生物基芳香平台化合物2,5-呋喃二甲酸的合成研究进展

doi:10.16085/j.issn.1000-6613.2017.02.038

摘要/Abstract

摘要： 生物基芳香平台化合物2，5-呋喃二甲酸（2，5-FDCA）有望替代现有的石油基单体对苯二甲酸用于高性能高分子材料的合成。如何通过高效、廉价的路线制备2，5-FDCA已经成为近几十年的研究热点。本文系统地介绍了从5-羟甲基糠醛（HMF）、糠酸、呋喃、二甘醇酸或己糖二酸制备2，5-FDCA的各种方法，并重点介绍了HMF的直接氧化法、贵金属氧化法、非贵金属氧化法和生物酶氧化法合成2，5-FDCA。在比较了现有各种路线优缺点的基础上，认为HMF路线是2，5-FDCA规模化制备最有希望的路线，长远发展应朝着以纤维素为起始原料的方向，打通纤维素到糖的关键制备技术。

关键词: 2,5-呋喃二甲酸, 生物基, 平台化合物, 合成, 进展

Abstract: 2,5-Furandicarboxylic acid(2,5-FDCA) is a promising bio-based aromatic platform chemical for the synthesis of high performance polymers and has been regarded as the most suitable alternative to the petroleum-derived terephthalic acid. The synthesis of 2,5-FDCA through efficient and low cost route has been a hot subject since last decade. In this review article,the popular starting materials,including 5-hydroxymethyl furfural(HMF),furoic acid,furan,diglycolic acid,and hexaric acid,for the fabrication of 2,5-FDCA,are introduced in detail. Perspectives are given based on the comparison of different synthetic routes. The most popular synthetic route is based on HMF by either directly oxidation,noble metal oxidation,non-noble metal oxidation or enzyme catalysis oxidation. This method is considered as the most promising one to achieve large scale preparation of 2,5-FDCA. More importantly,development of novel technology for the conversion of cellulose to glucose is critical to produce large amount of low cost HMF.

Key words: 2,5-furandicarboxylic acid, bio-based, platform chemical, synthesis, progress

中图分类号:

王静刚, 刘小青, 朱锦. 生物基芳香平台化合物2,5-呋喃二甲酸的合成研究进展[J]. 化工进展, 2017, 36(02): 672-682.

WANG Jinggang, LIU Xiaoqing, ZHU Jin. Research progress on the synthesis of bio-based aromatic platform chemical 2,5-furandicarboxylic acid[J]. Chemical Industry and Engineering Progree, 2017, 36(02): 672-682.

