Lignin-Derived Oil Palm Biomass Using Deep Eutectic Solvent

Abstract:

Deep Eutectic Solvent (DES) are eutectic mixes of hydrogen bond acceptors (HBA) and donors (HBD) with melting points significantly lower than their constituents. Choline chloride (ChCl) and glycerol were chosen as HBA and HBD because they are simple to prepare, have low toxicity, are biodegradable, and are environmentally friendly. As a result, the study aims to determine the feasibility of extracting lignin from oil palm fronds (OPF) and empty fruit bunches (EFB) using DES. The molar ratios of DESs were investigated to determine their effect on OPF solubility and lignin yield. The reaction is carried out at a solid loading ratio of 1:10, 150°C, and 6 hours. Because the DES medium induces homogeneous swelling and breakdown of small fibre fragments but not dissolution, both OPF and EFB are insoluble in DES. Small fragment disintegration suggests rapid dissolution, which will be easily dissolved in the DESs. The lignin yield and solubility of EFB and OPF in DESs are significantly reduced when the molar concentration of glycerol is increased. The highest lignin yields, 27.6% (EFB) and 16.1% (OPF) were obtained with a ChCl/glycerol molar ratio of 1:3. The comparatively low lignin yield achieved for both OPF and EFB is ascribed to the poor hydrogen bonding between the chloride ion and the hydroxyl group of the DES due to the low acidity of the DES. Despite this, lignin is extracted successfully due to the presence of chloride ions in ChCl, which target β-O-4 bonds and successfully cleave the ether bonds present in the lignin-carbohydrate linkage.

• Periodical: Materials Science Forum (Volume 1077)
• Pages: 145-151
• DOI: https://doi.org/10.4028/p-80x6p9
• Online since: December 2022
• Authors: Siti Khadijah Amran, Afiqah Liana Sazali, Mohamad Zulkeflee Sabri, Norfahana Abd Talib, Khairul Faizal Pa'ee, Siew Hway Teo Teo, Kelly Tau Len Yong*
• Keywords: Biomass, Deep Eutectic Solvent, Empty Fruit Bunch, Lignin, Oil Palm Frond

References

[1] W. Gindl-Altmutter, C. Fürst, A. raj Mahendran, M. Obersriebnig, G. Emsenhuber, M. Kluge, S. Veigel, J. Keckes, F. Liebner, Electrically conductive kraft lignin-based carbon filler for polymers, Carbon 89 (2015) 161-168.

DOI: 10.1016/j.carbon.2015.03.042

[2] T. L. Kelly-Yong, S. Lim, K. T. Lee, Gasification of oil palm Empty Fruit Bunch fibers in hot compressed water for synthesis gas production, J. Appl. Sci. 11 (2011) 3563–3570.

DOI: 10.3923/jas.2011.3563.3570

[3] T. L. K. Yong, M. Yukihiko, Kinetic analysis of guaiacol conversion in sub- and supercritical water, Ind. Eng. Chem. Res. 52 (2013) 9048–9059.

DOI: 10.1021/ie4009748

[4] T. L. K. Yong, Y. Matsumura, Reaction kinetics of the lignin conversion in supercritical water, Ind. Eng. Chem. Res. 51 (2012) 11975–11988.

DOI: 10.1021/ie300921d

[5] K. A. Khalid, A. A. Ahmad, T. L.-K. Yong, Lignin Extraction from Lignocellulosic Biomass Using Sub- and Supercritical Fluid Technology as Precursor for Carbon Fiber Production, J. Japan Inst. Energy 96 (2017) 255–260.

DOI: 10.3775/jie.96.255

[6] K. A. Khalid, V. Karunakaran, A. A. Ahmad, K. F. Pa'ee, N. Abd-Talib, and T. L. K. Yong, Lignin from oil palm frond under subcritical phenol conditions as a precursor for carbon fiber production, Malaysian J. Anal. Sci. 24 (2020) 484–494.

DOI: 10.1016/j.matpr.2020.01.252

[7] V. Karunakaran, N. Abd-Talib, T. L. Kelly Yong, Lignin from oil palm empty fruit bunches (EFB) under subcritical phenol conditions as a precursor for carbon fiber production, Mater. Today Proc. 31 (2020) 100–105.

DOI: 10.1016/j.matpr.2020.01.252

[8] D. Smink, A. Juan, B. Schuur, S. R. A. Kersten, Understanding the role of choline chloride in deep eutectic solvents used for biomass delignification, Ind. Eng. Chem. Res. 58 (2019) 16348–16357.

DOI: 10.1021/acs.iecr.9b03588

[9] D. Yongzhuang Liu, W. Chen, Q. Xia, B. Guo, Q. Wang, S. Liu, Y. Liu, J. Li, H. Yu, 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 (2017)1692–1700.

