离子液体在木质素研究中的应用

doi:10.3969/j.issn.0253-2417.2015.02.025

摘要/Abstract

摘要： 详细综述了离子液体溶解、提取木质素的研究,分析了离子液体溶解木质素的机理,讨论了不同因素对木质素提取率的影响,介绍了木质素在离子液体中不同的降解方法,并对离子液体在木质素研究中的应用进行了总结和展望。

Abstract: The recent progress in dissolution and extraction of lignin with ionic liquids (ILs) is reviewed in detail. The possible dissolution mechanisms of lignin in ILs are analyzed. The influencing factors on the lignin extraction efficiency are discussed, and different depolymerization techniques of lignin in ILs are summarized. Finally, the summary and prospect on the application of ILs in lignin processing are given.

Key words: ionic liquid, lignin, dissolution, extraction, depolymerization

中图分类号:

TQ35

李利芬, 胡英成. 离子液体在木质素研究中的应用[J]. 林产化学与工业, 2015, 35(2): 163-170.

LI Li-fen, HU Ying-cheng. Application of Ionic Liquids in Lignin Processing[J]. Chemistry and Industry of Forest Products, 2015, 35(2): 163-170.

参考文献

[1] HOLLADAY J E, BOZELL J J, WHITE J F, et al.Top Value-added Chemicals from Biomass, Volume II-Results of Screening for Potential Candidates from Biorefinery Lignin[M].Richland, WA:Pacific Northwest National Laboratory, 2007:39.
[2] ZAVREL M, BROSS D, FUNKE M, et al.High-throughput screening for ionic liquids dissolving (ligno-)cellulose[J].Bioresource Technology, 2009, 100(9):2580-2587.
[3] PU Yun-qiao, JIANG Nan, RAGAUSKAS A J.Ionic liquid as a green solvent for lignin[J].Journal of Wood Chemistry and Technology, 2007, 27(1):23-33.
[4] FORT D A, REMSING R C, SWATLOSKI R P, et al.Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride[J].Green Chemistry, 2007, 9(1):63-69.
[5] CHAKAR F S, RAGAUSKAS A J.Review of current and future softwood kraft lignin process chemistry[J].Industrial Crops and Products, 2004, 20(2):131-141.
[6] 杨淑惠.植物纤维化学[M].北京:中国轻工业出版社, 2011:69-72. YANG Shu-hui.Lignocellulosic Chemistry[M].Beijing:China Light Industry Press, 2011:69-72.
[7] MENG Ling-yan, KANG Su-min, ZHANG Xue-ming, et al.Comparative characterization of lignins extracted from cotton stalk based on complete dissolution in different systems[J].Industrial & Engineering Chemistry Research, 2012, 51(29):9858-9866.
[8] ZAKZESKI J, BRUIJNINCX P C A, JONGERIUS A L, et al.The catalytic valorization of lignin for the production of renewable chemicals[J].Chemical Reviews, 2010, 110(6):3552-3599.
[9] COLEMAN D, GATHERGOOD N.Biodegradation studies of ionic liquids[J].Chemical Society Reviews, 2010, 39(2):600-637.
[10] LIU Qiu-ping, HOU Xue-dan, LI Ning, et al.Ionic liquids from renewable biomaterials:Synthesis, characterization and application in the pretreatment of biomass[J].Green Chemistry, 2012, 14(2):304-307.
[11] HOU Xue-dan, LIU Qiu-ping, SMITH T J, et al.Evaluation of toxicity and biodegradability of cholinium amino acids ionic liquids[J].PLoS One, 2013, 8(3):e59145.
[12] FRANCISCO M, VAN DEN BRUINHORST A, KROON M C.New natural and renewable low transition temperature mixtures (LTTMs):Screening as solvents for lignocellulosic biomass processing[J].Green Chemistry, 2012, 14(8):2153-2157.
[13] ABBOTT A P, CAPPER G, DAVIES D L, et al.Novel solvent properties of choline chloride/urea mixtures[J].Chemical Communications, 2003(1):70-71.
[14] CASAS A, PALOMAR J, ALONSO M V, et al.Comparison of lignin and cellulose solubilities in ionic liquids by COSMO-RS analysis and experimental validation[J].Industrial Crops and Products, 2012, 37(1):155-163.
[15] GEORGE A, TRAN K, MORGAN T J, et al.The effect of ionic liquid cation and anion combinations on the macromolecular structure of lignins[J].Green Chemistry, 2011, 13(12):3375-3385.
[16] KILPELÄINEN I, XIE Hai-bo, KING A, et al.Dissolution of wood in ionic liquids[J].Journal of Agricultural and Food Chemistry, 2007, 55(22):9142-9148.
[17] 周红霞, 李露, 刘仕伟, 等.磷酸酯基离子液体对木质素的溶解性能[J].高分子材料科学与工程, 2012, 28(3):49-52. ZHOU Hong-xia, LI lu, LIU Shi-wei, et al.Dissolution of lignin in phosphoester ionic liquid[J].Polymer Materials Science and Engineering, 2012, 28(3):49-52.
