Chemistry and Industry of Forest Products ›› 2017, Vol. 37 ›› Issue (2): 22-34.doi: 10.3969/j.issn.0253-2417.2017.02.003
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CHEN Lungang1, LIU Yong1,2, ZHANG Xinghua1, ZHANG Qi1, WANG Tiejun1, MA Longlong1
Received:
2016-07-20
Online:
2017-04-25
Published:
2017-05-04
CLC Number:
CHEN Lungang, LIU Yong, ZHANG Xinghua, ZHANG Qi, WANG Tiejun, MA Longlong. Progress on Reaction and Catalyst for Production of C5/C6 Alkane Fuels from Cellulose by Catalytic Conversion[J]. Chemistry and Industry of Forest Products, 2017, 37(2): 22-34.
[1] IEA. World Energy Investment Outlook 2014[M]. International Energy Agency. [2] ALONSO D M, WETTSTEIN S G, DUMESIC J A. Bimetallic catalysts for upgrading of biomass to fuels and chemicals[J]. Chemical Society Reviews, 2012,41(24):8075-8098. [3] CORMA A, IBORRA S, VELTY A. Chemical routes for the transformation of biomass into chemicals[J]. Chemical Reviews, 2007, 107(6):2411-2502. [4] GRAY H L, STAUD C J. Recent advances in cellulose and starch chemistry[J]. Chemical Reviews, 1928, 4(4):355-373. [5] CLIMENT M J, CORMA A, IBORRA S. Heterogeneous catalysts for the one-pot synthesis of chemicals and fine chemicals[J]. Chemical Reviews, 2011, 111(2):1072-1133. [6] FUKUOKA A, DHEPE P L. Catalytic conversion of cellulose into sugar alcohols[J]. Angewandte Chemie, 2006, 118(31):5285-5287. [7] HUBER G W, IBORRA S, CORMA A. Synthesis of transportation fuels from biomass:Chemistry, catalysts, and engineering[J]. Chemical Reviews, 2006, 106(9):4044-4098. [8] NEGAHDAR L, OLTMANNS J U, PALKOVITS S, et al. Kinetic investigation of the catalytic conversion of cellobiose to sorbitol[J]. Applied Catalysis B:Environmental, 2014, 147:677-683. [9] OGASAWARA Y, ITAGAKI S, YAMAGUCHI K, et al. Saccharification of natural lignocellulose biomass and polysaccharides by highly negatively charged heteropolyacids in concentrated aqueous solution[J].ChemSusChem, 2011, 4(4):519-525. [10] PALKOVITS R, TAJVIDI K, RUPPERT A M, et al.Heteropoly acids as efficient acid catalysts in the one-step conversion of cellulose to sugar alcohols[J]. Chemical Communications, 2011, 47(1):576-578. [11] ZHU Y H, KONG Z N, STUBBS L P, et al.Conversion of cellulose to hexitols catalyzed by ionic liquid-stabilized ruthenium nanoparticles and a reversible binding agent[J]. ChemSusChem, 2010, 3(1):67-70. [12] LUO C, WANG S, LIU H C. Cellulose conversion into polyols catalyzed by reversibly formed acids and supported ruthenium clusters in hot water[J].Angewandte Chemie, 2007, 119(40):7780-7783. [13] HILGERT J, MEINE N, RINALDI R, et al.Mechanocatalytic depolymerization of cellulose combined with hydrogenolysis as a highly efficient pathway to sugar alcohols[J]. Energy & Environmental Science, 2013, 6(1):92-96. [14] PHILIPPAERTS A, GOOSSENS S, VERMANDEL W, et al. Design of Ru-zeolites for hydrogen-free production of conjugated linoleic acids[J]. ChemSusChem, 2011, 4(6):757-767. [15] KOBAYASHI H, MATSUHASHI H, KOMANOYA T, et al. Transfer hydrogenation of cellulose to sugar alcohols over supported ruthenium catalysts[J]. Chemical Communications, 2011, 47(8):2366-2368. [16] OP DE BEECK B, GEBOERS J, VAN