Abstract
A set of imidazolium-based ionic liquids: [C4mim][PF6], [C4mim][BF4], [C4mim][Cl], [C4mim][CF3COO], [C4mim][NTf2], [C4mim][OMs], [C4mim][Br], and [C4mim][OAc], was studied by molecular dynamics simulations to elucidate their solvent behavior around a crystallite model of cellulose I\(\beta\), through atomistic interactions and the degree of departure of its thermodynamic properties from their solvent pure phase. These departure changes were correlated with experimental values of the Kamlet-Taft solvent basicity parameter, and it was found that, even at room temperature, density changes, and vaporization enthalpy changes can be correlated with the capacity of ionic liquids for the preconditioning of the cellulose crystallite. Hydrogen bond occupancies indicate that ionic liquids can disrupt external chains of the cellulose crystallite by replacing and reducing the strong \(O6 - H \cdots O2/O3\) hydrogen bonds by weak hydrogen bonds such as \(O6 - H \cdots O4\) along the interchain network. Also, radial distribution functions indicated that structural changes in the cellulose-ionic liquid mixtures did not depart significantly with respect to the pure IL structure. The results of the free energy of solvation calculations for a cellulose chain, presented the following trend: [C4mim][Cl] > [C4mim][OAc] > [C4mim][CF3COO] > [C4mim][Br] > [C4mim][OMs] > [C4mim][BF4] > [C4mim][PF6] > water > [C4mim][NTf2]. It is important to emphasize, that the focus of this work was not the cellulose dissolution, but instead, the solvent behavior and cellulose preconditioning within each IL at room temperature. Our results can provide insights about the preconditioning stage of cellulose at low temperature, useful in the development of lignocellulosic materials and valuable cellulose derivatives by means of low energy requirements.
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References
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 12:1274–1280. https://doi.org/10.1039/C003976D
Abe M, Kuroda K, Sato D, Kunimura H, Ohno H (2015) Effects of polarity, hydrophobicity, and density of ionic liquids on cellulose solubility. Phys Chem Chem Phys 17:32276–32282. https://doi.org/10.1039/C5CP05808B
Anthony JL, Brennecke JF, Holbrey JD, et al (2002) Physicochemical properties of ionic liquids. In: Wasserscheid P, Welton T (eds) Ionic Liquids in Synthesis. Wiley-VCH Verlag, Weinheim, pp 41–126. https://doi.org/10.1002/3527600701
Banks JL, Beard HS, Cao Y et al (2005) Integrated modeling program, applied chemical theory (IMPACT). J Comput Chem 26:1752–1780. https://doi.org/10.1002/jcc.20292
Batista MLS, Pérez-Sánchez G, Gomes JRB et al (2015) Evaluation of the GROMOS 56ACARBO force field for the calculation of structural, volumetric, and dynamic properties of aqueous glucose Systems. J Phys Chem B 119:15310–15319. https://doi.org/10.1021/acs.jpcb.5b08155
Carpenter JE, Weinhold F (1988) Analysis of the geometry of the hydroxymethyl radical by the “different hybrids for different spins” natural bond orbital procedure. J Mol Struct THEOCHEM 169:41–62. https://doi.org/10.1016/0166-1280(88)80248-3
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 Prod Crop 37:155–163. https://doi.org/10.1016/j.indcrop.2011.11.032
Chipot C, Pohorille A (2007) Calculating free energy differences using perturbation theory. In: Chipot C, Pohorille A (eds) Free energy calculations: Theory and applications in chemistry and biology. Springer-Verlag, New York, pp 33–75
Chipot C, Shell MS, Pohorille A (2007) Introduction. In: Chipot C, Pohorille A (eds) Free energy calculations: Theory and applications in chemistry and biology. Springer-Verlag, New York, pp 1–31
Cláudio AFM, Swift L, Hallett JP et al (2014) Extended scale for the hydrogen-bond basicity of ionic liquids. Phys Chem Chem Phys 16:6593–6601. https://doi.org/10.1039/C3CP55285C
