A morpholinium ionic liquid for cellulose dissolution

Carbohydrate Polymers

Volumn 130, Issue , 2015, Pages 18-25

  Raut, Dilip G ^a   Sundman, Ola ^a   Su, Weiqing ^a   Virtanen, Pasi ^b   Sugano, Yasuhito ^c   Kordas, Krisztian ^d   Mikkola, Jyri Pekka ^a,b  

^a UMEÅ UNIVERSITY   (Sweden)

^b LABORATORY OF INDUSTRIAL CHEMISTRY AND REACTION ENGINEERING   (Finland)

^c ÅBO AKADEMI UNIVERSITY   (Finland)

^d UNIVERSITY OF OULU   (Finland)

Author keywords

Acetate; Allyl; Cellulose; Dissolution; Ionic liquid; Morpholinium

Indexed keywords

CELLULOSE; DISSOLUTION; LIQUIDS; ORGANIC POLYMERS; POLYMERIZATION; VOLATILE FATTY ACIDS;

ACETATE; ALLYL; CELLULOSE DISSOLUTIONS; CELLULOSIC MATERIAL; DEGREE OF POLYMERIZATION; MORPHOLINIUM; MORPHOLINIUM CATION; STRUCTURE AND MORPHOLOGY;

IONIC LIQUIDS;

2-(N-METHYLMORPHOLINIUM)ETHYL ACETATE; CELLULOSE; IONIC LIQUID; MORPHOLINE DERIVATIVE;

CHEMISTRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY; SOLUBILITY; SYNTHESIS; X RAY DIFFRACTION;

CELLULOSE; IONIC LIQUIDS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; MORPHOLINES; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; X-RAY DIFFRACTION;

EID: 84929990632     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.04.032     Document Type: Article

References (61)