DOI: 10.1002/cssc.201601795

[10] K. H. Kim, T. Dutta, J. Sun, B. Simmons, S. Singh, Biomass pretreatment using deep eutectic solvents from lignin derived phenols, Green Chem. 20 (2018) 809–815.

DOI: 10.1039/c7gc03029k

[11] T. Li, G. Lyu, Y. Liu, R. Lou, L.A. Lucia, G. Yang, J. Chen, H.A. Saeed, Deep eutectic solvents (DESs) for the isolation of willow lignin (salix matsudana cv. zhuliu), Int. J. Mol. Sci. 18 (2017) 2266.

DOI: 10.3390/ijms18112266

[12] Q. Xia, Y. Liu, J. Meng, W. Cheng, W. Chen, S. Liu, Y. Liu, J. Li, H. Yu, Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass, Green Chem. 20 (2018) 2711–2721.

DOI: 10.1039/c8gc00900g

[13] C. Alvarez-Vasco, R. Ma, M. Quintero, M. Guo, S. Geleynse, K.K. Ramasamy, M. Wolcott, X. Zhang, 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 (2016) 5133–5141.

DOI: 10.1039/c6gc01007e

[14] Y. T. Tan, G. C. Ngoh, A. S. M. Chua, Evaluation of fractionation and delignification efficiencies of deep eutectic solvents on oil palm empty fruit bunch, Ind. Crops Prod. 123 (2018) 271–277.

DOI: 10.1016/j.indcrop.2018.06.091

[15] M. Francisco, A. Van Den Bruinhorst, M. C. Kroon, New natural and renewable low transition temperature mixtures (LTTMs): Screening as solvents for lignocellulosic biomass processing, Green Chem. 14 (2012) 2153–2157.

DOI: 10.1039/c2gc35660k

[16] H. Malaeke, M. R. Housaindokht, H. Monhemi, M. Izadyar, Deep eutectic solvent as an efficient molecular liquid for lignin solubilization and wood delignification, J. Mol. Liq. 263 (2018) 193–199.

DOI: 10.1016/j.molliq.2018.05.001

[17] Y. T. Tan, G. C. Ngoh, A. S. M. Chua, Effect of functional groups in acid constituent of deep eutectic solvent for extraction of reactive lignin, Bioresour. Technol. 281 (2019) 359–366.

DOI: 10.1016/j.biortech.2019.02.010

[18] E. L. Smith, A. P. Abbott, K. S. Ryder, Deep eutectic solvents (DESs) and their applications, Chem. Rev. 114 (2014) 11060–11082.

DOI: 10.1021/cr300162p

[19] Q. Zhang, K.D.O. Vigier, S. Royer, F. Jérôme, Deep eutectic solvents: Syntheses, properties and applications, Chem. Soc. Rev. 41 (2012) 7108–7146.

DOI: 10.1039/c2cs35178a

[20] P. Kalhor, K. Ghandi, Deep eutectic solvents for pretreatment, extraction, and catalysis of biomass and food waste, Molecules 24 (2019) 4012.

DOI: 10.3390/molecules24224012

[21] Z. Maugeri, P. Domínguez De María, Novel choline-chloride-based deep-eutectic-solvents with renewable hydrogen bond donors: Levulinic acid and sugar-based polyols, RSC Adv. 2 (2012) 421–425.

DOI: 10.1039/c1ra00630d

[22] E. Abdulmalek, S. Zulkefli, M. Basyaruddin, A. Rahman, Deep eutectic solvent as a media in swelling and dissolution of oil palm trunk, Malaysian J. Anal. Sci. 21 (2017) 20-26.

DOI: 10.17576/mjas-2017-2101-03

[23] C. Cuissinat, P. Navard, T. Heinze, Swelling and dissolution of cellulose. Part IV: Free floating cotton and wood fibres in ionic liquids, Carbohydr. Polym. 72, (2008) 590–596.

DOI: 10.1016/j.carbpol.2007.09.029

[24] C. Li, C. Huang, Y. Zhao, C. Zheng, H. Su, L. Zhang, W. Luo, H. Zhao, S. Wang, L.J. Huang, Effect of choline-based deep eutectic solvent pretreatment on the structure of cellulose and lignin in bagasse, Processes 9 (2021) 384.

DOI: 10.3390/pr9020384

[25] T. Kanbayashi, H. Miyafuji, Effect of ionic liquid treatment on the ultrastructural and topochemical features of compression wood in Japanese cedar (Cryptomeria japonica), Sci. Rep. 6 (2016) 1–8.

DOI: 10.1038/srep30147

[26] A. Skulcova, A. Russ, M. Jablonsky, J. Sima, The pH behavior of seventeen deep eutectic solvents, Bioresources 3 (2018) 5042–5051.

DOI: 10.15376/biores.13.3.5042-5051