参考文献

[1] SHELDON R A. Utilisation of biomass for sustainable fuels and chemicals:molecules,methods and metrics[J]. Catal. Today,2011,167:3-13.
[2] GALLEZOT P. ChemInform abstract:conversion of biomass to selected chemical products[J]. Chem. Soc. Rev.,2012,41:1538-1558.
[3] IWATA T. Biodegradable and bio-based polymers:future prospects of eco-friendly plastics[J]. Angew. Chem. Int. Ed.,2015,54:3210-3215.
[4] BOND J Q,ALONSO D M,WANG D,et al. Integrated catalytic conversion of gamma-valerolactone to liquid alkenes for transportation fuels[J]. Science,2010,327:1110-1114.
[5] RHIM J W. Preparation and characterization of vacuum sputter silver coated PLA film[J]. LWT-Food Science and Technology,2013,54(2):477-484.
[6] HIROE A,USHIMARU K,TSUGE T. Characterization of polyhydroxyalkanoate (PHA) synthase derived from Delftia acidovorans DS-17 and the influence of PHA production in Escherichia coli[J]. Journal of Bioscience and Bioengineering,2013,115(6):633-638.
[7] TAKAHASHI K,KMURA L Y. Melt/solid polycondensation of glycolic acid to obtain high-molecular-weight poly(glycolic acid)[J]. Polymer,2000,41(24):8725-8731.
[8] YE H M,WANG R D,LIU J. Isomorphism in poly(butylene succinate-co-butylene fumarate) and its application as polymeric nucleating agent for poly(butylene succinate)[J]. Macromolecules,2012,45:5667-5675.
[9] BOZELL J J,PETERSEN G R. ChemInform abstract:technology development for the production of biobased products from biorefinery carbohydrates The US Department of Energy[J]. Green Chem.,2010,12(4):539-554.
[10] HAJJ E,MASROUA A,MARTIN J C,et al. Synthesis of 5-(hydroxymethyl)-furan-2-carboxaldehyde and its derivatives by acid treatment of sugars on ion-exchange resins[J]. Soc. Chim. Fr.,1987:855-860.
[11] GRABOWSKI G,LEWKOWSKI J,SKOWRONSK R. The electrochemical oxidation of 5-hydroxymethylfurfural with the nickel oxide/hydroxide electrode[J]. Electrochim. Acta.,1991,36(13):1995.
[12] MIURA T,HIROKAZU K,TAKENOBU K,et al. Method for producing furan-2,5-dicarboxylic acid:US20070232815[P]. 2007-10-04.
[13] VINKE P,POEL W V,BEKKUM H V. On the oxygen tolerance of noble metal catalysts in liquid phase alcohol oxidations the influence of the support on catalyst deactivation[J]. Heterogeneous Catalysis and Fine Chemicals Ⅱ,1991,59:385-394.
[14] VERDEGUER P,MERAT N,GASET A. Oxydation catalytique du HMF en acide 2,5-furane dicarboxylique[J]. Journal of Molecular Catalysis,1993,85(3):327-344.
[15] PARTENHEIMER W,GRUSHIN V V. Synthesis of 2,5-diformylfuran and furan-2,5-dicarboxylic acid by catalytic air-oxidation of 5-hydroxymethylfurfural[J]. Adv. Synth. Catal.,2001,343(1):102-111.
[16] PARTENHEIMER W. Methodology and scope of metal/bromide autoxidation of hydrocarbons[J]. Catalysis Today,1995,23(2):69-158.
[17] LILGA M A,HALLEN R T,Gray M. Production of oxidized derivatives of 5-hydroxymethylfurfural(HMF)[J]. Top. Catal.,2010,5:31264-1269.
[18] LILGA M A,HALLEN R T,HU J. Preparation of 2,5diformylduran from 5-HMF with a heterogeneous mesoporous silver containing manganese catalyst:US20080103318[P]. 2008-05-01.
[19] RASS H A,ESSAYEM N,BESSON M. Selective aqueous phase oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts:influence of the base and effect of bismuth promotion[J]. Green Chem.,2013,15:2240-2251.
[20] RASS H A,ESSAYEM N,BESSON M. Selective aerobic oxidation of 5-HMF into 2,5-furandicarboxylic acid with Pt catalysts supported on TiO₂-and ZrO₂-based supports[J]. Chemsuschem,2013,8(7):1206-1217.
[21] SIANKEVICH S,SAVOGLIDIS G,FEI Z F,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.
[22] CAI J Y,MA H,ZHANG J J,et al. Gold nanoclusters confined in a supercage of Y zeolite for aerobic oxidation of HMF under mild conditions[J]. Chem. Eur. J.,2013,19:14215-14223.
[23] LOLLI A,AMADORI R,LUCARELLI C,et al. Hard-template preparation of Au/CeO₂ mesostructured catalysts and their activity for the selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxlic acid[J]. Microporous and Mesoporous Materials,2016,226:466-475.
[24] HANG X W,LI C Q,GUO Y,et al. N-doped carbon supported Pt catalyst for base-free oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid[J]. Applied Catalysis A:General,2016,526:1-8.