1. M. Abe, Y. Fukaya, and H. Ohno Extraction of polysaccharides from bran with phosphonate or phosphinate-derived ionic liquids under short mixing time and low temperature Green Chemistry 12 2010 1274 1280
2. R. Ahlrichs, M. Ballauff, K. Eichkorn, O. Hanemann, G. Kettenbach, and P. Klufers Aqueous ethylenediamine dihydroxo palladium(II): A coordinating agent for low- and high-molecular weight carbohydrates Chemistry. European Journal 4 1998 835 844
3. M.A.S. Azizi Samir, F. Alloin, J.Y. Sanchez, and A. Dufresne Cellulose nanocrystals reinforced poly(oxyethylene) Polymer 45 2004 4149 4157
4. A. Brandt, J. Hallett, D. Leak, R. Murphy, and T. Welton The effect of the ionic liquid anion in the pretreatment of pine wood chips Green Chemistry 12 2010 672 679
5. C. Brigouleix, M. Anouti, J. Jacquemin, M. Caillon-Caravanier, H. Galiano, and D. Lemordant Physicochemical characterization of morpholinium cation based protic ionic liquids used as electrolytes Journal of Physical Chemistry B 114 2010 1757 1766
6. J. Cai, L. Zhang, S. Liu, Y. Liu, X. Xu, and X. Chen Dynamic self-assembly induced rapid dissolution of cellulose at low temperatures Macromolecules 41 2008 9345 9351
7. E. Carter, S. Culver, P. Fox, R. Goode, I. Ntai, and M. Tickell Sweet success: Ionic liquids derived from non-nutritive sweeteners Chemical Communication 6 2004 630 631
8. Chen, L. (1991). Production of high strength cellulose fiber using zinc chloride, organic solvents and aqueous solution. U.S. Patent 4999149.
9. S. Choi, K.-S. Kim, H. Lee, J. Oh, and B.-B. Lee Synthesis and ionic conductivities of lithium-doped morpholinium salts Korean Journal of Chemical Engineering 22 2005 281 284
10. Cross, C., Bevan, E., & Beadle, C. (1982). Improvements in dissolving cellulose and allied compounds. British Patent 8700.
11. R.L. Dudley, C.A. Fyfe, P.J. Stephenson, Y. Deslandes, G.K. Hamer, and R.H. Marchessault High resolution 13C CP/MAS NMR spectra of solid cellulose oligomers and the structure of cellulose II Journal of American Chemical Society 105 1983 2469 2472
12. K. Edgar, C. Buchanan, J. Debenham, P. Rundquist, B. Seiler, and M. Shelton Advances in cellulose ester performances and application Progress in Polymer Science 26 2001 1605 1688
13. T. Fujimoto, S. Takahashi, M. Tsuji, M. Miyamoto, and H. Inagaki Reaction of cellulose with formic acid and stability of cellulose formate Journal of Polymer Science, Part C: Polymer Letters 24 1986 495 501
14. Y. Fukaya, K. Hayashi, M. Wada, and H. Ohno Cellulose dissolution with polar ionic liquids under mild conditions: Required factors for anions Green Chemistry 10 2008 44
15. Y. Fukaya, A. Sugimoto, and H. Ohno Superior Solubility of Polysaccharides in Low Viscosity Polar, and Halogen-Free 1,3-Dialkylimidazolium Formates Biomacromolecules 7 2006 3295 3297
16. M. Galinski, and I. Stepniak Morpholinium-based ionic liquid mixtures as electrolytes in electrochemical double layer capacitors Journal of Applied Electrochemistry 39 2009 1949 1953
17. Graenacher, C., & Sallman, R. (1939). Cellulose solutions and process of making same. U.S. Patent 2179181.
18. J. Gräsvik, D. Raut, and J.-P. Mikkola T. Heinze, W.G. Glasser, Challenges and perspectives of ionic liquids vs. traditional solvents for cellulose processing 2012 Nova Science Publishers, Inc New York 1 34
19. T. Heinze, R. Dicke, A. Koschella, A.H. Kull, and W. Koch Effective preparation of cellulose derivatives in a new simple cellulose solvent Macromolecular Chemistry and Physics 201 2000 627 631
20. T. Heinze, K. Schwikal, and S. Barthel Ionic liquids as reaction medium in cellulose functionalization Macromolecular Bioscience 5 2005 520 525
21. T. Heinze, S. Dorn, M. Schöbitz, T. Liebert, S. Köhler, and F. Meister Interactions of ionic liquids with polysaccharides - 2: Cellulose Macromolecular Symposia 262 2008 8 22
22. G. Huber, S. Iborra, and A. Corma Synthesis of transportation fuels from biomass: Chemistry, catalysts, and engineering Chemical Reviews 106 2006 4044 4098
23. A. Isogai, and R. Atalla Dissolution of cellulose in aqueous NaOH Solutions Cellulose 5 1998 309 319
24. Johnson, D. (1969). Compounds dissolved in cyclic amine oxides. U.S. Patent 3447939.
25. Johnson, D. (1970). Method of preparing polymers from a mixture of cyclic amine oxides and polymers. U.S. Patent 3508941.
26. K. Johnson What's an ionic liquid? The Electrochemical Society Interface 16 2007 38 41
27. Y. Kataoka, and T. Kondo FT-IR microscopic analysis of changing cellulose crystalline structure during wood cell wall formation Macromolecules 31 1998 760 764
28. K.-S. Kim, S. Choi, D. Demberelnyamba, H. Lee, J. Oh, and B.-B. Lee Ionic liquids based on N-alkyl-N-methylmorpholinium salts as potential electrolytes Chemical Communication 2004 828 829
29. K.-S. Kim, S.-Y. Park, S.-H. Yeon, and H. Lee N-butyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide-PVdF(HFP) gel electrolytes Electrochimica Acta 50 2005 5673 5678
30. A. King, J. Asikkala, I. Mutikainen, P. Järvi, and I. Kilpeläinen Distillable acid-base conjugate ionic liquids for cellulose dissolution and processing Angewandte Chemie International Edition 50 2011 1 6
31. D. Klemm, B. Philipp, T. Heinze, U. Heinze, and W. Wagenknecht Comprehensive cellulose chemistry II 1998 Wiley VCH New York 140
