5-羟甲基糠醛(5-HMF)被认为是可由生物质原料制备、最具价值和潜力替代石化工业中基础化学品的生物基化合物,可用来制备诸多高附加值的化学品。金属-有机框架化合物(MOFs)具有独特的孔结构和极高的催化性能,在生物质催化转化领域拥有潜在应用价值。介绍了5-HMF的性质、用途及MOFs的合成和应用,综述了生物质制备5-HMF的主要途径以及MOFs在制备5-HMF中的应用进展,并展望了未来的研究方向。
5-Hydroxymethylfurfural (5-HMF) is considered to be the most valuable and potential bio-based compound to replace the basic chemicals in the petrochemical industry.It can be prepared from biomass raw materials and serve as a precursor for various high-value-added chemicals.Metal organic framework compounds (MOFs) have potential applications in the field of biomass catalytic conversion due to their unique pore structure and high catalytic performance.The properties and uses of 5-HMF as well as the synthesis and application of MOFs were introduced.The main pathways of preparing 5-HMF from biomass and the application progress of MOFs in the preparation of 5-HMF were reviewed.The future research directions were also prospected.
[1] Cao F,Schwartz T J,Mcclelland D J,et al.Dehydration of cellulose to levoglucosenone using polar aprotic solvents[J].Energy & Environmental Science,2015,8(6):1808-1815.
[2] Dutta S,Wu K C W.Enzymatic breakdown of biomass:enzyme active sites,immobilization,and biofuel production[J].Green Chemistry,2014,16(11):4615-4626.
[3] Rosillo-Calle F.A review of biomass energy-shortcomings and concerns[J].Journal of Chemical Technology & Biotechnology,2016,91(7):1933-1945.
[4] Yang F,Zhang S,Cho D W,et al.Porous biochar composite assembled with ternary needle-like iron-manganese-sulphur hybrids for high-efficiency lead removal[J].Bioresource Technology,2019,272:415-420.
[5] Ahemd M J,Okoye P U,Hummadi E H,et al.High-perfor-mance porous biochar from the pyrolysis of natural and renewable seaweed (Gelidiella acerosa) and its application for the adsorption of methylene blue[J].Bioresource Technology,2019,278:159-164.
[6] Liu X,Shen F,Qi X.Adsorption recovery of phosphate from aqueous solution by CaO-biochar composites prepared from eggshell and rice straw[J].Science of the Total Environment,2019,666:694-702.
[7] Yang F,Zhang S,Sun Y,et al.Fabrication and characterization of hydrophilic corn stalk biochar-supported nanoscale zero-valent iron composites for efficient metal removal[J].Bioresource Technology,2018,265:490-497.
[8] Chen J,Li K,Chen L,et al.Conversion of fructose into 5-hydroxymethylfurfural catalyzed by recyclable sulfonic acid-functionalized metal-organic frameworks[J].Green Chemistry,2014,16(5):2490-2499.
[9] Yang X,Liang Y,Cheng Y,et al.Hydrodeoxygenation of vanillin over carbon nanotube-supported Ru catalysts assembled at the interfaces of emulsion droplets[J].Catalysis Communications,2014,47:28-31.
[10] 胡磊,吴真,许家兴,等.5-羟甲基糠醛选择性加氢制备2,5二甲基呋喃的研究进展[J].林产化学与工业,2015,35(3):133-138.
[11] 卢思,王琼,李浔,等.5-羟甲基糠醛制备及其应用进展[J].林产化学与工业,2019,39(1):13-22.
[12] 白继峰,卢虹竹,杨雨,等.过渡金属催化5-羟甲基糠醛合成2,5-呋喃二甲酸研究进展[J].生物质化学工程,2022,56(2):49-59.
[13] Agarwal B,Kailasam K,Sangwan R S,et al.Traversing the history of solid catalysts for heterogeneous synthesis of 5-hydroxymethylfurfural from carbohydrate sugars:a review[J].Renewable and Sustainable Energy Reviews,2018,82:2408-2425.
[14] Chheda J N,Román-Leshkov Y D,James A.Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono-and poly-saccharides[J].Green Chemistry,2007,9(4):342-350.