[18] LEE S H, DOHERTY T V, LINHARDT R J, et al.Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis[J].Biotechnology and Bioengineering, 2009, 102(5):1368-1376.
[19] JI Wen-yan, DING Zhen-dong, LIU Jian-hua, et al.Mechanism of lignin dissolution and regeneration in ionic liquid[J].Energy Fuels, 2012, 26(10):6393-6403.
[20] TADESSE H, LUQUE R.Advances on biomass pretreatment using ionic liquids:An overview[J].Energy & Environmental Science, 2011, 4(10):3913-3929.
[21] ANUGWOM I, MÄKI-ARVELA P, VIRTANEN P, et al.Selective extraction of hemicelluloses from spruce using switchable ionic liquids[J].Carbohydrate Polymers, 2012, 87(3):2005-2011.
[22] SUN Ning, RAHMAN M, QIN Ying, et al.Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate[J].Green Chemistry, 2009, 11(5):646-655.
[23] MUHAMMAD N, MAN Z, BUSTAM M A, et al.Dissolution and delignification of bamboo biomass using amino acid-based ionic liquid[J].Applied Biochemistry and Biotechnology, 2011, 165(3/4):998-1009.
[24] TAN S S Y, MACFARLANE D R, UPFAL J, et al.Extraction of lignin from lignocellulose at atmospheric pressure using alkylbenzenesulfonate ionic liquid[J].Green Chemistry, 2009, 11(3):339-345.
[25] HOU Xue-dan, SMITH T J, LI Ning, et al.Novel renewable ionic liquids as highly effective solvents for pretreatment of rice straw biomass by selective removal of lignin[J].Biotechnology and Bioengineering, 2012, 109(10):2484-2493.
[26] PINKERT A, GOEKE D F, MARSH K N, et al.Extracting wood lignin without dissolving or degrading cellulose:Investigations on the use of food additive-derived ionic liquids[J].Green Chemistry, 2011, 13(11):3124-3136.
[27] MUHAMMAD N, MAN Z, BUSTAM M A, et al.Investigations of novel nitrile-based ionic liquids as pre-treatment solvent for extraction of lignin from bamboo biomass[J].Journal of Industrial and Engineering Chemistry, 2013, 19(1):207-214.
[28] ACHINIVU E C, HOWARD R M, LI Guo-qing, et al.Lignin extraction from biomass with protic ionic liquids[J].Green Chemistry, 2014, 16(3):1114-1119.
[29] FU Dong-bao, MAZZA G, TAMAKI Y.Lignin extraction from straw by ionic liquids and enzymatic hydrolysis of the cellulosic residues[J].Journal of Agricultural and Food Chemistry, 2010, 58(5):2915-2922.
[30] LI Wei-ying, SUN Ning, STONER B, et al.Rapid dissolution of lignocellulosic biomass in ionic liquids using temperatures above the glass transition of lignin[J].Green Chemistry, 2011, 13(8):2038-2047.
[31] WANG Hui, MAXIM M L, GURAU G, et al.Microwave-assisted dissolution and delignification of wood in 1-ethyl-3-methylimidazolium acetate[J].Bioresource Technology, 2013, 136:739-742.
[32] CASAS A, OLIET M, ALONSO M V, et al.Dissolution of Pinus radiata and Eucalyptus globulus woods in ionic liquids under microwave radiation:Lignin regeneration and characterization[J].Separation and Purification Technology, 2012, 97:115-122.
[33] BRANDT A, RAY M J, TO T Q, et al.Ionic liquid pretreatment of lignocellulosic biomass with ionic liquid-water mixtures[J].Green Chemistry, 2011, 13(9):2489-2499.
[34] HOU Xue-dan, LI Ning, ZONG Min-hua.Facile and simple pretreatment of sugar cane bagasse without size reduction using renewable ionic liquids-water mixtures[J].ACS Sustainable Chemistry & Engineering, 2013, 1(5):519-526.
[35] HOU Xue-dan, LI Ning, ZONG Min-hua.Significantly enhancing enzymatic hydrolysis of rice straw after pretreatment using renewable ionic liquid-water mixtures[J].Bioresource Technology, 2013, 136:469-474.
[36] HOU Xue-dan, LI Ning, ZONG Min-hua.Renewable bio-ionic liquids-water mixtures-mediated selective removal of lignin from rice straw:Visualization of changes in composition and cell wall structure[J].Biotechnology and Bioengineering, 2013, 110(7):1895-1902.
[37] WEERACHANCHAI P, LEE J M.Effect of organic solvent in ionic liquid on biomass pretreatment[J].ACS Sustainable Chemistry & Engineering, 2013, 1(8):894-902.
