生物质基2,5-二甲基呋喃制备对二甲苯的研究进展Advances in p-xylene production from biomass-derived 2,5-dimethylfuran
高哲邦,冯云超,曾宪海,孙勇,唐兴,雷廷宙,林鹿
摘要(Abstract):
对二甲苯(p-Xylene,pX)是一种十分重要的化工原料,其主要用途是生产对苯二甲酸(terephthalic acid,TA)和对苯二甲酸酯等聚合物单体产品。pX目前主要从石油化工路径制备得到。为了利用生物质资源绿色可持续地生产pX,从生物质基2,5-二甲基呋喃(2,5-Dimethylfuran,DMF)经Diels-Alder和脱水反应制备pX近年来逐渐成为研究热点。研究综述了近年来以生物质基DMF制备pX的研究进展,分析了该技术路线中催化体系和溶剂体系等方面的现状,并对生物质pX合成路径的发展趋势和前景进行展望。
关键词(KeyWords): 生物质;2,5-二甲基呋喃;对二甲苯;催化;溶剂体系
基金项目(Foundation): 国家自然科学基金(21506177,21676223);; 厦门大学校长基金(20720160077; 20720160087; 20720170062);; 福建省自然科学基金(2016J01077)
作者(Author): 高哲邦,冯云超,曾宪海,孙勇,唐兴,雷廷宙,林鹿
参考文献(References):
- [1]ESPOSITO D,ANTONIETTI M.Redefining biorefinery:the search for unconventional building blocks for materials[J].Chemical Society Reviews,2015,44(16):5821-5835.
- [2]CHEN L,XIN J Y,NI L L,et al.Conversion of lignin model compounds under mild conditions in pseudo-homogeneous systems[J].Green Chemistry,2016,18(8):2341-2352.
- [3]VLACHOS D G,CHEN J G,GORTE R J,et al.Catalysis center for energy innovation for biomass processing:research strategies and goals[J].Catalysis Letters,2010,140(3-4):77-84.
- [4]TOMAS R A,BORDADO J C,GOMES J F.p-Xylene oxidation to terephthalic acid:a literature review oriented toward process optimization and development[J].Chemical Reviews,2013,113(10):7421-7469.
- [5]FONG Y Y,ABDULLAH A Z,AHMAD A L,et al.Development of functionalized zeolite membrane and its potential role as reactor combined separator for para-xylene production from xylene isomers[J].Chemical Engineering Journal,2008,139(1):172-193.
- [6]MANEFFA A,PRIECEL P,LOPEZ-SANCHEZ J A.Biomass-derived renewable aromatics:selective routes and outlook for p-xylene commercialisation[J].ChemSusChem,2016,9(19):2736-2748.
- [7]刘俊霞,陈景润,王军峰,等.生物质基呋喃制备对二甲苯研究进展[J].工业催化,2017,25(4):13-16.LIU J X,CHEN J R,WANG J F,et al.Research progress in the preparation of p-xylene from biomass-based furan[J].Industrial Catalysis,2017,25(4):13-16.
- [8]ZHAO P P,ZHANG Y Y,WANG Y,et al.Conversion of glucose into 5-hydroxymethylfurfural catalyzed by acid-base bifunctional heteropolyacid-based ionic hybrids[J].Green Chemistry,2018,20(7):1551-1559.
- [9]刘迎新,曾茂,楼炯涛,等.5-羟甲基糠醛选择性加氢制备2,5-二甲基呋喃研究进展[J].高校化学工程学报,2018,32(2):255-265.LIU Y X,ZENG M,LOU J T,et al.Review on 2,5-dimethylfuran synthesis via selective hydrogenation of 5-hydroxymethylfufural[J].Journal of Chemical Engineering of Chinese Universities,2018,32(2):255-265.
- [10]BRANDVOLD T A.Carbohydrate route to para-xylene and terephthalic acid:US,8 314 267 B2[P].2012-11-20.
