深度共熔溶剂在生物质精炼过程中的应用
|
摘要
深度共熔溶剂通常是由一定化学计量比的胆碱盐(氢键受体)和氢键供体组合而成的低共熔混合物,具有绿色环保、不易挥发、可降解、价格低廉、容易得到且易于制备、反应产物分离简单等优点。目前,以氯化胆碱为基体合成的新型深度共熔溶剂体系被广泛应用于木质纤维生物质组分分级处理、生物油的组分萃取和平台化合物转化等。国内外大量实验研究表明,木质纤维生物质组分可以溶解在特定的深度共熔溶剂中,对纤维素和木素等组分进行分级分离处理。将这一新产品和工艺应用于生物质精炼或造纸工业生产过程中,可使过程生产能耗下降40%左右。尤其是由氯化胆碱和乳酸合成的深度共熔溶剂,它对酚类化合物和芳烃的萃取有着较高的选择性能,具有很强溶解木素的能力,能够将生物质中大量木素脱除,脱除效率远远高于稀酸预处理生物质的脱木素效率。本文从木素结构、深度共熔溶剂的组成分类、深度共熔溶剂分离木素效率和深度共熔溶剂的回用等方面综述深度共熔溶剂在木素分离中的应用,并对目前研究中存在的问题进行讨论。
Deep eutectic solvent is typically an eutectic mixture with the combination of choline salts(hydrogen bond acceptor,HBA)and hydrogen bond donor(HBD) at a certain molar ratio. It has the advantages of being green, non-volatile, degradable, cheap,common and preparation easily, and simple to separate reaction products. At present, a new deep eutectic solvent based on choline chloride is widely used in the classified of lignocellulosic biomass components, components extraction of bio-oil and conversion of platform compounds. Many studies at domestic and abroad showed that lignocellulosic biomass can be dissolved in specific deep eutectic solvents to fractionation cellulose and lignin. And this new solvent and technology can be applied into biomass refining or papermaking industrial production, the energy consumption in process production cost can be reduced by about 40%. Especially, the deep eutectic solvent mixed with choline chloride and lactic acid has a high selectivity to the extraction of phenolic compounds and aromatic hydrocarbons, and has a strong ability to dissolve lignin, which is great capable of delignin in biomass. Removal rate is much higher than the delignification efficiency of dilute acid pretreated biomass. This paper elaborated the application of deep eutectic solvent in lignin separation and reviewed lignin structure, composition classification of deep eutectic solvent, character of deep eutectic solvent in delignin efficiency and recycling in treatment, and also the problems in treatment of deep eutectic solvent were discussed.
Deep eutectic solvent is typically an eutectic mixture with the combination of choline salts(hydrogen bond acceptor,HBA)and hydrogen bond donor(HBD) at a certain molar ratio. It has the advantages of being green, non-volatile, degradable, cheap,common and preparation easily, and simple to separate reaction products. At present, a new deep eutectic solvent based on choline chloride is widely used in the classified of lignocellulosic biomass components, components extraction of bio-oil and conversion of platform compounds. Many studies at domestic and abroad showed that lignocellulosic biomass can be dissolved in specific deep eutectic solvents to fractionation cellulose and lignin. And this new solvent and technology can be applied into biomass refining or papermaking industrial production, the energy consumption in process production cost can be reduced by about 40%. Especially, the deep eutectic solvent mixed with choline chloride and lactic acid has a high selectivity to the extraction of phenolic compounds and aromatic hydrocarbons, and has a strong ability to dissolve lignin, which is great capable of delignin in biomass. Removal rate is much higher than the delignification efficiency of dilute acid pretreated biomass. This paper elaborated the application of deep eutectic solvent in lignin separation and reviewed lignin structure, composition classification of deep eutectic solvent, character of deep eutectic solvent in delignin efficiency and recycling in treatment, and also the problems in treatment of deep eutectic solvent were discussed.
引文
[1]程贤娃.生物质的重要组分--木质素的开发与应用[J].生物产业技术,2013(2):25-33.
[2]金显春.离子液体提取稻草木质素可有效促进纤维素酶解[J].江苏农业科学,2011,39(02):422-424.
[3]LI C,WANG Q,ZHAO Z K,et al.Acid in ionic liquid:An efficient system for hydrolysis of lignocellulose[J].Green Chem,2008,10(2):177-184.
[4]HIMMEL M E,DING S Y,JOHNSON D K,et al.Biomass Recalcitrance:Engineering Plants and Enzymes for Biofuels Production[J].Science,2007,315(5813):804-807.
