Mixed solvents for cellulose derivatization under homogeneous conditions: Kinetic, spectroscopic, and theoretical studies on the acetylation of the biopolymer in binary mixtures of an ionic liquid and molecular solvents

Cellulose

Volumn 21, Issue 3, 2014, Pages 1193-1204

  Nawaz, Haq ^a   Pires, Paulo A R ^a   Bioni, Thaís A ^a   Arêas, Elizabeth P G ^a   El Seoud, Omar A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

1 Allyl 3 methylimidazolium chloride; Acetonitrile; Ionic liquids; Kinetics of Cellulose acetylation; Mixtures of ionic liquids with molecular solvents; Molecular dynamics simulation of cellulose dissolution; N,N dimethylacetamide

Indexed keywords

ACETONITRILE; ACETYLATION; BINARY MIXTURES; CELLULOSE; CHLORINE COMPOUNDS; HYDROGEN BONDS; KINETICS; MOLECULAR DYNAMICS; ORGANIC SOLVENTS; RATE CONSTANTS; SOLVENTS;

1-ALLYL-3-METHYLIMIDAZOLIUM CHLORIDES; CELLULOSE ACETYLATIONS; CELLULOSE DISSOLUTIONS; MOLECULAR SOLVENTS; N , N-DIMETHYLACETAMIDE;

IONIC LIQUIDS;

EID: 84901232235     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-014-0184-8     Document Type: Article

References (58)

