生物质基2,5-二甲基呋喃制备对二甲苯的研究进展?
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摘要
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。
p-Xylene(pX) is an important chemical in the production of monomers such as terephthalic acid(TA) and related di-esters. Currently, it is prepared from petrochemical refinery processes. In order to produce pX from biomass resources in green and sustainable means, pX synthesis from biomass-based2,5-dimethyl-furan(DMF) via Diels-Alder and dehydration reactions has become a research hotspot. This article reviews pX preparation from biomass-derived DMF in recent years. The current progress of catalytic systems and solvents used in this reaction system is summarized. Moreover, prospects of pX production via biomass synthesis are also discussed.
p-Xylene(pX) is an important chemical in the production of monomers such as terephthalic acid(TA) and related di-esters. Currently, it is prepared from petrochemical refinery processes. In order to produce pX from biomass resources in green and sustainable means, pX synthesis from biomass-based2,5-dimethyl-furan(DMF) via Diels-Alder and dehydration reactions has become a research hotspot. This article reviews pX preparation from biomass-derived DMF in recent years. The current progress of catalytic systems and solvents used in this reaction system is summarized. Moreover, prospects of pX production via biomass synthesis are also discussed.
引文
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[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.
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[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.
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[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.
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