Microwave-assisted derivatization of cellulose, 2 - The surprising effect of the structure of ionic liquids on the dissolution and acylation of the biopolymer

Macromolecular Chemistry and Physics

Volumn 212, Issue 23, 2011, Pages 2541-2550

  El Seoud, Omar A ^a   Da Silva, Valdinéia C ^a   Possidonio, Shirley ^a   Casarano, Romeu ^a   Arêas, Elizabeth P G ^a   Gimenes, Paula ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

cellulose dissolution in ionic liquids; functionalization of polymers; imidazole based ionic liquids; microwave assisted acylation of cellulose; rheology of and solvatochromism in ionic liquids

Indexed keywords

DERIVATIZATIONS; FUNCTIONALIZATION OF POLYMERS; HEXANOIC ANHYDRIDE; HYDROPHOBIC INTERACTIONS; MICROWAVE-ASSISTED; SIDE-CHAINS; SOLVATOCHROMIC PROPERTIES;

ACYLATION; CELLULOSE; DISSOLUTION; FUNCTIONAL POLYMERS; HEPTANE; HYDROGEN; HYDROGEN BONDS; HYDROPHOBICITY;

IONIC LIQUIDS;

EID: 82555176749     PISSN: 10221352     EISSN: 15213935     Source Type: Journal    
DOI: 10.1002/macp.201100348     Document Type: Article

References (56)

