Reaserch progress in bifunctional catalysts for cellulose to polyols

doi:10.16085/j.issn.1000-6613.2015.09.018

Abstract

Abstract: The research on heterogeneous bifunctional catalysts (BFC) is the hot theme in cellulose processing to obtain green chemicals. But in this process,the BFC still had some fatal problems needed to be solved,such as the mechanism of the catalytic process,and its low selectivity for aimed products and hydrothermal stability. The research progress in most concerned BFC containing active metal components,such as Ru,Ni,W,and Pt,and the interacts between metal components and carriers for the application in cellulose to hexabasic alcohols and low carbon polyols (C₂-C₃),were introduced,and the recent advances in mono-metallic,bi-metallic BFC and the BFC based on different carriers were simply summarized. The analysis results demonstrated the ratios of different metal components and the internal interacts between active metals and carriers had a great influence on catalytic results. The future study should be focused on the mechanism of interacts of catalytic constituents and carriers.

Key words: biomass, degradation, hydrogenation, polyols, bifunctional catalysts

摘要： 双功能催化剂的研究一直是纤维素降解制备高值化学品过程中催化剂研究的热点问题,但其在催化纤维素降解过程中还存在着催化机理不明确、目标产物选择性不高、水热稳定性不好等问题。本文简述了目前最受关注的含Ru、Ni、W、Pt等体系的双功能催化剂和不同载体影响下的双功能催化剂在纤维素制备C₆多元醇、低碳多元醇(C₂~C₃)等化学品中的研究进展,初步总结了单金属、双金属体系和不同载体的双功能催化剂研究的前沿进展,分析表明不同活性金属之间配比以及活性金属与载体之间的相互作用均对催化效果产生重大影响;最后对其在纤维素制备多元醇中的应用前景进行了展望,指出继续研究活性金属之间及其与载体之间的相互作用将是今后研究的重点方向。

关键词: 生物质, 降解, 加氢, 多元醇, 双功能催化剂

CLC Number:

O629.12

XIAO Zhuqian, OUYANG Hongsheng, GE Qiuwei, WANG Zhenzhen, ZHANG Jinjian, JIANG Chengjun, JI Jianbing, MAO Jianwei. Reaserch progress in bifunctional catalysts for cellulose to polyols[J]. Chemical Industry and Engineering Progree, 2015, 34(09): 3323-3330.

肖竹钱, 欧阳洪生, 葛秋伟, 王珍珍, 张金建, 蒋成君, 计建炳, 毛建卫. 双功能催化剂在纤维素制多元醇中的研究进展[J]. 化工进展, 2015, 34(09): 3323-3330.

References

[1] Weingarten R,Cao F,Luterbacher J S,et al. Selective conversion of cellulose to hydroxymethylfurfural in polar aprotic solvents[J]. ChemCatChem,2014,6(8):2229-2234.

[2] Ramli N A S,Amin N A S. Catalytic hydrolysis of cellulose and oil palm biomass in ionic liquid to reducing sugar for levulinic acid production[J]. Fuel Processing Technology,2014,128:490-498.

[3] Tao F R,Song H L,Chou L J. Catalytic conversion of cellulose to chemicals in ionic liquid[J]. Carbohydrates Research,2011,346(1):58-63.

[4] Ding D Q,Wang J J,Xi J X,et al. High-yield production of levulinic acid from cellulose and its upgrading to gamma-valerolactone[J]. Green Chemistry,2014,16(8):3846-3853.

[5] 白净,张璐,方书起,等. 糖基生物质生产食品化工产品研究进展[J]. 化工进展,2015,34(1):212-218.

[6] Gardebje S,Larsson A,Lofgren C,et al. Controlling water permeability of composite films of polylactide acid,cellulose,and xyloglucan[J]. Journal of Applied Polymer Science,2015,132(1):41219-41226.

[7] Tao F R,Song H L,Yang J,et al. Catalytic hydrolysis of cellulose into furans in MnCl₂-ionic liquid system[J]. Carbohydrate Polymers,2011,85(2):363-368.