DE VYVER S, et al. Conversion of (ligno)cellulose feeds to isosorbide with heteropoly acids and ru on carbon[J]. ChemSusChem, 2013, 6(1):199-208. [17] PARK D S, YUN D, KIM T Y, et al. A mesoporous carbon-supported Pt nanocatalyst for the conversion of lignocellulose to sugar alcohols[J]. ChemSusChem, 2013, 6(12):2281-2289. [18] DING L N, WANG A Q, ZHENG M Y, et al. Selective transformation of cellulose into sorbitol by using a bifunctional nickel phosphide catalyst[J].ChemSusChem, 2010, 3(7):818-821. [19] HUANG Y B, DAI J J, DENG X J, et al.Ruthenium-catalyzed conversion of levulinic acid to pyrrolidines by reductive amination[J]. ChemSusChem, 2011, 4(11):1578-1581. [20] MIYAZAWA T, KOSO S, KUNIMORI K, et al. Development of a Ru/C catalyst for glycerol hydrogenolysis in combination with an ion-exchange resin[J]. Applied Catalysis A:General, 2007, 318:244-251. [21] OLIVIERO L, BARBIER-JR J, DUPREZ D, et al. Catalytic wet air oxidation of phenol and acrylic acid over Ru/C and Ru-CeO2/C catalysts[J]. Applied Catalysis B:Environmental, 2000, 25(4):267-275. [22] ROSSETTI I, FORNI L. Effect of Ru loading and of Ru precursor in Ru/C catalysts for ammonia synthesis[J]. Applied Catalysis A:General, 2005, 282(1/2):315-320. [23] FANG Z, ZHANG F, ZENG H Y, et al. Production of glucose by hydrolysis of cellulose at 423 K in the presence of activated hydrotalcite nanoparticles[J]. Bioresource Technology, 2011, 102(17):8017-8021. [24] KOBAYASHI H, YABUSHITA M, KOMANOYA T, et al. High-yielding one-pot synthesis of glucose from cellulose using simple activated carbons and trace hydrochloric acid[J].ACS Catalysis, 2013, 3(4):581-587. [25] LAI D M, DENG L, LI J A, et al.Hydrolysis of cellulose into glucose by magnetic solid acid[J]. ChemSusChem, 2011, 4(1):55-58. [26] LANZAFAME P, TEMI D M, PERATHONER S, et al. Direct conversion of cellulose to glucose and valuable intermediates in mild reaction conditions over solid acid catalysts[J]. Catalysis Today, 2012, 179(1):178-184. [27] PANG J F, WANG A Q, ZHENG M Y, et al. Hydrolysis of cellulose into glucose over carbons sulfonated at elevated temperatures[J]. Chemical Communications, 2010, 46(37):6935-6937. [28] TAKAGAKI A, TAGUSAGAWA C, DOMEN K. Glucose production from saccharides using layered transition metal oxide and exfoliated nanosheets as a water-tolerant solid acid catalyst[J]. Chemical Communications, 2008(42):5363-5365. [29] WANG H Y, ZHANG C B, HE H, et al. Glucose production from hydrolysis of cellulose over a novel silica catalyst under hydrothermal conditions[J]. Journal of Environmental Sciences, 2012, 24(3):473-478. [30] DENG W P, LIU M, TAN X S, et al.Conversion of cellobiose into sorbitol in neutral water medium over carbon nanotube-supported ruthenium catalysts[J]. Journal of Catalysis, 2010, 271(1):22-32. [31] LI J R, SOARES H S M P, MOULIJN J A, et al.Simultaneous hydrolysis and hydrogenation of cellobiose to sorbitol in molten salt hydrate media[J]. Catalysis Science & Technology, 2013, 3(6):1565-1572. [32] WANG D, NIU W Q, TAN M H, et al.Pt nanocatalysts supported on reduced graphene oxide for selective conversion of cellulose or cellobiose to sorbitol[J]. ChemSusChem, 