Efficient and eco-friendly isolation and purification of lignin from black liquor with choline chloride-based deep eutectic solvents
Source abstract
Abstract
Abstract This study developed an efficient and green method for isolating and purifying lignin from black liquor (BL) using deep eutectic solvents (DESs). After the short and mild process (700 W microwave-assisted, 100 °C, DES: BL 1:5 (v: v), 30 min) using optimized DES (lactic acid (LA): choline chloride (ChCl) 10:1, molar ratio), the yield and purity of lignin obtained from 100 mL BL was 1.58 g and 88.12%, respectively, which was more efficient than the results of 1.18 g and 78.54% of the conventional process. Furthermore, more than 95% of initial results were obtained after three cycles. The composition and structure of DESs and conventionally purified lignin were slightly different. The solvent costs for both processes were also evaluated, showing that the DES process has great potential to replace traditional bulky and environmentally unfriendly procedures for lignin isolation and purification and to help develop new strategies for the potential added value of lignin.
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Research context
OpenAlex topics: Lignin and Wood Chemistry · Fermentation and Sensory Analysis · Ionic liquids properties and applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
State Key Laboratory of Pulp and Paper Engineering , South China University of Technology , Guangzhou 510640 , P.R. China
International Innovation Center for Forest Chemicals and Materials and Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University , Nanjing 210037 , P.R. China
School of Food Science and Engineering , South China University of Technology , Guangzhou 510640 , P.R. China
Funding
Science and Technology Planning Project of Guangzhou City, China · Science and Technology Planning Project of Guangdong Province
References (50)
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1. Abbott, A.P., Boothby, D., Capper, G., Davies, D.L., and Rasheed, R.K. (2004). Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126: 9142–9147, https://doi.org/10.1021/ja048266j.10.1021/ja048266j ↗
2. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., and Tambyrajah, V. (2003). Novel solvent properties of choline chloride/urea mixtures. Chem. Commun.: 70–71, https://doi.org/10.1039/b210714g.10.1039/b210714g ↗
3. Alvarez-Vasco, C., Ma, R., Quintero, M., Guo, M., Geleynse, S., Ramasamy, K.K., Wolcott, M., and Zhang, X. (2016). Unique low-molecular-weight lignin with high purity extracted from wood by deep eutectic solvents (DES): a source of lignin for valorization. Green Chem. 18: 5133–5141, https://doi.org/10.1039/c6gc01007e.10.1039/C6GC01007E ↗
4. Billes, E., Onwukamike, K.N., Coma, V., Grelier, S., and Peruch, F. (2016). Cellulose oligomers production and separation for the synthesis of new fully bio-based amphiphilic compounds. Carbohydr. Polym. 154: 121–128, https://doi.org/10.1016/j.carbpol.2016.07.107.10.1016/j.carbpol.2016.07.107 ↗
5. Casas, A., Virginia Alonso, M., Oliet, M., Rojo, E., and Rodriguez, F. (2012). FTIR analysis of lignin regenerated from Pinus radiata and Eucalyptus globulus woods dissolved in imidazolium-based ionic liquids. J. Chem. Technol. Biotechnol. 87: 472–480, https://doi.org/10.1002/jctb.2724.10.1002/jctb.2724 ↗
6. Chen, Y., Zhang, L., Yu, J., Lu, Y., Jiang, B., Fan, Y., and Wang, Z. (2019a). High-purity lignin isolated from poplar wood meal through dissolving treatment with deep eutectic solvents. R. Soc. Open Sci. 6: 181757, https://doi.org/10.1098/rsos.181757.10.1098/rsos.181757 ↗
7. Chen, Z., Sun, Y., and Wan, C. (2019b). Effects of alkaline hydrogen peroxide treatment on cellulose accessibility of switchgrass pretreated by acidic deep eutectic solvent. Cellulose 26: 9439–9446, https://doi.org/10.1007/s10570-019-02759-5.10.1007/s10570-019-02759-5 ↗
