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24-10-2018 | Original Paper

Substituent effects on cellulose dissolution in imidazolium-based ionic liquids

Authors: Niwanthi Dissanayake, Vidura D. Thalangamaarachchige, Shelby Troxell, Edward L. Quitevis, Noureddine Abidi

Published in: Cellulose | Issue 12/2018

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Abstract

The dissolution of cotton cellulose with ionic liquids (ILs) has been extensively studied. However, the mechanism of cellulose dissolution, especially the role of the IL cation in the dissolution process, is not well understood. This paper describes a systematic study of the effects of the substituent groups on the cation in imidazolium-based ILs on cellulose dissolution. A series of imidazolium-based ILs with acetate as the anion, 1-hepyl-3-methylimidazolium acetate ([C₇C₁im][OAc]), 1-(cyclohexylmethyl)-3-methylimidazolium acetate ([CyhmC₁im][OAc]), 1-benzyl-3-methylimidazolium acetate ([BnzC₁im][OAc]), 1,3-dibenzylimidazolium acetate ([(Bnz)₂im][OAc]), and 1-(2-napthylmethyl)-3-methylimidazolium acetate ([NapmC₁im][OAc]) were synthesized. In each dissolution experiment, 5% (w/w) ground cotton fiber was dissolved in the ILs at 90 °C. The progress of the dissolution was monitored periodically with a polarized light microscope. This study revealed that [BnzC₁im][OAc] dissolved cotton cellulose more efficiently than the other four ILs. The results are discussed within the context of previous published theoretical and experimental studies on cellulose dissolution in ILs. For the five ILs that were investigated, we find that the effect of the cation can be rationalized on the basis of both the size and shape of the cation. In addition to the dissolution, cellulose was regenerated and characterized by Fourier transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM).

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Abe M, Fukaya Y, Ohno H (2010) Extraction of polysaccharides from bran with phosphonate or phosphinate-derived ionic liquids under short mixing time and low temperature. Green Chem 12:1274. https://doi.org/10.1039/c003976d CrossRef

Abidi N, Hequet E, Cabrales L et al (2008) Evaluating cell wall structure and composition of developing cotton fibers using fourier transform infrared spectroscopy and thermogravimetric analysis. J Appl Polym Sci 107:476–486. https://doi.org/10.1002/app.27100 CrossRef

Abidi N, Cabrales L, Haigler CH (2014) Changes in the cell wall and cellulose content of developing cotton fibers investigated by FTIR spectroscopy. Carbohydr Polym 100:9–16. https://doi.org/10.1016/j.carbpol.2013.01.074 CrossRefPubMed

Andanson J-M, Bordes E, Devémy J et al (2014) Understanding the role of co-solvents in the dissolution of cellulose in ionic liquids. Green Chem 16:2528. https://doi.org/10.1039/c3gc42244e CrossRef

Andanson JM, Pádua AAH, Costa Gomes MF (2015) Thermodynamics of cellulose dissolution in an imidazolium acetate ionic liquid. Chem Commun 51:4485–4487. https://doi.org/10.1039/c4cc10249e CrossRef

Azizi Samir MAS, Alloin F, Dufresne A (2005) Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromol 6:612–626CrossRef

Casas A, Palomar J, Alonso MV et al (2012) Comparison of lignin and cellulose solubilities in ionic liquids by COSMO-RS analysis and experimental validation. Ind Crops Prod 37:155–163. https://doi.org/10.1016/j.indcrop.2011.11.032 CrossRef

Casas A, Omar S, Palomar J et al (2013) Relation between differential solubility of cellulose and lignin in ionic liquids and activity coefficients. RSC Adv 3:3453–3460. https://doi.org/10.1039/c2ra22800a CrossRef

Dassanayake RS, Gunathilake C, Jackson T et al (2016) Preparation and adsorption properties of aerocellulose-derived activated carbon monoliths. Cellulose 23:1363–1374. https://doi.org/10.1007/s10570-016-0886-1 CrossRef

Derecskei B, Derecskei-Kovacs A (2006) Molecular dynamic studies of the compatibility of some cellulose derivatives with selected ionic liquids. Mol Simul 32:109–115. https://doi.org/10.1080/08927020600669627 CrossRef

Ding ZD, Chi Z, Gu WX et al (2012) Theoretical and experimental investigation on dissolution and regeneration of cellulose in ionic liquid. Carbohydr Polym 89:7–16. https://doi.org/10.1016/j.carbpol.2012.01.080 CrossRefPubMed

Endo T, Hosomi S, Fujii S et al (2016) Anion bridging-induced structural transformation of cellulose dissolved in ionic liquid. J Phys Chem Lett 7:5156–5161. https://doi.org/10.1021/acs.jpclett.6b02504 CrossRefPubMed