[15] Hu L,Lin L,Wu Z,et al.Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals[J].Renewable and Sustainable Energy Reviews,2017,74:230-257.
[16] De S,Saha B,Luque R.Hydrodeoxygenation processes:advances on catalytic transformations of biomass-derived platform chemicals into hydrocarbon fuels[J].Bioresource Technology,2015,178:108-118.
[17] 姜楠,齐崴,黄仁亮,等.生物质制备5-羟甲基糠醛的研究进展[J].化工进展,2011,30(9):1937-1945.
[18] Zhou L,He Y,Ma Z,et al.One-step degradation of cellulose to 5-hydroxymethylfurfural in ionic liquid under mild conditions[J].Carbohydrate Polymers,2015,117:694-700.
[19] Deng W,Zhang Q,Wang Y.Catalytic transformations of cellulose and its derived carbohydrates into 5-hydroxymethylfurfural,levulinic acid,and lactic acid[J].Science China Chemistry,2014,58(1):29-46.
[20] 陈茹茹,王雪,吕兴梅,等.离子液体在生物质转化中的应用与研究进展[J].轻工学报,2019,34(3):1-20.
[21] Bhanja P,Bhaumik A.Porous nanomaterials as green catalyst for the conversion of biomass to bioenergy[J].Fuel,2016,185:432-441.
[22] He R,Huang X,Zhao P,et al.The synthesis of 5-hydroxymethylfurfural from glucose in biphasic system by phosphotungstic acidified titanium-zirconium dioxide[J].Waste and Biomass Valorization,2017,9(4):657-668.
[23] Xu H,Miao Z,Zhao H,et al.Dehydration of fructose into 5-hydroxymethylfurfural by high stable ordered mesoporous zirconium phosphate[J].Fuel,2015,145:234-240.
[24] Chen J D,Kuster B F M,Wlele K V D.Reparation of 5-hydroxymethylfurfural via fructose acetonides in ethylene glycol dimethyl ether[J].Biomass and Bioenergy,1991,1:217-233.
[25] 杨凤丽,梁国斌,顾宇阳.H2SO4改性凹凸棒土在葡萄糖脱水制备5-羟甲基糠醛过程中的催化性能研究[J].轻工学报,2019,34(1):64-70.
[26] Zhang Y,Degirmenci V,Li C,et al.Phosphotungstic acid encapsulated in metal-organic framework as catalysts for carbohydrate dehydration to 5-hydroxymethylfurfural[J].ChemSusChem,2011,4(1):59-64.
[27] Hu Z,Peng Y,Gao Y,et al.Direct synthesis of hierarchically porous metal-organic frameworks with high stability and strong brønsted acidity:the decisive role of hafnium in efficient and selective fructose dehydration[J].Chemistry of Materials,2016,28(8):2659-2667.
[28] Nguyen C V,Liao Y T,Kang T C,et al.A metal-free,high nitrogen-doped nanoporous graphitic carbon catalyst for an effective aerobic HMF-to-FDCA conversion[J].Green Chemistry,2016,18(22):5957-5961.
[29] Burnett D L,Oozeerally R,Pertiwi R,et al.A hydrothermally stable ytterbium metal-organic framework as a bifunctional solid-acid catalyst for glucose conversion[J].Chemical Communications,2019,55(76):11446-11449.
[30] 潘学林.关于含稀土金属-有机骨架材料的合成及性能分析[J].当代化工研究,2022(4):45-47.
[31] 王茀学,王崇臣,王鹏,等.Uio系列金属-有机骨架的合成方法与应用[J].无机化学学报,2017,33(5):713-737.
[32] Stock N,Biswas S.Synthesis of metal-organic frameworks (MOFs):routes to various MOF topologies,morphologies,and composites[J].Chemical Reviews,2012,12(2):933-969.
[33] Hupp J T,Poeppelmeier K R.Better living through nanopore chemistry[J].Science,2005,309(5743):2008-2009.
[34] Luan Y,Zheng N,Qi Y,et al.Development of a SO3H-functionalized UiO-66 metal-organic framework by postsynthetic modification and studies of its catalytic activities[J].European Journal of Inorganic Chemistry,2014,2014(26):4268-4272.