[5]衣守志,石淑兰,李翠珍.制浆废液中木质素的分离与利用新进展[J].国际造纸,2000,20(6):56-58.
[6]邹瑾颖,庄蕾,黄治齐,等.木素抗氧化性的研究现状及展望[J].纸和造纸,2018,37(2):25-27.
[7]侯祥.离子液体法提取木质素的研究[D].大连:大连工业大学,2011.
[8]蒋挺大.木质素-第2版[M].化学工业出版社,2009:15-55.
[9]陶用珍,管映亭.木质素的化学结构及其应用[J].纤维素科学与技术,2003,11(1):42-55.
[10]苏寿承.木质素的化学结构和利用[J].浙江农林大学学报,1990(1):87-96.
[11]BJ?RKMAN A,PERSON B,et al.The properties of lignins extracted with neutral solvents f rom softwoods and hardwoods[J].Svensk Papperstidning,1957,60(5):158-169.
[12]CHAKAR F S,RAGAUSKAS A J,et al.Review of current and future softwood kraft lignin process chemistry[J].Industrial Crops&Products,2004,20(2):131-141.
[13]黄映芳,蔡明亮,吴敏雅.造纸黑液中木素降解的研究现状与进展[J].纸和造纸,2018,37(01):12-17.
[14]ZHOU Q,SONG Y,YU Y,et al.Density and Excess Molar Volume for Binary Mixtures of Naphthenic Acid Ionic Liquids and Ethanol[J].Journal of Chemical&Engineering Data,2010,55(3):1105-1108.
[15]常杰,刘钧,郭姝君,等.新型深度共熔溶剂选择性分离木质素的研究[J].华南理工大学学报(自然科学版),2016,44(6):14-20.
[16]ABBOTT A P,CAPPER G,DAVIES D L,et al.Novel solvent proper ties of cholnecloride/ureamixtures.[J].Chemical Communications,2002,9(1):70-71.
[17]ZHANG Q,Karine D O V,Royer S,et al.Deep eutectic solvents:syntheses,properties and applications[J].Chemical Society Reviews,2012,41(21):7108-7146.
[18]FRANCISCO M,Adriaan van den Bruinhorst,KROON MC.Low-Transition-Temperature Mixtures(LTTMs):A New Generation of Designer Solvents[J].Angewandte Chemie International Edition,2013,52(11):3074-3085.
[19]李利芬.基于氯化胆碱低共熔溶剂的木质素提取、改性和降解研究[D].东北林业大学,2015.
[20]FRANCISCO M,BRUINHORST A V D,KROON M C,et al.New natural and renew able low transition temperature mixtures(LTTMs):screening as solvents for lignocellulosic biomass processing[J].Green Chemistry,2012,14(8):2153-2157.
[21]SOARES B,TAVARES D J P,AMARALJOSéLUIS,et al.Enhanced Solubility of Lignin Monomeric Model Compounds and Technical Lignins in Aqueous Solutions of Deep Eutectic Solvents[J].ACS Sustainable Chemistry&Engineering,2017,5(5):4056-4065.
[22]王俊宏,常丽萍,谢克昌.现代仪器分析方法在煤热解研究中的应用[J].现代化工,2006(S2):386-390.
[23]PANG K,HOU Y,WU W,et al.Efficient separation of phenols f rom oils via forming deep eutectic solvents[J].Green Chemistry,2012,14-22.
[24]MALAEKE H,HOUSAINDOKHT M R,MONHEMI H,et al.Deep eutectic solvent as an efficient molecular liquid for lignin solubilization and wood delignification[J].Journal of Molecular Liquids,2015,263:193-199
[25]HILTUNEN J,KUUTTI L,ROVIO S,et al.Using a low melting solvent mixture to extract value from wood biomass[J].Scientific Reports,2016,6:32420.
[26]刘钧,王菊,岳莺莺,等.深度共熔溶剂对尾叶桉木质素的溶解选择性[J].精细化工,2016,33(11):1287-1294.
[27]JABLONSKY M,SKULCOVA A,KAMENSKA L,et al.Deep Eutectic S ol vents:Fractionation of W heat S traw[J].Bioresources,2015,10(4):8039-8047.
[28]CARRIAZO D,SERRANO,MARíA CONCEPCIóN,et al.Deep-eutectic sol vents play ing multiple roles in the synthesis of polymers and related materials[J].Chemical Society Reviews,2012,41(14):4996-5014.
[29]ASSANOSI A A,FARAH M M,WOOD J,et al.A facile acidic choline chloride-p-TSA DES-catalysed dehydration of f ructose to 5-hydroxymethylfurfural[J].Rsc Advances,2014,4(74):39359-39364.
