Cellulose dissolution and regeneration in ionic liquids: A computational perspective

Chemical Engineering Science

Volumn 121, Issue , 2015, Pages 180-189

  Gupta, Krishna M ^a   Jiang, Jianwen ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Anion; Cation; Hydrogen bonding; Interaction; Solvent

Indexed keywords

CELLULOSE; DISSOLUTION; HYDROGEN BONDS; NEGATIVE IONS; POSITIVE IONS; SOLVENTS;

CELLULOSE DISSOLUTIONS; CELLULOSE PRETREATMENT; CELLULOSE REGENERATION; COMPUTATIONAL EXPLORATION; COMPUTATIONAL STUDIES; ENVIRONMENTALLY BENIGN; GLOBAL ENERGY DEMAND; INTERACTION;

IONIC LIQUIDS;

EID: 84921834156     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ces.2014.07.025     Document Type: Article

References (64)

1. Andanson J.-M., Bordes E., Devemy J., Leroux F., Padua A.A.H., Gomes M.F.C. Understanding the role of cosolvents in the dissolution of cellulose in ionic liquids. Green Chem. 2014, 16:2528-2538.
2. Brandt A., Grasvik J., Hallett J.P., Welton T. Deconstruction of lignocellulosic biomass with ionic liquids. Green Chem. 2013, 15:550-583.
3. Cao Y., Wu J., Zhang J., Li H.Q., Zhang Y., He J.S. Room temperature ionic liquids: a new and versatile platform for cellulose processing and derivatization. Chem. Eng. J. 2009, 147:13-21.
4. Casas A., Palomar J., Alonso M.V., Oliet M., Omar S., Rodriguez F. Comparison of lignin and cellulose solubilities in ionic liquids by COSMO-RS analysis and experimental validation. Ind. Crops Prod. 2012, 37:155-163.
5. Casas A., Omar S., Palomar J., Oliet M., Alonso M.V., Rodriguez F. Relation between differential solubility of cellulose and lignin in ionic liquids and activity coefficients. RSC Adv. 2013, 3:3453-3460.
6. Cho H.M., Gross A.S., Chu J.W. Dissecting force interactions in cellulose deconstruction reveals the required solvent versatility for overcoming biomass recalcitrance. J. Am. Chem. Soc. 2011, 133:14033-14041.
7. Cruz H., Fanselow M., Holbrey J.D., Seddon K.R. Determining relative rates of cellulose dissolution in ionic liquids through in situ viscosity measurement. Chem. Commun. 2012, 48:5620-5622.
8. Derecskei B., Derecskei-Kovacs A. Molecular dynamic studies of the compatibility of some cellulose derivatives with selected ionic liquids. Mol. Simul. 2006, 32:109-115.
9. Ding Z.D., Chi Z., Gu W.X., Gu S.M., Liu J.H., Wang H.J. Theoretical and experimental investigation on dissolution and regeneration of cellulose in ionic liquid. Carbohydr. Polym. 2012, 89:7-16.
10. Freudenmann D., Wolf S., Wolff M., Feldmann C. Ionic liquids: new perspectives for inorganic synthesis?. Angew. Chem. Int. Ed. 2011, 50:11050-11060.
11. Fukaya Y., Hayashi K., Wada M., Ohno H. Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem. 2008, 10:44-46.
12. Graenacher, C., 1934. US Patent, 1943176.
13. Graziani M., Fornasiero P. Renewable Resources and Renewable Energy: A Global Challenge 2007, CRC Press/Taylor & Francis Group LLC, Boca Raton.
14. Gross A.S., Bell A.T., Chu J.-W. Thermodynamics of cellulose solvation in water and the ionic liquid 1-butyl-3-methylimidazolim chloride. J. Phys. Chem. B 2011, 115:13433-13440.
15. Gross A.S., Bell A.T., Chu J.W. Entropy of cellulose dissolution in water and in the ionic liquid 1-butyl-3-methylimidazolim chloride. Phys. Chem. Chem. Phys. 2012, 14:8425-8430.
16. Gupta K.M., Hu Z., Jiang J. Mechanistic understanding of interactions between cellulose and ionic liquids: a molecular simulation study. Polymer 2011, 52:5904-5911.
17. Gupta K.M., Hu Z., Jiang J. Molecular insight into cellulose regeneration from a cellulose/ionic liquid mixture: effects of water concentration and temperature. RSC Adv. 2013, 3:4425-4433.
18. Gupta K.M., Hu Z., Jiang J. Cellulose regeneration from a cellulose/ionic liquid mixture: the role of anti-solvents. RSC Adv. 2013, 3:12794-12801.