[25] HANGa X W,GENG L,GUO Y,et al. Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Pt/C-O-Mg catalyst[J]. Green Chem.,2016,18:1597-1604.
[26] ZHANG Y W,XUE Z M,WANG J F,et al. Controlled deposition of Pt nanoparticles on Fe₃O₄@carbon microspheres for efficient oxidation of 5-hydroxymethylfurfural[J]. RSC Adv.,2016,6:51229-51237.
[27] HARUTA M,KOBAYASHI T,SANO H,et al. Novel gold catalysts for the oxidation of carbon monoxide at a temperature far below 0℃[J]. Chemistry Letters,1987,16(2):405-408.
[28] PINA C D,FALLETTA E,PRATI L,et al. Selective oxidation using gold[J]. Chem. Soc. Rev.,2008,37:2077-2095.
[29] ZHENG N F,STUCKY G D. Promoting gold nanocatalysts in solvent-free selective aerobic oxidation of alcohols[J]. Chem. Commun.,2007,37:3862-3864.
[30] TAARNING E,NIELSEN I S,EGEBLAD K,et al. Chemicals from renewables:aerobic oxidation of furfural and hydroxymethylfurfural over gold catalysts[J]. ChemSusChem,2008,11:75-78.
[31] GORBANEV Y Y,KLITGAARD S K,WOODLEY J M,et al. Gold-catalyzed aerobic oxidation of 5-hydroxymethylfurfural in water at ambient temperature[J]. ChemSusChem,2009,2:672-675.
[32] 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.
[33] CASANOVA O,IORRA S,CORMA A. Biomass into chemicals:One pot-base free oxidative esterification of 5-hydroxymethyl-2-furfural into 2,5-dimethylfuroate with gold on nanoparticulated ceria[J]. Journal of Catalysis,2009,265(1):109-116.
[34] PASINI T,PICCININI M,BLOSIl M,et al. Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles[J]. Green Chem.,2011,13(8):2091-2099.
[35] AALBONETTI S,PASINI T,LOLLI A,et al. Selective oxidation of 5-hydroxymethyl-2-furfural over TiO₂-supported gold-copper catalysts prepared from preformed nanoparticles:effect of Au/Cu ratio[J]. Catalysis Today,2012,195(1):120-126.
[36] SAHA B,DUTTA S,ABU-OMAR M M. Aerobic oxidation of 5-hydroxylmethylfurfural with homogeneous and nanoparticulate catalysts[J]. Catal. Sci. Technol.,2012,2(1):79-81.
[37] VILLA D 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]. ChemSusChem,2013,6(4):609-612.
[38] ARDEMANI L,CIBIN C G,DENT A J,et al. Solid base catalysed 5-HMF oxidation to 2,5-FDCA over Au/hydrotalcites:fact or fiction?[J]. Chem. Sci.,2015,6:4940-4945.
[39] YI G S,TEONG S P,LI X C,et al. Purification of eiomass-derived 5-hydroxymethylfurfural and its catalytic conversion to 2,5-furandicarboxylic acid[J]. ChemSusChem,2014,7(8):2131-2135.
[40] YI G,TEONG S P,ZHANG Y G. The direct conversion of sugars into 2,5-furandicarboxylic acid in a triphasic system[J]. ChemSusChem,2015,8(7):1151-1155.
[41] YI G S,TEONG S P,ZHANG Y G. Base-free conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Ru/C catalyst[J]. Green Chem.,2016,18:979-983.
[42] WANG F,YUAN Z L,LIU B,et al. Catalytic oxidation of biomass derived 5-hydroxymethylfurfural (HMF) over RuIII-incorporated zirconium phosphate catalyst[J]. Journal of Industrial and Engineering Chemistry,2016,38:181-185.
[43] GORBANEV Y Y,KEGNAES S,RIISAAGER A. Effect of support in heterogeneous ruthenium catalysts used for the selective aerobic oxidation of HMF in water[J]. Topics in Catalysis,2011,54(16):1318-1324.
[44] GORBAN Y Y,KEGNAES S,RIISAGER A. Selective aerobic oxidation of 5-hydroxymethylfurfural in water over solid ruthenium hydroxide cwith magnesium-based supports[J]. Catal. Lett.,2011,141(12):1752-1760.
[45] ZHANG Z H,ZHEN J D,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 Chem.,2015,17:1308-1317.
[46] LIU B,REN Y S,ZHANG Z H. Aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid in water under mild conditions[J]. Catal. Green Chem.,2015,17:1610-1617.
[47] DAVIS S E,HOUK L R,TAMARGO E C,et al. Oxidation of 5-hydroxymethylfurfural over supported Pt,Pd and Au catalysts[J]. Catal. Today,2011,160(1):55-60.
[48] ROGR M,PRUBE U,VORLOP K D. A new approach for the production of 2,5-furandicarboxylic acid by in situ oxidation of 5-hydroxymethylfurfural starting from fructose[J]. Topics in Catalysis,2012,13(3):237-242.
[49] WAN X Y,ZHU C M,CHEN J S,et al. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au-Pd alloy nanoparticles[J]. ACS Catal.,2014,4:2175-2185.
[50] CHADDERDON D J,XIN L,QI J,et al. Electrocatalytic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid on supported Au and Pd bimetallic nanoparticles[J]. Green Chem.,2014,16:3778-3786.