[30]YIIN C L,QUITAIN A T,YUSUP S,et al.Characterization of natur allowtransition temperature mitures(LTTMs):Green solvents for biomass delignification[J].Bioresource Technology,2015,199:258-264
[31]MARINO D D,ST?CKMANN D,KRIESCHER S,et al.Wessling,M.Electrochemical depolymerisation of lignin in a deep eutectic solvent.Green Chem.,2016,18,6021-6028.
[32]WEI Z,QI X,LI T,et al.Application of natural deep eutectic solvents for extraction and determination of phenolics in Cajanus cajan leaves by ultra performance liquid chromatography.Sep.Purif.Technol.,2015,149,237-244.
[33]LYNAM J G,KUMAR N,WONG M J,et al.Deep eutectic solvents’abiity to solubilizelign in,cellu lose,and hemicellu lose;thermal stability;and density[J].Bioresource Technology,238:684-689
[34]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.Am.Chem.Soc.,2004,126,9142-9147.
[35]YAO X H,ZHANG D Y,DUAN M H,et al.Preparation and determination of phenolic compounds from Pyrola incarnata Fisch with a green polyols based-deep eutectic solvent[J].Sep.Purif.Technol.,2015,149,116-123.
[36]KUMAR A K,PARIKH B S,PRAVAKAR M,et al.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.
[37]DAI Y,WITKAMP G J,VERPOORTE R,et al.Tailoring properties of natural deep eutectic solvents with water to facilitate their applications[J].Food Chem.,2015,187,14-19.
[38]REN S H,XIAO Y,WANG Y M,et al.Effect of water on the separation of phenol from model oil with choline chloride via forming deep eutectic solvent.Fuel Process[J].Technol.2015,137,104-108.
[39]ABBOTT A,CAPPER G,GRAY S,et al.Design of improved deep eutectic solvents using hole theory[J].Chemphyschem,2010,7(4):803-806.
[2]金显春.离子液体提取稻草木质素可有效促进纤维素酶解[J].江苏农业科学,2011,39(02):422-424.
[3]LI C,WANG Q,ZHAO Z K,et al.Acid in ionic liquid:An efficient system for hydrolysis of lignocellulose[J].Green Chem,2008,10(2):177-184.
[4]HIMMEL M E,DING S Y,JOHNSON D K,et al.Biomass Recalcitrance:Engineering Plants and Enzymes for Biofuels Production[J].Science,2007,315(5813):804-807.
[5]衣守志,石淑兰,李翠珍.制浆废液中木质素的分离与利用新进展[J].国际造纸,2000,20(6):56-58.
[6]邹瑾颖,庄蕾,黄治齐,等.木素抗氧化性的研究现状及展望[J].纸和造纸,2018,37(2):25-27.
[7]侯祥.离子液体法提取木质素的研究[D].大连:大连工业大学,2011.
[8]蒋挺大.木质素-第2版[M].化学工业出版社,2009:15-55.
[9]陶用珍,管映亭.木质素的化学结构及其应用[J].纤维素科学与技术,2003,11(1):42-55.
[10]苏寿承.木质素的化学结构和利用[J].浙江农林大学学报,1990(1):87-96.
[11]BJ?RKMAN A,PERSON B,et al.The properties of lignins extracted with neutral solvents f rom softwoods and hardwoods[J].Svensk Papperstidning,1957,60(5):158-169.
[12]CHAKAR F S,RAGAUSKAS A J,et al.Review of current and future softwood kraft lignin process chemistry[J].Industrial Crops&Products,2004,20(2):131-141.
[13]黄映芳,蔡明亮,吴敏雅.造纸黑液中木素降解的研究现状与进展[J].纸和造纸,2018,37(01):12-17.
[14]ZHOU Q,SONG Y,YU Y,et al.Density and Excess Molar Volume for Binary Mixtures of Naphthenic Acid Ionic Liquids and Ethanol[J].Journal of Chemical&Engineering Data,2010,55(3):1105-1108.
[15]常杰,刘钧,郭姝君,等.新型深度共熔溶剂选择性分离木质素的研究[J].华南理工大学学报(自然科学版),2016,44(6):14-20.
[16]ABBOTT A P,CAPPER G,DAVIES D L,et al.Novel solvent proper ties of cholnecloride/ureamixtures.[J].Chemical Communications,2002,9(1):70-71.
[17]ZHANG Q,Karine D O V,Royer S,et al.Deep eutectic solvents:syntheses,properties and applications[J].Chemical Society Reviews,2012,41(21):7108-7146.
