Abstract
Development of efficient solvents to dissolve lignocellulose and its main components is of significant importance for the utilization/transformation of lignocellulose. Herein, several ionic liquid (IL)-based deep eutectic solvents (DESs) were prepared using four ILs as the hydrogen bond acceptors and four different hydrogen bond donors, including thiourea (TU), N-methylthiourea (NMTU), glycerol (Gly), and ethylene glycol (EG). Using the dissolution of xylan (a typical type of hemicellulose) as the example, it was observed that the synthesized IL-based DESs could efficiently dissolve xylan. Especially in the DES formed from 1-allyl-3-methylimidazolium chloride and EG, the xylan solubility could reach as high as 40.4 wt% at 343.15 K. More importantly, the solubility of xylan in IL-based DESs was much higher than that in the corresponding IL. The enhancement effect might be ascribed to that the formation of DESs could significantly decrease the viscosity and increase the hydrogen bond accepting ability. Additionally, the regeneration of the xylan from the DESs could be easily realized using ethanol as the anti-solvent, and the regenerated xylan kept a high consistency with the original xylan.
Graphic abstract
Ionic liquid-based deep eutectic solvents were designed for highly efficient dissolution of xylan owing to the decreased viscosity and the increased hydrogen-bond accepting ability.
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References
Ab Rani MA et al (2011) Understanding the polarity of ionic liquids. Phys Chem Chem Phys 13:16831–16840. https://doi.org/10.1039/c1cp21262a
Bastos R, Coelho E, Coimbra MA (2015) Modifications of Saccharomyces pastorianus cell wall polysaccharides with brewing process. Carbohydr Polym 124:322–330. https://doi.org/10.1016/j.carbpol.2015.02.031
Blumenkrantz N, Asboe-Hansen G (1973) New method for quantitative determination of uronic acids. Anal Biochem 54:484–489. https://doi.org/10.1016/0003-2697(73)90377-1
Chen Y-L, Zhang X, You T-T, Xu F (2018) Deep eutectic solvents (DESs) for cellulose dissolution: a mini-review. Cellulose 26:205–213. https://doi.org/10.1007/s10570-018-2130-7
Cui G, Wang J, Zhang S (2016) Active chemisorption sites in functionalized ionic liquids for carbon capture. Chem Soc Rev 45:4307–4339. https://doi.org/10.1039/c5cs00462d
Evtuguin DV, Tomas JL, Silva AMS, Neto CP (2003) Characterization of an acetylated heteroxylan from Eucalyptus globulus Labill. Carbohydr Res 338:597–604. https://doi.org/10.1016/s0008-6215(02)00529-3
Florindo C, Branco LC, Marrucho IM (2019) Quest for green-solvent design: from hydrophilic to hydrophobic (deep) eutectic solvents. Chemsuschem 12:1549–1559. https://doi.org/10.1002/cssc.201900147
Francisco M, van den Bruinhorst A, Kroon MC (2012) New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing. Green Chem 14:2153. https://doi.org/10.1039/c2gc35660k
Froschauer C, Hummel M, Laus G, Schottenberger H, Sixta H, Weber HK, Zuckerstaetter G (2012) Dialkyl phosphate-related ionic liquids as selective solvents for xylan. Biomacromol 13:1973–1980. https://doi.org/10.1021/bm300582s
Ghaedi H, Ayoub M, Sufian S, Shariff AM, Lal B (2017) The study on temperature dependence of viscosity and surface tension of several Phosphonium-based deep eutectic solvents. J Mol Liq 241:500–510. https://doi.org/10.1016/j.molliq.2017.06.024
Gilbert A, Bucher G, Haines RS, Harper JB (2019) Correlating ionic liquid solvent effects with solvent parameters for a reaction that proceeds through a xanthylium intermediate. Org Biomol Chem 17:9336–9342. https://doi.org/10.1039/C9OB01807G
Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. Chem Rev 111:3508–3576. https://doi.org/10.1021/cr1003248
Hao X et al (2015) Self-assembled nanostructured cellulose prepared by a dissolution and regeneration process using phosphoric acid as a solvent. Carbohydr Polym 123:297–304. https://doi.org/10.1016/j.carbpol.2015.01.055
Huang W, Wang Y, Zhang L, Chen L (2016) Rapid dissolution of spruce cellulose in H2SO4 aqueous solution at low temperature. Cellulose 23:3463–3473. https://doi.org/10.1007/s10570-016-1047-2
Jessop PG, Jessop DA, Fu D, Lam P (2012) Solvatochromic parameters for solvents of interest in green chemistry. Green Chem 14:1245–1259. https://doi.org/10.1039/c2gc16670d
Kasprzak D, Krystkowiak E, Stepniak I, Galinski M (2019) Dissolution of cellulose in novel carboxylate-based ionic liquids and dimethyl sulfoxide mixed solvents. Eur Polym J 113:89–97. https://doi.org/10.1016/j.eurpolymj.2019.01.053
Ke Y, Jin W, Yang Q, Suo X, Yang Y, Ren Q, Xing H (2018) Nanostructured branched-chain carboxylate ionic liquids: synthesis, characterization, and extraordinary solubility for bioactive molecules. ACS Sustain Chem Eng 6:8983–8991. https://doi.org/10.1021/acssuschemeng.8b01353
King AWT, Asikkala J, Mutikainen I, Jarvi P, Kilpelainen I (2011) Distillable acid-base conjugate ionic liquids for cellulose dissolution and processing. Angew Chem Int Ed 50:6301–6305. https://doi.org/10.1002/anie.201100274
Lee C, Teng Q, Zhong R, Ye Z-H (2014) Alterations of the degree of xylan acetylation in Arabidopsis xylan mutants. Plant Signal Behav 9:e27797–e27797
Lethesh KC, Evjen S, Venkatraman V, Shah SN, Fiksdahl A (2020) Highly efficient cellulose dissolution by alkaline ionic liquids. Carbohydr Polym. https://doi.org/10.1016/j.carbpol.2019.115594
Li X, Li H, You T, Chen X, Ramaswamy S, Wu Y-Y, Xu F (2019) Enhanced dissolution of cotton cellulose in 1-allyl-3-methylimidazolium chloride by the addition of metal chlorides. ACS Sustain Chem Eng 7:19176–19184. https://doi.org/10.1021/acssuschemeng.9b05159
Liu Q-P, Hou X-D, Li N, Zong M-H (2012) Ionic liquids from renewable biomaterials: synthesis, characterization and application in the pretreatment of biomass. Green Chem 14:304–307. https://doi.org/10.1039/c2gc16128a
Liu Q, Zhao X, Yu D, Yu H, Zhang Y, Xue Z, Mu T (2019) Novel deep eutectic solvents with different functional groups towards highly efficient dissolution of lignin. Green Chem 21:5291–5297. https://doi.org/10.1039/c9gc02306b
Lynam JG, Kumar N, Wong MJ (2017) Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. Biores Technol 238:684–689. https://doi.org/10.1016/j.biortech.2017.04.079
Ma Y et al (2019) Natural deep eutectic solvents as multifunctional media for the valorization of agricultural wastes. Chemsuschem 12:1310–1315. https://doi.org/10.1002/cssc.201900043
Mohanty AK, Vivekanandhan S, Pin J-M, Misra M (2018) Composites from renewable and sustainable resources: challenges and innovations. Science 362:536–542. https://doi.org/10.1126/science.aat9072
Morais ES, Mendonca PV, Coelho JFJ, Freire MG, Freire CSR, Coutinho JP, Silvestre AJD (2018) Deep eutectic solvent aqueous solutions as efficient media for the solubilization of hardwood xylans. Chemsuschem 11:753–762. https://doi.org/10.1002/cssc.201702007
Rashid T, Kait CF, Regupathi I, Murugesan T (2016) Dissolution of kraft lignin using protic ionic liquids and characterization. Ind Crop Prod 84:284–293. https://doi.org/10.1016/j.indcrop.2016.02.017