2014, 7(5):1398-1406. [33] PANG J F, ZHENG M Y, WANG A Q, et al. Catalytic hydrogenation of corn stalk to ethylene glycol and 1,2-propylene glycol[J]. Industrial & Engineering Chemistry Research, 2011, 50(11):6601-6608. [34] TAI Z J, ZHANG J Y, WANG A Q, et al.Catalytic conversion of cellulose to ethylene glycol over a low-cost binary catalyst of Raney Ni and tungstic acid[J]. ChemSusChem, 2013, 6(4):652-658. [35] ZHENG M Y, WANG A Q, JI N, et al.Transition metal-tungsten bimetallic catalysts for the conversion of cellulose into ethylene glycol[J]. ChemSusChem, 2010, 3(1):63-66. [36] HUBER G W, CORTRIGHT R D, DUMESIC J A. Renewable alkanes by aqueous-phase reforming of biomass-derived oxygenates[J]. Angewandte Chemie, 2004.116(12), 1575-1577. [37] LI N, TOMPSETT G A, HUBER G W. Renewable high-octane gasoline by aqueous-phase hydrodeoxygenation of C5 and C6 carbohydrates over Pt/Zirconium phosphate catalysts[J]. ChemSusChem, 2010, 3(10):1154-1157. [38] LI N, HUBER G W. Aqueous-phase hydrodeoxygenation of sorbitol with Pt/SiO2-Al2O3:Identification of reaction intermediates[J]. Journal of Catalysis, 2010, 270(1):48-59. [39] VILCOCQ L, CABIAC A, ESPECEL C, et al.Study of the stability of Pt/SiO2-Al2O3 catalysts in aqueous medium:Application for sorbitol transformation[J]. Catalysis Communications, 2011, 15(1):18-22. [40] VILCOCQ L, KOERIN R, CABIAC A, et al. New bifunctional catalytic systems for sorbitol transformation into biofuels[J]. Applied Catalysis B:Environmental, 2014, 148:499-508. [41] VILCOCQ L, CABIAC A, ESPECEL C, et al. Hydrocarbon fuel synthesis from sorbitol over bifunctional catalysts:Association of tungstated titania with platinum, palladium or iridium[J].Catalysis Today, 2015, 242:91-100. [42] AMADA Y, SHINMI Y, KOSO S, et al.Reaction mechanism of the glycerol hydrogenolysis to 1,3-propanediol over Ir-ReOx/SiO2 catalyst[J]. Applied Catalysis B:Environmental, 2011, 105(1/2):117-127. [43] DAVDA R R, SHABAKER J W, HUBER G W, et al.Aqueous-phase reforming of ethylene glycol on silica-supported metal catalysts[J]. Applied Catalysis B:Environmental, 2003, 43(1):13-26. [44] VILCOCQ L, CABIAC A, ESPECEL C, et al.New insights into the mechanism of sorbitol transformation over an original bifunctional catalytic system[J]. Journal of Catalysis, 2014, 320:16-25. [45] ZHANG Q, WANG T J, LI B, et al.Aqueous phase reforming of sorbitol to bio-gasoline over Ni/HZSM-5 catalysts[J]. Applied Energy, 2012, 97:509-513. [46] ZHANG Q, WANG T J, XU Y, et al.Production of liquid alkanes by controlling reactivity of sorbitol hydrogenation with a Ni/HZSM-5 catalyst in water[J]. Energy Conversion and Management, 2014, 77:262-268. [47] ZHANG Q, JIANG T, LI B, et al. Highly selective sorbitol hydrogenolysis to liquid alkanes over Ni/HZSM-5 catalysts modified with pure silica MCM-41[J].ChemCatChem, 2012, 4(8):1084-1087. [48] JIANG T, ZHANG Q, WANG T J, et al.High yield of pentane production by aqueous-phase reforming of xylitol over Ni/HZSM-5 and Ni/MCM22 catalysts[J]. Energy Conversion and Management, 2012, 59:58-65. [49] CHEN K Y, TAMURA M, YUAN Z L, et al. One-pot conversion of sugar and sugar polyols ton-alkanes without