Endo T, Hosomi S, Fujii S et al (2017) Nano-structural investigation on cellulose highly dissolved in ionic liquid: a small angle x-ray scattering study. Molecules. https://doi.org/10.3390/molecules22010178 CrossRefPubMed

Gericke M, Fardim P, Heinze T (2012) Ionic liquids—promising but challenging solvents for homogeneous derivatization of cellulose. Molecules 17:7458–7502CrossRef

Gupta KM, Jiang J (2015) Cellulose dissolution and regeneration in ionic liquids: a computational perspective. Chem Eng Sci 121:180–189. https://doi.org/10.1016/j.ces.2014.07.025 CrossRef

Gupta KM, Hu Z, Jiang J (2011) Mechanistic understanding of interactions between cellulose and ionic liquids: a molecular simulation study. Polymer (Guildf) 52:5904–5911. https://doi.org/10.1016/j.polymer.2011.10.035 CrossRef

Haigler CH, Betancur L, Stiff MR, Tuttle JR (2012) Cotton fiber: a powerful single-cell model for cell wall and cellulose research. Front Plant Sci. https://doi.org/10.3389/fpls.2012.00104 CrossRefPubMedPubMedCentral

Heinze T, Dorn S, Schöbitz M et al (2008) Interactions of ionic liquids with polysaccharides—2: Cellulose. In: Macromolecular Symposia, pp 8–22CrossRef

Holding AJ, Parviainen A, Kilpeläinen I et al (2017) Efficiency of hydrophobic phosphonium ionic liquids and DMSO as recyclable cellulose dissolution and regeneration media. RSC Adv 7:17451–17461. https://doi.org/10.1039/c7ra01662j CrossRef

Huo F, Liu Z, Wang W (2013) Cosolvent or antisolvent? A molecular view of the interface between ionic liquids and cellulose upon addition of another molecular solvent. J Phys Chem B 117:11780–11792. https://doi.org/10.1021/jp407480b CrossRefPubMed

Ilharco LM, Garcia AR, Lopes da Silva J, Vieira Ferreira LF (1997) Infrared approach to the study of adsorption on cellulose: influence of cellulose crystallinity on the adsorption of benzophenone. Langmuir 13:4126–4132. https://doi.org/10.1021/la962138u CrossRef

Kahlen J, Masuch K, Leonhard K (2010) Modelling cellulose solubilities in ionic liquids using COSMO-RS. Green Chem 12:2172–2181. https://doi.org/10.1039/c0gc00200c CrossRef

Kosan B, Michels C, Meister F (2008) Dissolution and forming of cellulose with ionic liquids. Cellulose 15:59–66. https://doi.org/10.1007/s10570-007-9160-x CrossRef

Lan W, Liu CF, Yue FX et al (2011) Ultrasound-assisted dissolution of cellulose in ionic liquid. Carbohydr Polym 86:672–677. https://doi.org/10.1016/j.carbpol.2011.05.013 CrossRef

Li Y, Liu X, Zhang S et al (2015) Dissolving process of a cellulose bunch in ionic liquids: a molecular dynamics study. Phys Chem Chem Phys 17:17894–17905. https://doi.org/10.1039/C5CP02009C CrossRefPubMed

Li Y, Liu X, Zhang Y et al (2017) Why only ionic liquids with unsaturated heterocyclic cations can dissolve cellulose: a simulation study. ACS Sustain Chem Eng 5:3417–3428. https://doi.org/10.1021/acssuschemeng.7b00073 CrossRef

Li Y, Wang J, Liu X, Zhang S (2018) Towards a molecular understanding of cellulose dissolution in ionic liquids: anion/cation effect, synergistic mechanism and physicochemical aspects. Chem Sci 9:4027–4043CrossRef

Lindman B, Karlström G, Stigsson L (2010) On the mechanism of dissolution of cellulose. J Mol Liq 156:76–81. https://doi.org/10.1016/j.molliq.2010.04.016 CrossRef

Liu H, Sale KL, Holmes BM et al (2010) Understanding the interactions of cellulose with ionic liquids: a molecular dynamics study. J Phys Chem B 114:4293–4301. https://doi.org/10.1021/jp9117437 CrossRefPubMed

Liu Y-R, Thomsen K, Nie Y et al (2016) Predictive screening of ionic liquids for dissolving cellulose and experimental verification. Green Chem 18:6246–6254. https://doi.org/10.1039/C6GC01827K CrossRef

Lu B, Xu A, Wang J (2014) Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids. Green Chem 16:1326–1335. https://doi.org/10.1039/C3GC41733F CrossRef

