5-羟甲基糠醛制备及其应用研究进展
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摘要
5-羟甲基糠醛(HMF)被认为是最重要的生物质基平台分子之一,广泛应用于制备精细化学品、关键医药中间体、功能聚酯、溶剂和液体燃料等多功能化合物。目前,HMF的制备是生物质领域研究的热点,大量的研究使得制备HMF的原料和方法得到不断扩展。简单介绍了HMF的主要制备方法及其反应机理,系统综述了制备HMF的催化体系,包括催化过程中所使用的催化剂(无机酸、离子液体、金属氯化物、固体酸及其他催化剂)种类及制备HMF的溶剂体系。归纳了HMF重要衍生物的制备路径及应用,总结了目前研究中所存在的问题,并展望了未来的研究方向。
5-Hydroxymethylfurfural(HMF) is one of the most important biomass-based platform molecules and widely used in the preparation of multifunctional compounds such as fine chemicals, key pharmaceutical intermediates, functional polyesters, solvents and liquid fuels. At present, the preparation of HMF is a hot spot in the field of biomass research, and the raw materials and methods for preparing HMF have been continuously expanded. This paper reviews the main preparation methods and research progress of HMF. Catalysis systems for HMF preparation is systematically described, including the types of the catalysts(mineral acids, ionic liquids, metal chlorides, solid acids and others) used in the catalytic process and the solvent systems. Then, the preparation paths and applications of important derivatives from HMF are summarized. Finally, suggestions for future research on HMF are provided based on the understanding of problems existing in the current research.
5-Hydroxymethylfurfural(HMF) is one of the most important biomass-based platform molecules and widely used in the preparation of multifunctional compounds such as fine chemicals, key pharmaceutical intermediates, functional polyesters, solvents and liquid fuels. At present, the preparation of HMF is a hot spot in the field of biomass research, and the raw materials and methods for preparing HMF have been continuously expanded. This paper reviews the main preparation methods and research progress of HMF. Catalysis systems for HMF preparation is systematically described, including the types of the catalysts(mineral acids, ionic liquids, metal chlorides, solid acids and others) used in the catalytic process and the solvent systems. Then, the preparation paths and applications of important derivatives from HMF are summarized. Finally, suggestions for future research on HMF are provided based on the understanding of problems existing in the current research.
引文
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[7]AKIEN G R,QI L,HORVáTH I T. Molecular mapping of the acid catalysed dehydration of fructose[J]. Chemical Communications,2012,48(47):5850-5852.
[8]AMARASEKARA A,WILLIAMS L,EBEDE C. Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 ℃:An NMR study[J]. Carbohydrate Research,2008,343(18):3021-3024.
[9]ROMáN-LESHKOV Y,CHHEDA J N,DUMESIC J A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose[J]. Science,2006,312(5782):1933-1937.
[10]CHHEDA J N,ROMáN-LESHKOV Y,DUMESIC J A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides[J]. Green Chemistry,2007,9(4):342-350.
[11]HANSEN T S,WOODLEY J M,RIISAGER A. Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose[J]. Carbohydrate Research,2009,344(18):2568-2572.
[12]LI C Z,ZHAO Z K,WANG A Q,et al. Production of 5-hydroxymethylfurfural in ionic liquids under high fructose concentration conditions[J]. Carbohydrate Research,2010,345(13):1846-1850.
[13]ANTAL J M J,MOK W S L,RICHARDS G N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from D-fructose and sucrose[J]. Carbohydrate Research,1990,199(1):91-109.
[14]SUN Y H,LIU P T,LIU Z. Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural from the waste liquid of acid hydrolysis NCC[J]. Carbohydrate Polymers,2016,142:177-182.
[15]DUTTA S,PAL S. Promises in direct conversion of cellulose and lignocellulosic biomass to chemicals and fuels:Combined solvent-nanocatalysis approach for biorefinary[J]. Biomass & Bioenergy,2014,62(1):182-197.
[16]MOREAU C,FINIELS A,VANOYE L. Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst[J]. Journal of Molecular Catalysis A:Chemical,2006,253(1):165-169.
[17]BAO Q X,QIAO K,TOMIDA D,et al. Preparation of 5-hydroymethylfurfural by dehydration of fructose in the presence of acidic ionic liquid[J]. Catalysis Communications,2008,9(6):1383-1388.
[18]LI C Z,ZHAO Z B K,CAI H L,et al. Microwave-promoted conversion of concentrated fructose into 5-hydroxymethylfurfural in ionic liquids in the absence of catalysts[J]. Biomass & Bioenergy,2011,35(5):2013-2017.
[19]RAMLI N A S,AMIN N A S. Thermo-kinetic assessment of glucose decomposition to 5-hydroxymethyl furfural and levulinic acid over acidic functionalized ionic liquid[J]. Chemical Engineering Journal,2018,335:221-230.
[20]SERI K I,INOUE Y,ISHIDA H. Highly efficient catalytic activity of Lanthanide(III) ions for conversion of saccharides to 5-hydroxymethyl-2-furfural in organic solvents[J]. Chemistry Letters,2000,29(1):22-23.
[21]ZHAO H B,HOLLADAY J E,BROWN H,et al. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural[J]. Science,2007,316:1597-1600.
[22]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.
[23]LIMA S,NEVES P,ANTUNES M M,et al. Conversion of mono/di/polysaccharides into furan compounds using 1-alkyl-3-methylimidazolium ionic liquids[J]. Applied Catalysis A:General,2009,363(1/2):93-99.
[24]ILGEN F,OTT D,KRALISCH D,et al. Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures[J]. Green Chemistry,2009,11:1948-1954.
[25]RASRENDRA C B,MAKERTIHARTHA I G B N,ADISASMITO S,et al. Green chemicals from D-glucose:Systematic studies on catalytic effects of inorganic salts on the chemo-selectivity and yield in aqueous solutions[J]. Topics in Catalysis,2010,53(15/16/17/18):1241-1247.
[26]CAO Q,GUO X C,YAO S X,et al. Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst[J]. Carbohydrate Research,2011,346(7):956-959.
[27]田玉奎,邓晋,潘涛,等. 离子液体中Lewis酸催化葡萄糖和果糖脱水制5-羟甲基呋喃甲醛[J]. 催化学报,2011,32(6):997-1002. TIAN Y K,DENG J,PAN T,et al. Dehydration of glucose and fructose into 5-hydroxymethylfural catalyzed by lewis acid in ionic liquids[J]. Chinese Journal of Catalysis,2011,32(6):997-1002.
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