生物质基呋喃衍生物选择氢解制备戊二醇和己二醇研究进展
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摘要
生物质基呋喃衍生物来源广泛,利用生物糠醛、5-羟甲基糠醛及他们的衍生物选择氢解制备戊二醇、己二醇具有重要的研究价值和意义.根据原料和催化剂体系不同对生物质基呋喃衍生物选择氢解制备高碳二元醇的代表性工作进行了归纳总结,对影响催化剂活性和选择性的关键因素如活性金属、载体、助剂及反应溶剂等进行了分析讨论,对反应可能涉及的路径和机理进行了阐述,并对未来的研究方向和发展趋势作了展望.
The selective hydrogenolysis of abundant biomass-based furan derivatives in nature,including furfural( FA),5-hydroxymethylfurfural( 5-HMF) and their derivatives,into pentanediols and hexanediol is significant for academic research and industrial application. The representative works on the selective hydrogenolysis of biomassbased furan derivatives into high-carbon glycols were summarized according to the different raw materials and catalyst systems. The important factors for activity and selectivity consisting of active metal,carrier,additives and solvents were remarked. The possible reaction pathways and mechanism were demonstrated,and prospect for the research directions as well as future development was proposed.
The selective hydrogenolysis of abundant biomass-based furan derivatives in nature,including furfural( FA),5-hydroxymethylfurfural( 5-HMF) and their derivatives,into pentanediols and hexanediol is significant for academic research and industrial application. The representative works on the selective hydrogenolysis of biomassbased furan derivatives into high-carbon glycols were summarized according to the different raw materials and catalyst systems. The important factors for activity and selectivity consisting of active metal,carrier,additives and solvents were remarked. The possible reaction pathways and mechanism were demonstrated,and prospect for the research directions as well as future development was proposed.
引文
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[41]Sulmonetti T P,Hu B,Lee S,et al.Reduced Cu-Co-Al mixed metal oxides for the ring-opening of furfuryl alcohol to produce renewable diols[J].ACS Sustain Chem Eng,2017,5(10):8959-8969.
[42]Lee J,Burt S P,Carrero C A,et al.Stabilizing cobalt catalysts for aqueous-phase reactions by strong metal-support interaction[J].J Catal,2015,330:19-27.
[43]Wijaya H W,Kojima T,Hara T,et al.Synthesis of 1,5-Pentanediol by hydrogenolysis of furfuryl alcohol over NiY2O3Composite Catalyst[J].Chem Cat Chem,2017,9(14):2869-2874.
[44]Wijaya H W,Sato T,Tange H,et al.Hydrogenolysis of furfural into 1,5-Pentanediol by employing Ni-M(M=Yor La)composite catalysts[J].Chem Lett,2017,46(5):744-746.
[45]Wijaya H W,Hara T,Ichikuni N,et al.Hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over a nickel-yttrium oxide catalyst containing ruthenium[J].Chem Lett,2018,47(1):103-106.
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[54]Waidmann C R,Pierpont A W,Batista E R,et al.Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings:An experimental and theoretical study[J].Catal Sci Technol,2013,3(1):106-115.
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[60]Yao S X,Wang X C,Jiang Y J,et al.One-step conversion of biomass-derived 5-hydroxymethylfurfural to 1,2,6-hexanetriol over Ni-Co-Al mixed oxide catalysts under mild conditions[J].ACS Sustain Chem Eng,2014,2(2):173-180.
[2]Li C,Zhao X,Wang A,et al.Catalytic transformation of lignin for the production of chemicals and fuels[J].Chem Rev,2015,115(21):11559-11624.
[3]Mariscal R,Maireles-Torres P,Ojeda,M,et al.Furfural:A renewable and versatile platform molecule for the synthesis of chemicals and fuels[J].Energy Environ Sci,2016,9(4):1144-1189.
[4]Hu L,Zhao G,Hao W W,et al.Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes[J].RSC Adv,2012,2(30):11184-11206.
[5]He J,Huang K,Barnett K J,et al.New catalytic strategies for alpha-omega diol production from lignocellulosic biomass[J].Faraday Discuss,2017,202:247-267.
[6]Besson M,Gallezot P,Pinel C.Conversion of biomass into chemicals over metal catalysts[J].Chem Rev,2014,114(3):1827-1870.
[7]Nakagawa Y,Tamura M,Tomishige K.Catalytic reduction of biomass-derived furanic compounds with hydrogen[J].ACS Catal,2013,3(12):2655-2668.
[8]van Putten R J,van der Waal J C,de Jong E,et al.Hydroxymethylfurfural,A versatile platform chemical made from renewable resources[J].Chem Rev,2013,113(3):1499-1597.
[9]Agirrezabal-Telleria I,Gandarias I,Arias P L.Heterogeneous acid-catalysts for the production of furan-derived compounds(furfural and hydroxymethylfurfural)from renewable carbohydrates:A review[J].Catal Today,2014,234:42-58.