Madeira Lau R, Sorgedrager MJ, Carrea G et al (2004) Dissolution of Candida antarctica lipase B in ionic liquids: effects on structure and activity. Green Chem 6:483–487. https://doi.org/10.1039/B405693K CrossRef

Meng X, Devemy J, Verney V et al (2017) Improving cellulose dissolution in ionic liquids by tuning the size of the ions: impact of the length of the alkyl chains in tetraalkylammonium carboxylate. Chemsuschem 10:1749–1760. https://doi.org/10.1002/cssc.201601830 CrossRefPubMed

Mostofian B, Smith JC, Cheng X (2011) The solvation structures of cellulose microfibrils in ionic liquids. Interdiscip Sci Comput Life Sci 3:308–320. https://doi.org/10.1007/s12539-011-0111-8 CrossRef

Mostofian B, Cheng X, Smith JC (2014) Replica-exchange molecular dynamics simulations of cellulose solvated in water and in the ionic liquid 1-butyl-3-methylimidazolium chloride. J Phys Chem B 118:11037–11049. https://doi.org/10.1021/jp502889c CrossRefPubMed

Oh SY, Il Yoo D, Shin Y et al (2005a) Crystalline structure analysis of cellulose treated with sodium hydroxide and carbon dioxide by means of X-ray diffraction and FTIR spectroscopy. Carbohydr Res 340:2376–2391. https://doi.org/10.1016/j.carres.2005.08.007 CrossRefPubMed

Oh SY, Il Yoo D, Shin Y, Seo G (2005b) FTIR analysis of cellulose treated with sodium hydroxide and carbon dioxide. Carbohydr Res 340:417–428. https://doi.org/10.1016/j.carres.2004.11.027 CrossRefPubMed

Ohno H, Fukaya Y (2009) Task specific ionic liquids for cellulose technology. Chem Lett 38:2–7. https://doi.org/10.1246/cl.2009.2 CrossRef

Olsson C, Westman G (2013) Direct dissolution of cellulose: background, means and applications. Cellul Asp. https://doi.org/10.5772/52144 CrossRef

Payal RS, Bharath R, Periyasamy G, Balasubramanian S (2012) Density functional theory investigations on the structure and dissolution mechanisms for cellobiose and xylan in an ionic liquid: gas phase and cluster calculations. J Phys Chem B 116:833–840. https://doi.org/10.1021/jp207989w CrossRefPubMed

Phillips DM, Drummy LF, Conrady DG et al (2004) Dissolution and regeneration of Bombyx mori silk fibroin using ionic liquids. J Am Chem Soc 126:14350–14351. https://doi.org/10.1021/ja046079f CrossRefPubMed

Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728. https://doi.org/10.1021/cr9001947 CrossRefPubMed

Rabideau BD, Agarwal A, Ismail AE (2013) Observed mechanism for the breakup of small bundles of cellulose Iα and Iβ in ionic liquids from molecular dynamics simulations. J Phys Chem B 117:3469–3479. https://doi.org/10.1021/jp310225t CrossRefPubMed

Rabideau BD, Agarwal A, Ismail AE (2014) The role of the cation in the solvation of cellulose by imidazolium-based ionic liquids. J Phys Chem B 118:1621–1629. https://doi.org/10.1021/jp4115755 CrossRefPubMed

Ragauskas AJ, Williams CK, Davison BH et al (2006) The path forward for biofuels and biomaterials. Science 311:484–489CrossRef

Remsing RC, Swatloski RP, Rogers RD, Moyna G (2006) Mechanism of cellulose dissolution in the ionic liquid 1-n-butyl-3-methylimidazolium chloride: a 13C and 35/37Cl NMR relaxation study on model systems. Chem Commun. https://doi.org/10.1039/b600586c CrossRef

Remsing RC, Hernandez G, Swatloski RP et al (2008) Solvation of carbohydrates in N, N′-dialkylimidazolium ionic liquids: a multinuclear NMR spectroscopy study. J Phys Chem B 112:11071–11078. https://doi.org/10.1021/jp8042895 CrossRefPubMed

Rogers RD, Seddon KR (2003) Ionic liquids—solvents of the future? Science 302:792–793CrossRef

Salmén L, Bergström E (2009) Cellulose structural arrangement in relation to spectral changes in tensile loading FTIR. Cellulose 16:975–982. https://doi.org/10.1007/s10570-009-9331-z CrossRef

Schutt TC, Bharadwaj VS, Hegde GA et al (2016) In silico insights into the solvation characteristics of the ionic liquid 1-methyltriethoxy-3-ethylimidazolium acetate for cellulosic biomass. Phys Chem Chem Phys 18:23715–23726. https://doi.org/10.1039/c6cp03235d CrossRefPubMed

