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氯化胆碱类低共熔溶剂对木质纤维素分离及其利用的研究进展
Lignocellulose Separation and Utilization Based on Choline Chloride Eutectic Solvents: A Review
为了去除木质纤维素固有复杂抗性结构,实现木质纤维素原料的高效利用,研究人员不断开发新的木质纤维素预处理技术。低共熔溶剂(Deep Eutectic Solvents, DESs)作为一种绿色溶剂,具有成本低、制备简单、热稳定性好、可设计性等优势,在促进木质纤维素原料预处理、原料酶解转化方面有着较好的应用潜力,得到了研究者们的广泛关注和认可。本研究在查阅国内外研究现状和研究成果的相关报道基础上,综述了氯化胆碱DESs的合成及性质,预处理木质纤维素的作用机理,对木质纤维素酶解效果及转化为生物乙醇的相关研究,指出不同氢键供体、不同的预处理条件对原料的木质素去除率及葡萄糖产量有很大影响,认为DESs预处理木质纤维素极大提高了后续纤维素酶解过程的糖化率,并对DESs预处理机理、循环使用、工艺参数优化方面提出了展望。
In order to remove the inherent complex resistance structure of lignocellulose and achieve efficient utilization of lignocellulose, new lignocellulosic pretreatment technologies have been improved continuously. As green solvents, Deep Eutectic Solvents (DESs) have the advantages of low cost, simple preparation, thermal stability, and designability. They have great application potential in promoting the pretreatment of lignocellulose and enzymatic hydrolysis, and have received widespread attention. Based on the analysis and summary of the research status and achievements at home and abroad, the research progress of synthesis and properties of DESs, pretreatment mechanism, enzymatic hydrolysis, and bioethanol conversion were discussed. It was pointed out that different hydrogen bond donors and different pre-treatment conditions had a significant impact on the lignin removal rate and glucose yield. It was believed that pretreatment of lignocellulose with DESs could greatly improve the saccharification rate. Prospects for DESs pretreatment mechanism, recycling, and process parameter optimization were proposed.
低共熔溶剂 / 木质纤维素 / 酶解 / 生物乙醇 {{custom_keyword}} /
deep eutectic solvents / lignocellulose / enzymolysis / bioethanol {{custom_keyword}} /
表1 部分DESs的物理化学性质 |
DESs | 熔点/℃ | 黏度/Pa.S | 密度/(g/cm3) | 表面张力/(mN/N) | 电导率/(S/m) | 参考文献 |
---|---|---|---|---|---|---|
ChCl/尿素(1:2) | 12 | 0.75(25℃) | 1.25 | 52.00 | 0.075(25℃) | [37] |
ChCl/丙三醇(1:2) | -36.15 | 0.26(25℃) | 1.18 | -- | 0.105(25℃) | [37] |
ChCl/乙二醇(1:2) | -66.01 | 0.037(25℃) | 1.12 | 48.91 | 0.761(25℃) | [38] |
ChCl/1,4-丁二醇(1:3) | -32 | 0.14(25℃) | 1.06 | 47.17 | 0.164(25℃) | [38] |
ChCl/草酸(1:1) | 34 | -- | -- | -- | -- | [16] |
ChCl/苹果酸(1:1) | -- | 3.34(25℃) | -- | 65.68 | 0.0036 | [39,40] |