[10]Climent M J,Corma A,Iborra S.Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels[J].Green Chem,2014,16(2):516-547.
[11]Bicker M,Hirth J,Vogel H.Dehydration of fructose to5-hydroxymethylfurfural in sub-and supercritical acetone[J].Green Chem,2003,5(2):280-284.
[12]Xu W,Wang H,Liu X,et al.Direct catalytic conversion of furfural to 1,5-pentanediol by hydrogenolysis of the furan ring under mild conditions over Pt/Co2Al O4catalyst[J].Chem Commun,2011,47(13):3924-3926.
[13]Ma R F,Wu X P,Tong T,et al.The critical role of water in the ring opening of furfural alcohol to 1,2-pentanediol[J].ACS Catal,2017,7(1):333-337.
[14]Tong T,Xia Q,Liu X,et al.Direct hydrogenolysis of biomass-derived furans over Pt/Ce O2catalyst with high activity and stability[J].Catal Commun,2017,101:129-133.
[15]Mizugaki T,Yamakawa T,Nagatsu Y,et al.Direct transformation of furfural to 1,2-Pentanediol using a hydrotalcite-supported platinum nanoparticle catalyst[J].ACS Sustain Chem Eng,2014,2(10):2243-2247.
[16]Feng S X,Nagao A,Aihara T,et al.Selective hydrogenolysis of tetrahydrofurfuryl alcohol on Pt/WO3/Zr O2catalysts:Effect of WO3loading amount on activity[J].Catal Today,2018,303:207-212.
[17]Wang C,Lee J D,Ji Y C,et al.A Study of tetrahydrofurfuryl alcohol to 1,5-Pentanediol over Pt-WOx/C[J].Catal Lett,2018,148(4):1047-1054.
[18]Dias E L,Shoemaker J A W,Boussie T R,et al.Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor:US[P],20130184495A1,2013.
[19]He J,Burt S P,Ball M,et al.Synthesis of 1,6-Hexanediol from cellulose derived tetrahydrofuran-dimethanol with Pt-WOx/Ti O2catalysts[J].ACS Catal,2018,8(2):1427-1439.
[20]Liu S B,Amada Y,Tamura M,et al.One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir-Re Ox/Si O2bifunctional catalyst[J].Green Chem,2014,16(2):617-626.
[21]Liu S B,Amada Y,Tamura M,et al.Performance and characterization of rhenium-modified Rh-Ir alloy catalyst for one-pot conversion of furfural into 1,5-pentanediol[J].Catal Sci Technol,2014,4(8):2535-2549.
[22]Chen K,Mori K,Watanabe H,et al.C-O bond hydrogenolysis of cyclic ethers with OH groups over rheniummodified supported iridium catalysts[J].J Catal,2012,294:171-183.
[23]Wang Z Q,Pholjaroen B,Li M X,et al.Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Ir-Mo Ox/Si O2catalyst[J].J Energy Chem,2014,23(4):427-434.
[24]Pholjaroen B,Li N,Huang Y Q,et al.Selective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over vanadium modified Ir/Si O2catalyst[J].Catal Today,2015,245:93-99.
[25]Wan W,Jenness G R,Xiong K,et al.Ring-opening reaction of furfural and tetrahydrofurfuryl alcohol on hydrogen-predosed iridium(111)and cobalt/iridium(111)surfaces[J].Chem Cat Chem,2017,9(9):1701-1707.
[26]Xiao B,Zheng M,Li X,et al.Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/Si O2+Ir-Re Ox/Si O2in a fixed-bed reactor[J].Green Chem,2016,18(7):2175-2184.
[27]Zhang B,Zhu Y L,Ding G Q,et al.Selective conversion of furfuryl alcohol to 1,2-pentanediol over a Ru/Mn Oxcatalyst in aqueous phase[J].Green Chem,2012,14(12):3402-3409.
[28]G9tz D,Lucas M,Claus P.C-O bond hydrogenolysis vs.C=C group hydrogenation of furfuryl alcohol:Towards sustainable synthesis of 1,2-pentanediol[J].React Chem Eng,2016,1(2):161-164.
[29]Koso S,Furikado I,Shimao A,et al.Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol[J].Chem Commun,2009,2009(15):2035-2037.
[30]Koso S,Ueda N,Shinmi Y,et al.Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to1,5-pentanediol over Rh/Si O2[J].J Catal,2009,267(1):89-92.
[31]Chen K Y,Koso S,Kubota T,et al.Chemoselective hydrogenolysis of tetrahydropyran-2-methanol to 1,6-hexanediol over rhenium-modified carbon-supported rhodium catalysts[J].Chem Cat Chem,2010,2(5):547-555.
[32]Chia M,Pagan-Torres Y J,Hibbitts D,et al.Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts[J].JAm Chem Soc,2011,133(32):12675-12689.