Contreras-García J, Johnson ER, Keinan S et al (2011) NCIPLOT: a program for plotting noncovalent interaction regions. J Chem Theory Comput 7:625–632. https://doi.org/10.1021/ct100641a
Contreras-García J, Boto RA, Izquierdo-Ruiz F et al (2016) A benchmark for the non-covalent interaction (NCI) index or… is it really all in the geometry? Theor Chem Acc 135:242. https://doi.org/10.1007/s00214-016-1977-7
Deyko A, Lovelock KRJ, Corfield J-A et al (2009) Measuring and predicting ΔvapH298 values of ionic liquids. Phys Chem Chem Phys 11:8544–8555. https://doi.org/10.1039/B908209C
Doherty B, Zhong X, Acevedo O (2018) Virtual site OPLS force field for imidazolium-based ionic liquids. J Phys Chem B 122:2962–2974. https://doi.org/10.1021/acs.jpcb.7b11996
Essmann U, Perera L, Berkowitz ML et al (1995) A smooth particle mesh Ewald method. J Chem Phys 103:8577–8592. https://doi.org/10.1063/1.470117
Fang D-W, Zhang F, Jia R et al (2017) Physicochemical properties of [Cnmim][TFA] (n=2,3, 4, 5, 6) ionic liquids. RSC Adv 7:11616–11625. https://doi.org/10.1039/C7RA00197E
Feller SE, Zhang Y, Pastor RW, Brooks BR (1995) Constant pressure molecular dynamics simulation: the Langevin piston method. J Chem Phys 103:4613–4620. https://doi.org/10.1063/1.470648
Foster JP, Weinhold F (1980) Natural hybrid orbitals. J Am Chem Soc 102:7211–7218. https://doi.org/10.1021/ja00544a007
Frenkel D, Smith B (2002) Understanding molecular simulations: From algorithms to applications. Academic Press, California. https://doi.org/10.1016/B978-0-12-267351-1.X5000-7
Frisch MJ, Trucks GW, Schlegel HB, et al (2013). Gaussian 09, revision D.01. Wallingford, CT, Gaussian Inc.
Fuentes-Azcatl R, Mendoza N, Alejandre J (2015) Improved SPC force field of water based on the dielectric constant: SPC/ε. Phys A 420:116–123. https://doi.org/10.1016/j.physa.2014.10.072
Fukaya Y, Sugimoto A, Ohno H (2006) Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates. Biomacromol 7:3295–3297. https://doi.org/10.1021/bm060327d
Fukaya Y, Hayashi K, Wada M, Ohno H (2008) Cellulose dissolution with polar ionic liquids under mild conditions: Required factors for anions. Green Chem 10:44–46. https://doi.org/10.1039/B713289A
Geppert-Rybczyńska M, Lehmann JK, Safarov J, Heintz A (2013) Thermodynamic surface properties of [BMIm][NTf2] or [EMIm][NTf2] binary mixtures with tetrahydrofuran, acetonitrile or dimethylsulfoxide. J Chem Thermodyn 62:104–110. https://doi.org/10.1016/j.jct.2013.02.021
Gericke M, Fardim P, Heinze T (2012) Ionic liquids—promising but challenging solvents for homogeneous derivatization of cellulose. Molecules 17:7458–7502. https://doi.org/10.3390/molecules17067458
Gomes TC, Skaf MS (2012) Cellulose-builder: a toolkit for building crystalline structures of cellulose. J Comput Chem 33:1338–1346. https://doi.org/10.1002/jcc.22959
Govinda V, Attri P, Venkatesu P, Venkateswarlu P (2011) Thermophysical properties of dimethylsulfoxide with ionic liquids at various temperatures. Fluid Phase Equilib 304:35–43. https://doi.org/10.1016/j.fluid.2011.02.010
Grest GS, Kremer K (1986) Molecular dynamics simulation for polymers in the presence of a heat bath. Phys Rev A 33:3628–3631. https://doi.org/10.1103/PhysRevA.33.3628
Griffin P, Ramer S, Winfough M, Kostal J (2020) Practical guide to designing safer ionic liquids for cellulose dissolution using a tiered computational framework. Green Chem 22:3626–3637. https://doi.org/10.1039/D0GC00923G
Gross AS, Bell AT, Chu J-W (2011) Thermodynamics of cellulose solvation in water and the ionic liquid 1-butyl-3-methylimidazolim chloride. J Phys Chem B 115:13433–13440. https://doi.org/10.1021/jp202415v
