Abstract
Cellulose (7% water) was thoroughly dispersed in various ionic liquids (IL) and the turbidity of the mixture was investigated to distinguish real dissolution from fine dispersion. The dissolving ability of 1-butyl-3-methylimidazolium chloride (BMIMCl know cellulose solvent) and 11 other commercial IL (not reported as cellulose solvents) was studied. From the latter, only 1,3-dimethylimidazolium dimethylphosphate (DMIMDMP) could dissolve cellulose. The influence of water content on the real dissolution of cellulose in these two IL was investigated. The maximum theoretical amount of dissolved anhydrous cellulose in the IL was determined by extrapolation methodology at different temperatures. For cellulose in BMIMCl, it was 8.75 g/100 g of IL at 95 °C. DMIMDMP could achieve real cellulose dissolution only in a practically anhydrous system (2.3 g/100 g of IL at 30 °C) but dissolution was physically limited by high viscosity.
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References
Apelblat A, Korin E (1998) The vapor pressures of saturated aqueous solutions of sodium chloride, sodium bromide, sodium nitrate, sodium nitrite, potassium iodate, and rubidium chloride at temperatures from 227 K to 323 K. J Chem Thermodyn 30:59–71. doi:10.1006/jcht.1997.0275
Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8:301–306. doi:10.1039/b513157j
Chrapava S, Touraud D, Rosenau T, Potthast A, Kunz W (2003) The investigation of the influence of water and temperature on the LiCl/DMAc/cellulose system. Phys Chem Chem Phys 5:1842–1847. doi:10.1039/b212665f
El Seoud OA, Heinze T (2005) Organic esters of cellulose: new perspectives for old polymers. Adv Polym Sci 186:103–149. doi:10.1007/b136818
El Seoud OA, Koschella A, Fidale LC, Dorn S, Heinze T (2007) Applications of ionic liquids in carbohydrate chemistry: a window of opportunities. Biomacromolecules 8:2629–2647. doi:10.1021/bm070062i
Heinze T (2005) Chemical functionalization of cellulose. In: Severian D (ed) Polysaccharides, 2nd edn. Marcel Dekker, New York, pp 551–590
Heinze T, Schwikal K, Barthel S (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromol Biosci 5:520–525. doi:10.1002/mabi.200500039
Johnson DC (1985) Solvents for cellulose. In: Nevel TP, Zeronian SH (eds) Cellulose chemistry and its application. Horwood, Chichester, pp 181–201
Moulthrop JS, Swatloski RP, Moyna G, Rogers RD (2005) High-resolution 13C NMR studies of cellulose and cellulose oligomers in ionic liquid solutions. Chem Commun pp 1557–1559. doi:10.1039/b417745b
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 pp 1271–1273. doi:10.1039/b600586c
Schlufter K, Schmauder H-P, Dorn S, Heinze T (2006) Efficient homogeneous chemical modification of bacterial cellulose in the ionic liquid 1-N-butyl-3-methylimidazolium chloride. Macromol Rapid Commun 27:1670–1676. doi:10.1002/marc.200600463
Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975. doi:10.1021/ja025790m
Swatloski RP, Rogers RD, Holbrey JD (2003) Dissolution and processing of cellulose using ionic liquids, cellulose solution, and regenerating cellulose. World Patent number 1,029,329
Vaca-Garcia C, Thiebaud S, Borredon ME, Gozzelino G (1998) Cellulose esterification with fatty acids and acetic anhydride in lithium chloride/N,N-dimethylacetamide medium. J Am Oil Chem Soc 75:315–319
Zhang H, Wu J, Zhang J, He J (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful non-derivatizing solvent for cellulose. Macromolecules 38:8272–8277. doi:10.1021/ma0505676
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The authors wish to thank TEMBEC France and the ANRT agency (France) for financial support.
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Mazza, M., Catana, DA., Vaca-Garcia, C. et al. Influence of water on the dissolution of cellulose in selected ionic liquids. Cellulose 16, 207–215 (2009). https://doi.org/10.1007/s10570-008-9257-x
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DOI: https://doi.org/10.1007/s10570-008-9257-x