[33]Guan J,Peng G M,Cao Q,et al.Role of Mo O3on a rhodium catalyst in the selective hydrogenolysis of biomass-derived tetrahydrofurfuryl alcohol into 1,5-pentanediol[J].J Phys Chem C,2014,118(44):25555-25566.
[34]Chatterjee M,Kawanami H,Ishizaka T,et al.An attempt to achieve the direct hydrogenolysis of tetrahydrofurfuryl alcohol in supercritical carbon dioxide[J].Catal Sci Technol,2011,1(8):1466-1471.
[35]Buntara T,Noel S,Phua P H,et al.From 5-hydroxymethylfurfural(HMF)to polymer precursors:Catalyst screening studies on the conversion of 1,2,6-hexanetriol to 1,6-hexanediol[J].Top Catal,2012,55(7/10):612-619.
[36]Chem Sus Chem,Tuteja J,Choudhary H,et al.Direct synthesis of 1,6-hexanediol from HMF over a heterogeneous Pd/Zr P catalyst using formic acid as hydrogen source[J].Chem Sus Chem,2014,7(1):96-100.
[37]Adkins H,Connor P.The catalytic hydrogenation of organic compounds[J].J Am Chem Soc,1931,53:1091-1095.
[38]Liu H L,Huang Z W,Zhao F,et al.Efficient hydrogenolysis of biomass-derived furfuryl alcohol to 1,2-and 1,5-pentanediols over a non-precious Cu-Mg3Al O4.5bifunctional catalyst[J].Catal Sci Technol,2016,6(3):668-671.
[39]Liu H L,Huang Z W,Kang H X,et al.Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and1,5-pentanediol over highly dispersed Cu-Al2O3catalysts[J].Chin J Catal,2016,37(5):700-710.
[40]Gotz D,Lucas M,Claus P.Aqueous phase hydrogenolysis of bio-derivable furfuryl alcohol to pentanediols using copper catalysts[J].Catal,2017,7(2):1-7.
[41]Sulmonetti T P,Hu B,Lee S,et al.Reduced Cu-Co-Al mixed metal oxides for the ring-opening of furfuryl alcohol to produce renewable diols[J].ACS Sustain Chem Eng,2017,5(10):8959-8969.
[42]Lee J,Burt S P,Carrero C A,et al.Stabilizing cobalt catalysts for aqueous-phase reactions by strong metal-support interaction[J].J Catal,2015,330:19-27.
[43]Wijaya H W,Kojima T,Hara T,et al.Synthesis of 1,5-Pentanediol by hydrogenolysis of furfuryl alcohol over NiY2O3Composite Catalyst[J].Chem Cat Chem,2017,9(14):2869-2874.
[44]Wijaya H W,Sato T,Tange H,et al.Hydrogenolysis of furfural into 1,5-Pentanediol by employing Ni-M(M=Yor La)composite catalysts[J].Chem Lett,2017,46(5):744-746.
[45]Wijaya H W,Hara T,Ichikuni N,et al.Hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over a nickel-yttrium oxide catalyst containing ruthenium[J].Chem Lett,2018,47(1):103-106.
[46]Lee J C,Xu Y,Huber G W.High-throughput screening of monometallic catalysts for aqueous-phase hydrogenation of biomass-derived oxygenates[J].Appl Catal B-Environ,2013,140:98-107.
[47]Nakagawa Y,Tomishige K.Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol[J].Catal Today,2012,195(1):136-143.
[48]Ma C Y,Mu Z,Li J J,et al.Mesoporous Co3O4and Au/Co3O4catalysts for low-temperature oxidation of trace ethylene[J].J Am Chem Soc,2010,132:2608-2613.
[49]Zeitsch K J.The Chemistry and Technology of Furfural and Its Many By-products.Elsevier Science[M].Amsterdam,2000.
[50]Choura M,Belgacem N M,Gandini A.Acid-catalyzed polycondensation of furfuryl alcohol:Mechanisms of chromophore formation and cross-linking[J].Macromolecules,1996,29:3839-3850.
[51]Koso S,Watanabe H,Okumura K,et al.,Stable low-valence Re Oxcluster attached on Rh metal particles formed by hydrogen reduction and its formation mechanism[J].J Phys Chem C,2012,116(4):3079-3090.
[52]Tomishige K,Nakagawa Y,Tamura M.Selective hydrogenolysis and hydrogenation using metal catalysts directly modified with metal oxide species[J].Green Chem,2017,19(13):2876-2924.
[53]Ding Jing(丁璟),Zhao Jun-qi(赵俊琦),Cheng Shibiao(程时标),et al.Advances in production of biobased 1,6-HDO(生物基1,6-己二醇的研究进展)[J].Chem Ind&Engineer Pro(China)(化工进展),2015,32(12):4209-4213.
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