[18]FRANCISCO M,Adriaan van den Bruinhorst,KROON MC.Low-Transition-Temperature Mixtures(LTTMs):A New Generation of Designer Solvents[J].Angewandte Chemie International Edition,2013,52(11):3074-3085.
[19]李利芬.基于氯化胆碱低共熔溶剂的木质素提取、改性和降解研究[D].东北林业大学,2015.
[20]FRANCISCO M,BRUINHORST A V D,KROON M C,et al.New natural and renew able low transition temperature mixtures(LTTMs):screening as solvents for lignocellulosic biomass processing[J].Green Chemistry,2012,14(8):2153-2157.
[21]SOARES B,TAVARES D J P,AMARALJOSéLUIS,et al.Enhanced Solubility of Lignin Monomeric Model Compounds and Technical Lignins in Aqueous Solutions of Deep Eutectic Solvents[J].ACS Sustainable Chemistry&Engineering,2017,5(5):4056-4065.
[22]王俊宏,常丽萍,谢克昌.现代仪器分析方法在煤热解研究中的应用[J].现代化工,2006(S2):386-390.
[23]PANG K,HOU Y,WU W,et al.Efficient separation of phenols f rom oils via forming deep eutectic solvents[J].Green Chemistry,2012,14-22.
[24]MALAEKE H,HOUSAINDOKHT M R,MONHEMI H,et al.Deep eutectic solvent as an efficient molecular liquid for lignin solubilization and wood delignification[J].Journal of Molecular Liquids,2015,263:193-199
[25]HILTUNEN J,KUUTTI L,ROVIO S,et al.Using a low melting solvent mixture to extract value from wood biomass[J].Scientific Reports,2016,6:32420.
[26]刘钧,王菊,岳莺莺,等.深度共熔溶剂对尾叶桉木质素的溶解选择性[J].精细化工,2016,33(11):1287-1294.
[27]JABLONSKY M,SKULCOVA A,KAMENSKA L,et al.Deep Eutectic S ol vents:Fractionation of W heat S traw[J].Bioresources,2015,10(4):8039-8047.
[28]CARRIAZO D,SERRANO,MARíA CONCEPCIóN,et al.Deep-eutectic sol vents play ing multiple roles in the synthesis of polymers and related materials[J].Chemical Society Reviews,2012,41(14):4996-5014.
[29]ASSANOSI A A,FARAH M M,WOOD J,et al.A facile acidic choline chloride-p-TSA DES-catalysed dehydration of f ructose to 5-hydroxymethylfurfural[J].Rsc Advances,2014,4(74):39359-39364.
[30]YIIN C L,QUITAIN A T,YUSUP S,et al.Characterization of natur allowtransition temperature mitures(LTTMs):Green solvents for biomass delignification[J].Bioresource Technology,2015,199:258-264
[31]MARINO D D,ST?CKMANN D,KRIESCHER S,et al.Wessling,M.Electrochemical depolymerisation of lignin in a deep eutectic solvent.Green Chem.,2016,18,6021-6028.
[32]WEI Z,QI X,LI T,et al.Application of natural deep eutectic solvents for extraction and determination of phenolics in Cajanus cajan leaves by ultra performance liquid chromatography.Sep.Purif.Technol.,2015,149,237-244.
[33]LYNAM J G,KUMAR N,WONG M J,et al.Deep eutectic solvents’abiity to solubilizelign in,cellu lose,and hemicellu lose;thermal stability;and density[J].Bioresource Technology,238:684-689
[34]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.Am.Chem.Soc.,2004,126,9142-9147.
[35]YAO X H,ZHANG D Y,DUAN M H,et al.Preparation and determination of phenolic compounds from Pyrola incarnata Fisch with a green polyols based-deep eutectic solvent[J].Sep.Purif.Technol.,2015,149,116-123.
[36]KUMAR A K,PARIKH B S,PRAVAKAR M,et al.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.
[37]DAI Y,WITKAMP G J,VERPOORTE R,et al.Tailoring properties of natural deep eutectic solvents with water to facilitate their applications[J].Food Chem.,2015,187,14-19.
[38]REN S H,XIAO Y,WANG Y M,et al.Effect of water on the separation of phenol from model oil with choline chloride via forming deep eutectic solvent.Fuel Process[J].Technol.2015,137,104-108.
[39]ABBOTT A,CAPPER G,GRAY S,et al.Design of improved deep eutectic solvents using hole theory[J].Chemphyschem,2010,7(4):803-806.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |