A convenient solvent system for cellulose dissolution and derivatization: Mechanistic aspects of the acylation of the biopolymer in tetraallylammonium fluoride/dimethyl sulfoxide

Carbohydrate Polymers

Volumn 86, Issue 3, 2011, Pages 1395-1402

  Casarano, Romeu ^a   Nawaz, Haq ^a   Possidonio, Shirley ^a   Da Silva, Valdinéia C ^a   El Seoud, Omar A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Acyl fluoride formation; Cellulose carboxylic esters; Cellulose mixed carboxylic esters; Convenient solvent for cellulose; Mechanistic aspects of cellulose acylation; Tetraallylammonium fluoride DMSO

Indexed keywords

ACYL FLUORIDE FORMATION; CARBOXYLIC ACID ANHYDRIDES; CONVENIENT SOLVENT FOR CELLULOSE; DERIVATIZATIONS; ELECTROLYTE SOLUTIONS; EMF MEASUREMENT; FIBROUS CELLULOSE; FTIR SPECTROSCOPY; H NMR SPECTROSCOPY; HEXANOATE; HOMOGENEOUS REACTION; INTERMEDIATE FORMATION; LOW DEGREE; MECHANISTIC ASPECTS; MIXED ESTERS; SOLVENT SYSTEM; TETRAALLYLAMMONIUM FLUORIDE/DMSO;

ACYLATION; BIOMOLECULES; CARBOXYLIC ACIDS; DISSOLUTION; ELECTROLYTES; ESTERIFICATION; ESTERS; FLUORINE COMPOUNDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; ION SELECTIVE ELECTRODES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMIC STABILITY;

CELLULOSE;

EUCALYPTUS; GOSSYPIUM HIRSUTUM;

EID: 79961027796     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.06.051     Document Type: Article

References (59)

1. D. Albanese, D. Landini, and M. Penso Hydrated tetrabutylammonium fluoride as a powerful nucleophilic fluorinitaing agent Journal of Organic Chemistry 63 1998 9558 9589
2. W.L.F. Armagero, and C.L.L. Chai Purification of laboratory chemicals 5th ed. 2003 Elsevier New York
3. B.A.P. Ass, E. Frollini, and T. Heinze Studies on the homogeneous acetylation of cellulose in the novel solvent dimethyl sulfoxide/ tetrabutylammonium fluoride trihydrate Macromolecular Bioscience 4 2004 1008 1013 (Pubitemid 39578092)
4. ASTM D1795-94 (2001). Standard test methods for intrinsic viscosity of cellulose.
5. ASTM D871-96 (2004). Standard test methods of testing cellulose acetate (solution method; procedure A).
6. C.A. Bunton, and J.H. Fendler Fluoride ion catalyzed hydrolysis of carboxylic anhydrides Journal of Organic Chemistry 32 1967 1547 1551
7. R. Casarano, L.C. Fidale, C.M. Lucheti, T. Heinze, and O.A. El Seoud Expedient, accurate methods for the determination of the degree of substitution of cellulose carboxylic esters: Application of UV-vis spectroscopy (dye solvatochromism) and FTIR Carbohydrate Polymer 83 2011 1285 1292
8. R.B. Chavan, and A.K. Patra Development and processing of lyocell Indian Journal of Fibre & Textile Research 29 2004 483 492
9. S. Chempath, J.M. Boncella, L.R. Pratt, N. Henson, and B.S. Pivovar Density functional theory study of degradation of tetraalkylammonium hydroxides Journal of Physical Chemistry C 114 2010 11977 11983
10. G.T. Ciacco, T.F. Liebert, E. Frollini, and T.J. Heinze Application of the solvent dimethyl sulfoxide/tetrabutyl-ammonium fluoride trihydrate as reaction medium for the homogeneous acylation of sisal cellulose Cellulose 10 2003 125 132 (Pubitemid 36861748)
11. T.R. Dawsey, and C.L. McCormick The lithium chloride/dimethylacetamide solvent for cellulose: A literature review Journal of Macromolecular Science, Reviews in Macromolecular Chemistry and Physics C30 3-4 1990 405 440 (Pubitemid 21654635)
12. O.A. El Seoud, and T. Heinze Organic esters of cellulose: New perspectives for old polymers Advances in Polymer Science 186 2005 103 149
13. O.A. El Seoud, L.C. Fidale, N. Ruiz, M.L.O. D'Almeida, and E. Frollini Cellulose swelling by protic solvents: Which properties of the biopolymer and the solvent matter? Cellulose 15 2008 371 392
14. O.A. El Seoud, A. Koschella, L.C. Fidale, S. Dorn, and T. Heinze Applications of ionic liquids in carbohydrate chemistry: A window of opportunities Biomacromolecules 8 2007 2629 2647 (Pubitemid 47516909)
15. O.A. El Seoud, G.A. Marson, G.T. Ciacco, and E. Frollini An efficient, one-pot acylation of cellulose under homogeneous reaction conditions Macromolecular Chemistry and Physics 201 2000 882 889
16. J. Emsley, V. Gold, F. Hibbert, and W.T.A. Szeto Kinetic and equilibrium studies by fluorine-19 NMR of the formation of acetyl fluoride from acetyl chloride and tetraethylammonium fluoride in ethanoic acid Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry 6 1988 923 925
17. L.C. Fidale, S. Koehler, M.H.G. Prechtl, T. Heinze, and O.A. El Seoud Simple, expedient methods for the determination of water and electrolyte contents of cellulose solvent systems Cellulose 13 2006 581 592 (Pubitemid 44219571)
18. L.C. Fidale, N. Ruiz, T. Heinze, and O.A. El Seoud Cellulose swelling by aprotic and protic solvents: What are the similarities and differences? Macromolecular Chemistry and Physics 209 2008 1240 1254
19. L.C. Fidale, S. Possidonio, and O.A. El Seoud Application of 1-allyl-3-(1-butyl)imidazolium chloride in the synthesis of cellulose esters: Properties of the ionic liquid, and comparison with other solvents Macromolecular Bioscience 9 2009 813 821
20. H.-P. Fink, P. Weigel, H.J. Purz, and J. Ganster Structure formation of regenerated cellulose materials from NMMO-solutions Progress in Polymer Science 26 2001 1473 1524 (Pubitemid 33090642)
21. 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
22. T. Heinze, T. Liebert, and A. Koschella Esterification of polysaccharides 2006 Springer Germany
23. T. Heinze, T. Lincke, D. Fenn, and A. Koschella Efficient allylation of cellulose in dimethyl sulfoxide/tetrabutylammonium fluoride trihydrate Polymer Bulletin 61 2008 1 9
24. L. Imeson Thickening and gelling agents for food 1999 Aspen Publication New York p. 60
25. T. IWata, J. Azuma, K. Okamura, M. Muramoto, and B. Chun Preparation and NMR assignments of cellulose mixed esters regioselectively substituted by acetyl and propanoyl groups Carbohydrate Research 224 1992 277 283
26. A. Kivinen Mechanisms of substitution at the COX group S. Patai, The chemistry of acyl halides 1972 John Wiley & Sons New York 177 230
27. S. Kluge, and J. Weston Can a hydroxide ligand trigger a change in the coordination number of magnesium ions in biological systems? Biochemistry 44 2005 4877 4885 (Pubitemid 40403088)
28. S. Koehler, and T. Heinze New solvents for cellulose: Dimethyl sulfoxide/ammonium fluorides Macromolecular Bioscience 7 2007 307 314 (Pubitemid 47264651)
29. N. Le Moigne, M. Spinu, T. Heinze, and P. Navard Restricted dissolution and derivatization capacities of cellulose fibres under uniaxial elongational stress Polymer 51 2010 447 453
30. M. Makosza, and A.A. Chesnokov Study of the mechanism of base induced dehydrobromination of trans-β-bromostyrene Tetrahedron 59 2003 1995 2000 (Pubitemid 36255682)
31. M. Marek Jr., K. Fukuta, and T. Kunitake Preparation of a multilayered film of ultrathin poly(tetraallylammonium bromide) network Chemistry Letters 2 1993 291 294
32. 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 1360 (Pubitemid 30507476)
33. G.A. Marson, and O.A. El Seoud Cellulose dissolution in lithium chloride/N,N-dimethylacetamide solvent system: Relevance of kinetics of decrystallization to cellulose derivatization under homogeneous solution conditions Journal of Polymer Science, Part A: Polymer Chemistry 37 1999 3738 3744 (Pubitemid 30510565)
34. A. Matsumoto, Y. Kohama, and M. Oiwa Gelation in the copolymerization of tetraallylammonium chloride with diallyldimethylammonium chloride and diallylammonium chloride Polymer 31 1990 2141 2145
35. A. Matsumoto, H. Mano, M. Oiwa, and G.B. Butler Polymerization of tetraallyl ammonium chloride Journal of Polymer Science, Part A: Polymer Chemistry 27 1989 1811 1816
36. M.C.V. Nagel, and T. Heinze Esterification of cellulose with acyl-1H-benzotriazole Polymer Bulletin 65 2010 873 881
37. A. Oestlund, D. Lundberg, L. Nordstierna, K. Holmberg, and M. Nyden Dissolution and gelation of cellulose in TBAF/DMSO solutions: The roles of fluoride ions and water Biomacromolecules 10 2009 2401 2407
38. G. Olah, and I. Kuhn Organic fluorine compounds. XXVII. Preparation of acyl fluorides with anhydrous hydrogen fluoride. General use of the method of Colson and Fredenhagen Journal of Organic Chemistry 26 1961 237 238
39. A.G. Pittman, D.L. Sharp, and R.E. Lundin Polymers derived from fluoroketones. I. Preparation of fluoroalkyl acrylates and methacrylates Journal of Polymer Science, Part A: Polymer Chemistry 10 1966 2637 2647
40. S. Possidonio, L.C. Fidale, and O.A. El Seoud Microwave-assisted derivatization of cellulose in an ionic liquid: An efficient, expedient synthesis of simple and mixed carboxylic esters Journal of Polymer Science, Part A: Polymer Chemistry 48 2010 134 143
41. A. Potthast, T. Rosenau, R. Buchner, T. Roeder, G. Ebner, and H. Bruglachner The cellulose solvent system N,N-dimethylacetamide/lithium chloride revisited: The effect of water on physicochemical properties and chemical stability Cellulose 9 2002 41 53 (Pubitemid 34817268)
42. L.A. Ramos, J.M. Assaf, O.A. El Seoud, and E. Frollini Influence of the supramolecular structure and physicochemical properties of cellulose on its dissolution in a lithium chloride/N,N-dimethylacetamide solvent system Biomacromolecules 6 2005 2638 2647 (Pubitemid 41388276)
43. L.A. Ramos, D.L. Morgado, O.A. El Seoud, V.C. da Silva, and E. Frollini Acetylation of cellulose in LiCl-N,N-dimethylacetamide: First report on the correlation between the reaction efficiency and the aggregation number of dissolved cellulose Cellulose 18 2011 385 392
44. J.A. Ramsey, and J.A. Ladd Infrared spectra and vibrational assignments of the acetyl halides Journal of the Chemical Society [Section] B: Physical Organic 1968 118 122
45. E. Rohleder, and T. Heinze Comparison of benzyl celluloses synthesized in aqueous NaOH and dimethyl sulfoxide/tetrabutylammonium fluoride Macromolecular Symposia 294 2010 107 116
46. T. Rosenau, A. Potthast, I. Adorjan, A. Hofinger, H. Sixta, and H. Firgo Cellulose solutions in N-methylmorpholine-N-oxide (NMMO) - degradation processes and stabilizers Cellulose 9 2002 283 291 (Pubitemid 36036460)
47. P. Rustemeyer P. Rustemeyer, Cellulose acetates: Properties and applications 2004 Wiley-VCH Weinheim 267
48. R.K. Sharma, and J.L. Fry Instability of anhydrous tetra-n-alkylammonium fluorides Journal of Organic Chemistry 48 1983 2112 2114
49. E. Sjoholm, K. Gustafsson, B. Pettersson, and A. Colmsjo Characterization of the cellulosic residues from lithium chloride/N,N-dimethylacetamide dissolution of softwood kraft pulp Carbohydrate Polymers 32 1997 57 63 (Pubitemid 127382678)
50. S. Spange, K. Fischer, S. Prause, and T. Heinze Empirical polarity parameters of celluloses and related materials Cellulose 10 2003 201 212 (Pubitemid 37160118)
51. A.M. Striegel Theory and applications of DMAc/LiCl in the analysis of polysaccharides Carbohydrate Polymers 34 1997 267 274
52. G. Swain, and C.B. Scott Quantitative acorrelation of relative rates. Comparison of hydroxide ion with other nucleophilic reagents toward alkyl halides, esters, epoxides and acyl halides Journal of the American Chemical Society 75 1953 141 147
53. M. Terbojevich, A. Cosani, M. Camilot, and B. Focher Solution studies of cellulose tricarbanilates obtained in homogeneous phase Journal of Applied Polymer Science 55 1995 1663 1671
54. Y. Tezuka Carbon-13 NMR structural studies on cellulose derivatives with carbonyl groups as a sensitive probe. 7. Carbon-13 NMR determination of the distribution of two ester substituents in cellulose ethanoate butanoate Carbohydrate Research 241 1993 285 290
55. I. Toyoshima J.F. Kennedy, G.O. Phillips, P.A. Williams, Cellulosics: Chemical, biochemical and material aspects 1993 Ellis Horwood Chichester 125
56. D.S. Trifan, and J.J. Hoglen Generalized polymerization mechanism of multi-vinyl monomers. Bicyclo- and tricyclointramolecular propagation Journal of the American Chemical Society 83 1961 2021 2022
57. M. Ueki, K. Kai, M. Amemiya, H. Horino, and H. Oyamada Facile removal of a peptide chain from a solid phase resin support by hydrolysis using tetrabutylammonium fluoride trihydrate in N,N-dimethylformamide Journal of the Chemical Society, Chemical Communications 1988 414 415
58. V.M. Vlasov Fluoride ion as a nucleophile and a leaving group in aromatic nucleophilic substitution reactions Journal of Fluorine Chemistry 61 1993 193 216
59. Y. Yamasi On the studies of Friedel-Crafts acylation. II The relative reactivity of some acyl halides Bulletin of the Chemical Society of Japan 34 1961 480 484