生物基平台分子2,5-呋喃二甲酸的制备研究进展
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摘要
2,5-呋喃二甲酸(FDCA)被认为是对苯二甲酸的潜在替代物,可以作为多种绿色聚合物的单体,受到广泛关注。采用5-羟甲基糠醛(HMF)选择氧化制备FDCA是目前较为有效的方法。综述了HMF选择氧化制备FDCA的研究进展,并着重分析了HMF选择氧化制备FDCA的多相催化体系(包括Ru、Pt、Au、Pd贵金属和非贵金属催化剂)。分析了不同催化体系的问题和难点,对其今后的研究方向提供了建议,制备高活性和高稳定性的催化剂是该研究的重点,同时合理评估有碱和无碱体系的经济性也是放大生产的关键。
2,5-furandicarboxylic(FDCA) is a potential substitute for petroleum-derived terephthalic acid, and has been considered as a good precursor for producing green polymers, which have got wide attention. Aerobic oxidation of HMF provides an efficient route to synthesis of FDCA. Research progress about preparations from 5-hydroxymethyl furfural(HMF) to 2,5-Furandicarboxylic acid(FDCA), is overviewed, and present researches mainly focus on preparing supported Ru, Pt, Au, Pd and non-noble catalysts. Problems and difficulties in the preparation process are analyzed to provide advices for the further research. It is recommended that future works should be focused on, but not limited to, the preparation of highly active and stable catalysts, and reasonable evaluation between basic and base-free system is also the key of industrialization.
2,5-furandicarboxylic(FDCA) is a potential substitute for petroleum-derived terephthalic acid, and has been considered as a good precursor for producing green polymers, which have got wide attention. Aerobic oxidation of HMF provides an efficient route to synthesis of FDCA. Research progress about preparations from 5-hydroxymethyl furfural(HMF) to 2,5-Furandicarboxylic acid(FDCA), is overviewed, and present researches mainly focus on preparing supported Ru, Pt, Au, Pd and non-noble catalysts. Problems and difficulties in the preparation process are analyzed to provide advices for the further research. It is recommended that future works should be focused on, but not limited to, the preparation of highly active and stable catalysts, and reasonable evaluation between basic and base-free system is also the key of industrialization.
引文
[1]Sajid M,Zhao X,Liu D.Production of 2,5-furandicarboxylic acid(FDCA)from 5-hydroxymethylfurfural(HMF):recent progress focusing on the chemical-catalytic routes[J].Green Chemistry,2018,20(24):5427-5453.
[2]Zhang Z,Huber G W.Catalytic oxidation of carbohydrates into organic acids and furan chemicals[J].Chemical Society Reviews,2018,47(4):1351-1390.
[3]Kucherov F A,Romashov L V,Galkin K I,et al.Chemical Transformations of Biomass-Derived C6-Furanic Platform Chemicals for Sustainable Energy Research,Materials Science,and Synthetic Building Blocks[J].ACSSustainable Chemistry&Engineering,2018,6(7):8064-8092.
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[6]Nie J,Xie J,Liu H.Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts[J].Journal of Catalysis,2013,301(5):83-91.
[7]Xie J,Nie J,Liu H.Aqueous-phase selective aerobic oxidation of5-hydroxymethylfurfural on Ru/C in the presence of base[J].Chinese Journal of Catalysis,2014,35(6):937-944.
[8]Zheng L,Zhao J,Du Z,et al.Efficient aerobic oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid on Ru/Ccatalysts[J].Science China Chemistry,2017,60(7):950-957.
[9]Yi G,Teong S P,Zhang Y.Base-free conversion of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Ru/C catalyst[J].Green Chemistry,2015,18(4):979-983.
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[11]Verdeguer P,Merat N,Gaset A.Oxydation catalytique du HMF en acide2,5-furane dicarboxylique[J].Journal of molecular catalysis,1993,85(3):327-344.
[12]Ait Rass H,Essayem N,Besson M.Selective aqueous phase oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts:influence of the base and effect of bismuth promotion[J].Green Chemistry,2013,15(8):2240-2251.
