Competing forces during cellulose dissolution: From solvents to mechanisms

Current Opinion in Colloid and Interface Science

Volumn 19, Issue 1, 2014, Pages 32-40

  Medronho, Bruno ^a   Lindman, Björn ^b,c  

^a UNIVERSITY OF ALGARVE   (Portugal)

^b LUND UNIVERSITY   (Sweden)

^c NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

Cellulose dissolution; Cellulose solvents; Hydrogen bonding; Hydrophobic interactions

Indexed keywords

DISSOLUTION; HYDROGEN BONDS; HYDROPHOBICITY; SOLVENTS;

CELLULOSE DISSOLUTIONS; CELLULOSE SOLVENT; ENTROPY EFFECTS; HYDROPHOBIC INTERACTIONS;

CELLULOSE;

ANION; CATION; CELLULOSE; IONIC LIQUID; SOLVENT;

ALKALINITY; AQUEOUS SOLUTION; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; DERIVATIZATION; DISSOLUTION; FORCE; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; LOW TEMPERATURE; MOLECULAR DYNAMICS; REVIEW; SOLUBILITY; SOLVENT EFFECT;

EID: 84896056479     PISSN: 13590294     EISSN: 18790399     Source Type: Journal    
DOI: 10.1016/j.cocis.2013.12.001     Document Type: Review

References (99)

