Fast and highly efficient acetylation of xylans in ionic liquid systems

Cellulose

Volumn 20, Issue 6, 2013, Pages 2813-2824

  Stepan, Agnes M ^a   King, Alistair W T ^b   Kakko, Tia ^b   Toriz, Guillermo ^a,c   Kilpeläinen, Ilkka ^b   Gatenholm, Paul ^a  

^a CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF HELSINKI   (Finland)

^c UNIVERSITY OF GUADALAJARA   (Mexico)

Author keywords

Acetylation; Ionic liquid; Rye; Spruce; Xylan

Indexed keywords

ACETIC ANHYDRIDES; ACETYLATED XYLAN; DIMETHYL CARBONATE; HIGH MOLECULAR WEIGHT; RYE; SPRUCE; TRANSPARENT FILMS; XYLAN;

ACETYLATION; CASTING; CHLORINE COMPOUNDS; DISSOLUTION; GEL PERMEATION CHROMATOGRAPHY; MOLECULAR WEIGHT; ORGANIC SOLVENTS; POLYSACCHARIDES; SOLVENTS;

IONIC LIQUIDS;

EID: 84888002392     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-013-0028-y     Document Type: Article

References (49)

1. Abbott AP, Bell TJ, Handa S, Stoddart B (2005) O-Acetylation of cellulose and monosaccharides using a zinc based ionic liquid. Green Chem 7(10): 705-707. doi: 10. 1039/b511691k.
2. Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8(3): 301-306. doi: 10. 1039/b513157j.
3. Buchanan CM, Buchanan NL (2009) Cellulose esters and their production in halogenated ionic liquids. WO2009102306A1.
4. Buchanan CM, Buchanan NL, Hembre RT, Lambert JL, Donelson ME, Gorbunova MG, Kuo T, Wang B (2010) Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom. US20100029927A1.
5. Escalante A, Goncalves A, Bodin A, Stepan A, Sandstroem C, Toriz G, Gatenholm P (2012) Flexible oxygen barrier films from spruce xylan. Carbohydr Polym 87(4): 2381-2387. doi: 10. 1016/j. carbpol. 2011. 11. 003.
6. Fang JM, Sun RC, Tomkinson J, Fowler P (2000) Acetylation of wheat straw hemicellulose B in a new non-aqueous swelling system. Carbohydr Polym 41(4): 379-387. doi: 10. 1016/S0144-8617(99)00102-2.
7. Fukaya Y, Hayashi K, Wada M, Ohno H (2008) Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem 10(1): 44-46. doi: 10. 1039/b713289a.
8. Gericke M, Liebert T, Heinze T (2009) Interaction of ionic liquids with polysaccharides, 8-synthesis of cellulose sulfates suitable for polyelectrolyte complex formation. Macromol Biosci 9(4): 343-353. doi: 10. 1002/mabi. 200800329.
9. 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(6): 483-493. doi: 10. 1002/mame. 201000330.
10. Gericke M, Fardim P, Heinze T (2012) Ionic liquids - promising but challenging solvents for homogeneous derivatization of cellulose. Molecules 17(6): 7458-7502.
11. Glasser WG, Jain RK, Sjostedt MA (1995) Thermoplastic pentosan-rich polysaccharides from biomass. 5430142.
12. Grondahl M, Gatenholm P (2005) Role of acetyl substitution in hardwood xylan. In: Marcel Dekker, Inc. pp 509-514.
13. Grondahl M, Teleman A, Gatenholm P (2003) Effect of acetylation on the material properties of glucuronoxylan from aspen wood. Carbohydr Polym 52(4): 359-366. doi: 10. 1016/s0144-8617(03)00014-6.
14. Grondahl M, Eriksson L, Gatenholm P (2004) Material properties of plasticized hardwood xylans for potential application as oxygen barrier films. Biomacromolecules 5(4): 1528-1535.
15. Hansen NML, Plackett D (2011) Synthesis and characterization of birch wood xylan succinoylated in 1-n-butyl-3-methylimidazolium chloride. Polym Chem 2(9): 2010-2020. doi: 10. 1039/c1py00086a.