ChCl/乙酰苯 (1:2) | -- | -- | -- | 41.86 | -- | [40] |
表2 木质纤维素不同组分在部分DESs中的溶解度 |
DESs | 摩尔比 | 木质素溶解度/% | 木聚糖溶解度/% | 纤维素溶解度/% | 参考文献 |
---|---|---|---|---|---|
ChCl/甲酸 | 1:2 | 14 | <1 | <1 | [45] |
ChCl/乳酸 | 1:10 | 13 | <5 | <3 | |
ChCl/乙酸 | 1:2 | 12 | <1 | <1 | |
甜菜碱/乳酸 | 1:2 | 9 | <1 | <1 | |
脯氨酸/乳酸 | 1:3.3 | 9 | <1 | <1 |
表3 不同种类DESs对木质素的分离效果 |
原料 | DESs | 摩尔比 | 预处理条件 | 木质素去除率/% | 参考文献 |
---|---|---|---|---|---|
小麦秸秆 | ChCl/单乙醇胺 | 1:2 | 90 ℃,12 h | 81.0 | [59] |
小麦秸秆 | ChCl/二乙醇胺 | 1:8 | 90 ℃,12 h | 73.5 | |
小麦秸秆 | ChCl/甲基二乙醇胺 | 1:10 | 90 ℃,12 h | 44.6 | |
小麦秸秆 | ChCl/乙酰胺 | 1:2 | 90 ℃,12 h | 3.4 | |
小麦秸秆 | ChCl/尿素 | 1:2 | 70 ℃,12 h | 76.4 | |
小麦秸秆 | ChCl/单乙醇胺 | 1:6 | 110 ℃,12 h | 87.7 | |
玉米芯 | ChCl/尿素 | 1:2 | 80 ℃,15 h | 40.0 | [50] |
玉米芯 | ChCl/咪唑 | 3:7 | 115 ℃,15 h | 70.0 | |
玉米芯 | ChCl/咪唑 | 3:7 | 150 ℃,15 h | 88.0 | |
玉米芯 | ChCl/咪唑 | 3:7 | 120 ℃,4 h | 11.1 | |
核桃壳 | ChCl/乳酸 | 1:2 | 145 ℃,6 h | 64.3 | [60] |
桃核 | ChCl/乳酸 | 1:2 | 145 ℃,6 h | 70.2 | |
油棕空果壳 | ChCl/苹果酸 | 1:1 | 120 ℃,8 h | 22.9 | [58] |
油棕空果壳 | ChCl/柠檬酸 | 1:1 | 120 ℃,8 h | 20.6 | |
油棕空果壳 | ChCl/甲酸 | 1:2 | 120 ℃,8 h | 61.9 | |
油棕空果壳 | ChCl/甲酸 | 1:5 | 120 ℃,8 h | 25.0 | |
油棕空果壳 | ChCl/乙酸 | 1:2 | 120 ℃,8 h | 28.0 | |
油棕空果壳 | ChCl/乙酸 | 1:5 | 120 ℃,8 h | 40.0 | |
油棕空果壳 | ChCl/丙酸 | 1:2 | 120 ℃,8 h | 20.4 | |
油棕空果壳 | ChCl/丁酸 | 1:2 | 120 ℃,8 h | 14.3 | |
油棕空果壳 | ChCl/琥珀酸 | 2:1 | 120 ℃,8 h | 10.7 | |
玉米芯 | ChCl/乙二醇 | 1:2 | 90 ℃,24 h | 87.6 | [11] |
玉米芯 | ChCl/丙三醇 | 1:2 | 90 ℃,24 h | 71.3 | |
玉米芯 | ChCl/丙三醇/聚乙二醇 | 1:2:1 | 60 ℃,2 h | 62.9 | [61] |
稻草 | ChCl/乙二醇 | 1:1 | 120 ℃,3 h | 28.7 | [55] |
稻草 | ChCl/1,2-丙二醇 | 1:1 | 120 ℃,3 h | 32.9 | |
稻草 | ChCl/1,3-丙二醇 | 1:1 | 120 ℃,3 h | 34.2 | |
杨木 | ChCl/乳酸 | 1:2 | 170 ℃,4 h | 49.2 | [62] |
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木质纤维素生物质转化为生物燃料或化工产品一般需经历预处理、酶解及发酵过程,因其复杂的化学结构,在酶解前通常进行预处理以破坏其致密结构,提高酶与纤维素的可及性。深度共熔溶剂(DES)是一类新型的“绿色”溶剂,具有制备简单、价格低廉、性质可调、可生物降解、可循环使用等优势,可有效去除木质素组分,同时保留大部分纤维素,在生物质预处理方面具有巨大的潜力。本文介绍了DES的构成、分类及理化性质,总结了DES预处理对生物质组分的影响,并对预处理效果的影响因素如底物和DES的类型、溶剂黏度、温度、生物载量、微波及超声波辅助工艺和两阶段处理工艺等方面进行分析,探讨了DES和生物的相容性,最后针对DES存在的问题及缺点,提出了理性设计和大规模利用DES的机遇与挑战,本文可为实现生物质的低成本预处理和高价值利用提供新的思路。
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解先利, 刘云云, 余强, 等. 低共熔溶剂预处理提高甘草渣酶解效果优化[J]. 化工进展, 2022, 41(3):1349-1356.