1. O'Sullivan A.C. Cellulose: the structure slowly unravels. Cellulose 1997, 4:173-208.
2. Krässig H., Schurz J., Steadman R.G., Schliefer K., Albrecht W., Mohring M., et al. Cellulose Ullmann's encyclopedia of industrial chemistry 2000, Wiley-VCH Verlag GmbH & Co. KGaA.
3. Marsh J.T. An introduction to the chemistry of cellulose 1942, Chapman & Hall, London. 2nd ed.
4. Liebert T. Cellulose solvents - remarkable history, bright future. Acs Sym Ser 2009, 3-54. T.F. Liebert, T.J. Heinze, K.J. Edgar (Eds.).
5. Klemm D., Heublein B., Fink H.P., Bohn A. Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed Engl 2005, 44:3358-3393.
6. Medronho B., Romano A., Miguel M.G., Stigsson L., Lindman B. Rationalizing cellulose (in)solubility: reviewing basic physicochemical aspects and role of hydrophobic interactions. Cellulose 2012, 19:581-587.
7. Lindman B., Karlström G., Stigsson L. On the mechanism of dissolution of cellulose. J Mol Liq 2010, 156:76-81.
8. Biermann O., Hadicke E., Koltzenburg S., Muller-Plathe F. Hydrophilicity and lipophilicity of cellulose crystal surfaces. Angew Chem Int Ed Engl 2001, 40:3822-3825.
9. Yamane C., Aoyagi T., Ago M., Sato K., Okajima K., Takahashi T. Two different surface properties of regenerated cellulose due to structural anisotropy. Polym J 2006, 38:819-826.
10. Miyamoto H., Umemura M., Aoyagi T., Yamane C., Ueda K., Takahashi K. Structural reorganization of molecular sheets derived from cellulose II by molecular dynamics simulations. Carbohydr Res 2009, 344:1085-1094.
11. Klemm D., Philipp B., Heinze T., Heinze U., Wagenknecht W. Fundamentals and analytical methods. Comprehensive cellulose chemistry 1998, vol. 1. Wiley - VCH, Weinheim.
12. Kolpak F.J., Blackwell J. Structure of regenerated cellulose. Macromolecules 1975, 8:563-564.
13. Raymond S., Kvick A., Chanzy H. The structure of cellulose-Ii - a revisit. Macromolecules 1995, 28:8422-8425.
14. Krassig H.A. Cellulose: structure, accessibility and reactivity 1993, Gordon and Breach Science Publishers, Amsterdam. 1st ed.
15. Hudson S.M., Cuculo J.A. The solubility of unmodified cellulose - a critique of the literature. J Macromol Sci R M C 1980, C18:1-82.
16. Zhang L.N., Ruan D., Gao S.J. Dissolution and regeneration of cellulose in NaOH/thiourea aqueous solution. J Polym Sci Polym Phys 2002, 40:1521-1529.
17. Bergenstråhle M., Wohlert J., Himmel M.E., Brady J.W. Simulation studies of the insolubility of cellulose. Carbohyd Res 2010, 345:2060-2066.
18. Grulke E.A. Solubility parameter values. Polymer handbook 1999, Vol. 7. Wiley, New York, NY. 4th ed. J. Brandrup, E.H. Immergut, E.A. Grulke (Eds.).
19. Holmberg K., Jönsson B., Kronberg B., Lindman B. Surfactants and polymers in aqueous solution 2002, Wiley, Hoboken.
20. Cuissinat C., Navard P., Heinze T. Swelling and dissolution of cellulose. Part IV: free floating cotton and wood fibres in ionic liquids. Carbohydr Polym 2008, 72:590-596.
21. Ramos L.A., Morgado D.L., Gessner F., Frollini E., El Seoud O.A. A physical organic chemistry approach to dissolution of cellulose: effects of cellulose mercerization on its properties and on the kinetics of its decrystallization. Arkivoc 2011, 416-425.
22. Morgenstern B., Kammer H.W. On the particulate structure of cellulose solutions. Polymer 1999, 40:1299-1304.
23. Miller-Chou B.A., Koenig J.L. A review of polymer dissolution. Prog Polym Sci 2003, 28:1223-1270.
24. Turbak A.F., Hammer R.B., Davies R.E., Hergert H.L. Cellulose solvents. Chemtech 1980, 10:51-57.
25. Philipp B., Lukanoff B., Schleicher H., Wagenknecht W. Homogenous reactions of cellulose in organic-solvents systems. Z Chem 1986, 26:50-58.
26. Heinze T., Liebert T. Unconventional methods in cellulose functionalization. Prog Polym Sci 2001, 26:1689-1762.
27. Schoenbein F. Pogg Ann 1846, 70:220.
28. Schweiger R.G. DE 2120964 1971, [Germany].
29. Wilkes A.G. The viscose process. fibres 2001, Woodhead Publishing, Cambridge. WCeRc (Ed.).
30. Woodings C. Regenerated Cellulose Fibres. In: CRC Press LLC: Boca Raton U, editor.2001.
31. Ekman K, Turenen OT, Huttunen JI. Finnish Patent 61,033. 1982.
32. Jacobson R.A. J Am Chem Soc 1938, 60:1742.
33. Schuetzenberger P. Compt Rendus 1865, 61:485.
34. Rudy H. Cellulosechemie 1931, 13:49.
35. Liebert T., Klemm D. New soluble and hydrolytically cleavable intermediate in cellulose functionalization: cellulose dichloroacetate (CDCA). Acta Polym 1998, 49:124-128.