- [11]WILLIAMS C L,VINTER K P,CHANG C C,et al.Kinetic regimes in the tandem reactions of H-BEA catalyzed formation of p-xylene from dimethylfuran[J].Catalysis Science&Technology,2016,6(1):178-187.
- [12]NIKBIN N,FENG S,CARATZOULAS S,et al.p-Xylene formation by dehydrative aromatization of a Diels-Alder product in Lewis and br?nsted acidic zeolites[J].The Journal of Physical Chemistry C,2014,118(42):24415-24424.
- [13]XIONG R C,SANDLER S I,VLACHOS D G,et al.Solvent-tuned hydrophobicity for faujasite-catalyzed cycloaddition of biomass-derived dimethylfuran for renewable p-xylene[J].Green Chemistry,2014,16(9):4086-4091.
- [14]WALKER T W,CHEW A K,LI H X,et al.Universal kinetic solvent effects in acid-catalyzed reactions of biomass-derived oxygenates[J].Energy&Environmental Science,2018,11(3):617-628.
- [15]MELLMER M A,SENER C,GALLO J M R,et al.Solvent effects in acid-catalyzed biomass conversion reactions[J].Angewandte Chemie,2014,53(44):11872-11875.
- [16]SALAVATI-FARD T,CARATZOULAS S,DOREN D J.Solvent effects in acid-catalyzed dehydration of the Diels-Alder cycloadduct between 2,5-dimethylfuran and maleic anhydride[J].Chemical Physics,2017,485-486:118-124.
- [17]WILLIAMS C L,CHANG C C,DO P,et al.Cycloaddition of biomass-derived furans for catalytic production of renewable p-xylene[J].ACS Catalysis,2012,2(6):935-939.
- [18]WIJAYA Y P,SUH D J,JAE J.Production of renewable p-xylene from 2,5-dimethylfuran via Diels-Alder cycloaddition and dehydrative aromatization reactions over silica-alumina aerogel catalysts[J].Catalysis Communications,2015,70:12-16.
- [19]CHIAPPE C,MALVALDI M,POMELLI C S.The solvent effect on the Diels-Alder reaction in ionic liquids:multiparameter linear solvation energy relationships and theoretical analysis[J].Green Chemistry,2010,12(8):1330-1339.
- [20]AGGARWAL A,LANCASTER N L,SETHI A R,et al.The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids[J].Green Chemistry,2002,4(5):517-520.
- [21]VIDI?A,OHLIN C A,LAURENCZY G,et al.Rationalisation of solvent effects in the Diels-Alder reaction between cyclopentadiene and methyl acrylate in room temperature ionic liquids[J].Advanced Synthesis&Catalysis,2005,347(2-3):266-274.
- [22]NI L L,XIN J Y,DONG H X,et al.A simple and mild approach for the synthesis of p-xylene from bio-based 2,5-dimethyfuran by using metal triflates[J].ChemSusChem,2017,10(11):2394-2401.
- [23]NI L L,XIN J Y,JIANG K,et al.One-step conversion of biomass-derived furanics into aromatics by br?nsted acid ionic liquids at room temperature[J].ACS Sustainable Chemistry&Engineering,2018,6(2):2541-2551.
- [24]CHANG C C,GREEN S K,WILLIAMS C L,et al.Ultra-selective cycloaddition of dimethylfuran for renewable p-xylene with H-BEA[J].Green Chemistry,2014,16(2):585-588.
- [25]TEIXEIRA I F,LO B T W,KOSTETSKYY P,et al.From biomass-derived furans to aromatics with ethanol over zeolite[J].Angewandte Chemie,2016,55(42):13061-13066.
- [26]WECKHUYSEN B M,YU J H.Recent advances in zeolite chemistry and catalysis[J].Chemical Society Reviews,2015,44(20):7022-7024.
- [27]YU J Y,ZHU S Y,DAUENHAUER P J,et al.Adsorption and reaction properties of SnBEA,ZrBEA and H-BEA for the formation of p-xylene from DMF and ethylene[J].Catalysis Science&Technology,2016,6(14):5729-5736.