[38] KÖHLER S, LIEBERT T, HEINZE T J.Interactions of ionic liquids with polysaccharides.VI:Pure cellulose nanoparticles from trimethylsilyl cellulose synthesized in ionic liquids[J].Journal of Polymer Science Part A:Polymer Chemistry, 2008, 46(12):4070-4080.
[39] GERICKE M, LIEBERT T, HEINZE T.Interaction of ionic liquids with polysaccharides, 8-synthesis of cellulose sulfates suitable for polyelectrolyte complex formation[J].Macromolecular Bioscience, 2009, 9(4):343-353.
[40] KIM J Y, SHIN E J, EOM I Y, et al.Structural features of lignin macromolecules extracted with ionic liquid from poplar wood[J].Bioresource Technology, 2011, 102(19):9020-9025.
[41] WEN Jia-long, SUN Shao-long, XUE Bai-liang, et al.Quantitative structures and thermal properties of birch lignins after ionic liquid pretreatment[J].Journal of Agricultural and Food Chemistry, 2013, 61(3):635-645.
[42] VARANASI P, SINGH P, ARORA R, et al.Understanding changes in lignin of Panicum virgatum and Eucalyptus globulus as a function of ionic liquid pretreatment[J].Bioresource Technology, 2012, 126:156-161.
[43] ZHAO Dong-bin, WU Min, KOU Yuan, et al.Ionic liquids:Applications in catalysis[J].Catalysis Today, 2002, 74(1/2):157-189.
[44] JIA Song-yan, COX B J, GUO Xin-wen, et al.Hydrolytic cleavage of β-O-4 ether bonds of lignin model compounds in an ionic liquid with metal chlorides[J].Industrial & Engineering Chemistry Research, 2011, 50(2):849-855.
[45] BINDER J B, GRAY M J, WHITE J F, et al.Reactions of lignin model compounds in ionic liquids[J].Biomass and Bioenergy, 2009, 33(9):1122-1130.
[46] JIA Song-yan, COX B J, GUO Xin-wen, et al.Cleaving the β-O-4 bonds of lignin model compounds in an acidic ionic liquid, 1-H-3-methylimidazolium chloride:An optional strategy for the degradation of lignin[J].ChemSusChem, 2010, 3(9):1078 -1084.
[47] 贾松岩.木质素模型化合物的β-O-4键在离子液体中断裂的研究[D].大连:大连理工大学博士学位论文, 2012. JIA Song-yan.Study on the cleavage of β-O-4 bonds of lignin model compounds in ionic liquid[D].Doctoral Dissertation of Dalian University of Technology, 2012.
[48] COX B J, JIA Song-yan, ZHANG Z C, et al.Catalytic degradation of lignin model compounds in acidic imidazolium based ionic liquids:Hammett acidity and anion effects[J].Polymer Degradation and Stability, 2011, 96(4):426-431.
[49] COX B J, EKERDT J G.Depolymerization of oak wood lignin under mild conditions using the acidic ionic liquid 1-H-3-methylimidazolium chloride as both solvent and catalyst[J].Bioresource Technology, 2012, 118:584-588.
[50] JIA Song-yan, COX B J, GUO Xin-wen, et al.Decomposition of a phenolic lignin model compound over organic N-bases in an ionic liquid[J].Holzforschung, 2010, 64(5):577-580.
[51] TAVARES A P M, RODRIGUES O, MACEDO E A.Ionic liquids as alternative co-solvents for laccase:Study of enzyme activity and stability[J].Biotechnology and Bioengineering, 2008, 101(1):201-207.
[52] SGALLA S, FABRIZI G, CACCHI S, et al.Horseradish peroxidase in ionic liquids:Reactions with water insoluble phenolic substrates[J].Journal of Molecular Catalysis B:Enzymatic, 2007, 44(3/4):144-148.
[53] CHEN Ai-cheng, ROGERS E I, COMPTON R G.Abrasive stripping voltammetric studies of lignin and lignin model compounds[J].Electroanalysis, 2010, 22(10):1037-1044.
[54] REICHERT E, WINTRINGER R, VOLMER D A, et al.Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid[J].Physical Chemistry Chemical Physics, 2012, 14(15):5214-5221.
[55] STÄRK K, TACCARDI N, BÖSMANN A, et al.Oxidative depolymerization of lignin in ionic liquids[J].ChemSusChem, 2010, 3(6):719-723.
[56] LIU Shi-wei, SHI Zhong-liang, LI Lu, et al.Process of lignin oxidation in an ionic liquid coupled with separation[J].RSC Advances, 2013, 3(17):5789-5793.
[57] YAN Ning, YUAN Yuan, DYKEMAN R, et al.Hydrodeoxygenation of lignin-derived phenols into alkanes by using nanoparticle catalysts combined with brnsted acidic ionic liquids[J].Angewandte Chemie International Edition, 2010, 49(32):5549-5553.