19. Hauru L.K.J., Hummel M., King A.W.T., Kilpeläinen I., Sixta H. Role of solvent parameters in the regeneration of cellulose from ionic liquid solutions. Biomacromolecules 2012, 13:2896-2905.
20. Hermanutz F., Gaehr F., Uerdingen E., Meister F., Kosan B. New developments in dissolving and processing of cellulose in ionic liquids. Macromol. Symp. 2008, 262:23-27.
21. Huo F., Liu Z., Wang W. Cosolvent or antisolvent? a molecular view of the interface between ionic liquids and cellulose upon addition of another molecular solvent. J. Phys. Chem. B 2013, 117:11780-11792.
22. Janesko B.G. Modeling interactions between lignocellulose and ionic liquids using DFT-D. Phys. Chem. Chem. Phys. 2011, 13:11393-11401.
23. Kahlen J., Masuch K., Leonhard K. Modelling cellulose solubilities in ionic liquids using COSMO-RS. Green Chem. 2010, 12:2172-2181.
24. Klamt A. COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design 2005, Elsevier, Amsterdam.
25. Klemm D., Heublein B., Fink H.-P., Bohn A. Cellulose: fascinating biopolymer and sustainable raw material. Angew. Chem. Int. Ed. 2005, 44:3358-3393.
26. Kunkes E.L., Simonetti D.A., West R.M., Serrano-Ruiz J.C., Gärtner C.A., Dumesic J.A. Catalytic conversion of biomass to monofunctional hydrocarbons and targeted liquid-fuel classes. Science 2008, 322:417-421.
27. Li C., Zhao Z.K. Efficient acid-catalyzed hydrolysis of cellulose in ionic liquid. Adv. Synth. Catal. 2007, 349:1847-1850.
28. Li W.Y., Sun N., Stoner B., Jiang X.Y., Lu X.M., Rogers R.D. Rapid dissolution of lignocellulosic biomass in ionic liquids using temperatures above the glass transition of lignin. Green Chem. 2011, 13:2038-2047.
29. Liebert T. Cellulose solvents - remarkable history, bright future. ACS Symp. Ser. 2010, 1033:3-54.
30. Liu H.B., Sale K.L., Holmes B.M., Simmons B.A., Singh S. Understanding the interactions of cellulose with ionic liquids: a molecular dynamics study. J. Phys. Chem. B 2010, 114:4293-4301.
31. Liu H.B., Sale K.L., Simmons B.A., Singh S. Molecular dynamics study of polysaccharides in binary solvent mixtures of an ionic liquid and water. J. Phys. Chem. B 2011, 115:10251-10258.
32. Liu H.B., Cheng G., Kent M., Stavila V., Simmons B.A., Sale K.L., Singh S. Simulations reveal conformational changes of methylhydroxyl groups during dissolution of cellulose Iβ in ionic liquid 1-ethyl-3-methylimidazolium acetate. J. Phys. Chem. B 2012, 116:8131-8138.
33. Liu Z.W., Remsing R.C., Moore P.B., Moyna G. Molecular dynamics study of the mechanism of cellulose dissolution in the ionic liquid 1-n-butyl-3-methylimidazolium chloride. ACS Symp. Ser. 2007, 975:335-350.
34. Lu B., Xu A., Wang J. Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids. Green Chem. 2014, 16:1326-1335.
35. Mostofian B., Smith J., Cheng X. The solvation structures of cellulose microfibrils in ionic liquids. Interdiscip. Sci. Comput. Life Sci. 2011, 3:308-320.
36. Mostofian B., Smith J., Cheng X. Simulation of a cellulose fiber in ionic liquid suggests a synergistic approach to dissolution. Cellulose 2014, 21:983-997.
37. Muhammad N., Man Z., Khalil M.A.B. Ionic liquid-a future solvent for the enhanced uses of wood biomass. Eur. J. Wood Prod. 2012, 70:125-133.
38. Novoselov N.P., Sashina E.S., Petrenko V.E., Zaborsky M. Study of dissolution of cellulose in ionic liquids by computer modeling. Fibre Chem. 2007, 39:153-158.
39. Olivier-Bourbigou H., Magna L., Morvan D. Ionic liquids and catalysis: recent progress from knowledge to applications. Appl. Catal. 2010, 373:1-56.
40. Petrus L., Noordermeer M.A. Biomass to biofuels, a chemical perspective. Green Chem. 2006, 8:861-867.
41. Pinkert A., Marsh K.N., Pang S.S., Staiger M.P. Ionic liquids and their interaction with cellulose. Chem. Rev. 2009, 109:6712-6728.
42. Plechkova N.V., Seddon K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37:123-150.