- [28]PATET R E,FAN W,VLACHOS D G,et al.Tandem Diels-Alder reaction of dimethylfuran and ethylene and dehydration to para-xylene catalyzed by zeotypic Lewis acids[J].ChemCatChem,2017,9(13):2523-2535.
- [29]PACHECO J J,DAVIS M E.Synthesis of terephthalic acid via Diels-Alder reactions with ethylene and oxidized variants of5-hydroxy-methylfurfural[J].Proceedings of the National Academy of Sciences of the United States of America,2014,111(23):8363-8367.
- [30]PACHECO J J,LABINGER J A,SESSIONS A L,et al.Route to renewable PET:reaction pathways and energetics of Diels-Alder and dehydrative aromatization reactions between ethylene and biomass-derived furans catalyzed by Lewis acid molecular sieves[J].ACS Catalysis,2015,5(10):5904-5913.
- [31]PATET R E,CARATZOULAS S,VLACHOS D G.Tandem aromatization of oxygenated furans by framework zinc in zeolites:a computational study[J].The Journal of Physical Chemistry C,2017,121(40):22178-22186.
- [32]NIKBIN N,CARATZOULAS S,VLACHOS D G.On the Bronsted acid-catalyzed homogeneous hydrolysis of furans[J].ChemSusChem,2013,6(11):2066-2068.
- [33]PATET R E,KOEHLE M,LOBO R F,et al.General acid-type catalysis in the dehydrative aromatization of furans to aromatics in H-[Al]-BEA,H-[Fe]-BEA,H-[Ga]-BEA,and H-[B]-BEA zeolites[J].The Journal of Physical Chemistry C,2017,121(25):13666-13679.
- [34]CHO H J,REN L M,VATTIPALLI V,et al.Renewable p-xylene from 2,5-dimethylfuran and ethylene using phosphorus-containing zeolite catalysts[J].ChemCatChem,2017,9(3):398-402.
- [35]ROHLING R Y,USLAMIN E,ZIJLSTRA B,et al.An active alkali-exchanged faujasite catalyst for para-xylene production via the one-pot Diels-Alder cycloaddition/dehydration reaction of 2,5-dimethylfuran with ethylene[J].ACS Catalysis,2018,8(2):760-769..
- [36]PATET R E,NIKBIN N,WILLIAMS C L,et al.Kinetic regime change in the tandem dehydrative aromatization of furan Diels-Alder products[J].ACS Catalysis,2015,5(4):2367-2375.
- [37]ENNAERT T,AELST J V,DIJKMANS J,et al.Potential and challenges of zeolite chemistry in the catalytic conversion of biomass[J].Chemical Society Reviews,2016,45(3):584-611.
- [38]LUO H Y,LEWIS J D,ROMAN-LESHKOV Y.Lewis acid zeolites for biomass conversion:perspectives and challenges on reactivity,synthesis,and stability[J].Annual Review of Chemical and Biomolecular Engineering,2016,7:663-692.
- [39]MOLINER M.State of the art of Lewis acid-containing zeolites:lessons from fine chemistry to new biomass transformation processes[J].Dalton Transactions,2014,43(11):4197-4208.
- [40]NIKBIN N,DO P T,CARATZOULAS S,et al.A DFT study of the acid-catalyzed conversion of 2,5-dimethylfuran and ethylene to p-xylene[J].Journal of Catalysis,2013,297:35-43.
- [41]FENG X Q,SHEN C,TIAN C C,et al.Highly selective production of biobased p-xylene from 2,5-dimethylfuran over SiO2-SO3Hcatalysts[J].Industrial&Engineering Chemistry Research,2017,56(20):5852-5859.
- [42]KIM J C,KIM T W,KIM Y J,et al.Mesoporous MFI zeolites as high performance catalysts for Diels-Alder cycloaddition of bio-derived dimethylfuran and ethylene to renewable p-xylene[J].Applied Catalysis B:Environmental,2017,206:490-500.