[8] Tao F R,Song H L,Chou L J. Hydrolysis of cellulose in SO₃H-functionalized ionic liquids[J]. Bioresource Technology,2011,102:9000-9006.

[9] Taherzadeh M J,Karimi K. Acid-based hydrolysis processes for ethanol from lignocellulosic materials:A review[J]. Bioresources,2007,2(3):472-499.

[10] Yan Y J,Jiang G H. Recent advances in catalytic conversion of cellulose into variable chemicals and bio-fuels[J]. Journal of Biobased Materials and Bioenergy,2014,8(6):553-569.

[11] Kim S B,Lee Y Y. Diffusion of sulfuric acid within lignocellulosic biomass particles and its impact on dilute-acid pretreatment[J]. Bioresource Technology,2002,83(2):165-171.

[12] Zhang H Y,Cheng Y T,Vispute T P,et al. Catalytic conversion of biomass-derived feedstocks into olefins and aromatics with ZSM-5:The hydrogen to carbon effective ratio[J]. Energy & Environmenatl Science,2009,4(6):2297-2307.

[13] Robert R,Ferdi S. Design of solid catalysts for the conversion of biomass[J]. Energy & Environmental Science,2009,2:610-626.

[14] Wang A Q,Zhang T. One-pot conversion of cellulose to ethylene glycol with multifunctional tungsten-based catalyst[J]. Accounts of Chemical Research,2013,46(7):1377-1386.

[15] Liu Y,Luo C,Liu H C. Tungsten trioxide selective conversion of cellulose into propylene glycol and ethylene glycol on a ruthenium catalyst[J]. Angewandte Chemie:International Edition,2012,51(13):3249-3253.

[16] Ji N,Zhang T,Zheng M Y,et al. Catalytic conversion of cellulose into ethylene glycol over supported carbide catalysts[J]. Catalysis Today,2009,147(2):77-85.

[17] Ding L N,Wang A Q,Zheng M Y,et al. Selective transformation of cellulose into sorbitol by using a bifunctional nichkel phosphide catalyst[J]. ChemSusChem,2010,3(7):818-821.

[18] Zhang J J,Lu F,Yu W Q,Chen J Z,et al. Selective hydrogenative cleavage of C-C bonds in sorbitol using Ni-Re/C catalyst under nitrogen atmosphere[J]. Catalysis Today,2014,234:107-112.

[19] 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,320:16-25.

[20] Kobayashi H,Ito Y,Komanoya T,et al. Synthesis of sugar alcohols by hydrolytic hydrogenation of cellulose over supported metal catalysts[J]. Green Chemistry,2011,13(2):326-333.

[21] Kobayashi H,Yamakoshi Y,Fukuoka A,et al. Production of sugar alcohols from real biomass by supported platinum catalyst[J]. Catalysis Today,2014,226:204-209.

[22] Gorp K V,Boerman E,Cavenaghi C V,et al. Catalytic hydrogenation of fine chemicals:Sorbitol production[J]. Catalysis Today,1999,52(2):349-361.

[23] 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:International Edition,2007,46(40):7636-7639.

[24] 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.

[25] Deng W P,Wang Y L,Zhang Q H,et al. Development of bifunctional catalysts for the conversions of cellulose or cellobiose into polyols and organic acids in water[J]. Catalysis Surveys from Asia,2012,16(2):91-105.

[26] Zhu W W,Yang H M,Chen J Z,et al. Efficient hydrogenolysis of cellulose into sorbitol catalyzed by a bifunctional catalyst[J]. Green Chemistry,2014,16(30):1534-1542.

[27] Han J W,Lee H. Direct conversion of cellulose into sorbitol using dual-functionalized catalysts in neutral aqueous solution[J]. Catalysis Communications,2012,19:115-118.

[28] Onda A,Ochi K,Yanaqisawa K. Selective hydrolysis of cellulose into glucose over solid acid catalysts[J]. Green Chemistry,2008,10:1033-1037.

[29] Kobayashi H,Komanoya T,Fukuoka A,et al. Conversion of cellulose into renewable chemicals by supported metal catalysis[J]. Applied Catalysis A:General,2011,409-410:13-20.