[51] ALBONETTI S,LOLLIA A,MORANDI V,et al. Conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylicacid over Au-based catalysts:optimization of active phaseand metal-support interaction[J]. Applied Catalysis B:Environmental,2015,163:520-530.
[52] HANSEN T S,SADABA I,GARCIA E J,et al. Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions[J]. Applied Catalysis A:General,2013,456:44-50.
[53] RIBEIRO M L,SCHUCHARD U. Cooperative effect of cobalt acetylacetonate and silica in the catalytic cyclization and oxidation of fructose to 2,5-furandicarboxylic acid[J]. Catalysis Communications,2003,4(2):83-86.
[54] WANG S G,ZHANG Z H,LIU B. Catalytic conversion of fructose and 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid over a recyclable Fe₃O₄-CoO_x magnetite nanocatalyst[J]. ACS Sustainable Chem. Eng.,2015,3:406-412.
[55] GAO L C,DENG K J,ZHENG J D,et al. Efficient oxidation of biomass derived 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid catalyzed by Merrifield resin supported cobalt porphyrin[J]. Chemical Engineering Journal,2015,270:444-449.
[56] ZUO X B,VENKITASUBARAMANIAN P,BUSH D H,et al. Optimization of Co/Mn/Br-catalyzed oxidation of 5-hydroxymethylfurfural to enhance 2,5-furandicarboxylic acid yield and minimize substrate burning[J]. ACS Sustainable Chem. Eng.,2016,4:3659-3668.
[57] DIJKMAN W P,GROOTHUIS D E,FRAAIJE M W. Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid[J]. Angew. Chem. Int. Ed.,2014,53(25):6515-6518.
[58] MCKENNA S M,LEIKKULER S,HERTER S,et al. Enzyme cascade reactions:synthesis of furandicarboxylic acid (FDCA) and carboxylic acids using oxidases in tandem[J]. Green Chem.,2015,17:3271-3275.
[59] QIN Y Z,LI Y M,ZONG M H,et al. Enzyme-catalyzed selective oxidation of 5-hydroxymethylfurfural (HMF) and separation of HMF and 2,5-diformylfuran using deep eutectic solvents[J]. Green Chem.,2015,17:3718-3722.
[60] RAECKE B. Synthese von Diund Tricarbonsäuren aromatischer ringsysteme durch verschiebung von carboxyl-gruppen[J]. Angew. Chem. Int. Ed.,1958,70:1-5.
[61] THIYAGARAJAN S,PUKIN A,HAVEREN J V,et al. Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid:unexpected aspects of the Henkel reaction[J]. RSC Adv.,2013,3:15678-15686.
[62] PAN T,DENG J,XU Q,et al. Catalytic conversion of furfural into a 2,5-furandicarboxylic acid-based polyester with total carbon utilization[J]. ChemSusChem,2013,6:47-50.
[63] BANERJEE A,DICK G R,et al. Carbon dioxide utilization via carbonate-promoted C-H carboxylation[J]. Nature,2016,531:215-219.
[64] 刘浪,杨顺利,李鸿波,等. 2,5-呋喃二甲酸的合成[J]. 精细化工,2011,28(4):410-412. LIU L,YANG S L,LI H B,et al. The synthesis of 2,5-furandicarboxylic acid[J]. Fine Chemicals,2011,28(4):410-412.
[65] 王静刚,刘小青,朱锦,等. 一种2,5-二酰基呋喃化合物的制备方法:201410763313.2[P]. 2014-12-11. WANG J G,LIU X Q,ZHU J,et al. One method for preparation of 2,5-diacetylfuran:201410763313.2[P]. 2014-12-11.
[66] 王静刚,刘小青,朱锦,等. 一种2,5-呋喃二甲酸的制备方法:201410787166.2[P]. 2014-12-17. WANG J G,LIU X Q,ZHU J,et al. One method for preparation of 2,5-dicarboxylic acid:201410787166.2[P]. 2014-12-17.
[67] WANG J G,LIU X Q,ZHU J,et al. Preparation method for 2,5-furandicarboxylic acid:WO₂016095122[P]. 2016-07-23.
[68] LEWKOWSK J. Convenient synthesis of furan-2,5-dicarboxylic acid and its derivative[J]. Polish J. Chem.,2001,75(12):1943-1946.
[69] BRĂTULESCU G. Mass spectra of aromatic azoethers and azoxyethers[J]. Rev. Roum. Chim.,2000,45(9):883-885.
[70] TAGUCHI Y,OISSHI A,IIDA H. One-step synthesis of dibutyl furandicarboxylates from galactaric acid[J]. Chem. Lett.,2008,37(1):50-51.
[71] 李伟杰,陆豫. 合成3,4-二取代呋喃-2,5-二甲酸的简便方法[J]. 化学试剂,2006,28(5):309-310. LI W J,LU Y. Concise synthesis of 3,4-disubstitutedfuran-2,5-dicarboxylic acids[J]. Chemical Reagents,2006,28(5):309-310.
[72] FITTING R,HEINZELMAN H. Ueber neue derivate der schleimsaure[J]. Chem. Ber.,1876,9:1198-1201.
[73] DIEGO C M,DAM M A,GRUTER G J M. Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandi-carboxylic acid[J:WO₂011043661[P]. 2011.
[74] DIEGO C M,DAM M A,GRUTER G J M. Method for the preparation of furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicaeboxylic acid:US8865921[P]. 2014-10-21.
[75] JANKA M J,PARKER K R,SHAIKH A S,et al. Oxidation process to produce a crude dry carboxylic acid product:US8772513[P]. 2014-07-08.