- [43]KIM T W,KIM S Y,KIM J C,et al.Selective p-xylene production from biomass-derived dimethylfuran and ethylene over zeolite beta nanosponge catalysts[J].Applied Catalysis B:Environmental,2016,185:100-109.
- [44]FENG X Q,SHEN C,JI K Y,et al.Production of p-xylene from bio-based 2,5-dimethylfuran over high performance catalyst WO3/SBA-15[J].Catalysis Science&Technology,2017,7(23):5540-5549.
- [45]WANG D,OSMUNDSEN C M,TAARNING E,et al.Selective production of aromatics from alkylfurans over solid acid catalysts[J].ChemCatChem,2013,5(7):2044-2050.
- [46]YIN J B,SHEN C,FENG X Q,et al.Highly selective production of p-xylene from 2,5-dimethylfuran over hierarchical NbOx-based catalyst[J].ACS Sustainable Chemistry&Engineering,2017,6(2):1891-1899.
- [47]KOZHEVNIKOV I V.Sustainable heterogeneous acid catalysis by heteropoly acids[J].Journal of Molecular Catalysis A:Chemical,2007,262(1-2):86-92.
- [48]WANG S S,YANG G Y.Recent advances in polyoxometalate-catalyzed reactions[J].Chemical Reviews,2015,115(11):4893-4962.
- [49]LU R,LU F,CHEN J Z,et al.Production of diethyl terephthalate from biomass-derived muconic acid[J].Angewandte Chemie,2016,55(1):249-253.
- [50]WIJAYA Y P,WINOTO H P,PARK Y K,et al.Heteropolyacid catalysts for Diels-Alder cycloaddition of 2,5-dimethylfuran and ethylene to renewable p-xylene[J].Catalysis Today,2017,293-294:167-175.
- [51]BOKADE V V,YADAV G D.Heteropolyacid supported on montmorillonite catalyst for dehydration of dilute bio-ethanol[J].Applied Clay Science,2011,53(2):263-271.
- [52]ALHARBI W,BROWN E,KOZHEVNIKOVA E F,et al.Dehydration of ethanol over heteropoly acid catalysts in the gas phase[J].Journal of Catalysis,2014,319:174-181.
- [53]SETTLE A E,BERSTIS L,RORRER N A,et al.Heterogeneous Diels-Alder catalysis for biomass-derived aromatic compounds[J].Green Chemistry,2017,19(15):3468-3492.
- [54]TAO M L,XUE L F,SUN Z,et al.Tailoring the synergistic Bronsted-Lewis acidic effects in heteropolyacid catalysts:applied in esterification and transesterification reactions[J].Scientific Reports,2015,5:13764.
- [55]KISHIDA T,YAMAUCHI T,KUBOTA Y,et al.Rare-earth metal triflates as versatile catalysts for the chloromethylation of aromatic hydrocarbons[J].Green Chemistry,2004,6(1):57-62.
- [56]SARMA D,KUMAR A.Rare earth metal triflates promoted Diels-Alder reactions in ionic liquids[J].Applied Catalysis A:General,2008,335(1):1-6.
- [57]SONG S,WU G J,DAI W L,et al.Diels-Alder and dehydration reactions of furan derivatives with ethylene catalyzed by liquid Br?nsted acids and Lewis acids[J].Journal of Molecular Catalysis A:Chemical,2016,420:134-141.
- [58]SHUAI L,LUTERBACHER J.Organic solvent effects in biomass conversion reactions[J].ChemSusChem,2016,9(2):133-155.
- [59]SHIRAMIZU M,TOSTE F D.On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate(PET):conversion of 2,5-dimethylfuran and acrolein into p-xylene[J].Chemistry,2011,17(44):12452-12457.
- [60]MAHMOUD E,WATSON D A,LOBO R F.Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride[J].Green Chemistry,2014,16(1):167-175.
- [61]XIAO Y,MALHOTRA S V.Diels-Alder reactions in pyridinium based ionic liquids[J].Tetrahedron Letters,2004,45(45):8339-8342.