16. Heinze T, Schwikal K, Barthel S (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromol Biosci 5(6): 520-525. doi: 10. 1002/mabi. 200500039.
17. Hoije A, Sternemalm E, Heikkinen S, Tenkanen M, Gatenholm P (2008) Material properties of films from enzymatically tailored arabinoxylans. Biomacromolecules 9(7): 2042-2047.
18. Jain RK, Sjostedt M, Glasser WG (2000) Thermoplastic xylan derivatives with propylene oxide. Cellulose (Dordrecht, Neth) 7(4): 319-336.
19. Karatzos SK, Edye LA, Wellard RM (2012) The undesirable acetylation of cellulose by the acetate ion of 1-ethyl-3-methylimidazolium acetate. Cellulose (Dordrecht, Neth) 19(1): 307-312. doi: 10. 1007/s10570-011-9621-0.
20. Kilpelaeinen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS (2007) Dissolution of wood in ionic liquids. J Agric Food Chem 55(22): 9142-9148. doi: 10. 1021/jf071692e.
21. King AWT, Holding A, Parviainen A, Hauru LKJ, Hummel M, Sixta H, Kilpeläinen I (2013) Development of recyclable ionic liquids for lignocellulose processing. Paper presented at the 245th ACS National Meeting, New Orleans.
22. King AWT, Kilpelainen I, Heikkinen S, Jarvi P, Argyropoulos DS (2009a) Hydrophobic interactions determining functionalized lignocellulose solubility in dialkylimidazolium chlorides, as probed by 31p nmr. Biomacromolecules 10(2): 458-463. doi: 10. 1021/bm8010159.
23. King AWT, Zoia L, Filpponen I, Olszewska A, Xie H, Kilpelainen I, Argyropoulos DS (2009b) In situ determination of lignin phenolics and wood solubility in imidazolium chlorides using 31P NMR. J Agric Food Chem 57(18): 8236-8243. doi: 10. 1021/jf901095w.
24. King AWT, Parviainen A, Karhunen P, Matikainen J, Hauru LKJ, Sixta H, Kilpelaeinen I (2012) Relative and inherent reactivities of imidazolium-based ionic liquids: the implications for lignocellulose processing applications. RSC Adv 2(21): 8020-8026. doi: 10. 1039/c2ra21287k.
25. Kosan B, Dorn S, Meister F, Heinze T (2010) Preparation and Subsequent Shaping of Cellulose Acetates Using Ionic Liquids. Macromol Mater Eng 295 (7): 676-681. doi: 10. 1002/mame. 201000022.
26. Leskinen T, King AWT, Kilpelainen I, Argyropoulos DS (2011) Fractionation of lignocellulosic materials with ionic liquids. 1. effect of mechanical treatment. Ind Eng Chem Res 50(22): 12349-12357. doi: 10. 1021/ie200063x.
27. Liu C-F, Zhang A-P, Li W-Y, Yue F-X, Sun R-C (2009a) Homogeneous modification of cellulose in ionic liquid with succinic anhydride using N-bromosuccinimide as a catalyst. J Agric Food Chem 57(5): 1814-1820.
28. Liu C, Zhang A, Sun R (2009b) Method for homogeneous modification of cellulose in ionic liquid. CN101497668A.
29. Lu F, Ralph J (2003) Non-degradative dissolution and acetylation of ball-milled plant cell walls: high-resolution solution-state NMR. Plant J 35(4): 535-544. doi: 10. 1046/j. 1365-313X. 2003. 01817. x.
30. Massonne K, Stegmann V, D'Andola G, Mormann W, Wezstein M, Leng W (2007) Preparation of silylated polysaccharides or cellulose in ionic liquids. WO2007147813A1.
31. Parviainen A, King AWT, Mutikainen I, Hummel M, Selg C, Hauru LKJ, Sixta H, Kilpeläinen I (2013) Predicting cellulose solvating capabilities of acid-base conjugate ionic liquids. ChemSusChem. doi: 10. 1002/cssc. 201300143.
