Ionic liquid mediated technology for synthesis of cellulose acetates using different co-solvents

Carbohydrate Polymers

Volumn 135, Issue , 2016, Pages 341-348

  Jogunola, Olatunde ^a,b   Eta, Valerie ^a,b   Hedenström, Mattias ^a   Sundman, Ola ^a   Salmi, Tapio ^b   Mikkola, Jyri Pekka ^a,b  

^a UMEÅ UNIVERSITY   (Sweden)

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

Author keywords

Cellulose acetates; Cellulose acetylation; Cellulose dissolution; Dispersing agents; Ionic liquid; Recycling

Indexed keywords

ACETONE; ACETYLATION; CELLULOSE; DICHLOROMETHANE; DISPERSIONS; DISTILLATION; INDIUM COMPOUNDS; ORGANIC SOLVENTS; RECYCLING;

ACETIC ANHYDRIDES; CELLULOSE ACETATES; CELLULOSE ACETYLATIONS; CELLULOSE DISSOLUTIONS; DEGREE OF POLYMERIZATION; DISPERSING AGENT; HOMOGENEOUS CONDITIONS; NATIVE CELLULOSE;

IONIC LIQUIDS;

EID: 84941670432     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.08.092     Document Type: Article

References (50)

1. A. Abbott, T. Bell, S. Handa, and B. Stoddart O-acetylation of cellulose and monosaccharides using zinc based ionic liquid Green Chemistry 7 2005 705 707
2. J.-M. Andanson, E. Bordes, J. Devémy, F. Leroux, A.A.H. Padua, and M.F.C. Gomes Understanding the role of co-solvents in the dissolution of cellulose in ionic liquids Green Chemistry 16 2014 2528 2538
3. B.A.P. Ass, G.T. Ciacco, and E. Frollini Cellulose acetates from linters and sisal: Correlation between synthesis conditions in DMAc/LiCl and product properties Bioresource Technology 97 2006 1696 1702
4. S. Barthel, and T. Heinze Acylation and carbanilation of cellulose in ionic liquids Green Chemistry 8 2006 301 306
5. X. Cao, X. Peng, L. Zhong, S. Sun, D. Yang, X. Zhang, and et al. A novel transesterification system to rapidly synthesize cellulose aliphatic esters Cellulose 2 2014 581 594
6. Y. Cao, J. Wu, T. Meng, J. Zhang, J. He, H. Li, and et al. Acetone-soluble cellulose acetates prepared by one-step homogeneous acetylation of cornhusk cellulose in an ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) Carbohydrate Polymers 69 2007 665 672
7. Y. Cao, J. Zhang, J. He, H. Li, and Y. Zhang Homogeneous acetylation of cellulose at relatively high concentration in an ionic liquid Chinese Journal of Chemical Engineering 18 2010 515 522
8. J. Catalan Toward a generalized treatment of the solvent effect based on four empirical scales: Dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium The Journal of Physical Chemistry B 113 2009 5951 5960
9. C.Y. Chen, M.J. Chen, X.Q. Zhang, C.F. Liu, and R.C. Sun Per-O-acetylation of cellulose in dimethyl sulfoxide with catalyzed transesterification Journal of Agriculture and Food Chemistry 62 2014 3446 3452
10. H. Cho, A. Gross, and J.-W. Chu Dissecting force interactions in cellulose deconstruction reveals the required solvent versatility for overcoming biomass recalcitrance Journal of the American Chemical Society 133 2011 14033 14041
11. K.J. Edgar Cellulose esters, organic H.F. Mark, Encyclopedia of polymer science and technology Vol. 2 2004 Wiley New York
12. K. Edgar, K. Arnold, W. Blount, J. Lawniczak, and D. Lowman Synthesis and properties of cellulose acetoacetates Macromolecules 28 1995 4122 4128
13. O.A. El seound, G.A. Marson, G.T. Ciacco, and E. Frollini An efficient, one pot acylation of cellulose under homogeneous reaction conditions Macromolcular Chemistry and Physics 201 2000 882 889
14. W. Fawcett, R.P. Brooksby, D. Verbovy, I. Bako, and G. Palinkas Studies of anion solvation in polar aprotic solvents Journal of Molecular Liquids 118 2005 171 178
15. G.R. Filho, D.S. Monteiro, C.-d.-S. Meireles, R.M. Nascimento de Assunçəo, D.A. Cerqueira, H.S. Barud, and et al. Synthesis and characterization of cellulose acetate produced from recycled newspaper Carbohydrate Polymers 73 2008 74 82
16. S. Fischer, K. Thümmler, K. Pfeiffer, T. Liebert, and T. Heinze Evaluation of molten inorganic salt hydrates as reaction medium for the derivatization of cellulose Cellulose 9 2002 293 300
17. M. Gericke, T. Liebert, O.A. El Seoud, and T. Heinze Tailored media for homogeneous cellulose chemistry: Ionic liquid/co-solvent mixtures Macromolecular Material and Engineering 296 2011 483 493
18. V.W. Goodlett, J.-T. Doughert, and H.W. Patton Characterization of cellulose acetates by nuclear magnetic resonance Journal of Polymer Science 9 1971 155 161
19. T. Heinze, T. Liebert, and A. Koschella Esterification of polysaccharides 2006 Springer-Verlag Berlin Heidelberg, Germany 41 116
20. T. Heinze, K. Schwikal, and S. Barthel Ionic liquids as reaction medium in cellulose functionalization Macromolecular Bioscience 5 2005 520 525
21. K. Kamide, K. Okajima, K. Kowsaka, and T. Matsui Solubility of cellulose acetate prepared by different methods and its correlationships with average acetyl group distribution on glucopyranose units Polymer Journal 19 1987 1405 1412