43. Rabideau B.D., Agarwal A., Ismail A.E. Observed mechanism for the breakup of small bundles of cellulose Iα and Iβ in ionic liquids from molecular dynamics simulations. J. Phys. Chem. B 2013, 117:3469-3479.
44. Ragauskas A.J., Williams C.K., Davison B.H., Britovsek G., Cairney J., Eckert C.A., Frederick W.J., Hallett J.P., Leak D.J., Liotta C.L. The path forward for biofuels and biomaterials. Science 2006, 311:484-489.
45. Remsing R.C., Swatloski R.P., Rogers R.D., Moyna G. 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. 2006, 1271-1273.
46. Remsing R.C., Hernandez G., Swatloski R.P., Massefski W.W., Rogers R.D., Moyna G. Solvation of carbohydrates in n,n[U+05F3]-dialkylimidazolium ionic liquids: a multinuclear nmr spectroscopy study. J. Phys. Chem. B 2008, 112:11071-11078.
47. Remsing R.C., Petrik I.D., Liu Z., Moyna G. Comment on "NMR spectroscopic studies of cellobiose solvation in emimac aimed to understand the dissolution mechanism of cellulose in ionic liquids". Phys. Chem. Chem. Phys. 2010, 12:14827-14828.
48. Rosenau T., Potthast A., Sixta H., Kosma P. The chemistry of side reactions and byproduct formation in the system nmmo/cellulose (lyocell process). Prog. Polym. Sci. 2001, 26:1763-1837.
49. Swatloski R.P., Spear S.K., Holbrey J.D., Rogers R.D. Dissolution of cellose with ionic liquids. J. Am. Chem. Soc. 2002, 124:4974-4975.
50. Tadesse H., Luque R. Advances on biomass pretreatment using ionic liquids: an overview. Energy Environ. Sci. 2011, 4:3913-3929.
51. Vitz J., Erdmenger T., Haensch C., Schubert U.S. Extended dissolution studies of cellulose in imidazolium based ionic liquids. Green Chem. 2009, 11:417-424.
52. Wang H., Gurau G., Rogers R.D. Ionic liquid processing of cellulose. Chem. Soc. Rev. 2012, 41:1519-1537.
53. Xu A.R., Zhang Y.J., Zhao Y., Wang J.J. Cellulose dissolution at ambient temperature: role of preferential solvation of cations of ionic liquids by a cosolvent. Carbohydr. Polym. 2013, 92:540-544.
54. Xu H., Pan W.X., Wang R.X., Zhang D.J., Liu C.B. 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. 2012, 26:329-337.
55. Youngs T.G.A., Holbrey J.D., Deetlefs M., Nieuwenhuyzen M., Gomes M.F.C., Hardacre C. A molecular dynamics study of glucose solvation in the ionic liquid 1,3-dimethylimidazolium chloride. ChemPhysChem 2006, 7:2279-2281.
56. Youngs T.G.A., Hardacre C., Holbrey J.D. Glucose solvation by the ionic liquid 1,3-dimethylimidazolium chloride: a simulation study. J. Phys. Chem. B 2007, 111:13765-13774.
57. Youngs T.G.A., Holbrey J.D., Mullan C.L., Norman S.E., Lagunas M.C., D'Agostino C., Mantle M.D., Gladden L.F., Bowron D.T., Hardacre C. Glucose solvation by the ionic liquid 1,3-dimethylimidazolium chloride: a simulation study. Chem. Sci. 2011, 2:1594-1605.
58. Zhang H., Wu J., Zhang J., He J. 1-allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 2005, 38:8272-8277.
59. Zhao H., Baker G.A., Song Z., Olubajo O., Crittle T., Peters D. Designing enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem. 2008, 10:696-705.
60. Zhao H., Jones C.I.L., Baker G.A., Xia S., Olubajo O., Person V.N. Regenerating cellulose from ionic liquids for an accelerated enzymatic hydrolysis. J. Biotechnol. 2009, 139:47-54.
61. Zhao Y.L., Liu X.M., Wang J.J., Zhang S.J. Effects of cationic structure on cellulose dissolution in ionic liquids: a molecular dynamics study. ChemPhysChem 2012, 13:3126-3133.
62. Zhao Y.L., Liu X.M., Wang J.J., Zhang S.J. Effects of anionic structure on the dissolution of cellulose in ionic liquids revealed by molecular simulation. Carbohydr. Polym. 2013, 94:723-730.
63. Zhao Y.L., Liu X.M., Wang J.J., Zhang S.J. Insight into the cosolvent effect of cellulose dissolution in imidazolium-based ionic liquid systems. J. Phys. Chem. B 2013, 117:9042-9049.
64. Zhu S., Wu Y., Chen Q., Yu Z., Wang C., Jin S., Ding Y., Wu G. Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem. 2006, 8:325-327.