[13]Sahu R,Dhepe P L.Synthesis of 2,5-furandicarboxylic acid by the aerobic oxidation of 5-hydroxymethyl furfural over supported metal catalysts[J].Reaction Kinetics,Mechanisms and Catalysis,2014,112(1):173-187.
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[15]Miao Z,Wu T,Li J,et al.Aerobic oxidation of 5-hydroxymethylfurfural(HMF)effectively catalyzed by a Ce0.8Bi0.2O2-δsupported Pt catalyst at room temperature[J].RSC Advances,2015,5(26):19823-19829.
[16]Siankevich S,Savoglidis G,Fei Z,et al.A novel platinum nanocatalyst for the oxidation of 5-Hydroxymethylfurfural into 2,5-Furandicarboxylic acid under mild conditions[J].Journal of Catalysis,2014,315:67-74.
[17]Zhou C,Deng W,Wan X,et al.Functionalized Carbon Nanotubes for Biomass Conversion:The Base-Free Aerobic Oxidation of5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid over Platinum Supported on a Carbon Nanotube Catalyst[J].Chem Cat Chem,2015,7(18):2853-2863.
[18]Yu H,Kim K,Kang M J,et al.Carbon Support with Tunable Porosity Prepared by Carbonizing Chitosan for Catalytic Oxidation of5-Hydroxylmethylfurfural[J].ACS Sustainable Chemistry&Engineering,2019,7(4):3742-3748.
[19]Pan M,Brush A J,Pozun Z D,et al.Model Studies of Heterogeneous Catalytic Hydrogenation Reactions with Gold[J].Chemical Society Reviews,2013,42(12):5002-5013.
[20]Casanova O,Iborra S,Corma A.Biomass into Chemicals:Aerobic Oxidation of 5-Hydroxymethyl-2-furfural into 2,5-Furandicarboxylic Acid with Gold Nanoparticle Catalysts[J].ChemSusChem,2009,2(12):1138-1144.
[21]Miao Z,Zhang Y,Pan X,et al.Superior catalytic performance of Ce1-xBixO2-δsolid solution and Au/Ce1-xBixO2-δfor 5-hydroxymethylfurfural conversion in alkaline aqueous solution[J].Catalysis Science&Technology,2015,5(2):1314-1322.
[22]Cai J,Ma H,Zhang J,et al.Gold nanoclusters confined in a supercage of Y zeolite for aerobic oxidation of HMF under mild conditions[J].Chemistry-A European Journal,2013,19(42):14215.
[23]Rasul S.A Highly Selective Copper-Indium Bimetallic Electrocatalyst for the Electrochemical Reduction of Aqueous CO2 to CO[J].Angewandte Chemie International Edition,2014,127(7):2146-2150.
[24]Pasini T,Piccinini M,Blosi M,et al.Selective oxidation of5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles[J].Green Chemistry,2011,13(8):2091-2099.
[25]Villa A,Schiavoni M,Campisi S,et al.Pd-modified Au on Carbon as an Effective and Durable Catalyst for the Direct Oxidation of HMF to 2,5-Furandicarboxylic Acid[J].Chem Sus Chem,2013,6(4):609-612.
[26]Wan X,Zhou C,Chen J,et al.Base-Free Aerobic Oxidation of5-Hydroxymethyl-furfural to 2,5-Furandicarboxylic Acid in Water Catalyzed by Functionalized Carbon Nanotube-Supported Au-Pd Alloy Nanoparticles[J].Acs Catalysis,2014,4(7):2175-2185.
[27]Wang Q,Hou W,Li S,et al.Hydrophilic mesoporous poly(ionic liquid)-supported Au-Pd alloy nanoparticles towards aerobic oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions[J].Green Chemistry,2017,19(16):3820-3830.
[28]Gao Z,Xie R,Fan G,et al.Highly Efficient and Stable Bimetallic AuPd over La-Doped Ca-Mg-Al Layered Double Hydroxide for Base-Free Aerobic Oxidation of 5-Hydroxymethylfurfural in Water[J].ACS Sustainable Chemistry&Engineering,2017,5(7):5852-5861.