近年来,低共熔溶剂(deep eutectic solvent,DES)以易制备、成本低、易回收等优势,在生物质预处理方面受到广泛关注。本研究以氯化胆碱为氢键受体,乙醇胺为氢键供体,合成DES,研究了不同温度、时间和固液比预处理条件对中药渣组分和酶解效果的影响。结果表明:固液比1∶20、120℃、预处理4h后原料中木质素去除率达到78.42%,纤维素回收率为83.89%。随后对不同条件下所得底物进行酶水解,反应96h后发现,较优条件下所得底物酶解效率为78.57%,较未处理中药渣(30.40%)提高了1.58倍。类分形动力学分析表明,预处理温度对酶解效果影响最大。SEM、XRD和FTIR检测发现,预处理后底物形貌、结晶指数和官能团变化有利于酶解效果的提高。
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Ionic liquid (ILs) pretreatment of lignocellulosic biomass has attracted broad scientific interest, despite high costs, possible toxicity and energy intensive recycling. An alternative group of ionic solvents with similar physicochemical properties are deep eutectic solvents (DESs). Corncob residues were pretreated with three different DES systems: choline chloride and glycerol, choline chloride and imidazole, choline chloride and urea. The pretreated biomass was characterised in terms of lignin content, sugars concentration, enzymatic digestibility and crystallinity index. A reduction of lignin and hemicellulose content resulted in increased crystallinity of the pretreated biomass while the crystallinity of the cellulose fraction could be reduced, depending on DES system and operating conditions. The subsequent enzymatic saccharification was enhanced in terms of rate and extent. A total of 41 g fermentable sugars (27 g glucose and 14 g xylose) could be recovered from 100g corncob, representing 76% (86% and 63%) of the initially available carbohydrates.Copyright © 2015 Elsevier Ltd. All rights reserved.
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In this study, a novel biomass pretreatment process using three kinds of deep eutectic solvents (DESs) was developed to improve saccharification efficiency and lignin valorization. The major components of xylose residue including cellulose and lignin fractions were released, recovered and utilized. Pretreatment with betaine/lactic acid system at 120 °C for 2 h was found to be the optimal conditions with prominently increased enzymatic digestibility (from 55.3% to 96.8%). The efficient conversion was mainly ascribed to the significant delignification efficiency of 81.6% after betaine/lactic acid pretreatment, which caused incompact structure and corrosive surface of treated xylose residue. The recoverable lignin had high purity, low molecular weight (630-2040 g/mol) and polydispersity (1.07-1.76). Based on the comprehensive analysis, the one-pot DESs system provides us a facile and effective approach for whole components valorization of lignocellulosic materials.Copyright © 2018 Elsevier Ltd. All rights reserved.
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陈鑫东, 熊莲, 黎海龙, 等. 低共熔溶剂在木质纤维素预处理促进酶水解效率的研究进展[J]. 新能源进展, 2019, 7(5):415-422.
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Here, the potential use of herbal residues of Akebia as feedstock for ethanol production is evaluated. Additionally, five deep eutectic solvents from hemicellulose-derived acids were prepared to overcome biomass recalcitrance. Reaction temperatures had more significant influences on solid loss and chemical composition than the molar ratios of choline chloride (ChCl) to derived acids. Glycolic acid resulted in the maximum levels of lignin, xylan and glucan removal, which were 60.0%, 100% and 71.5%, respectively, at 120°C with a 1:6M ratio of ChCl-glycolic acid. In contrast, ChCl-formic acid resulted in the greatest level of glucan retention, at 97.8%, with a lignin removal rate of 40.7% under the same pretreatment conditions. Moreover, ChCl loading could significantly enhance the selectivity of carboxylic acid for lignin dissolution. A 98.0% level of subsequent enzymatic saccharification and a 100% ethanol yield were achieved after ChCl-formic acid pretreatments of Akebia' herbal residues.Copyright © 2017 Elsevier Ltd. All rights reserved.
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In this study, acidic deep eutectic solvents (DES) synthesized from various organic carboxylic acid hydrogen bond donors were applied to lignocellulosic oil palm empty fruit bunch (EFB) pretreatment. The influence of functional group types on acid and their molar ratios with hydrogen bond acceptor on lignin extraction were evaluated. The result showed presence of hydroxyl group and short alkyl chain enhanced biomass fractionation and lignin extraction. Choline chloride:lactic acid (CC-LA) with the ratio of 1:15 and choline chloride:formic acid (CC-FA) with 1:2 ratio extracted more than 60 wt% of lignin. CC-LA DES-extracted lignin (DEEL) exhibited comparable reactivity with technical and commercial lignin based on its phenolic hydroxyl content (3.33-3.72 mmol/g). Also, the DES-pretreated EFB comprised of enriched glucan content after biopolymer fractionation. Both DES-pretreated EFB and DEEL can be potential feedstock for subsequent conversion processes. This study presented DES as an effective and facile pretreatment method for reactive lignin extraction.Copyright © 2019. Published by Elsevier Ltd.
