Citation: | Xu Feng, Cheng Peng, Guo Zongwei, Xu Yanglei. Research progress on the fractionation and structural properties of lignin based on deep eutectic solvents[J]. Journal of Beijing Forestry University, 2021, 43(4): 158-168. DOI: 10.12171/j.1000-1522.20200410 |
[1] |
裴继诚, 杨淑慧, 平清伟, 等. 植物纤维化学[M]. 北京: 中国轻工业出版社, 2016.
Pei J C, Yang S H, Ping Q W, et al. Lignocellulosic chemistry[M]. Beijing: China Light Industry Press, 2016.
|
[2] |
Chen L, Dou J, Ma Q, et al. Rapid and near-complete dissolution of wood lignin at ≤ 80 ℃ by a recyclable acid hydrotrope[J]. Science Advances, 2017, 3(9): e1701735. doi: 10.1126/sciadv.1701735
|
[3] |
刘金科, 杨桂花, 齐乐天, 等. 胆碱类低共熔溶剂选择性分离杨木中木质素的研究[J]. 中国造纸, 2020, 39(4):1−9.
Liu J K, Yang G H, Qi L T, et al. Selective extraction of poplar lignin with choline-based deep eutectic solvents[J]. China Pulp & Paper, 2020, 39(4): 1−9.
|
[4] |
van Osch D, Kollau L, van den Bruinhorst A, et al. Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation[J]. Physical Chemistry Chemical Physics, 2017, 19(4): 2636−2665. doi: 10.1039/C6CP07499E
|
[5] |
Lyu G, Wu Q, Li T, et al. Thermochemical properties of lignin extracted from willow by deep eutectic solvents (DES)[J]. Cellulose, 2019, 26(15): 8501−8511. doi: 10.1007/s10570-019-02489-8
|
[6] |
马晓振, 罗清, 秦冬冬, 等. 木质素基生物质聚氨酯[J]. 化学进展, 2020, 32(5):617−626.
Ma X Z, Luo Q, Qin D D, et al. Lignin-based polyurethane[J]. Progress in Chemistry, 2020, 32(5): 617−626.
|
[7] |
罗通, 吕高金, 王超, 等. 工业木质素活化改性及其在复合材料中的应用进展[J]. 中国造纸, 2020, 39(9):60−67.
Luo T, Lü G J, Wang C, et al. Modification of industrial lignin and its application in composite materials: a review[J]. China Pulp & Paper, 2020, 39(9): 60−67.
|
[8] |
李小玉, 李广慈, 李学兵. 不同化学法分离解聚过程对木质素结构的影响[J]. 辽宁石油化工大学学报, 2020, 40(1):1−9. doi: 10.3969/j.issn.1672-6952.2020.01.001
Li X Y, Li G C, Li X B, et al. Effect of chemical separation and depolymerization processes on lignin structure[J]. Journal of Liaoning Petrochemical University, 2020, 40(1): 1−9. doi: 10.3969/j.issn.1672-6952.2020.01.001
|
[9] |
Haldar D, Purkait M K. A review on the environment-friendly emerging techniques for pretreatment of lignocellulosic biomass: mechanistic insight and advancements[J]. Chemosphere, 2021, 264: 128523. doi: 10.1016/j.chemosphere.2020.128523
|
[10] |
Li C L, Knierim B, Manisseri C, et al. Comparison of dilute acid and ionic liquid pretreatment of switchgrass: biomass recalcitrance, delignification and enzymatic saccharification[J]. Bioresource Technology, 2010, 101(13): 4900−4906. doi: 10.1016/j.biortech.2009.10.066
|
[11] |
刘振, 孙海红, 郝静静. 离子液体对玉米秸秆组分的溶解选择性[J]. 可再生能源, 2014, 32(6):871−875.
Liu Z, Sun H H, Hao J J. Solubility selectivity of ionic liquids to components of corn straw[J]. Renewable Energy Resources, 2014, 32(6): 871−875.
|
[12] |
周全伟. 基于醇胺型离子液体处理的奇岗草木质素的分离机制及其用于膜材料制备[D]. 济南: 齐鲁工业大学, 2020.