36. Boerstoel H., Maatman H., Westerink J.B., Koenders B.M. Liquid crystalline solutions of cellulose in phosphoric acid. Polymer 2001, 42:7371-7379.
37. Schweitzer E.J. Prakt Chem 1857, 72:109.
38. Johnson D.C. Cellulose chemistry and its applications 1985, Northwood, New York. T.P. Nevell, S.H. Zeronian (Eds.).
39. Achwal W.B., Sai B.S. Angew Macromol Chem 1970, 14:165.
40. Sobue H., Kiessig H.H. K Z Phys Chem 1939, 43:309.
41. Kamide K., Okajima K., Matsui T., Kowsaka K. Study on the solubility of cellulose in aqueous alkali solution by deuteration Ir and C-13 Nmr. Polym J 1984, 16:857-866.
42. Isogai A., Atalla R.H. Dissolution of cellulose in aqueous NaOH solutions. Cellulose 1998, 5:309-319.
43. Yamashiki T., Matsui T., Saitoh M., Okajima K., Kamide K. Characterization of cellulose treated by the steam explosion method.1. Influence of cellulose resources on changes in morphology, degree of polymerization, solubility and solid structure. Brit Polym J 1990, 22:73-83.
44. Yamashiki T., Kamide K., Okajima K., Kowsaka K., Matsui T., Fukase H. Some characteristic features of dilute aqueous alkali solutions of specific alkali concentration (2.5moll-1) which possess maximum solubility power against cellulose. Polym J 1988, 20:447-457.
45. Yan L.F., Gao Z.J. Dissolving of cellulose in PEG/NaOH aqueous solution. Cellulose 2008, 15:789-796.
46. Cai J., Zhang L. Rapid dissolution of cellulose in LiOH/Urea and NaOH/Urea aqueous solutions. Macromol Biosci 2005, 5:539-548.
47. Jin H.J., Zha C.X., Gu L.X. Direct dissolution of cellulose in NaOH/thiourea/urea aqueous solution. Carbohydr Res 2007, 342:851-858.
48. Fischer S., Leipner H., Thummler K., Brendler E., Peters J. Inorganic molten salts as solvents for cellulose. Cellulose 2003, 10:227-236.
49. Dawsey T.R., Mccormick C.L. The lithium chloride/dimethylacetamide solvent for cellulose - a literature-review. J Macromol Sci R M C 1990, C30:405-440.
50. Letters K. Kolloidzeitschrift 1932, 58:229.
51. Warwicker J.O., White E.B. A review of the literature on the effect of caustic soda and other swelling agents on the fine structure of cotton, Shirley Institute Pamphlet No. 93 1966, Manchester, UK.
52. Lukanoff B., Schleicher H., Philipp B. Untersuchungen zur Auflösung und Verformung von Cellulose in Schmelzen und konzentrierten Lösungen verschiedener Thiocyanate. Cell Chem Technol 1983, 17:593-599.
53. Kuga S. The porous structure of cellulose gel regenerated from calcium thiocyanate solution. J Colloid Interface Sci 1980, 77:413-417.
54. Hattori M., Koga T., Shimaya Y., Saito M. Aqueous calcium thiocyanate solution as a cellulose solvent. Structure and interactions with cellulose. Polym J 1998, 30:43-48.
55. Leipner H., Fischer S., Brendler E., Voigt W. Structural changes of cellulose dissolved in molten salt hydrates. Macromol Chem Phys 2000, 201:2041-2049.
56. Heinze T., Koschella A. Solvents applied in the field of cellulose chemistry - a mini review. Polímeros: Ciência e Tecnologia 2005, 15:84-90.
57. Isogai A., Ishizu A., Nakano J. J Appl Polym Sci 1987, 33:1283.
58. Cuculo J.A., Smith C.B., Sangwatanaroj U., Stejskal E.O., Sankar S.S. A study on the mechanism of dissolution of the cellulose/NH3/NH4SCN system.1. J Polym Sci Pol Chem 1994, 32:229-239.
59. Hattori K., Cuculo J.A., Hudson S.M. J Polym Sci, Part A: Polym Chem 2000, 40:601.
60. Hattori K., Abe E., Yoshida T., Cuculo J.A. Polym J 2004, 36:123.
61. Frey M.W., Chan H., Carranco K. Rheology of cellulose/KSCN/ethylenediamine solutions and coagulation into filaments and films. J Polym Sci Polym Phys 2005, 43:2013-2022.
62. Heinze T., Dicke R., Koschella A., Kull A.H., Klohr E.-A., Koch W. Macromol Chem Phys 2000, 201:627.
63. Frey M.W., Li L., Xiao M., Gould T. Dissolution of cellulose in ethylene diamine/salt solvent systems. Cellulose 2006, 13:147-155.
64. McCormick C.L., Lichatowich D.K. J Polym Sci, Part B: Polym Lett Ed 1979, 17:479.
65. McCorsley CC, Varga JK. U.S. Patent 4,142,913. 1979.
66. Fink H.P., Weigel P., Purz H.J., Ganster J. Structure formation of regenerated cellulose materials from NMMO-solutions. Prog Polym Sci 2001, 26:1473-1524.
67. Plechkova N.V., Seddon K.R. Applications of ionic liquids in the chemical industry. Chem Soc Rev 2008, 37:123-150.
68. Graenacher C. U.S. Patent 1,943,176. 1934.
69. Swatloski R.P., Spear S.K., Holbrey J.D., Rogers R.D. Dissolution of cellulose with ionic liquids. J Am Chem Soc 2002, 124:4974-4975.