22. H. Kern, S.W. Choi, G. Wenz, J. Heinrich, L. Ehrhardt, P. Mischnick, and et al. Synthesis, control of substitution pattern and phase transitions of 2,3-di-O-methylcellulose Carbohydrate Research 326 2000 67 79
23. B. Kosan, S. Dorn, F. Meister, and T. Heinze Preparation and subsequent shaping of cellulose acetates using ionic liquids Macromolecular Material and Engineering 295 2010 676 681
24. T.F. Liebert, and T.J. Heinze Exploitation of reactivity and selectivity in cellulose functionalization using unconventional media for the design of products showing new superstructures Biomacromolecules 2 2001 1124 1132
25. J. Luo, and Y. Sun Acetylation of cellulose using recyclable polymer catalysts Journal of Applied Polymer Science 100 2006 3288 3296
26. G.A. Marson, and O.A. El Seoud A novel, efficient procedure for acylation of cellulose under homogeneous solution conditions Journal of Applied Polymer Science 74 1999 1355 13360
27. 13C NMR studies of cellulose and cellulose oligomers in ionic liquid solutions Chemical Communications 2005 1557 1559
28. A. Parviainen, A.W.T. King, I. Mutikainen, M. Hummel, C. Selg, L.K.J. Hauru, and et al. Predicting cellulose solvating capabilities of acid-base conjugate ionic liquids ChemSusChem 6 2013 2161 2169
29. S. Possidonio, L.C. Fidale, and O.A. El Seoud Journal of Polymer Science Part A: Polymer Chemistry 48 2009 134 143
30. A.M. Regiani, E. Frollini, G.A. Marson, G.M. Arantes, and O. El Seoud Some aspects of acylation of cellulose under homogeneous solution conditions Journal of Polymer Science Part A: Polymer Chemistry 37 1999 1357 1363
31. 35/37Cl NMR relaxation study on model systems Chemical Communications 2006 1271 1273
32. R. Rinaldi Instantaneous dissolution of cellulose in organic electrolyte solutions Chemical Communications 47 2011 511 513
33. T. Rosenau, A. Potthast, H. Sixta, and P. Kosma The chemistry of side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process) Progress in Polymer Science 26 2001 1763 1837
34. E. Ruiz, V.R. Ferro, J. Palomar, J. Ortega, and J.J. Rodriguez Interactions of ionic liquids and acetone: Thermodynamic properties, quantum-chemical calculations, and NMR analysis The Journal of Physical Chemistry B 117 2013 7388 7398
35. F. Shafizadeh Cellulose chemistry: Perspective and retrospect Pure and Applied Chemistry 35 1973 195 208
36. A.M. Stepan, W.T.A. King, T. Kakko, G. Toriz, I. Kilpeläinen, and P. Gatenholm Fast and highly efficient acetylation of xylans in ionic liquid Cellulose 20 2013 2813 2824
37. A. Stoppa, J. Hunger, and R. Buchner Conductivities of binary mixtures of ionic liquids with polar solvents Journal of Chemical & Engineering Data 54 2008 472 479
38. X. Sun, C. Lu, W. Zhang, D. Tian, and X. Zhang Acetone-soluble cellulose acetate extracted from waste blended fabrics via ionic liquid catalyzed acetylation Carbohydrate Polymers 96 2013 405 411
39. R.P. Swatloski, S.K. Spear, J.D. Holbrey, and R.D. Rogers Dissolution of cellulose with ionic liquids Journal of the American Chemical Society 124 2002 4974 4975
40. A. Takaragi, M. Minoda, T. Miyamoto, H.Q. Liu, and L.N. Zhang Reaction characteristics of cellulose in the LiCl/1,3-dimethyl-2-imidazolidinone solvent system Cellulose 6 1999 93 102
41. X. Tian, Z. Fang, D. Jiang, and X. Sun Pretreatment of microcrystalline cellulose in organic electrolyte solutions for enzymatic hydrolysis Biotechnology for Biofuels 4 2011 53 67
42. H. Wang, G. Gurau, and R.D. Rogers Ionic liquid processing of cellulose Chemical Society Reviews 41 2012 1519 1537
43. P. Wasserscheid, and W. Keim Ionic liquids - New "solutions" for transition metal catalysis Angewandte Chemie International Edition 39 2000 3772 3789
44. J. Wu, J. Zhang, H. Zhang, J. He, Q. Ren, and M. Guo Homogeneous acetylation of cellulose in a new ionic liquid Biomacromolecules 5 2004 266 268
45. A.R. Xu, J.J. Wang, and H.Y. Wang Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquids solvent systems Green Chemistry 12 2010 268 275
46. A. Xu, Y. Zhang, Y. Zhao, and J. Wang Cellulose dissolution at ambient temperature: Role of preferential solvation of cations of ionic liquids by a cosolvent Carbohydrate Polymers 92 2013 540 544
47. Y. Yang, H. Xie, and E. Liu Acylation of cellulose in reversible ionic liquids Green Chemistry 16 2014 3018 3023
48. C. Zhai, J. Wang, Y. Zhao, J. Tang, and H. Wang A NMR study on the interactions of 1-alkyl-3-methylimidazolium ionic liquids with acetone Zeitschrift für Physikalische Chemie 220 2006 775 785
49. H. Zhang, J. Wu, J. Zhang, and J. He 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: A new and powerful nonderivative solvent for cellulose Macromolecules 38 2005 8272 8277
50. Y. Zhao, X. Liu, J. Wang, and H. Zhang Insight into the cosolvent effect of cellulose dissolution in imidazolium-based ionic liquid systems Journal of Physical Chemistry B 117 2013 9042 9049