Zhou Q W. Separation of Miscanthus × giganteus lignin based on the treatment of alcoholamine-type ionic liquid system and its application in preparation of composite membrane material[D]. Jinan: Qilu University of Technology, 2020.
|
[13] |
Maki-Arvela P, Anugwom I, Virtanen P, et al. Dissolution of lignocellulosic materials and its constituents using ionic liquids: a review[J]. Industrial Crops and Products, 2010, 32(3): 175−201. doi: 10.1016/j.indcrop.2010.04.005
|
[14] |
Shen Y, Sun J K, Yi Y X, et al. One-pot synthesis of levulinic acid from cellulose in ionic liquids[J]. Bioresource Technology, 2015, 192: 812−816. doi: 10.1016/j.biortech.2015.05.080
|
[15] |
Abbott A P, Boothby D, Capper G, et al. Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids[J]. Journal of the American Chemical Society, 2004, 126(29): 9142−9147. doi: 10.1021/ja048266j
|
[16] |
Sanchez P B, Gonzalez B, Salgado J, et al. Physical properties of seven deep eutectic solvents based on L-proline or betaine[J]. Journal of Chemical Thermodynamics, 2019, 131: 517−523. doi: 10.1016/j.jct.2018.12.017
|
[17] |
Tian D, Guo Y, Hu J, et al. Acidic deep eutectic solvents pretreatment for selective lignocellulosic biomass fractionation with enhanced cellulose reactivity[J]. International Journal of Biological Macromolecules, 2020, 142: 288−297. doi: 10.1016/j.ijbiomac.2019.09.100
|
[18] |
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. doi: 10.1039/c2gc35660k
|
[19] |
Francisco M, van den Bruinhorst A, Kroon M C. Low-transition-temperature mixtures (LTTMs): a new generation of designer solvents[J]. Angewandte Chemie International Edition, 2013, 52(11): 3074−3085. doi: 10.1002/anie.201207548
|
[20] |
Smith E L, Abbott A P, Ryder K S. Deep eutectic solvents (DESs) and their applications[J]. Chemical Reviews, 2014, 114(21): 11060−11082. doi: 10.1021/cr300162p
|
[21] |
Liu Q, Zhao X, Yu D, et al. Novel deep eutectic solvents with different functional groups towards highly efficient dissolution of lignin[J]. Green Chemistry, 2019, 21(19): 5291−5297. doi: 10.1039/C9GC02306B
|
[22] |
Nam M W, Zhao J, Lee M S, et al. Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae[J]. Green Chemistry, 2015, 17(3): 1718−1727. doi: 10.1039/C4GC01556H
|
[23] |
Lim W L, Gunny A A N, Kasim F H, et al. Alkaline deep eutectic solvent: a novel green solvent for lignocellulose pulping[J]. Cellulose, 2019, 26(6): 4085−4098. doi: 10.1007/s10570-019-02346-8
|
[24] |
Skulcova A, Majova V, Sima J, et al. Mechanical properties of pulp delignified by deep eutectic solvents[J]. Bioresources, 2017, 12(4): 7479−7486.
|
[25] |
Li P, Sirviö J A, Hong S, et al. Preparation of flame-retardant lignin-containing wood nanofibers using a high-consistency mechano-chemical pretreatment[J]. Chemical Engineering Journal, 2019, 375: 122050. doi: 10.1016/j.cej.2019.122050
|
[26] |
Sirvio J A, Visanko M. Highly Transparent nanocomposites based on poly (vinyl alcohol) and sulfated UV-absorbing wood nanofibers[J]. Biomacromolecules, 2019, 20(6): 2413−2420. doi: 10.1021/acs.biomac.9b00427
|
[27] |
Xu G C, Ding J C, Han R Z, et al. Enhancing cellulose accessibility of corn stover by deep eutectic solvent pretreatment for butanol fermentation[J]. Bioresource Technology, 2016, 203: 364−369. doi: 10.1016/j.biortech.2015.11.002
|
[28] |
Cai Z, Long J, Li Y, et al. Selective production of diethyl maleate via oxidative cleavage of lignin aromatic unit[J]. Chem, 2019, 5(9): 2365−2377. doi: 10.1016/j.chempr.2019.05.021
|
[29] |
Kumar A K, Sharma S, Shah E, et al. Technical assessment of natural deep eutectic solvent (NADES) mediated biorefinery process: a case study[J]. Journal of Molecular Liquids, 2018, 260: 313−322. doi: 10.1016/j.molliq.2018.03.107
|
[30] |
Alvarez-Vasco C, Ma R, Quintero M, et al. Unique low-molecular-weight lignin with high purity extracted from wood by deep eutectic solvents (DES): a source of lignin for valorization[J]. Green Chemistry, 2016, 18(19): 5133−5141. doi: 10.1039/C6GC01007E
|
[31] |
Tan Y T, Ngoh G C, Chua A S M. Evaluation of fractionation and delignification efficiencies of deep eutectic solvents on oil palm empty fruit bunch[J]. Industrial Crops and Products, 2018, 123: 271−277. doi: 10.1016/j.indcrop.2018.06.091
|
[32] |
Teh S S, Loh S K, Mah S H. Development of choline-based deep eutectic solvents for efficient concentrating of hemicelluloses in oil palm empty fruit bunches[J]. Korean Journal of Chemical Engineering, 2019, 36(10): 1619−1625. doi: 10.1007/s11814-019-0348-1
|
[33] |
周敏姑, 郭英杰, 郝子越, 等. 氯化胆碱/乳酸低共熔溶剂预处理对杨木酶水解特性的影响[J]. 西北农林科技大学学报(自然科学版), 2020, 48(12):1−8.