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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):55-63.
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杨露敏. 深度共熔溶剂结构性质对甘蔗渣预处理效率的影响研究[D]. 广州: 广州工业大学, 2020.
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Background: Waste biomass from agro-food industries are a reliable and readily exploitable resource. From the circular economy point of view, direct residues from these industries exploited for production of fuel/chemicals is a winning issue, because it reduces the environmental/cost impact and improves the eco-sustainability of productions.Results: The present paper reports recent results of deep eutectic solvent (DES) pretreatment on a selected group of the agro-industrial food wastes (AFWs) produced in Europe. In particular, apple residues, potato peels, coffee silver-skin, and brewer's spent grains were pretreated with two DESs, (choline chloride-glycerol and choline chloride-ethylene glycol) for fermentable sugar production. Pretreated biomass was enzymatic digested by commercial enzymes to produce fermentable sugars. Operating conditions of the DES pretreatment were changed in wide intervals. The solid to solvent ratio ranged between 1:8 and 1:32, and the temperature between 60 and 150 degrees C. The DES reaction time was set at 3 h. Optimal operating conditions were: 3 h pretreatment with choline chloride-glycerol at 1:16 biomass to solvent ratio and 115 degrees C. Moreover, to assess the expected European amount of fermentable sugars from the investigated AFWs, a market analysis was carried out. The overall sugar production was about 217 kt yr(-1), whose main fraction was from the hydrolysis of BSGs pretreated with choline chloride-glycerol DES at the optimal conditions.Conclusions: The reported results boost deep investigation on lignocellulosic biomass using DES. This investigated new class of solvents is easy to prepare, biodegradable and cheaper than ionic liquid. Moreover, they reported good results in terms of sugars' release at mild operating conditions (time, temperature and pressure).
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In this study, an acidified, aqueous DES comprising choline chloride: glycerol (ChCl:Gly) was used to fractionate switchgrass into three major streams under a relatively mild condition: cellulose-rich pulp, lignin, and xylose-rich liquor. The pulp showed good digestibility with about 89% glucose yield. The solvent can be recycled successfully and reused for at least four more pretreatment cycles while maintaining its pretreatment capability. The solvent recycling also improved the lignin recovery from the pretreatment liquor. Lignin recovered from different pretreatment cycles had the β-O-4 bonds preserved, and shared similar structures with native lignin. Using the pretreatment liquor as a substrate, the oleaginous yeast Rhodotorula toruloides produced 18.7 g/L biomass with lipid and carotenoid titers of 8.1 g/L and 15.0 mg/L, respectively. Overall, this study demonstrated a green process integrating chemical and biological methods toward full utilization of lignocellulosic biomass.Copyright © 2018 Elsevier Ltd. All rights reserved.
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Deep Eutectic Solvents (DESs) have recently emerged as a new generation of ionic liquids for lignocellulose pretreatment. However, DESs contain salt components which tend to inactivate cellulase in the subsequent saccharification process. To alleviate this problem, it is necessary to evaluate the applicability of the DESs-Cellulase system. This was accomplished in the present study by first studying the stability of cellulase in the presence of selected DESs followed by applicability evaluation based on glucose production, energy consumption and kinetic performance. Results showed that the cellulase was able to retain more than 90% of its original activity in the presence of 10% (v/v) for glycerol based DES (GLY) and ethylene glycol based DES (EG). Furthermore, both DESs system exhibited higher glucose percentage enhancement and lower energy consumption as compared to diluted alkali system. Among the two DESs studied, EG showed comparatively better kinetic performance. Copyright © 2015 Elsevier Ltd. All rights reserved.
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王冬梅, 刘云. 低共熔溶剂(DES)分级分离木质纤维素组分新技术[J]. 北京化工大学学报, 2018, 45(6):40-47.
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汝娟坚, 张远, 卜骄骄, 等. 低共熔溶剂在电沉积金属及其合金方面的研究进展[J]. 科学技术创新, 2019, 20:191.
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