Gruzdev MS, Ramenskaya LM, Chervonova UV, Kumeev RS (2009) Preparation of 1-butyl-3-methylimidazolium salts and study of their phase behavior and intramolecular intractions. Russ J Gen Chem 79:1720–1727. https://doi.org/10.1134/S1070363209080246
Harris KR, Woolf LA (2004) Temperature and volume dependence of the viscosity of water and heavy water at low temperatures. J Chem Eng Data 49:1064–1069. https://doi.org/10.1021/je049918m
Hermanutz F, Vocht M, Panzier N, Buchmeise MR (2019) Processing of cellulose using ionic liquids. Macromol Mater Eng 304:1800450. https://doi.org/10.1002/mame.201800450
Hernández-Ríos S, Sánchez-Badillo J, Gallo M et al (2017) Thermodynamic properties of the 1-butyl-3-methylimidazolium mesilate ionic liquid [C4mim][OMs] in condensed phase, using molecular simulations. J Mol Liq 244:422–432. https://doi.org/10.1016/j.molliq.2017.09.031
Humphrey W, Dalke A, Schulten K (1996) VMD: Visual molecular dynamics. J Mol Graphics 14:33–38. https://doi.org/10.1016/0263-7855(96)00018-5
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
Isik M, Sardon H, Mecerreyes D (2014) Ionic liquids and cellulose: dissolution, chemical modification and preparation of new cellulosic materials. Int J Mol Sci 15:11922–11940. https://doi.org/10.3390/ijms150711922
Jacquemin J, Husson P, Padua AAH, Majer V (2006) Density and viscosity of several pure and water-saturated ionic liquids. Green Chem 8:172–180. https://doi.org/10.1039/B513231B
Jadhav VH, Jeong H-J, Lim ST et al (2011) Tailor-made hexaethylene glycolic ionic liquids as organic catalysts for specific chemical reactions. Org Lett 13:2502–2505. https://doi.org/10.1021/ol200751e
Jedvert K, Heinze T (2017) Cellulose modification and shaping – A review. J Polym Eng 37:845–860. https://doi.org/10.1515/polyeng-2016-0272
Johnson ER, Keinan S, Mori-Sánchez P et al (2010) Revealing noncovalent interactions. J Am Chem Soc 132:6498–6506. https://doi.org/10.1021/ja100936w
Kabiri K, Zohuriaan-Mehr MJ, Mirzadeh H, Kheirabadi M (2010) Solvent-, Ion- and pH-specific swelling of poly(2-acrylamido-2-methylpropane sulfonic acid) superabsorbing gels. J Polym Res 17:203–212. https://doi.org/10.1007/s10965-009-9306-7
Kavitha T, Vasantha T, Venkatesu P et al (2014) Thermophysical properties for the mixed solvents of N-methyl-2-pyrrolidone with some of the imidazolium-based ionic liquids. J Mol Liq 198:11–20. https://doi.org/10.1016/j.molliq.2014.07.002
Khazraji AC, Robert S (2013) Interaction effects between cellulose and water in nanocrystalline and amorphous regions: A novel approach using molecular modeling. J Nanomater. https://doi.org/10.1155/2013/409676
Komeiji Y, Uebayasi M, Someya J, Yamato I (1993) A molecular dynamics study of solvent behavior around a protein. Proteins Struct Funct Genet 16:268–277. https://doi.org/10.1002/prot.340160305
Krossing I, Slattery JM, Daguenet C et al (2006) Why are ionic liquids liquid? a simple explanation based on lattice and solvation energies. J Am Chem Soc 128:13427–13434. https://doi.org/10.1021/ja0619612
Kumar B, Bhardwaj N, Agrawal K et al (2020) Current perspective on pretreatment technologies using lignocellulosic biomass: an emerging biorefinery concept. Fuel Process Technol. https://doi.org/10.1016/j.fuproc.2019.106244
Leach AR (2001) Computer simulations methods. Molecular modelling: Principles and applications. Prentice Hall, New York, pp 303–352
Lee JW, Shin JY, Chun YS et al (2010) Toward understanding the origin of positive effects of ionic liquids on catalysis: Formation of more reactive catalysts and stabilization of reactive intermediates and transition states in ionic liquids. Acc Chem Res 43:985–994. https://doi.org/10.1021/ar9002202
Lei Z, Dai C, Chen B (2014) Gas solubility in ionic liquids. Chem Rev 114:1289–1326. https://doi.org/10.1021/cr300497a