Zhou M G, Guo Y J, Hao Z Y, et al. Effects of choline chloride/lactic acid deep eutectic solvents pretreatment on enzymatic hydrolysis of poplar[J]. Journal of Northwest A&F University (Natural Science Edition), 2020, 48(12): 1−8.
|
[34] |
Wang S Z, Su S H, Xiao L P, et al. Catechyl lignin extracted from castor seed coats using deep eutectic solvents: characterization and depolymerization[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(18): 7031−7038.
|
[35] |
Li T, Lyu G, Liu Y, et al. Deep eutectic solvents (DESs) for the isolation of willow lignin (Salix matsudana cv. Zhuliu)[J]. International Journal of Molecular Sciences, 2017, 18(11): 2266. doi: 10.3390/ijms18112266
|
[36] |
Shen X J, Wen J L, Mei Q Q, et al. Facile fractionation of lignocelluloses by biomass-derived deep eutectic solvent (DES) pretreatment for cellulose enzymatic hydrolysis and lignin valorization[J]. Green Chemistry, 2019, 21(2): 275−283. doi: 10.1039/C8GC03064B
|
[37] |
Guo Z W, Zhang Q L, You T T, et al. Short-time deep eutectic solvent pretreatment for enhanced enzymatic saccharification and lignin valorization[J]. Green Chemistry, 2019, 21(11): 3099−3108. doi: 10.1039/C9GC00704K
|
[38] |
Lynam J G, Kumar N, Wong M J. Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density[J]. Bioresource Technology, 2017, 238: 684−689. doi: 10.1016/j.biortech.2017.04.079
|
[39] |
Kohli K, Katuwal S, Biswas A, et al. Effective delignification of lignocellulosic biomass by microwave assisted deep eutectic solvents[J]. Bioresource Technology, 2020, 303: 122897. doi: 10.1016/j.biortech.2020.122897
|
[40] |
Tan Y T, Ngoh G C, Chua A S M. Effect of functional groups in acid constituent of deep eutectic solvent for extraction of reactive lignin[J]. Bioresource Technology, 2019, 281: 359−366. doi: 10.1016/j.biortech.2019.02.010
|
[41] |
Liang Y, Duan W J, An X X, et al. Novel betaine-amino acid based natural deep eutectic solvents for enhancing the enzymatic hydrolysis of corncob[J]. Bioresource Technology, 2020, 310: 123389. doi: 10.1016/j.biortech.2020.123389
|
[42] |
Zhang C W, Xia S Q, Ma P S. Facile pretreatment of lignocellulosic biomass using deep eutectic solvents[J]. Bioresource Technology, 2016, 219: 1−5. doi: 10.1016/j.biortech.2016.07.026
|
[43] |
Ling Z, Guo Z W, Huang C X, et al. Deconstruction of oriented crystalline cellulose by novel levulinic acid based deep eutectic solvents pretreatment for improved enzymatic accessibility[J]. Bioresource Technology, 2020, 305: 123025. doi: 10.1016/j.biortech.2020.123025
|
[44] |
Kim K H, Dutta T, Sun J, et al. Biomass pretreatment using deep eutectic solvents from lignin derived phenols[J]. Green Chemistry, 2018, 20(4): 809−815. doi: 10.1039/C7GC03029K
|
[45] |
Mamilla J L K, Novak U, Grilc M, et al. Natural deep eutectic solvents (DES) for fractionation of waste lignocellulosic biomass and its cascade conversion to value-added bio-based chemicals[J]. Biomass and Bioenergy, 2019, 120: 417−425. doi: 10.1016/j.biombioe.2018.12.002
|
[46] |
Yu Q, Zhang A, Wang W, et al. Deep eutectic solvents from hemicellulose-derived acids for the cellulosic ethanol refining of Akebia’ herbal residues[J]. Bioresource Technology, 2018, 247: 705−710. doi: 10.1016/j.biortech.2017.09.159
|
[47] |
Chen Z, Reznicek W D, Wan C X. Deep eutectic solvent pretreatment enabling full utilization of switchgrass[J]. Bioresource Technology, 2018, 263: 40−48. doi: 10.1016/j.biortech.2018.04.058
|
[48] |
Xia Q, Liu Y, Meng J, et al. Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass[J]. Green Chemistry, 2018, 20(12): 2711−2721. doi: 10.1039/C8GC00900G
|
[49] |