1. H. A. Krässig, Cellulose Structure, Accessibility and Reactivity, Gordon and Breach, New York 1992, 167.
2. D. Klemm, B. Philipp, T. Heinze, U. Heinze, W. Wagenknecht, Comprehensive Cellulose Chemistry, Vol. 2, Wiley-VCH, Weinheim, Germany 1998, 9.
3. S. Köehler, T. Liebert, M. Schoebitz, J. Schaller, F. Meister, W. Guenther, T. Heinze, Macromol. Rapid Commun. 2007, 28, 2311.
4. C. L. McCormick, P. A. Callais, B. H. Hutchinson Jr,., Macromolecules 1985, 18, 2394.
5. C. L. McCormick, P. A. Callais, Polym. Prepr. 1986, 27, 91.
6. C. L. McCormick, P. A. Callais, Polymer 1987, 28, 2317.
7. O. A. El Seoud, T. Heinze, Adv. Polym. Sci. 2005, 186, 103.
8. S. Köhler, T. Heinze, Macromol. Biosci. 2007, 7, 307.
9. N. Le Moige, M. Spinu, T. Heinze, P. Navard, Polymer 2010, 51, 447.
10. R. P. Swatloski, R. D. Rogers, J. D. Holbrey, WO 2003029329, 2003.
11. G. Laus, G. Bentivoglio, H. Schottenberger, V. Kahlenberg, H. Kopacka, H. Röder, T. Röder, H. Sixta, Lenzinger Ber. 2005, 84, 71.
12. S. Zhu, Y. Wu, Q. Chen, Z. Yu, C. Wang, S. Jin, Y. Ding, G. Wu, Green Chem. 2006, 8, 325.
13. S. Barthel, T. Heinze, Green Chem. 2006, 8, 301.
14. T. Liebert, T. Heinze, BioResources 3, 576.
15. R. P. Swatloski, S. K. Spear, J. D. Holbrey, R. D. Rogers, J. Am. Chem. Soc. 2002, 124, 4974.
16. O. A. El Seoud, A. Koschella, L. C. Fidale, S. Dorn, T. Heinze, Biomacromolecules 2007, 8, 2629.
17. H. Zhao, G. A. Baker, Z. Song, O. Olubajo, T. Crittle, D. Peters, Green Chem. 2008, 10, 696.
18. Q.-L. Kuang, J.-C. Zhao, Y.-H. Niu, J. Zhang, Z.-G. Wang, J. Phys. Chem. B 2008, 112, 10234.
19. A. Pinkert, K. N. Marsh, S. Pang, M. P. Staiger, Chem. Rev. 2009, 109, 6712.
20. M. E. Zakrewska, E. Bogel-Lukasik, R. Bogel-Lukasik, Energy Fuels 2010, 24, 737.
21. P. Maeki-Arvela, I. Anugwom, P. Virtanen, R. Sjöholm, J. P. Mikkola, Ind. Crop. Prod. 2010, 32, 175.
22. Z. Fei, W. H. Ang, D. Zhao, R. Scopelliti, E. E. Zvereva, S. A. Katsyuba, P. J. Dyson, J. Phys. Chem. B 2007, 111, 10095.
23. W. L. F. Armarego, C. L. L. Chai, Purification of Laboratory Chemicals, Elsevier, New York 2009.
24. B. R. Osterby, R. D. McKelvey, J. Chem. Educ. 1996, 73, 260.
25. ASTM D1795-94, Standard Test Methods for Intrinsic Viscosity of Cellulose, 2001.
26. G. Buschle-Diller, S. H. Zeronian, J. Appl. Polym. Sci. 1992, 45, 967.
27. B. L. Browning, Methods of Wood Chemistry, Vol. 2, Interscience, New York 1967, 499.
28. V. Gudipati, D. P. Curran, C. S. Wilcox, J. Org. Chem. 2006, 71, 3599.
29. R. Casarano, L. C. Fidale, C. M. Lucheti, T. Heinze, O. A. El Seoud, Carbohydr. Polym. 2011, 83, 1285.
30. ASTM D 871-96, Standard Test Methods of Testing Cellulose Acetate (solution method; procedure A), 2002.
31. E. S. Sashina, N. P. Novoselov, Russ. J. Gen. Chem. 2009, 79, 1057.
32. S. Possidonio, L. C. Fidale, O. A. El Seoud, J. Polym. Sci. A 2009, 48, 134.
33. L. A. Ramos, J. M. Assaf, O. A. El Seoud, E. Frollini, Biomacromolecules 2005, 6, 2638.
34. L. C. Branco, J. N. Rosa, J. J. M. Ramos, C. A. M Afonso, Chem. Eur. J. 2002, 8, 3671.
35. G. T. Ciacco, T. Liebert, E. Frollini, T. Heinze, Cellulose 2003, 10, 125.
36. T. Heinze, S. Dorn, M. Schöbitz, T. Liebert, S. Köhler, F. Meister, Macromol. Symp. 2008, 262, 8.
37. S. T. Handy, Curr. Org. Chem. 2005, 9, 959.
38. Y. Cao, J. Wu, J. Zhang, H. Li, Y. Zhang, J. He, Chem. Eng. J. 2009, 147, 13.
39. R. L. Brinkley, R. B. Gupta, Ind. Eng. Chem. Res. 1998, 37, 4823.
40. J. Vitz, T. Erdmenger, C. Hänsch, U. S. Schubert, Green Chem. 2009, 11, 417.
41. A. Xu, J. Wang, H. Wang, Green Chem. 2010, 12, 268.
42. C. Reichardt, T. Welton, Solvents and Solvents Effects in Organic Chemistry, 4th ed, Wiley-VCH, Weinheim, Germany 2010, 425.
43. C. Reichardt, Chem. Rev. 1994, 94, 2319.
44. O. A. El Seoud, Pure Appl. Chem. 2007, 79, 1135.
45. O. A. El Seoud, Pure Appl. Chem. 2009, 81, 697.
46. G. A. Marson, O. A. El Seoud, J. Polym. Sci. A 1999, 37, 3738.
47. L. C. Fidale, N. Ruiz, T. Heinze, O. A. El Seoud, Macromol. Chem. Phys. 2008, 209, 1240.
48. Y. Fukaya, K. Hayashi, M. Wada, H. Ohno, Green Chem. 2008, 10, 44.
49. H. Zhang, J. Wu, J. Zhang, J. He, Macromolecules 2005, 38, 8272.
50. H. Liu, K. L. Sale, B. M. Holmes, B. A. Simmons, S. Singh, J. Phys. Chem. B 2010, 114, 4293.
51. S. M. Urahata, M. C. C. Ribeiro, J. Chem. Phys. 2004, 120, 1855.
52. S. M. Urahata, M. C. C. Ribeiro, J. Chem. Phys. 2005, 122, 024511/1.
53. J. N. C. Lopes, A. A. H. Padua, J. Phys. Chem. B 2006, 110, 3330.
54. Y. Wang, G. A. Voth, J. Phys. Chem. B 2006, 110, 18601.
55. A. F. Lagalante, M. Spadi, T. J. Bruno, J. Chem. Eng. Data 2000, 45, 382.
56. E. B. Tada, L. P. Novaki, O. A. El Seoud, J. Phys. Org. Chem. 2000, 13, 679.