8. Ci, Y.-H., Yu, F., Zhou, C.-X., Mo, H.-E., Li, Z.-Y., Ma, Y.-Q., and Zang, L.-H. (2020). New ternary deep eutectic solvents for effective wheat straw deconstruction into its high-value utilization under near-neutral conditions. Green Chem. 22: 8713–8720, https://doi.org/10.1039/d0gc03240a.10.1039/D0GC03240A ↗
9. da Costa Lopes, A.M., Gomes, J.R.B., Coutinho, J.A.P., and Silvestre, A.J.D. (2020). Novel insights into biomass delignification with acidic deep eutectic solvents: a mechanistic study of beta-O-4 ether bond cleavage and the role of the halide counterion in the catalytic performance. Green Chem. 22: 2474–2487, https://doi.org/10.1039/c9gc02569c.10.1039/C9GC02569C ↗
10. Dai, Y., Witkamp, G.-J., Verpoorte, R., and Choi, Y.H. (2015). Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem. 187: 14–19, https://doi.org/10.1016/j.foodchem.2015.03.123.10.1016/j.foodchem.2015.03.123 ↗
11. Dallinger, D. and Kappe, C.O. (2007). Microwave-assisted synthesis in water as solvent. Chem. Rev. 107: 2563–2591, https://doi.org/10.1021/cr0509410.10.1021/cr0509410 ↗
12. Dwamena, A.K. and Raynie, D.E. (2020). Solvatochromic parameters of deep eutectic solvents: effect of different carboxylic acids as hydrogen bond donor. J. Chem. Eng. Data 65: 640–646, https://doi.org/10.1021/acs.jced.9b00872.10.1021/acs.jced.9b00872 ↗
13. Fernandes, C., Melro, E., Magalhaes, S., Alves, L., Craveiro, R., Filipe, A., Valente, A.J.M., Martins, G., Antunes, F.E., Romano, A., et al.. (2021). New deep eutectic solvent assisted extraction of highly pure lignin from maritime pine sawdust (Pinus pinaster Ait.). Int. J. Biol. Macromol. 177: 294–305, https://doi.org/10.1016/j.ijbiomac.2021.02.088.10.1016/j.ijbiomac.2021.02.088 ↗
14. Francisco, M., van den Bruinhorst, A., and Kroon, M.C. (2012). New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing. Green Chem. 14: 2153–2157, https://doi.org/10.1039/c2gc35660k.10.1039/c2gc35660k ↗
15. Gonzalez-Rivera, J., Husanu, E., Mero, A., Ferrari, C., Duce, C., Tine, M.R., D’Andrea, F., Pomelli, C.S., and Guazzelli, L. (2020). Insights into microwave heating response and thermal decomposition behavior of deep eutectic solvents. J. Mol. Liq. 300: 300, https://doi.org/10.1016/j.molliq.2019.112357.10.1016/j.molliq.2019.112357 ↗
16. Gonzalez-Rivera, J., Mero, A., Husanu, E., Mezzetta, A., Ferrari, C., D’Andrea, F., Bramanti, E., Pomelli, C.S., and Guazzelli, L. (2021). Combining acid-based deep eutectic solvents and microwave irradiation for improved chestnut shell waste valorization. Green Chem. 23: 10101–10115, https://doi.org/10.1039/d1gc03450b.10.1039/D1GC03450B ↗
17. Hammond, O.S., Bowron, D.T., and Edler, K.J. (2017). The effect of water upon deep eutectic solvent nanostructure: an unusual transition from ionic mixture to aqueous solution. Angew. Chem., Int. Ed. 56: 9782–9785, https://doi.org/10.1002/ange.201702486.10.1002/anie.201702486 ↗
18. Hubbe, M.A., Alen, R., Paleologou, M., Kannangara, M., and Kihlman, J. (2019). Lignin recovery from spent alkaline pulping liquors using acidification, membrane separation, and related processing steps: a review. Bioresources 14: 2300–2351, https://doi.org/10.15376/biores.14.1.2300-2351.10.15376/biores.14.1.2300-2351 ↗
19. Li, A.-L., Hou, X.-D., Lin, K.-P., Zhang, X., and Fu, M.-H. (2018). Rice straw pretreatment using deep eutectic solvents with different constituents molar ratios: biomass fractionation, polysaccharides enzymatic digestion and solvent reuse. J. Biosci. Bioeng. 126: 346–354, https://doi.org/10.1016/j.jbiosc.2018.03.011.10.1016/j.jbiosc.2018.03.011 ↗
20. Li, M.-F., Yu, P., Li, S.-X., Wu, X.-F., Xiao, X., and Bian, J. (2017a). Sequential two-step fractionation of lignocellulose with formic acid organosolv followed by alkaline hydrogen peroxide under mild conditions to prepare easily saccharified cellulose and value-added lignin. Energy Convers. Manag. 148: 1426–1437, https://doi.org/10.1016/j.enconman.2017.07.008.10.1016/j.enconman.2017.07.008 ↗