Chen Z, Jacoby W A, Wan C. Ternary deep eutectic solvents for effective biomass deconstruction at high solids and low enzyme loadings[J]. Bioresource Technology, 2019, 279: 281−286. doi: 10.1016/j.biortech.2019.01.126
|
[50] |
Guo Z W, Ling Z, Wang C, et al. Integration of facile deep eutectic solvents pretreatment for enhanced enzymatic hydrolysis and lignin valorization from industrial xylose residue[J]. Bioresource Technology, 2018, 265: 334−339. doi: 10.1016/j.biortech.2018.06.027
|
[51] |
Chen Z, Bai X L, Lusi A, et al. High-solid lignocellulose processing enabled by natural deep eutectic solvent for lignin extraction and industrially relevant production of renewable chemicals[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(9): 12205−12216.
|
[52] |
Ji Q, Yu X, Yagoub A G A, et al. Efficient removal of lignin from vegetable wastes by ultrasonic and microwave-assisted treatment with ternary deep eutectic solvent[J]. Industrial Crops and Products, 2020, 149: 112357. doi: 10.1016/j.indcrop.2020.112357
|
[53] |
Thi S, Lee K M. Comparison of deep eutectic solvents (DES) on pretreatment of oil palm empty fruit bunch (OPEFB): cellulose digestibility, structural and morphology[J]. Bioresource Technology, 2019, 282: 525−529. doi: 10.1016/j.biortech.2019.03.065
|
[54] |
Procentese A, Johnson E, Orr V, et al. Deep eutectic solvent pretreatment and subsequent saccharification of corncob[J]. Bioresource Technology, 2015, 192: 31−36. doi: 10.1016/j.biortech.2015.05.053
|
[55] |
Tan Y T, Chua A S M, Ngoh G C. Deep eutectic solvent for lignocellulosic biomass fractionation and the subsequent conversion to bio-based products: a review[J]. Bioresource Technology, 2020, 297: 122522. doi: 10.1016/j.biortech.2019.122522
|
[56] |
金永灿, 谷峰. 木质素清洁高效分离研究进展[J]. 中国造纸, 2019, 38(6):65−72. doi: 10.11980/j.issn.0254-508X.2019.06.010
Jin Y C, Gu F. Research progress in clean and efficient separation of lignin[J]. China Pulp & Paper, 2019, 38(6): 65−72. doi: 10.11980/j.issn.0254-508X.2019.06.010
|
[57] |
Kumar A K, Parikh B S, Pravakar M. Natural deep eutectic solvent mediated pretreatment of rice straw: bioanalytical characterization of lignin extract and enzymatic hydrolysis of pretreated biomass residue[J]. Environmental Science Pollution Research, 2016, 23(10): 9265−9275. doi: 10.1007/s11356-015-4780-4
|
[58] |
D’Agostino C, Harris R C, Abbott A P, et al. Molecular motion and ion diffusion in choline chloride based deep eutectic solvents studied by 1H pulsed field gradient NMR spectroscopy[J]. Physical Chemistry Chemical Physics, 2011, 13(48): 21383−21391. doi: 10.1039/c1cp22554e
|
[59] |
Liu Y, Chen W, Xia Q, et al. Efficient cleavage of lignin-carbohydrate complexes and ultrafast extraction of lignin oligomers from wood biomass by microwave-assisted treatment with deep eutectic solvent[J]. ChemSusChem, 2017, 10(8): 1692−1700. doi: 10.1002/cssc.201601795
|
[60] |
Li C, Tanjore D, He W, et al. Scale-up and evaluation of high solid ionic liquid pretreatment and enzymatic hydrolysis of switchgrass[J]. Biotechnology for Biofuels, 2013, 6: 154. doi: 10.1186/1754-6834-6-154
|
[61] |
Yuan X, Duan Y, He L, et al. Characterization of white poplar and eucalyptus after ionic liquid pretreatment as a function of biomass loading using X-ray diffraction and small angle neutron scattering[J]. Bioresource Technology, 2017, 232: 113−118. doi: 10.1016/j.biortech.2017.02.014
|
[62] |
Chen Z, Ragauskas A, Wan C. Lignin extraction and upgrading using deep eutectic solvents[J]. Industrial Crops and Products, 2020, 147: 112241. doi: 10.1016/j.indcrop.2020.112241
|
[63] |
Das L, Li M, Stevens J, et al. Characterization and catalytic transfer hydrogenolysis of deep eutectic solvent extracted sorghum lignin to phenolic compounds[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(8): 10408−10420.