Li C, Strachan A (2018) Cohesive energy density and solubility parameter evolution during the curing of thermoset. Polymer 135:162–170. https://doi.org/10.1016/j.polymer.2017.12.002
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
Liu Z, Wu X, Wang W (2006) A novel united-atom force field for imidazolium-based ionic liquids. Phys Chem Chem Phys 8:1096–1104. https://doi.org/10.1039/B515905A
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
Liu H, Cheng G, Kent M et al (2012) Simulations reveal conformational changes of methylhydroxyl groups during dissolution of cellulose Iβ in ionic liquid 1-ethyl-3-methylimidazolium acetate. J Phys Chem B 116:8131–8138. https://doi.org/10.1021/jp301673h
Loerbroks C, Boulanger E, Thiel W (2015) Solvent influence on cellulose 1,4-β-glycosidic bond cleavage: a molecular dynamics and metadynamics study. Chem Eur J 21:5477–5487. https://doi.org/10.1002/chem.201405507
Lopes JM, Bermejo MD, Martín Á, Cocero MJ (2017) Ionic liquid as reaction media for the production of cellulose-derived polymers from cellulosic biomass. ChemEngineering 1:10. https://doi.org/10.3390/chemengineering1020010
Lungwitz R, Spange S (2008) A hydrogen bond accepting (HBA) scale for anions, including room temperature ionic liquids. New J Chem 32:392–394. https://doi.org/10.1039/B714629A
Lv Y, Wu J, Zhang J et al (2012) Rheological properties of cellulose/ionic liquid/dimethylsulfoxide (DMSO) solutions. Polymer 53:2524–2531. https://doi.org/10.1016/j.polymer.2012.03.037
Mäki-Arvela P, Anugwom I, Virtanem P et al (2010) Dissolution of lignocellulosic materials and its constituents using ionic liquids-a review. Ind Crop Prod 32:175–201. https://doi.org/10.1016/j.indcrop.2010.04.005
Manna B, Ghosh A (2018) Dissolution of cellulose in ionic liquid and water mixtures as revealed by molecular dynamics simulations. J Biomol Struct Dyn 37:3987–4005. https://doi.org/10.1080/07391102.2018.1533496
Marciniak A (2010) The solubility parameters of ionic liquids. Int J Mol Sci 11:1973–1990. https://doi.org/10.3390/ijms11051973
Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378–6396. https://doi.org/10.1021/jp810292n
Martínez-Palou R, Flores Sanchez P (2011) Perspectives of ionic liquids applications for clean oilfield technologies. In: Kokorin A (Ed) Ionic liquids: Theory, properties, new approaches. In Tech, Croatia, pp. 567–630. https://doi.org/10.5772/14529
Miranda AD, Gallo M, Domíguez JM et al (2019) Experimental and theoretical assessment of the interactions of ionic liquids (ILs) with fluoridated compounds (HF, R-F) in organic medium. J Mol Liq 276:779–793. https://doi.org/10.1016/j.molliq.2018.12.040
Morrison G, Chadwick AV, Richard C, Catlow CRA (2002) Computational studies of the structural and transport properties of the cellulose–water–amine oxide system. Phys Chem Chem Phys 4:3407–3414. https://doi.org/10.1039/B107346J
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
Muhammad N, Man Z, Mutalib MIA et al (2015) Dissolution and separation of wood biopolymers using ionic liquids. Chem Bio Eng Rev 2:257–278. https://doi.org/10.1002/cben.201500003
Muranaka Y, Suzuki T, Sawanishi H et al (2014) Effective production of levulinic acid from biomass through pretreatment using phosphoric acid, hydrochloric acid, or ionic liquid. Ing Eng Chem Res 53:11611–11621. https://doi.org/10.1021/ie501811x
Naert P, Rabaey K, Stevens CV (2018) Ionic liquid ion exchange: Exclusion from strong interactions condemns cations to the most weakly interacting anions and dictates reaction equilibrium. Green Chem 20:4277–4286. https://doi.org/10.1039/C8GC01869C
Nakaya N, Hosoya T, Miyafuji H (2018) Ionic liquids as formaldehyde-free wood adhesives. J Wood Sci 64:794–801. https://doi.org/10.1007/s10086-018-1769-x
Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron x-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–9082. https://doi.org/10.1021/ja0257319
Paduszyński K, Domańska U (2014) Viscosity of ionic liquids: An extensive database and a new group contribution model based on a feed-forward artificial neural network. J Chem Inf Model 54:1311–1324. https://doi.org/10.1021/ci500206u
Parthasarathi R, Balamurugan K, Shi J et al (2015) Theoretical insights into the role of water in the dissolution of cellulose using IL/water mixed solvent systems. J Phys Chem B 119:14339–14349. https://doi.org/10.1021/acs.jpcb.5b02680
Patel H, Vaid ZS, More UU et al (2016) Thermophysical, acoustic and optical properties of binary mixtures of imidazolium based ionic liquids + polyethylene glycol. J Chem Thermodyn 99:40–53. https://doi.org/10.1016/j.jct.2016.02.025
Paul S, Panda AK (2012) Physicochemical investigations on the aqueous solution of an ionic liquid, 1-butyl-3-methylimidazolium methanesulfonate, [Bmim][MS], in a concentrated and dilute regime. Colloids Surf A 404:1–11. https://doi.org/10.1016/j.colsurfa.2012.01.034
Payal RS, Bejagam KK, Mondal A, Balasubramanian S (2015) Dissolution of cellulose in room temperature ionic liquids: Anion dependence. J Phys Chem B 119:1654–1659. https://doi.org/10.1021/jp512240t
Phillips JC, Braun R, Wang W et al (2005) Scalable molecular dynamics with NAMD. J Comput Chem 26:1781–1802. https://doi.org/10.1002/jcc.20289
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
Pinkert A, Goeke DF, Marsh KN, Pang S (2011) Extracting wood lignin without dissolving or degrading cellulose: Investigations on the use of food additive-derived ionic liquids. Green Chem 13:3124–3136. https://doi.org/10.1039/C1GC15671C
Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150. https://doi.org/10.1039/B006677J
Procentese A, Johnson E, Orr V et al (2015) Deep eutectic solvent pretreatment and subsequent saccharification of corncob. Bioresour Technol 192:31–36. https://doi.org/10.1016/j.biortech.2015.05.053
Rabideau BD, Ismail AE (2015) Mechanisms of hydrogen bond formation between ionic liquids and cellulose and the influence of water content. Phys Chem Chem Phys 17:5767–5775. https://doi.org/10.1039/c4cp04060k
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
Ravula S, Larm NE, Mottaleb MA et al (2019) Vapor pressure mapping of ionic liquids and low-volatility fluids using graded isothermal thermogravimetric analysis. Chemengineering 3:42. https://doi.org/10.3390/chemengineering3020042
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
Rinaldi R, Reece J (2017) Solution-based deconstruction of (ligno)-cellulose. In: Behrens M, Datye AK (eds) Catalysis for the conversion of biomass and its derivatives. WILEY-VCH Verlag, Weinheim, pp 435–462
Rogers RD, Seddon KR (2003) Ionic liquids - solvents of the future? Science 302:792–793. https://doi.org/10.1126/science.1090313
Ryckaert J-P, Ciccotti G, Berendsen HJC (1977) Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 23:327–341. https://doi.org/10.1016/0021-9991(77)90098-5
Sánchez-Badillo J, Gallo M, Guirado-López RA, González-García R (2020) Potential of mean force calculations for an SN2 fluorination reaction in five different imidazolium ionic liquids solvents using quantum mechanics/molecular mechanics molecular dynamics simulations. J Phys Chem B 124:4338–4357. https://doi.org/10.1021/acs.jpcb.0c03192
Santos LM, Canongia Lopes JN, Coutinho JAP et al (2007) Ionic liquids: first direct determination of their cohesive energy. J Am Chem Soc 129:284–285. https://doi.org/10.1021/ja067427b
Sashina ES, Kashirskii DA, Busygin KN (2016) Dissolution of cellulose with pyridinium-based ionic liquids: effect of chemical structure and interaction mechanism. Cellul Chem Technol 50:199–211