1. Ananikov VP (2011) Characterization of molecular systems and monitoring of chemical reactions in ionic liquids by nuclear magnetic resonance spectroscopy. Chem Rev 111: 418-454.
2. Anslyn EV, Dougherty DA (2006) Modern physical organic chemistry. University Science Books, Sausalito, p 382.
3. Armagero WLF, Chai CLL (2003) Purification of laboratory chemicals, 5th edn. Elsevier, New York.
4. Arvela PM, Anugwom I, Virtanen P, Sjöholma R, Mikkola JP (2010) Dissolution of lignocellulosic materials and its constituents using ionic liquids-a review. Ind Crops Prod 32: 175-201.
5. ASTM D1795-94 (2001) Standard test methods for intrinsic viscosity of cellulose.
6. ASTM D871-96 (2002) Standard test methods of testing cellulose acetate (solution method; procedure A).
7. Bayly CI, Cieplak P, Cornell WD, Kollman PA (1993) A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model. J Phys Chem 97: 10269-10280.
8. Berry RS, Rice SA, Ross J (2000) Journal of Physics Chemistry. Oxford University Press, Oxford, p 524.
9. Bester-Rogac M, Stopp A, Johannes HJ, Hefter G, Buchner R (2011) Association of ionic liquids in solution: a combined dielectric and conductivity study of [bmim][Cl] in water and in acetonitrile. Phys Chem Chem Phys 13: 17588-17598.
10. Bruice TC (2006) Computational approaches: reaction trajectories, structures, and atomic motions. Enzyme reactions and proficiency. Chem Rev 106: 3119-3139.
11. Buschle-diller G, Zeronian SH (1992) Enhancing the reactivity and strength of cotton fibres. J Appl Polym Sci 45: 967-979.
12. Caleman C, van Maaren PJ, Hong M, Hub JS, Costa LT, van der Spoel D (2012) Force field benchmark of organic liquids: density, enthalpy of vaporization, heat capacities, surface tension, isothermal compressibility, volumetric expansion coefficient, and dielectric constant. J Chem Theory Comput 8: 61-74.
13. Catalán J (2009) 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. J Phys Chem B 113: 5951-5960.
14. Ciocirlan O, Croitoru O, Iulian O (2011) Densities for binary mixtures of 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid with molecular solvents. J Chem Eng Data 56: 1526-1534.
15. Crosthwaite JM, Aki SNVK, Maginn EJ, Brennecke JF (2005) Liquid phase behavior of imidazolium-based ionic liquids with alcohols: effects of hydrogen bonding and non-polar interactions. Fluid Phase Equilib 228-229: 303-309.
16. Dong K, Zhang SJ, Wang DX, Yao XQ (2006) Hydrogen bonds in imidazolium ionic liquids. J Phys Chem A 110: 9775-9782.
17. El Seoud OA (2007) Solvation in pure and mixed solvents: some recent developments. Pure Appl Chem 79: 1135-1151.
18. El Seoud OA (2009) Understanding solvation. Pure Appl Chem 81: 697-707.
19. El Seoud OA, Koschella A, Fidale LC, Dorn S, Heinze T (2007) Applications of ionic liquids in carbohydrate chemistry: a window of opportunities. Biomacromolecules 8: 2629-2647.
20. El Seoud OA, Nawaz H, Arêas EPG (2013) Chemistry and applications of polysaccharide solutions in strong electrolytes/dipolar aprotic solvents: an overview. Molecules 18: 1270-1313.
21. Fidale LC, Ruiz N, Heinze T, El Seoud OA (2008) Cellulose swelling by aprotic and protic solvents: what are the similarities and differences? Macromol Chem Phys 209: 1240-1254.
22. Fidale LC, Possidonio S, El Seoud OA (2009) 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. Macromol Biosci 9: 813-821.
23. Gericke M, Liebert T, El Seoud OA, Heinze T (2011) Tailored media for homogeneous cellulose chemistry: ionic liquid/CO-solvent mixtures. Macromol Mater Eng 296: 483-493.
24. Gericke M, Fardim P, Heinze T (2012) Ionic liquids-promising but challenging solvents for homogeneous derivatization of cellulose. Molecules 17: 7458-7502.
25. Gomes TCF, Skaf MS (2012) Cellulose-builder: a toolkit for building crystalline structures of cellulose. J Comput Chem 33: 1338-1346.
26. Hanbin L, Kenneth L, Holmes BM, Simmons BA, Singh S (2010) Understanding the interactions of cellulose with ionic liquids: a molecular dynamics study. J Phys Chem B 114: 4293-4301.
27. Hauru LKJ, Hummel M, King AWT, Kilpeläinen I, Sixta H (2012) Role of solvent parameters in the regeneration of cellulose from ionic liquid solutions. Biomacromolecules 13: 2896-2905.
28. Hesse-Ertelt S, Heinze T, Kosan B, Schwikal K, Meister F (2010) Solvent effects on the NMR chemical shifts of imidazolium-based ionic liquids and cellulose therein. Macromol Symp 294-II: 75-89.
29. Humphrey W, Dalke A, Schulten K (1996) VMD-Visual molecular dynamics. J Mol Graphics 14: 33-38.
30. Jain RK, Agnish SL, Lal K, Bhatnagar HL (1985) Reactivity of hydroxyl groups in cellulose towards chloro(p-tolyl)methane. Makromol Chem 186: 2501-2512.