Ruiz-Olles J, Slavik P, Whitelaw NK, Smith DK (2019) Self-assembled gels formed in deep eutectic solvents: supramolecular eutectogels with high ionic conductivity. Angew Chem Int Ed 58:4173–4178. https://doi.org/10.1002/anie.201810600
Schutyser W, Renders T, Van den Bosch S, Koelewijn SF, Beckham GT, Sels BF (2018) Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem Soc Rev 47:852–908. https://doi.org/10.1039/c7cs00566k
Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082. https://doi.org/10.1021/cr300162p
Soares B, Tavares DJP, Amaral JL, Silvestre AJD, Freire CSR, Coutinho JAP (2017) Enhanced solubility of lignin monomeric model compounds and technical lignins in aqueous solutions of deep eutectic solvents. ACS Sustain Chem Eng 5:4056–4065. https://doi.org/10.1021/acssuschemeng.7b00053
Sudarsanam P, Peeters E, Makshina EV, Parvulescu VI, Sels BF (2019) Advances in porous and nanoscale catalysts for viable biomass conversion. Chem Soc Rev 48:2366–2421. https://doi.org/10.1039/c8cs00452h
Sun R, Fang JM, Rowlands P, Bolton J (1998) Physicochemical and thermal characterization of wheat straw hemicelluloses and cellulose. J Agric Food Chem 46:2804–2809. https://doi.org/10.1021/jf971078a
Sun SN, Yuan TQ, Li MF, Cao XF, Xu F, Liu QY (2012) Structural characterization of hemicelluloses from bamboo culms (Neosinocalamus affinis). Cellul Chem Technol 46:165–176
Sun X, Xue Z, Mu T (2014) Precipitation of chitosan from ionic liquid solution by the compressed CO2 anti-solvent method. Green Chem 16:2102–2106. https://doi.org/10.1039/c3gc42166j
Sun Z, Fridrich B, de Santi A, Elangovan S, Barta K (2018) Bright side of lignin depolymerization: toward new platform chemicals. Chem Rev 118:614–678. https://doi.org/10.1021/acs.chemrev.7b00588
Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose correction of cellose with ionic liquids. J Am Chem Soc 124:4974–4975. https://doi.org/10.1021/ja025790m
Xu A, Guo X, Zhang Y, Li Z, Wang J (2017) Efficient and sustainable solvents for lignin dissolution: aqueous choline carboxylate solutions. Green Chem 19:4067–4073. https://doi.org/10.1039/c7gc01886j
Xue Z, Zhao X, Sun R-c, Mu T (2016) Biomass-derived γ-valerolactone-based solvent systems for highly efficient dissolution of various lignins: dissolution behavior and mechanism study. ACS Sustain Chem Eng 4:3864–3870. https://doi.org/10.1021/acssuschemeng.6b00639
Yuan L et al (2019) Dissolution of bamboo hemicellulose in 1-butyl-3-methylimidazolium halide-based ionic liquids. BioResources 14:2097–2112. https://doi.org/10.15376/biores.14.1.2097-2112
Zhang H, Wu J, Zhang J, He JS (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38:8272–8277. https://doi.org/10.1021/ma0505676
Zhang Q, Vigier KDO, Royer S, Jerome F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/c2cs35178a
Zhang Z, Song J, Han B (2017) Catalytic transformation of lignocellulose into chemicals and fuel products in ionic liquids. Chem Rev 117:6834–6880. https://doi.org/10.1021/acs.chemrev.6b00457
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The authors thank the National Natural Science Foundation of China (21873012) for financial support.
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Yu, H., Xue, Z., Lan, X. et al. Highly efficient dissolution of xylan in ionic liquid-based deep eutectic solvents. Cellulose 27, 6175–6188 (2020). https://doi.org/10.1007/s10570-020-03213-7
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DOI: https://doi.org/10.1007/s10570-020-03213-7