[29]Davis S E,Houk L R,Tamargo E C,et al.Oxidation of5-hydroxymethylfurfural over supported Pt,Pd and Au catalysts[J].Catalysis Today,2011,160(1):55-60.
[30]Siyo B,Schneider M,Pohl M M,et al.Synthesis,Characterization,and Application of PVP-Pd NP in the Aerobic Oxidation of5-Hydroxymethylfurfural(HMF)[J].Catalysis Letters,2014,144(3):498-506.
[31]Zhang Z,Zhen J,Liu B,et al.Selective aerobic oxidation of the biomass-derived precursor 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions over a magnetic palladium nanocatalyst[J].Green Chemistry,2015,17(2):1308-1317.
[32]Liu B,Ren Y,Zhang Z.Aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water under mild conditions[J].Green Chemistry,2015,17(3):1610-1617.
[33]Mei N,Liu B,Zheng J,et al.A novel magnetic palladium catalyst for the mild aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water[J].Catalysis Science&Technology,2015,5(6):3194-3202.
[34]Saha B,Gupta D,Abu-Omar M M,et al.Porphyrin-based porous organic polymer-supported iron(III)catalyst for efficient aerobic oxidation of5-hydroxymethyl-furfural into 2,5-furandicarboxylic acid[J].Journal of Catalysis,2013,299(2):316-320.
[35]Jain A,Jonnalagadda S C,Ramanujachary K V,et al.Selective oxidation of 5-hydroxymethyl-2-furfural to furan-2,5-dicarboxylic acid over spinel mixed metal oxide catalyst[J].Catalysis Communications,2015,58:179-182.
[36]Wang S,Zhang Z,Liu B.Catalytic conversion of fructose and5-hydroxymethylfurfural into 2,5-furandicarboxylic acid over a recyclable Fe3O4-CoOx magnetite nanocatalyst[J].Acs Sustainable Chemistry&Engineering,2015,3(3):406-412.
[37]Jebaraj A J J,Scherson D A.Microparticle Electrodes and Single Particle Microbatteries:Electrochemical and in Situ MicroRaman Spectroscopic Studies[J].Accounts of Chemical Research,2013,46(5):1192-1205.
[38]Zhang K,Han X,Hu Z,et al.Nanostructured Mn-based oxides for electrochemical energy storage and conversion[J].Chemical Society Reviews,2014,46(15):699-728.
[39]Hayashi E,Komanoya T,Kamata K,et al.Heterogeneously-catalyzed Aerobic Oxidation of 5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid with Manganese Dioxide[J].Chemsuschem,2017,10(4):654-658.
[40]Han X,Li C,Liu X,et al.Selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over MnOx-CeO2 composite catalysts[J].Green Chemistry,2017,19(4):996-1004.
[2]Zhang Z,Huber G W.Catalytic oxidation of carbohydrates into organic acids and furan chemicals[J].Chemical Society Reviews,2018,47(4):1351-1390.
[3]Kucherov F A,Romashov L V,Galkin K I,et al.Chemical Transformations of Biomass-Derived C6-Furanic Platform Chemicals for Sustainable Energy Research,Materials Science,and Synthetic Building Blocks[J].ACSSustainable Chemistry&Engineering,2018,6(7):8064-8092.
[4]Partenheimer W,Grushin V V.Synthesis of 2,5‐Diformylfuran and Furan‐2,5‐Dicarboxylic Acid by Catalytic Air‐Oxidation of5‐Hydroxymethylfurfural.Unexpectedly Selective Aerobic Oxidation of Benzyl Alcohol to Benzaldehyde with Metal=Bromide Catalysts[J].Advanced Synthesis&Catalysis,2001,343(1):102-111.
[5]Saha B,Dutta S,Abu-Omar M M.Aerobic oxidation of5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts[J].Catal Sci Technol,2012,2(1):79-81.
[6]Nie J,Xie J,Liu H.Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran on supported Ru catalysts[J].Journal of Catalysis,2013,301(5):83-91.
[7]Xie J,Nie J,Liu H.Aqueous-phase selective aerobic oxidation of5-hydroxymethylfurfural on Ru/C in the presence of base[J].Chinese Journal of Catalysis,2014,35(6):937-944.
[8]Zheng L,Zhao J,Du Z,et al.Efficient aerobic oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid on Ru/Ccatalysts[J].Science China Chemistry,2017,60(7):950-957.
[9]Yi G,Teong S P,Zhang Y.Base-free conversion of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Ru/C catalyst[J].Green Chemistry,2015,18(4):979-983.
[10]Mishra D K,Lee H J,Kim J,et al.MnCo2O4 Spinels Supported Ruthenium Catalyst for Air-Oxidation of HMF to FDCA under Aqueous Phase and Base-Free Conditions[J].Green Chemistry,2017.
[11]Verdeguer P,Merat N,Gaset A.Oxydation catalytique du HMF en acide2,5-furane dicarboxylique[J].Journal of molecular catalysis,1993,85(3):327-344.
[12]Ait Rass H,Essayem N,Besson M.Selective aqueous phase oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts:influence of the base and effect of bismuth promotion[J].Green Chemistry,2013,15(8):2240-2251.
[13]Sahu R,Dhepe P L.Synthesis of 2,5-furandicarboxylic acid by the aerobic oxidation of 5-hydroxymethyl furfural over supported metal catalysts[J].Reaction Kinetics,Mechanisms and Catalysis,2014,112(1):173-187.
[14]Hicham A R,Nadine E,Michèle B.Selective aerobic oxidation of 5-HMFinto 2,5-furandicarboxylic acid with Pt catalysts supported on Ti O2-and ZrO2-based supports[J].Chemsuschem,2015,8(7):1206-1217.
[15]Miao Z,Wu T,Li J,et al.Aerobic oxidation of 5-hydroxymethylfurfural(HMF)effectively catalyzed by a Ce0.8Bi0.2O2-δsupported Pt catalyst at room temperature[J].RSC Advances,2015,5(26):19823-19829.
[16]Siankevich S,Savoglidis G,Fei Z,et al.A novel platinum nanocatalyst for the oxidation of 5-Hydroxymethylfurfural into 2,5-Furandicarboxylic acid under mild conditions[J].Journal of Catalysis,2014,315:67-74.
[17]Zhou C,Deng W,Wan X,et al.Functionalized Carbon Nanotubes for Biomass Conversion:The Base-Free Aerobic Oxidation of5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid over Platinum Supported on a Carbon Nanotube Catalyst[J].Chem Cat Chem,2015,7(18):2853-2863.
[18]Yu H,Kim K,Kang M J,et al.Carbon Support with Tunable Porosity Prepared by Carbonizing Chitosan for Catalytic Oxidation of5-Hydroxylmethylfurfural[J].ACS Sustainable Chemistry&Engineering,2019,7(4):3742-3748.
[19]Pan M,Brush A J,Pozun Z D,et al.Model Studies of Heterogeneous Catalytic Hydrogenation Reactions with Gold[J].Chemical Society Reviews,2013,42(12):5002-5013.
[20]Casanova O,Iborra S,Corma A.Biomass into Chemicals:Aerobic Oxidation of 5-Hydroxymethyl-2-furfural into 2,5-Furandicarboxylic Acid with Gold Nanoparticle Catalysts[J].ChemSusChem,2009,2(12):1138-1144.
[21]Miao Z,Zhang Y,Pan X,et al.Superior catalytic performance of Ce1-xBixO2-δsolid solution and Au/Ce1-xBixO2-δfor 5-hydroxymethylfurfural conversion in alkaline aqueous solution[J].Catalysis Science&Technology,2015,5(2):1314-1322.
[22]Cai J,Ma H,Zhang J,et al.Gold nanoclusters confined in a supercage of Y zeolite for aerobic oxidation of HMF under mild conditions[J].Chemistry-A European Journal,2013,19(42):14215.
[23]Rasul S.A Highly Selective Copper-Indium Bimetallic Electrocatalyst for the Electrochemical Reduction of Aqueous CO2 to CO[J].Angewandte Chemie International Edition,2014,127(7):2146-2150.