32. Peng X-w, Ren J-l, Sun R-c (2010) Homogeneous esterification of xylan-rich hemicelluloses with maleic anhydride in ionic liquid. Biomacromolecules 11(12): 3519-3524. doi: 10. 1021/bm1010118.
33. Peng X, Ren J, Zhong L, Sun R (2011) Homogeneous synthesis of hemicellulosic succinates with high degree of substitution in ionic liquid. Carbohydr Polym 86(4): 1768-1774. doi: 10. 1016/j. carbpol. 2011. 07. 018.
34. Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev (Washington, DC, U S) 109 (12): 6712-6728. doi: 10. 1021/cr9001947.
35. Qu C, Kishimoto T, Kishino M, Hamada M, Nakajima N (2011) Heteronuclear single-quantum coherence nuclear magnetic resonance (hsqc nmr) characterization of acetylated fir (Abies sachallnensis MAST) Wood Regenerated from Ionic Liquid. J Agric Food Chem 59(10): 5382-5389. doi: 10. 1021/jf200498n.
36. Qu C, Kishimoto T, Ogita S, Hamada M, Nakajima N (2012) Dissolution and acetylation of ball-milled birch (Betula platyphylla) and bamboo (Phyllostachys nigra) in the ionic liquid [Bmim]Cl for HSQC NMR analysis. Holzforschung 66(5): 607-614. doi: 10. 1515/hf. 2011. 186.
37. Ragauskas AJ, Williams CK, Davison BH, Britovsek G, Cairney J, Eckert CA, Frederick WJ, Hallett JP, Leak DJ, Liotta CL, Mielenz JR, Murphy R, Templer R, Tschaplinski T (2006) The path forward for biofuels and biomaterials. Science 311(5760): 484-489.
38. Ren J, Sun R, Liu C (2007a) Ionic liquid as solvent for biopolymer: acetylation of hemicelluloses. In 2007a. American Chemical Society, pp CARB-141.
39. Ren JL, Sun RC, Liu CF, Cao ZN, Luo W (2007b) Acetylation of wheat straw hemicelluloses in ionic liquid using iodine as a catalyst. Carbohydr Polym 70(4): 406-414. doi: 10. 1016/j. carbpol. 2007. 04. 022.
40. Ren J, Peng X, Sun R (2011) Method for preparation of maleoyl hemicellulose. CN101974109A.
41. Renard CMGC, Jarvis MC (1999) Acetylation and methylation of homogalacturonans 1: optimisation of the reaction and characterisation of the products. Carbohydr Polym 39(3): 201-207. doi: 10. 1016/S0144-8617(99)00006-5.
42. Stepan AM, Hoeije A, Schols HA, de Waard P, Gatenholm P (2012) Arabinose content of arabinoxylans contributes to flexibility of acetylated arabinoxylan films. J Appl Polym Sci 125(3): 2348-2355. doi: 10. 1002/app. 36458.
43. Sun R, Fang JM, Tomkinson J, Jones GL (1999) Acetylation of wheat straw hemicelluloses in N N-dimethylacetamide/LiCl solvent system. Ind Crops Prod 10(3): 209-218. doi: 10. 1016/s0926-6690(99)00025-4.
44. Sun R, Sun XF, Tomkinson J (2004) Hemicelluloses and their derivatives. ACS Symp Ser 864(Hemicelluloses): 2-22.
45. Timell TE (1967) Recent progress in the chemistry of wood hemicelluloses. Wood Sci Technol 1(1): 45-70. doi: 10. 1007/bf00592255.
46. Tombs M, Harding S (1997) An introduction to polysaccharide biotechnology. Taylor and Francis.
47. Welton T (1999) Room-Temperature ionic liquids. solvents for synthesis and catalysis. Chem Rev (Washington, D C) 99 (8): 2071-083. doi: 10. 1021/cr980032t.
48. Xie H, King A, Kilpelainen I, Granstrom M, Argyropoulos DS (2007) Thorough chemical modification of wood-based lignocellulosic materials in ionic liquids. Biomacromolecules 8(12): 3740-3748. doi: 10. 1021/bm700679s.
49. Zoia L, King AWT, Argyropoulos DS (2011) Molecular weight distributions and linkages in lignocellulosic materials derivatized from ionic liquid media. J Agric Food Chem 59(3): 829-838. doi: 10. 1021/jf103615e.