32. T. Liebert T. Heinze, W.G. Glasser, Cellulose solvents - Remarkable history, bright future, ACS Symposium Series 1033 2010 American Chemical Society Washington, DC 3 54
33. T. Liebert, and T. Heinze T. Heinze, W.G. Glasser, Cellulose derivatives: Modification, characterization and nanostructures, ACS Symposium Series 688 1998 American Chemical Society Washington, DC 61
34. C. McCormick, and D. Lichatowich Homogeneous solution reactions of cellulose, chitin, and other polysaccharides to produce controlled-activity pesticide systems Journal Polymer Science, Part B: Polymer Letter 17 1979 479 484
35. F. Moutos, L. Freed, and F. Guilak A biomimetic three-dimensional woven composite scaffold for functional tissue engineering of cartilage Nature Materials 6 2007 162 167
36. H. Ngo, K. LeCompte, L. Hargens, and A. McEwen Thermal properties of imidazolium ionic liquids Thermochimica Acta 357 2000 97 102
37. J. Pernak, N. Borucka, F. Walkiewicz, B. Markiewicz, P. Fochtman, and S. Stolte Synthesis, toxicity, biodegradability and physicochemical properties of 4-benzyl-4-methylmorpholinium-based ionic liquids Green Chemistry 13 2011 2901 2910
38. J. Pernak, R. Kordala, B. Markiewicz, F. Walkiewicz, P. Mikołaj, and A. Fabiańska Synthesis and properties of ammonium ionic liquids with cyclohexyl substituent and dissolution of cellulose RSC Advances 2 2012 8429 8438
39. B. Philipp, W. Wagenknecht, I. Nehls, J. Ludwig, M. Schnabelrauch, and H. Kim Comparison of cellulose formate and cellulose acetate under homogeneous reaction conditions Cellulose Chemical Technology 24 1990 667 668
40. A. Pinkert, K. Marsh, S. Pang, and M. Staiger Ionic liquids and their interaction with cellulose Chemical Reviews 109 2009 6712
41. A. Pinkert, K. Marsh, and S. Pang Reflections on the solubility of cellulose Industrial & Engineering Chemistry Research 49 2010 11121 11130
42. R. Rinaldi Instantaneous dissolution of cellulose in organic electrolyte solutions Chemical Communication 47 2011 511 513
43. C. Roy, T. Budtova, and P. Navard Rheological properties and gelation of aqueous cellulose-NaOH solutions Biomacromolecules 4 2003 259 264
44. P. Schuetzenberger Action de l'acide acétique anhydre sur la cellulose, l'amidon, les sucres, la mannite et ses congénères, les glucosides et certaines matières colorantes végétales Comptes Rendus 61 1865 485 486
45. R. Swatloski, S. Spear, J. Holbrey, and R. Rogers Dissolution of cellulose with ionic liquids Journal of American Chemical Society 124 2002 4974 4975
46. S. Tang, G. Baker, S. Ravula, J. Jones, and H. Zhao PEG-functionalized ionic liquids for cellulose dissolution and saccharification Green Chemistry 14 2012 2922 2932
47. J. Vitz, T. Erdmenger, C. Haensch, and U. Schubert Extended dissolution studies of cellulose in imidazolium based ionic liquids Green Chemistry 11 2009 417
48. H. Wang, G. Gurau, and R. Rogers Ionic liquid processing of cellulose Chemical Society Reviews 41 2012 1519 1537
49. P. Weimarn Zur Dispersoidchemie der Zellulose, I Kolloidzeitschrift 11 1912 41 43
50. A. Xu, J. Wang, and H. Wang Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems Green Chemistry 12 2010 268 275
51. L. Yan, and Z. Gao Dissolving of cellulose in PEG/NaOH aqueous solution Cellulose 15 2008 789 796
52. F. Yang, L. Li, Q. Li, W. Tan, W. Liu, and M. Xian Enhancement of enzymatic in situ saccharification of cellulose in aqueous-ionic liquid media by ultrasonic intensification Carbohydrate Polymer 81 2010 311
53. T. Yim, H. Yeong Lee, H.-J. Kim, J. Mun, S. Kim, and S. Oh Synthesis and properties of pyrrolidinium and piperidinium bis(trifluoromethanesulfonyl)imide ionic liquids with allyl substituents Bulletin Korean Chemical Society 28 2007 1567 1572
54. L. Zhang, D. Ruan, and J.P. Zhou Structure and properties of regenerated cellulose films prepared from cotton linters in NaOH/urea aqueous solution Industrial & Engineering Chemical Research 40 2001 5923
55. H. Zhang, J. Wu, J. Zhang, and J. He 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: A new and powerful nonderivatizing solvent for cellulose Macromolecules 38 2005 8272 8277
56. J. Zhang, J. Zhang, L. Lin, T. Chen, J. Zhang, and S. Liu Dissolution of microcrystalline cellulose in phosphoric acid - Molecular changes and kinetics Molecules 14 2009 5027 5041
57. Q. Zhang, X. Ma, S. Liu, B. Yang, L. Lu, and Y. He Hydrophobic 1-allyl-3-alkylimidazolium dicyanamide ionic liquids with low densities Journal of Material Chemistry 21 2011 6864 6868
58. D. Zhao, Z. Fei, T. Geldbach, R. Scopelliti, G. Laurenczy, and P. Dyson Allyl functionalized ionic liquids: Synthesis, characterization, and reactivity Helvetica Chimica Acta 88 2005 665 675
59. D. Zhao, H. Li, J. Zhang, L. Fu, M. Liu, and J. Fu Dissolution of cellulose in phosphate-based ionic liquids Carbohydrate Polymer 87 2012 1490 1494
60. S. Zhou, K. Tashiro, T. Hongo, H. Shirataki, C. Yamane, and T. Ii Influence of water on structure and mechanical properties of regenerated cellulose studied by an organized combination of infrared spectra, X-ray diffraction, and dynamic viscoelastic data measured as functions of temperature and humidity Macromolecules 34 2001 1274 1280
61. S. Zhu, Y. Wu, Q. Chen, Z. Yu, C. Wang, and S. Jin Dissolution of cellulose with ionic liquids and its application: A mini-review Green Chemistry 8 2006 325 327