21. Li, T., Lyu, G., Liu, Y., Lou, R., Lucia, L.A., Yang, G., Chen, J., and Saeed, H.A.M. (2017b). Deep eutectic solvents (DESs) for the isolation of willow lignin (Salix matsudana cv. Zhuliu). Int. J. Mol. Sci. 18: 2266, https://doi.org/10.3390/ijms18112266.10.3390/ijms18112266 ↗
22. Li, T., Ma, H., Wu, S., and Yin, Y. (2020). Effect of highly selective oxypropylation of phenolic hydroxyl groups on subsequent lignin pyrolysis: toward the lignin valorization. Energy Convers. Manag. 207: 112551.10.1016/j.enconman.2020.112551 ↗
23. Liu, X., Li, T.F., Wu, S.B., Ma, H., and Yin, Y.H. (2020a). Structural characterization and comparison of enzymatic and deep eutectic solvents isolated lignin from various green processes: toward lignin valorization. Bioresour. Technol. 310: 310, https://doi.org/10.1016/j.biortech.2020.123460.10.1016/j.biortech.2020.123460 ↗
24. Liu, Y., Chen, W., Xia, Q., Guo, B., Wang, Q., Liu, S., Liu, Y., Li, J., and Yu, H. (2017). Efficient cleavage of lignin-carbohydrate complexes and ultrafast extraction of lignin oligomers from wood biomass by microwave-assisted treatment with deep eutectic solvent. Chemsuschem 10: 1692–1700, https://doi.org/10.1002/cssc.201601795.10.1002/cssc.201601795 ↗
25. Liu, Z., Hou, Y., Hu, S., and Li, Y. (2020b). Possible dissolution mechanism of alkali lignin in lactic acid-choline chloride under mild conditions. Rsc Adv. 10: 40649–40657, https://doi.org/10.1039/d0ra07808e.10.1039/D0RA07808E ↗
26. Lourencon, T.V., Hansel, F.A., da Silva, T.A., Ramos, L.P., de Muniz, G.I.B., and Magalhaes, W.L.E. (2015). Hardwood and softwood kraft lignins fractionation by simple sequential acid precipitation. Sep. Purif. Technol. 154: 82–88, https://doi.org/10.1016/j.seppur.2015.09.015.10.1016/j.seppur.2015.09.015 ↗
27. Manara, P., Zabaniotou, A., Vanderghem, C., and Richel, A. (2014). Lignin extraction from Mediterranean agro-wastes: impact of pretreatment conditions on lignin chemical structure and thermal degradation behavior. Catal. Today 223: 25–34, https://doi.org/10.1016/j.cattod.2013.10.065.10.1016/j.cattod.2013.10.065 ↗
28. Martins, M.A.R., Pinho, S.P., and Coutinho, J.A.P. (2019). Insights into the nature of eutectic and deep eutectic mixtures. J. Solution Chem. 48: 962–982, https://doi.org/10.1007/s10953-018-0793-1.10.1007/s10953-018-0793-1 ↗
29. Maugeri, Z. and de Maria, P.D. (2012). Novel choline-chloride-based deep-eutectic-solvents with renewable hydrogen bond donors: levulinic acid and sugar-based polyols. Rsc Adv. 2: 421–425, https://doi.org/10.1039/c1ra00630d.10.1039/C1RA00630D ↗
30. Morais, E.S., Da Costa Lopes, A.M., Freire, M.G., Freire, C.S.R., and Silvestre, A.J.D. (2021). Unveiling modifications of biomass polysaccharides during thermal treatment in cholinium chloride: lactic acid deep eutectic solvent. Chemsuschem 14: 686–698, https://doi.org/10.1002/cssc.202002301.10.1002/cssc.202002301 ↗
31. Morais, E.S., Freire, M.G., Freire, C.S.R., Coutinho, J.A.P., and Silvestre, A.J.D. (2020). Enhanced conversion of xylan into furfural using acidic deep eutectic solvents with dual solvent and catalyst behavior. Chemsuschem 13: 784–790, https://doi.org/10.1002/cssc.201902848.10.1002/cssc.201902848 ↗
32. Muley, P.D., Mobley, J.K., Tong, X., Novak, B., Stevens, J., Moldovan, D., Shi, J., and Boldor, D. (2019). Rapid microwave-assisted biomass delignification and lignin depolymerization in deep eutectic solvents. Energy Convers. Manag. 196: 1080–1088, https://doi.org/10.1016/j.enconman.2019.06.070.10.1016/j.enconman.2019.06.070 ↗
33. Pan, X., Kadla, J.F., Ehara, K., Gilkes, N., and Saddler, J.N. (2006). Organosolv ethanol lignin from hybrid poplar as a radical scavenger: relationship between lignin structure, extraction conditions, and antioxidant activity. J. Agric. Food Chem. 54: 5806–5813, https://doi.org/10.1021/jf0605392.10.1021/jf0605392 ↗
34. Schutyser, W., Renders, T., Van den Bosch, S., Koelewijn, S.F., Beckham, G.T., and Sels, B.F. (2018). Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem. Soc. Rev. 47: 852–908, https://doi.org/10.1039/c7cs00566k.10.1039/C7CS00566K ↗