[30] Liu M,Deng W P,Zhang Q H,et al. Polyoxometalate-supported ruthenium nanoparticles as bifunctional heterogeneous catalysts for the conversions of cellobiose and cellulose into sorbitol under mild conditions[J]. Chemical Commnication,2011,47(34):9717-9719.

[31] Deng W P,Zhang Q H,Wang Y. Polyoxometalates as efficient catalysts for transformations of cellulose into platform chemicals[J]. Dalton Transactions,2012,41(33):9817-9831.

[32] Palkovits R,Tajvidi K,Ruppertc A M,et al. Heteropoly acids as efficient acid catalysts in the one-step conversion of cellulose to sugar alcohols[J]. Chemical Communication,2011,47(1):576-578.

[33] Van de Vyver S,Thomas J,Geboers J,et al. Catalytic production of levulinic acid from cellulose and other biomass-derived carbohydrates with sulfonated hyperbranched poly(arylene oxindole)s[J]. Energy & Environmental Science,2011,4(9):3601-3610.

[34] Shimizu K I,Furukawa H,Kobayashi N,et al. Effects of Bronsted and Lewis acidities on activity and selectivity of heteropolyacid-based catalysts for hydrolysis of cellobiose and cellulose[J]. Green Chemisrty,2009,11:1627-1632.

[35] Deng W P,Liu M,Wang Y,et al. Acid-catalysed direct transformation of cellulose into methyl glucosides in methanol at moderate temperatures[J]. Chemical Communication,2010,46(15):2668-2670.

[36] Deng W P,Zhu E Z,Wang Y,et al. Cs-substituted tungstophosphate-supported ruthenium nanoparticles as efficient and robust bifunctional catalysts for the conversion of inulin and cellulose into hexitols in water in the presence of H₂[J]. RSC Advances,2014,81(4):43131-43141.

[37] Chen J Z,Wang S P,Huang J,et al. Conversion of cellulose and cellobiose into sorbitol catalyzed by ruthenium supported on a polyoxometalate/metal-organic framework hybrid[J]. ChemSusChem,2013,6(8):1545-1555.

[38] Geboers J,Van de Vyver S,Carpentier K,et al. Efficient catalytic conversion of concentrated cellulose feeds to hexitols with heteropoly acids and Ru on carbon[J]. Chemical Communication,2010,46(20):3577-3579.

[39] Fukuoka A,Dhepe P L. Catalytic conversion of cellulose into sugar alcohols[J]. Angewandte Chemie:International Edition,2006,45(31):5161-5163.

[40] Liang G F,Cheng H Y,Zhao F Y,et al. Selective conversion of microcrystalline cellulose into hexitols on nickel particles encapsulated within ZSM-5 zeolite[J]. Green Chemistry,2012,14:2146-2149.

[41] Van de Vyver S,Geboers J,Dusselier M,et al. Selective bifunctional catalytic conversion of cellulose over reshaped Ni particles at the tip of carbon nanofiber[J]. ChemSusChem,2010,3(6):698-701.

[42] Wang X C,Meng L Q,Wu F,et al. Efficient conversion of microcrystalline cellulose to 1,2-alkanediols over supported Ni catalysts[J]. Green Chemistry,2012,14(3):758-765.

[43] Sun J Y,Liu H C. Selective hydrogenolysis of biomass-derived xylitol to ethylene glycol and propylene glycol on Ni/C and basic oxide-promoted Ni/C catalysts[J]. Catalysis Today,2014,234:75-82.

[44] Ding L N,Wang A Q,Zheng M Y,et al. Selective transformation of cellulose in to sorbitol by using a bifunctional nickel phosphide catalyst[J]. ChemSusChem,2010,3(7):818-821.

[45] Negoi A,Triantafyllidis K,Parvulescu V I,et al. The hydrolytic hydrogenation of cellulose to sorbitol over M (Ru,Ir,Pd,Rh)-BEA-zeolite catalysts[J]. Catalysis Today,2014,223:122-128.

[46] Deng W P,Tan X S,Wang Y,et al. Conversion of cellulose into sorbitol over carbon nanotube-supported ruthenium catalyst[J]. Catalsis Letters,2009,133(1-2):167-174.