C-C Dissociation over the Ir-ReOx/SiO2 catalyst combined with H-ZSM-5[J]. ChemSusChem, 2013,6(4):613-21. [50] LV D C, LIU Y Q, ZHANG B B, et al. Production of liquid hydrocarbons from sorbitol by reduction with hydroiodic acid[J]. Energy & Fuels, 2014, 28(6):3802-3807. [51] XI J X, XIA Q N, SHAO Y, et al. Production of hexane from sorbitol in aqueous medium over Pt/NbOPO4 catalyst[J]. Applied Catalysis B:Environmental, 2016, 181:699-706. [52] MCLAUGHLIN M P, ADDUCI L L, BECKER J J, et al. Iridium-catalyzed hydrosilylative reduction of glucose to hexane(s)[J]. Journal of the American Chemical Society, 2013, 135(4):1225-1227. [53] ADDUCI L L, MCLAUGHLIN M P, BENDER, T A, et al. Metal-free deoxygenation of carbohydrates[J].Angewandte Chemie-International Edition, 2014, 53(6):1646-1649. [54] GEVORGYAN V, LIU J X, RUBIN M, et al.A novel reduction of alcohols and ethers with a HSiEt3/catalytic B(C6F5)3 system[J]. Tetrahedron Letters, 1999, 40(50):8919-8922. [55] OP DE BEECK B, DUSSELIER M, GEBOERS J, et al. Direct catalytic conversion of cellulose to liquid straight-chain alkanes[J]. Energy & Environmental Science, 2015, 8(1):230-240. [56] OSAKA Y, IKEDA Y, HASHIZUME D, et al.Direct hydrodeoxygenation of cellulose and xylan to lower alkanes on ruthenium catalysts in subcritical water[J]. Biomass and Bioenergy, 2013, 56:1-7. [57] MURATA K, LIU Y Y, INABA M, et al.Hydrocracking of biomass-derived materials into alkanes in the presence of platinum-based catalyst and hydrogen[J]. Catalysis Letters, 2010, 140(1):8-13. [58] KATO Y, SEKINE Y. One pot direct catalytic conversion of cellulose to hydrocarbon by decarbonation using Pt/H-beta zeolite catalyst at low temperature[J]. Catalysis Letters, 2013, 143(5):418-423. [59] LIAO Y H, LIU Q Y, WANG T J, et al.Zirconium phosphate combined with Ru/C as a highly efficient catalyst for the direct transformation of cellulose to C6 alditols[J]. Green Chemistry, 2014, 16(6):3305-3312. [60] MEINE N, RINALDI R, SCHUTH F. Solvent-free catalytic depolymerization of cellulose to water-soluble oligosaccharides[J]. ChemSusChem, 2012, 5(8):1449-1454. [61] SHROTRI A, LAMBERT L K, TANKSALE A, et al. Mechanical depolymerisation of acidulated cellulose:Understanding the solubility of high molecular weight oligomers[J]. Green Chemistry, 2013, 15(10):2761-2770. [62] LIU S B, TAMURA M, NAKAGAWA Y, et al. One-pot conversion of cellulose into n-Hexane over the Ir-ReOx/SiO2 catalyst combined with HZSM-5[J]. ACS Sustainable Chemistry & Engineering, 2014, 2(7):1819-1827. [63] LIU Y, CHEN L G, WANG T J, et al. High yield of renewable hexanes by direct hydrolysis-hydrodeoxygenation of cellulose in aqueous phase catalytic system[J]. RSC Advances, 2015, 5:11649-11657. [64] LIU Y, CHEN L G, WANG T J, et al. One-pot catalytic conversion of raw lignocellulosic biomass into gasoline alkanes and chemicals over LiTaMoO6 and Ru/C in aqueous phosphoric acid[J]. ACS Sustainable Chemistry & Engineering, 2015, 3(8):1745-1755. [65] XIA Q N, CHEN Z J, SHAO Y, et al. Direct hydrodeoxygenation of raw woody biomass into liquid alkanes[J]. Nature Communications, 2016, 7:11162. |
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