35. Shen, X.-J., Wen, J.-L., Mei, Q.-Q., Chen, X., Sun, D., Yuan, T.-Q., and Sun, R.-C. (2019). Facile fractionation of lignocelluloses by biomass-derived deep eutectic solvent (DES) pretreatment for cellulose enzymatic hydrolysis and lignin valorization. Green Chem. 21: 275–283, https://doi.org/10.1039/c8gc03064b.10.1039/C8GC03064B ↗
36. Smink, D., Juan, A., Schuur, B., and Kersten, S.R.A. (2019). Understanding the role of choline chloride in deep eutectic solvents used for biomass delignification. Ind. Eng. Chem. Res. 58: 16348–16357, https://doi.org/10.1021/acs.iecr.9b03588.10.1021/acs.iecr.9b03588 ↗
37. Smith, E.L., Abbott, A.P., and Ryder, K.S. (2014). Deep eutectic solvents (DESs) and their applications. Chem. Rev. 114: 11060–11082, https://doi.org/10.1021/cr300162p.10.1021/cr300162p ↗
38. Soares, B., Tavares, D.J.P., Amaral, J.L., Silvestre, A.J.D., Freire, C.S.R., and Coutinho, J.A.P. (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.7b00053.10.1021/acssuschemeng.7b00053 ↗
39. Tan, Y.T., Chua, A.S.M., and Ngoh, G.C. (2020). Deep eutectic solvent for lignocellulosic biomass fractionation and the subsequent conversion to bio-based products - a review. Bioresour. Technol. 297: 122522.10.1016/j.biortech.2019.122522 ↗
40. Tan, Y.T., Ngoh, G.C., and Chua, A.S.M. (2019). Effect of functional groups in acid constituent of deep eutectic solvent for extraction of reactive lignin. Bioresour. Technol. 281: 359–366, https://doi.org/10.1016/j.biortech.2019.02.010.10.1016/j.biortech.2019.02.010 ↗
41. Tan, Y.T., Ngoh, G.C., and Chua, A.S.M. (2018). Evaluation of fractionation and delignification efficiencies of deep eutectic solvents on oil palm empty fruit bunch. Ind. Crops Prod. 123: 271–277, https://doi.org/10.1016/j.indcrop.2018.06.091.10.1016/j.indcrop.2018.06.091 ↗
42. Wen, J.-L., Yuan, T.-Q., Sun, S.-L., Xu, F., and Sun, R.-C. (2014). Understanding the chemical transformations of lignin during ionic liquid pretreatment. Green Chem. 16: 181–190, https://doi.org/10.1039/c3gc41752b.10.1039/C3GC41752B ↗
43. Xia, Q., Liu, Y., Meng, J., Cheng, W., Chen, W., Liu, S., Liu, Y., Li, J., and Yu, H. (2018). Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass. Green Chem. 20: 2711–2721, https://doi.org/10.1039/c8gc00900g.10.1039/C8GC00900G ↗
44. Xue, Y., Li, Y., Liu, Z., and Hou, Y. (2019). Structural changes of lignin in soda delignification process and associations with pollution load. Bioresources 14: 7869–7885.10.15376/biores.14.4.7869-7885 ↗
45. Zafarani-Moattar, M.T., Asadzadeh, B., and Shekaari, H. (2016). Phase equilibrium of aqueous Glycine plus choline chloride ionic liquid solutions. J. Solution Chem. 45: 1842–1856, https://doi.org/10.1007/s10953-016-0537-z.10.1007/s10953-016-0537-z ↗
46. Zhang, C.-W., Xia, S.-Q., and Ma, P.-S. (2016). Facile pretreatment of lignocellulosic biomass using deep eutectic solvents. Bioresour. Technol. 219: 1–5, https://doi.org/10.1016/j.biortech.2016.07.026.10.1016/j.biortech.2016.07.026 ↗
47. Zhang, Q., Vigier, K.D.O., Royer, S., and Jerome, F. (2012). Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 41: 7108–7146, https://doi.org/10.1039/c2cs35178a.10.1039/c2cs35178a ↗
48. Zhang, Y., Lu, X., Feng, X., Shi, Y., and Ji, X. (2013). Properties and applications of choline-based deep eutectic solvents. Prog. Chem. 25: 881–892.
49. Zhao, X., Wu, R., and Liu, D. (2011). Production of pulp, ethanol and lignin from sugarcane bagasse by alkali-peracetic acid delignification. Biomass Bioenergy 35: 2874–2882, https://doi.org/10.1016/j.biombioe.2011.03.033.10.1016/j.biombioe.2011.03.033 ↗
50. Zhong, L., Wang, C., Yang, G., Chen, J., Xu, F., Yoo, C.G., and Lyu, G. (2022). Rapid and efficient microwave-assisted guanidine hydrochloride deep eutectic solvent pretreatment for biological conversion of castor stalk. Bioresour. Technol. 343: 343, https://doi.org/10.1016/j.biortech.2021.126022.10.1016/j.biortech.2021.126022 ↗