[47] Wang H J,Zhu L L,Yang J,et al. High efficient conversion of cellulose to polyols with Ru/CNTs as catalyst[J]. Renewable Energy,2012,37(1):192-196.

[48] Yan N,Zhao C,Luo C,et al. One-step conversion of cellobiose to C₆-alcohols using a ruthenium nanocluster catalyst[J]. Journal of the American Chemical Society,2006,128(27):8714-8715.

[49] Sun R Y,Wang T T,Zhang T,et al. Versatile nickel-lanthanum (Ⅲ) catalyst for direct conversion of cellulose to glycols[J]. ACS Catalysis,2015,5(2):874-883.

[50] Zhang Y H,Wang A Q,Zhang T. A new 3D mesoporous carbon replicated from commercial silica as a catalyst support for direct conversion of cellulose into ethylene glycol[J]. Chemical Communication,2010,46(6):862-864.

[51] Geboers J,Van de Vyver S,Carpentier K,et al. Efficient hydrolytic hydrogenation of cellulose in the presence of Ru-loaded zeolites and trace amounts of mineral acid[J]. Catalysis Communication,2011,47(19):5590-5592.

[52] Ji N,Zhang T,Zheng M Y,et al. Direct catalytic conversion of cellulose into ethylene glycol using nickel-promoted tungsten carbide catalysts[J]. Angewandte Chemie:International Edition,2008,47:8510-8513.

[53] 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.

[54] Li C Z,Zheng M Y,Wang A Q,et al. One-pot catalytic hydrocracking of raw woody biomass into chemicals over supported carbide catalysts:Simultaneous conversion of cellulose,hemicellulose and lignin[J]. Energy & Environmental Science,2012,5(4):6383-6390.

[55] Zhao G H,Zheng M Y,Wang A Q,et al. Catalytic conversion of cellulose to ethylene glycol over tungsten phosphide catalysts[J]. Chinese Journal of Catalysis,2010,31(8):928-932.

[56] Zheng M Y,Pang J F,Wang A Q,et al. One-pot catalytic conversion of cellulose to ethylene glycol and other chemicals:From fundamental discovery to potential commercialization[J]. Chinese Journal of Catalysis,2014,35(5):602-613.

[57] Cao Y L,Wang J W,Kang M Q,et al. Efficient synthesis of ethylene glycol from cellulose over Ni-WO₃/SBA-15 catalysts[J]. Journal of Molecular Catalysis A:Chemical,2014,381:46-53.

[58] Baek I G,You S J,Park E D. Direct conversion of cellulose into polyols over Ni/W/SiO₂-Al₂O₃[J]. Bioresource Technology,2012,114:684-690.

[59] Zhao J Y,Hou B L,Wang A Q,et al. Kinetic study of Retro-Aldol condensation of glucose glycolaldehyde with ammonium metatungstate as the catalyst[J]. American Institute of Chemical Engineers,2014,60(11):3804-3813.

[60] Kourieh R,Bennici S,Marzo M,et al. Investigation of the WO₃/ZrO₂ surface acidic properties for the aqueous hydrolysis of cellobiose[J]. Catalysis Communications,2012,19:119-126.

[61] Levy R B,Boudart M. Platinum-like behavior of tungsten carbide in surface catalysis[J]. Science,1973,181:547-549.

[62] Zhang J Y,Hou B L,Wang A Q,et al. Kinetic study of the competitive hydrogenation of glycolaldehyde and glucose on Ru/C with or without AMT[J]. American Institute of Chemical Engineers,2015,61:224-238.

[63] Ji N,Zheng M Y,Wang A Q,et al. Nickel-promoted tungsten carbide catalysts for cellulose conversion:Effect of preparation methods[J]. ChemSusChem,2012,5(5):939-944.

[64] Zhou L K,Pang J F,Wang A Q,et al. Catalytic converion of jerusalem artichoke stalk to ethylene glycol over a combined catalyst of WO₃ and Raney Ni[J]. Chinese Journal of Catalysis,2013,34(11):2041-2046.