[35] Loiseau T,Serre C,Huguenand C,et al.A rationale for the large breathing of the porous aluminum terephthalate (MIL-53) upon hydration[J].Chemistry,2004,10(6):1373-1382.
[36] Al-Janabi N,Hill P,Torrente-murciano L,et al.Mapping the Cu-BTC metal-organic framework (HKUST-1) stability envelope in the presence of water vapour for CO2 adsorption from flue gases[J].Chemical Engineering Journal,2015,281:669-677.
[37] Al-Janabi N,Deng H,Borges J,et al.A facile post-synthetic modification method to improve hydrothermal stability and CO2 selectivity of CuBTC metal-organic framework[J].Industrial & Engineering Chemistry Research,2016,55(29):7941-7949.
[38] Güner M,Yilmaz E,Yüceer Y.Off-odor removal from fish oil by adsorbent treatment with selected metal-organic frameworks[J].Flavour and Fragrance Journal,2019,34(3):163-174.
[39] 刘晓芳,张衡,杨凯丽,等.金属有机框架材料的特性、制备方法及应用研究进展[J].贵州大学学报(自然科学版),2015,32(4):15-19.
[40] Fu Z,Xu G.Crystalline,highly oriented MOF thin film:the fabrication and application[J].Chemical Record,2017,17(5):518-534.
[41] Ma B,Guo H,Wang M,et al.Electrocatalysis of Cu-MOF/graphene composite and its sensing application for electrochemical simultaneous determination of dopamine and paracetamol[J].Electroanalysis,2019,31(6):1002-1008.
[42] Mortazavi S S,Abbasi A,Masteri-farahani M,et al.Sulfonic acid functionalized MIL-101(Cr) metal-organic framework for catalytic production of acetals[J].ChemistrySelect,2019,4(25):7495-7501.
[43] Silva P,Vilela S M,Tome J P,et al.Multifunctional metal-organic frameworks:from academia to industrial applications[J].Chemical Society Reviews,2015,44(19):6774-6803.
[44] Feng D,Gu Z Y,Li J R,et al.Zirconium-metalloporphyrin PCN-222:mesoporous metal-organic frameworks with ultrahigh stability as biomimetic catalysts[J].Angewandte Chemie International Edition,2012,51(41):10307-10310.
[45] Johnson J A,Luo J,Zhang X,et al.Porphyrin-metalation-mediated tuning of photoredox catalytic properties in metal-organic frameworks[J].ACS Catalysis,2015,5(9):5283-5291.
[46] Su Y,Chang G,Zhang Z,et al.Catalytic dehydration of glucose to 5-hydroxymethylfurfural with a bifunctional metal-organic framework[J].AIChE Journal,2016,62(12):4403-4417.
[47] Oozeerally R,Burnett D L,Chamberlain T W,et al.Exceptionally efficient and recyclable heterogeneous metal-organic framework catalyst for glucose isomerization in water[J].ChemCatChem,2018,10(4):706-709.
[48] Zhang Y,Guan W,Song H,et al.Coupled acid and base UiO-66-type MOFs supported on g-C3N4 as a bi-functional catalyst for one-pot production of 5-HMF from glucose[J].Microporous and Mesoporous Materials,2020,305:110328.
[49] Zhang Y,Li B,Wei Y,et al.Direct synthesis of metal-organic frameworks catalysts with tunable acid-base strength for glucose dehydration to 5-hydroxymethylfurfural[J].Journal of the Taiwan Institute of Chemical Engineers,2019,96:93-103.
[50] Riezzati N,Krisnandi Y K,Zulys A.Metal organic frameworks of lanthanum and iron using BDC linker as catalysts for glucose conversion into 5-hydroxymethylfurfural (5-HMF)[J].IOP Conference Series:Materials Science and Engineering,2020,902(1):12044.
[51] Pertiwi R,Oozeerally R,Burnett D L,et al.Replacement of chromium by non-toxic metals in Lewis-acid MOFs:assessment of stability as glucose conversion catalysts[J].Catalysts,2019,9(5):437.
基金资助
辽宁省“兴辽英才计划”(XLYC1907173);辽宁省教育厅科学研究经费项目(LJKMZ20221835,LQ2019003);国家环境保护近岸海域生态环境重点实验室开放课题(202103)
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