Schuermann J, Huber T, LeCorre D et al (2016) Surface tension of concentrated cellulose solutions in 1-ethyl-3-methylimidazolium acetate. Cellulose 23:1043–1050. https://doi.org/10.1007/s10570-015-0850-5
Sedano-Mendoza M, Lopez-Albarran P, Pizzi A (2010) Natural lignans as adhesives for cellulose: Computational interaction energy vs experimental results. J Adhes Sci Technol 24:1769–1786. https://doi.org/10.1163/016942410X507777
Seki S, Kobayashi T, Kobayashi Y et al (2010) Effects of cation and anion on physical properties of room-temperature ionic liquids. J Mol Liq 152:9–13. https://doi.org/10.1016/j.molliq.2009.10.008
Shen T, Gnanakaran S (2009) The stability of cellulose: A statistical perspective from a coarse-grained model of hydrogen-bond networks. Biophys J 96:3032–3040. https://dx.doi.org/10.1016%2Fj.bpj.2008.12.3953
Shirts MR, Pande VS (2005) Comparison of efficiency and bias of free energies computed by exponential averaging, the Bennett acceptance ratio, and thermodynamic integration. J Chem Phys. https://doi.org/10.1063/1.1873592
Stark A, Sellin M, Ondruschka B, Massonne K (2012) The effect of hydrogen bond acceptor properties of ionic liquids on their cellulose solubility. Sci China Chem 55:1663–1670. https://doi.org/10.1007/s11426-012-4685-8
Stortz CA, Johnson GP, French AD, Csonka GI (2009) Comparison of different force fields for the study of disaccharides. Carbohydr Res 344:2217–2228. https://doi.org/10.1016/j.carres.2009.08.019
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
Teixeira J, Bellissent-Funel M-C (1990) Dynamics of water studied by neutron scattering. J Phys Condens Matter 2:SA105-SA108. https://doi.org/10.1088/0953-8984/2/S/011
Teodorescu M (2014) Isothermal vapor + liquid equilibrium and thermophysical properties for 1-butyl-3-methylimidazolium bromide + 1-butanol binary system. Ind Eng Chem Res 53:13522–13528. https://doi.org/10.1021/ie502247d
Tokuda H, Hayamizu K, Ishii K et al (2004) Physicochemical properties and structures of room temperature ionic liquids. 1. variation of anionic species. J Phys Chem B 108:16593–16600. https://doi.org/10.1021/jp047480r
Tshibangu PN, Ndwandwe SN, Dikio ED (2011) Density, viscosity and conductivity study of 1-butyl-3-methylimidazolium bromide. Int J Electrochem Sci 6:2201–2213
van Osch DJGP, Kollau LJBM, van den Bruinhorst A et al (2017) Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation. Phys Chem Chem Phys 19:2636–2665. https://doi.org/10.1039/C6CP07499E
van Putten R-J, van der Waal JC, de Jong E et al (2013) Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem Rev 113:1499–1597. https://doi.org/10.1021/cr300182k
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
Verevkin SP (2008) Predicting enthalpy of vaporization of ionic liquids: a simple rule for a complex property. Angew Chem Int Ed 47:5071–5074. https://doi.org/10.1002/anie.200800926
Wang J, Hou T (2011) Application of molecular dynamics simulations in molecular property prediction. 1. density and heat of vaporization. J Chem Theory Comput 7:2151–2165. https://doi.org/10.1021/ct200142z
Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537. https://doi.org/10.1039/C2CS15311D
Wei J, Bu X, Guan W et al (2015) Measurement of vaporization enthalpy by isothermogravimetrical method and prediction of the polarity for 1-alkyl-3-methylimidazolium acetate [Cnmim][OAc] (n = 4, 6) ionic liquids. RSC Adv 5:70333–70338. https://doi.org/10.1039/C5RA12626F
Welton T (1999) Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 99:2071–2083. https://doi.org/10.1021/cr1003248
Xia S, Baker GA, Li H et al (2014) Aqueous ionic liquids and deep eutectic solvents for cellulosic biomass pretreatment and saccharification. RSC Adv 4:10586–10596. https://doi.org/10.1039/c3ra46149a
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