70. Pinkert A., Marsh K.N., Pang S.S., Staiger M.P. Ionic liquids and their interaction with cellulose. Chem Rev 2009, 109:6712-6728.
71. Zhang H., Wu J., Zhang J., He J.S. 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 2005, 38:8272-8277.
72. 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.
73. Fukaya Y., Sugimoto A., Ohno H. Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates. Biomacromolecules 2006, 7:3295-3297.
74. Sun N., Rahman M., Qin Y., Maxim M.L., Rodriguez H., Rogers R.D. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 2009, 11:646-655.
75. Phillips D.M., Drummy L.F., Conrady D.G., Fox D.M., Naik R.R., Stone M.O., et al. Dissolution and regeneration of Bombyx mori Silk fibroin using ionic liquids. J Am Chem Soc 2004, 126:14350-14351.
76. Garcia H., Ferreira R., Petkovic M., Ferguson J.L., Leitao M.C., Gunaratne H.Q.N., et al. Dissolution of cork biopolymers in biocompatible ionic liquids. Green Chem 2010, 12:367-369.
77. Zhao H., Baker G.A., Song Z.Y., Olubajo O., Crittle T., Peters D. Designing enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem 2008, 10:696-705.
78. Kluefers P., Kunte T. Angew Chem, Int Ed 2001, 40:4210.
79. Vu-Manh H., Öztürk H., Bechtold T. Swelling and dissolution mechanism of regenerated cellulose fibres in aqueous alkaline solution containing ferric tartrate acid complex Part I. Viscose fibres. Carbohydr Polym 2010, 82:761-767.
80. Cai J., Zhang L., Liu S.L., Liu Y.T., Xu X.J., Chen X.M., et al. Dynamic self-assembly induced rapid dissolution of cellulose at low temperatures. Macromolecules 2008, 41:9345-9351.
81. Liu W.Q., Budtova T., Navard P. Influence of ZnO on the properties of dilute and semi-dilute cellulose-NaOH-water solutions. Cellulose 2011, 18:911-920.
82. Pinkert A., Marsh K.N., Pang S.S. Reflections on the solubility of cellulose. Ind Eng Chem Res 2010, 49:11121-11130.
83. Östlund A., Lundberg D., Nordstierna L., Holmberg K., Nyden M. Dissolution and gelation of cellulose in TBAF/DMSO solutions: the roles of fluoride ions and water. Biomacromolecules 2009, 10:2401-2407.
84. Brendler E., Fischer S., Leipner H. Li-7 NMR as probe for solvent-cellulose interactions in cellulose dissolution. Cellulose 2001, 8:283-288.
85. Nehls I., Wagenknecht W., Philipp B., Stscherbina D. Characterization of cellulose and cellulose derivatives in solution by high-resolution C-13-Nmr spectroscopy. Prog Polym Sci 1994, 19:29-78.
86. Lu X.K., Shen X.Y. Solubility of bacteria cellulose in zinc chloride aqueous solutions. Carbohydr Polym 2011, 86:239-244.
87. Fischer S. Unconventional dissolution and derivatization of cellulose. Lenzinger Berichte 2004, 83:71-78.
88. 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 C-13 and Cl-35/37 NMR relaxation study on model systems. Chem Commun 2006, 1271-1273.
89. 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.
90. Lindman B., Forsen S., Forslind E. Nuclear quadrupole relaxation of 79Br in aqueous solutions of quaternary ammonium bromides. J Phys Chem-Us 1968, 72:2805-2813.
91. Wennerström H., Lindman B., Forsen S. Interaction of halide ions with organic cations containing charged nitrogen, phosphorus, or sulfur in aqueous solutions studied by nuclear quadrupole relaxation. J Phys Chem-Us 1971, 75:2936-2942.
92. Lindman B., Wennerström H., Forsen S. Halide ion quadrupole relaxation in aqueous-solutions containing organic cations. J Phys Chem-Us 1992, 96:5669-5670.
93. Sashina E.S., Novoselov N.P. Effect of structure of ionic liquids on their dissolving power toward natural polymers. Russ J Gen Chem 2009, 79:1057-1062.
94. Zhang J.M., Zhang H., Wu J., Zhang J., He J.S., Xiang J.F. NMR spectroscopic studies of cellobiose solvation in EmimAc aimed to understand the dissolution mechanism of cellulose in ionic liquids. Phys Chem Chem Phys 2010, 12:1941-1947.
95. Kahlen J., Masuch K., Leonhard K. Modelling cellulose solubilities in ionic liquids using COSMO-RS. Green Chem 2010, 12:2172-2181.
96. Rabideau B.D., Agarwal A., Ismail A.E. Observed mechanism for the breakup of small bundles of cellulose I alpha and I beta in ionic liquids from molecular dynamics simulations. J Phys Chem B 2013, 117:3469-3479.
97. Le K.A., Sescousse R., Budtova T. Influence of water on cellulose-EMIMAc solution properties: a viscometric study. Cellulose 2012, 19:45-54.
98. Cousins S.K., Brown R.M. Polym Bull 1995, 36:3885-3888.
99. 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.