imidazolium ionic liquid on the dehydration of fructose to 5-hydroxymethylfurfural,and a room tempera-ture catalytic system[J]. Chem. Sus. Chem.,2010,3(11):1257-1259.

[13] 邓友全. 离子液体——性质,制备与应用[M]. 北京:中国石化出版社,2006.

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Preparation of 5-HMF from sucrose catalyzed in DMF-[BMIm]Cl mixed solvent

蔗糖在DMF-[BMIm]Cl溶剂中催化制备5-HMF

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