[24]Pasini T,Piccinini M,Blosi M,et al.Selective oxidation of5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles[J].Green Chemistry,2011,13(8):2091-2099.
[25]Villa A,Schiavoni M,Campisi S,et al.Pd-modified Au on Carbon as an Effective and Durable Catalyst for the Direct Oxidation of HMF to 2,5-Furandicarboxylic Acid[J].Chem Sus Chem,2013,6(4):609-612.
[26]Wan X,Zhou C,Chen J,et al.Base-Free Aerobic Oxidation of5-Hydroxymethyl-furfural to 2,5-Furandicarboxylic Acid in Water Catalyzed by Functionalized Carbon Nanotube-Supported Au-Pd Alloy Nanoparticles[J].Acs Catalysis,2014,4(7):2175-2185.
[27]Wang Q,Hou W,Li S,et al.Hydrophilic mesoporous poly(ionic liquid)-supported Au-Pd alloy nanoparticles towards aerobic oxidation of5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions[J].Green Chemistry,2017,19(16):3820-3830.
[28]Gao Z,Xie R,Fan G,et al.Highly Efficient and Stable Bimetallic AuPd over La-Doped Ca-Mg-Al Layered Double Hydroxide for Base-Free Aerobic Oxidation of 5-Hydroxymethylfurfural in Water[J].ACS Sustainable Chemistry&Engineering,2017,5(7):5852-5861.
[29]Davis S E,Houk L R,Tamargo E C,et al.Oxidation of5-hydroxymethylfurfural over supported Pt,Pd and Au catalysts[J].Catalysis Today,2011,160(1):55-60.
[30]Siyo B,Schneider M,Pohl M M,et al.Synthesis,Characterization,and Application of PVP-Pd NP in the Aerobic Oxidation of5-Hydroxymethylfurfural(HMF)[J].Catalysis Letters,2014,144(3):498-506.
[31]Zhang Z,Zhen J,Liu B,et al.Selective aerobic oxidation of the biomass-derived precursor 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions over a magnetic palladium nanocatalyst[J].Green Chemistry,2015,17(2):1308-1317.
[32]Liu B,Ren Y,Zhang Z.Aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water under mild conditions[J].Green Chemistry,2015,17(3):1610-1617.
[33]Mei N,Liu B,Zheng J,et al.A novel magnetic palladium catalyst for the mild aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water[J].Catalysis Science&Technology,2015,5(6):3194-3202.
[34]Saha B,Gupta D,Abu-Omar M M,et al.Porphyrin-based porous organic polymer-supported iron(III)catalyst for efficient aerobic oxidation of5-hydroxymethyl-furfural into 2,5-furandicarboxylic acid[J].Journal of Catalysis,2013,299(2):316-320.
[35]Jain A,Jonnalagadda S C,Ramanujachary K V,et al.Selective oxidation of 5-hydroxymethyl-2-furfural to furan-2,5-dicarboxylic acid over spinel mixed metal oxide catalyst[J].Catalysis Communications,2015,58:179-182.
[36]Wang S,Zhang Z,Liu B.Catalytic conversion of fructose and5-hydroxymethylfurfural into 2,5-furandicarboxylic acid over a recyclable Fe3O4-CoOx magnetite nanocatalyst[J].Acs Sustainable Chemistry&Engineering,2015,3(3):406-412.
[37]Jebaraj A J J,Scherson D A.Microparticle Electrodes and Single Particle Microbatteries:Electrochemical and in Situ MicroRaman Spectroscopic Studies[J].Accounts of Chemical Research,2013,46(5):1192-1205.
[38]Zhang K,Han X,Hu Z,et al.Nanostructured Mn-based oxides for electrochemical energy storage and conversion[J].Chemical Society Reviews,2014,46(15):699-728.
[39]Hayashi E,Komanoya T,Kamata K,et al.Heterogeneously-catalyzed Aerobic Oxidation of 5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid with Manganese Dioxide[J].Chemsuschem,2017,10(4):654-658.
[40]Han X,Li C,Liu X,et al.Selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over MnOx-CeO2 composite catalysts[J].Green Chemistry,2017,19(4):996-1004.