Schwanninger M, Rodrigues JC, Pereira H, Hinterstoisser B (2004) Effects of short-time vibratory ball milling on the shape of FT-IR spectra of wood and cellulose. Vib Spectrosc 36:23–40. https://doi.org/10.1016/j.vibspec.2004.02.003 CrossRef

Sun N, Rodríguez H, Rahman M, Rogers RD (2011) Where are ionic liquid strategies most suited in the pursuit of chemicals and energy from lignocellulosic biomass? Chem Commun 47:1405–1421. https://doi.org/10.1039/C0CC03990J CrossRef

Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellose with ionic liquids. J Am Chem Soc 124:4974–4975. https://doi.org/10.1021/ja025790m CrossRefPubMed

Thakurathi M, Gurung E, Cetin MM et al (2018) The Stokes-Einstein equation and the diffusion of ferrocene in imidazolium-based ionic liquids studied by cyclic voltammetry: effects of cation ion symmetry and alkyl chain length. Electrochim Acta. https://doi.org/10.1016/j.electacta.2017.10.149 CrossRef

Velioglu S, Yao X, Devémy J et al (2014) Solvation of a cellulose microfibril in imidazolium acetate ionic liquids: effect of a cosolvent. J Phys Chem B 118:14860–14869. https://doi.org/10.1021/jp508113a CrossRefPubMed

Vitz J, Erdmenger T, Haensch C, Schubert US (2009) Extended dissolution studies of cellulose in imidazolium based ionic liquids. Green Chem 11:417–424. https://doi.org/10.1039/b818061j CrossRef

Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2084. https://doi.org/10.1021/cr980032t CrossRefPubMed

Xu A, Wang J, Wang H (2010) Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems. Green Chem 12:268–275. https://doi.org/10.1039/B916882F CrossRef

Xu H, Pan W, Wang R et al (2012) Understanding the mechanism of cellulose dissolution in 1-butyl-3-methylimidazolium chloride ionic liquid via quantum chemistry calculations and molecular dynamics simulations. J Comput Aided Mol Des 26:329–337. https://doi.org/10.1007/s10822-012-9559-9 CrossRefPubMed

Yao Y, Li Y, Liu X et al (2015) Mechanistic study on the cellulose dissolution in ionic liquids by density functional theory. Chin J Chem Eng 23:1894–1906. https://doi.org/10.1016/j.cjche.2015.07.018 CrossRef

Youngs TGA, Holbrey JD, Deetlefs M et al (2006) A molecular dynamics study of glucose solvation in the ionic liquid 1,3-dimethylimidazolium chloride. ChemPhysChem 7:2279–2281. https://doi.org/10.1002/cphc.200600569 CrossRefPubMed

Youngs TGA, Hardacre C, Holbrey JD (2007) Glucose solvation by the ionic liquid 1,3-dimethylimidazolium chloride: a simulation study. J Phys Chem B 111:13765–13774. https://doi.org/10.1021/jp076728k CrossRefPubMed

Youngs TGA, Holbrey JD, Mullan CL et al (2011) Neutron diffraction, NMR and molecular dynamics study of glucose dissolved in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Chem Sci 2:1594. https://doi.org/10.1039/c1sc00241d CrossRef

Zavrel M, Bross D, Funke M et al (2009) High-throughput screening for ionic liquids dissolving (ligno-)cellulose. Bioresour Technol 100:2580–2587. https://doi.org/10.1016/j.biortech.2008.11.052 CrossRefPubMed

Zhang H, Wu J, Zhang J, He J (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 CrossRef

Zhang S, Sun N, He X et al (2006) Physical properties of ionic liquids: database and evaluation. J Phys Chem Ref Data 35:1475–1517CrossRef

Zhao H, Baker GA, Song Z et al (2008) Designing enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem 10:696–705. https://doi.org/10.1039/b801489b CrossRef

Zhao D, Li H, Zhang J et al (2012) Dissolution of cellulose in phosphate-based ionic liquids. Carbohydr Polym 87:1490–1494. https://doi.org/10.1016/j.carbpol.2011.09.045 CrossRef

Zhao Y, Liu X, Wang J, Zhang S (2013) Insight into the cosolvent effect of cellulose dissolution in imidazolium-based ionic liquid systems. J Phys Chem B 117:9042–9049. https://doi.org/10.1021/jp4038039 CrossRefPubMed

Title: Substituent effects on cellulose dissolution in imidazolium-based ionic liquids
Authors: Niwanthi Dissanayake
Vidura D. Thalangamaarachchige
Shelby Troxell
Edward L. Quitevis
Noureddine Abidi
Publication date: 24-10-2018
Publisher: Springer Netherlands
Published in: Cellulose / Issue 12/2018
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-018-2055-1

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