Xu A, Wang J, Zhang Y, Chen Q (2012a) Effect of alkyl chain length in anions on thermodynamic and surface properties of 1-butyl-3-methylimidazolium carboxylate ionic liquids. Ind Eng Chem Res 51:3458–3465. https://doi.org/10.1021/ie201345t
Xu W-G, Li L, Ma X-X et al (2012b) Density, surface tension, and refractive index of ionic liquids homologue of 1-alkyl-3-methylimidazolium tetrafluoroborate [Cnmim][BF4] (n = 2,3,4,5,6). J Chem Eng Data 57:2177–2184. https://doi.org/10.1021/je3000348
Xu A, Zhang Y, Zhao Y, Wang J (2013) Cellulose dissolution at ambient temperature: Role of preferential solvation of cations of ionic liquids by a cosolvent. Carbohydr Polym 92:540–544. https://doi.org/10.1016/j.carbpol.2012.09.028
Yuan X, Cheng G (2015) From cellulose fibrils to single chains: understanding cellulose dissolution in ionic liquids. Phys Chem Chem Phys 17:31592–31607. https://doi.org/10.1039/C5CP05744B
Yui T, Nihimura S, Akiba S, Hayashi S (2006) Swelling behavior of the cellulose Iβ crystal models by molecular dynamics. Carbohydr Res 341:2521–2530. https://doi.org/10.1016/j.carres.2006.04.051
Zacharias M, Straatsma TP, McCammon JA (1994) Separation-shifted scaling, a new scaling method for Lennard-Jones interactions in thermodynamic integration. J Chem Phys 100:9025–9031. https://doi.org/10.1063/1.466707
Zaitsau DH, Kabo GJ, Strechan AA et al (2006) Experimental vapor pressures of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides and a correlation scheme for estimation of vaporization enthalpies of ionic liquids. J Phys Chem A 110:7303–7306. https://doi.org/10.1021/jp060896f
Zhang N, Li W, Chen C, Zuo J (2013) Molecular dynamics simulation of aggregation in dimethyl sulfoxide–water binary mixture. Comput Theor Chem 1017:126–135. https://doi.org/10.1016/j.comptc.2013.05.018
Zhao Y, Truhlar DG (2008) Density functionals with broad applicability in chemistry. Acc Chem Res 41:157–167. https://doi.org/10.1021/ar700111a
Zhong X, Liu Z, Cao D (2011) Improved classical united-atom force field for imidazolium-based ionic liquids: Tetrafluoroborate, hexafluorophosphate, methylsulfate, trifluoromethylsulfonate, acetate, trifluoroacetate, and bis(trifluoromethylsulfonyl)amide. J Phys Chem B 115:10027–10040. https://doi.org/10.1021/jp204148q
Zhu S, Wu Y, Chen Q et al (2006) Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem 8:325–327. https://doi.org/10.1039/B601395C
Zorębski E, Musiał M, Bałuszyńska K et al (2018) Isobaric and isochoric heat capacities as well as isentropic and isothermal compressibilities of di-and trisubstituted imidazolium-based ionic liquids as a function of temperature. Ind Eng Chem Res 57:5161–5172. https://doi.org/10.1021/acs.iecr.8b00506
Acknowledgments
J.S.-B. acknowledges a postdoctoral fellowship from PRODEP through the 511-6/2019.-9878 grant. All authors acknowledge the computational resources provided by the Facultad de Ingeniería en Tecnología de la Madera at Universidad Michoacana de San Nicolás de Hidalgo (UMSNH) and by Dr. Pedro Navarro-Santos at Instituto de Investigaciones Químico-Biológicas both at UMSNH. Also, the computational resources provided by Dr. Raúl González-García at Universidad Autónoma de San Luis Potosí (UASLP) are acknowledged, as well as the help of Andrea López-Martínez at Instituto Tecnológico de Estudios Superiores de Monterrey (ITESM)-Querétaro.
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Sánchez-Badillo, J.A., Gallo, M., Rutiaga-Quiñones, J.G. et al. Solvent behavior of an ionic liquid set around a cellulose Iβ crystallite model through molecular dynamics simulations. Cellulose 28, 6767–6795 (2021). https://doi.org/10.1007/s10570-021-03992-7
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DOI: https://doi.org/10.1007/s10570-021-03992-7