|
[64] |
Haldar D, Purkait M K. Lignocellulosic conversion into value-added products: a review[J]. Process Biochemistry, 2020, 89: 110−133. doi: 10.1016/j.procbio.2019.10.001
|
[65] |
Hong S, Shen X, Pang B, et al. In-depth interpretation of the structural changes of lignin and formation of diketones during acidic deep eutectic solvent pretreatment[J]. Green Chemistry, 2020, 22(6): 1851−1858. doi: 10.1039/D0GC00006J
|
[66] |
Guo Z, Li D, You T, et al. New Lignin streams derived from heteropoly acids enhanced neutral deep eutectic solvent fractionation: toward structural elucidation and antioxidant performance[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(32): 12110−12119.
|
[67] |
Wang Z K, Hong S, Wen J L, et al. Lewis acid-facilitated deep eutectic solvent (DES) pretreatment for producing high-purity and antioxidative lignin[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(2): 1050−1057.
|
[68] |
Li W, Amos K, Li M, et al. Fractionation and characterization of lignin streams from unique high-lignin content endocarp feedstocks[J]. Biotechnology for Biofuels, 2018, 11: 304. doi: 10.1186/s13068-018-1305-7
|
[69] |
Cronin D, Chen X, Moghaddam L, et al. Deep eutectic solvent extraction of high purity lignin from a corn stover hydrolysate[J]. ChemSusChem, 2020, 13: 4678−4690. doi: 10.1002/cssc.202001243
|
[70] |
周金梅, 李思明, 覃春芳, 等. 有机溶剂法纯化蔗渣木质素[J]. 应用化工, 2017, 46(8):1447−1450. doi: 10.3969/j.issn.1671-3206.2017.08.001
Zhou J M, Li S M, Qin C F, et al. Organic solvent purify bagasse lignin[J]. Applied Chemical Industry, 2017, 46(8): 1447−1450. doi: 10.3969/j.issn.1671-3206.2017.08.001
|
[71] |
康玉. 木质素基防晒霜与纳米纤维素复合膜产品的开发[D]. 北京: 北京化工大学, 2017.
Kang Y. Preparation of lignin-based sunscreens and cellulose nanocomposite film[D]. Beijing: Beijing University of Chemical Technology, 2017.
|
[72] |
Ragauskas A J, Beckham G T, Biddy M J, et al. Lignin valorization: improving lignin processing in the biorefinery[J]. Science, 2014, 344: 1246843. doi: 10.1126/science.1246843
|
[73] |
刘天勤, 连海兰, 洪枢, 等. 氯化胆碱/尿素低共熔溶剂改性木质素的环氧固化体系[J]. 东北林业大学学报, 2018, 46(4):78−87. doi: 10.3969/j.issn.1000-5382.2018.04.016
Liu T Q, Lian H L, Hong S, et al. Effect of modified lignin by choline chloride/urea deep-eutectic solvent on curing properties of epoxy resin[J]. Journal of Northeast Forestry University, 2018, 46(4): 78−87. doi: 10.3969/j.issn.1000-5382.2018.04.016
|
[74] |
Xu P, Zheng G W, Zong M H, et al. Recent progress on deep eutectic solvents in biocatalysis[J]. Bioresources and Bioprocessing, 2017, 4(1): 34. doi: 10.1186/s40643-017-0165-5
|
[75] |
Satlewal A, Agrawal R, Bhagia S, et al. Natural deep eutectic solvents for lignocellulosic biomass pretreatment: recent developments, challenges and novel opportunities[J]. Biotechnology Advances, 2018, 36(8): 2032−2050. doi: 10.1016/j.biotechadv.2018.08.009
|
[76] |
Liang X, Fu Y, Chang J, et al. Effective separation, recovery and recycling of deep eutectic solvent after biomass fractionation with membrane-based methodology[J]. Separation and Purification Technology, 2019, 210: 409−416. doi: 10.1016/j.seppur.2018.08.021
|