31. Jiang JC, Lin KH, Li SC, Pao-Ming SPM, Hung KC, Lin SH, Chang HC (2011) Association structures of ionic liquid/DMSO mixtures studied by high-pressure infrared spectroscopy. J Chem Phys 134: 044506.
32. Jorgensen WL, Maxwell DS, Tirado-Rives J (1996) Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J Am Chem Soc 118: 11225-11236.
33. Kwatra HS, Caruthers JM, Tao BY (1992) Synthesis of long chain fatty acids esterified onto cellulose via the vacuum-acid chloride process. Ind Eng Chem Res 31: 2647-2651.
34. Le KA, Sescousse R, Budtova T (2012) Influence of water on cellulose-EMIMAc solution properties: a viscometric study. Cellulose 19: 45-54.
35. Lide DR (2004) CRC Handbook of chemistry and physics, 85th edn. CRC Press, Boca Raton.
36. Makowska A, Dyoniziak E, Siporska A, Szydlowski J (2010) Miscibility of ionic liquids with polyhydric alcohols. J Phys Chem B 114: 2504-2508.
37. Malm CJ, Tanghe LO, Laird BC, Smith GD (1953) Relative rates of acetylation of the hydroxyl groups in cellulose acetate. J Am Chem Soc 75: 80-84.
38. Martínez L, Andrade R, Birgin EG, Martínez JM (2009) Packmol: a package for building initial configurations for molecular dynamics simulations. J Comput Chem 30: 2157-2164.
39. Nawaz H, Casarano R, El Seoud OA (2012) First report on the kinetics of the uncatalyzed esterification of cellulose under homogeneous reaction conditions: a rationale for the effect of carboxylic acid anhydride chain-length on the degree of biopolymer substitution. Cellulose 19: 199-207.
40. Nawaz H, Pires PAR, El Seoud OA (2013) Kinetics and mechanism of imidazole-catalyzed acylation of cellulose in LiCl/N, N-dimethylacetamide. Carbohydr Polym 92: 997-1005.
41. Neese F, Becker U, Ganiouchine D, Kobmann S, Petrenko T, Riplinger C (2011) Orca - an ab initio, DFT and semiempirical SCF-MO package (Version 2. 9). Germany: University of Bonn.
42. Perepelkin KE (2007) Lyocell fibers based on direct dissolution of cellulose in N-methylmorpholine N-oxide: development and prospects. Fiber Chem 39: 163-172.
43. Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109: 6712-6728.
44. Possidonio S, Fidale LC, El Seoud OA (2010) Microwave-assisted derivatization of cellulose in an ionic liquid: an efficient, expedient synthesis of simple and mixed carboxylic esters. J Polym Sci Part A Polym Chem 48: 134-143.
45. Press WH, Teukolsky SA, Vetterling WT, Flannergy BP (2007) Numerical recipes: the art of scientific computing, 3rd edn. Cambridge University Press, Cambridge.
46. Punyiczki M, Rosenberg A (1992) The effect of viscosity on the accessibility of the single tryptophan in human serum albumin. Biophys Chem 42: 93-100.
47. Sashina ES, Novoselov NP, Kuzmina OG, Troshenkova SV (2008) Ionic liquids as new solvents of natural polymers. Fibre Chem 40: 270-277.
48. Sato BM, Oliveira CG, Clarissa TM, El Seoud OA (2010) Thermo-solvatochromism in binary mixtures of water and ionic liquids: on the relative importance of solvophobic interactions. Phys Chem Chem Phys 12: 1764-1771.
49. Sato BM, Martins CT, El Seoud OA (2012) Solvation in aqueous binary mixtures: consequences of the hydrophobic character of the ionic liquids and the solvatochromic probes. New J Chem 2353-2360.
50. Silva AWS, Vranken WF (2012) ACPYPE-AnteChamber PYthon Parser interfacE. BMC Res Notes 5: 367.
51. Sitnitsky AE (2008) Solvent viscosity dependence for enzymatic reactions. Physica A 387: 5483-5497.
52. Somogyi B, Norman JA, Zempel L, Rosenberg A (1988) Viscosity and transient solvent accessibility Trp-63 in the native confirmation of lysozyme. Biophys Chem 32: 1-13.
53. Tada EB, Novaki LP, El Seoud OA (2000) Solvatochromism in pure and binary solvent mixtures: effects of the molecular structure of the zwitterionic probe. J Phys Org Chem 13: 679-687.
54. Tosh B, Saikia CN, Dass NN (2000) Homogeneous esterification of cellulose in the lithium chloride-N, N-dimethylacetamide solvent system: effect of temperature and catalyst. Carbohydr Res 327: 345-352.
55. van der Spoel D, Lindahl E, Hess B, Groenhof G, Mark AE, Berendsen HJ (2005) GROMACS: fast, flexible and free. J Comput Chem 26: 1701-1718.
56. Vanquelef E, Simon S, Marquant G, Garcia E, Klimerak G, Delepine JC (2011) R. E. D. Server: a web service for deriving RESP and ESP charges and building force field libraries for new molecules and molecular fragments. Nucleic Acids Res (Web server issue) 39: W511-W517.
57. Wang J, Wang W, Kollman PA, Case DA (2004) Development and testing of a general amber force field. J Comput Chem 25: 1157-1174.
58. Wang J, Wang W, Kollman PA, Case DA (2006) Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 25: 247-260.