Functional comparison of polar ionic liquids and onium hydroxides for chitin dissolution and deacetylation to chitosan

ACS Sustainable Chemistry and Engineering

Volumn 4, Issue 7, 2016, Pages 3722-3727

  Shimo, Mizuki ^a   Abe, Mitsuru ^a,b   Ohno, Hiroyuki ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Deacetylation; Ethylenediamine; Hydrogen bond; Hydroxide anion; Mild conditions; Proton accepting ability

Indexed keywords

ACETYLATION; CHITOSAN; DISSOLUTION; HYDROGEN BONDS; IONIC LIQUIDS; MIXTURES;

DEACETYLATION; DISSOLUTION ABILITY; DISSOLUTION PROCESS; ETHYLENE DIAMINE; HYDROXIDE ANIONS; IONIC LIQUID (ILS); MILD CONDITIONS; TETRAALKYLAMMONIUM;

CHITIN;

EID: 84979018876     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b00368     Document Type: Review

References (25)

1. Kurita, K.; Sannan, T.; Iwakura, Y. Studies on chitin, 4. Evidence for formation of block and random copolymers of N-acetyl-D-glucosamine and D-glucosamine by hetero- and homogeneous hydrolyses Makromol. Chem. 1977, 178, 3197-3202 10.1002/macp.1977.021781203
2. Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. Dissolution of cellulose with ionic liquids J. Am. Chem. Soc. 2002, 124, 4974-4975 10.1021/ja025790m
3. Fukaya, Y.; Hayashi, K.; Wada, M.; Ohno, H. Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions Green Chem. 2008, 10, 44-46 10.1039/B713289A
4. Fort, D. A.; Remsing, R. C.; Swatloski, R. P.; Moyna, P.; Moyna, G.; Rogers, R. D. Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride Green Chem. 2007, 9, 63-69 10.1039/B607614A
5. Kilpeläinen, I.; Xie, H.; King, A.; Granstrom, M.; Heikkinen, S.; Argyropoulos, D. S. Dissolution of wood in ionic liquids J. Agric. Food Chem. 2007, 55, 9142-9148 10.1021/jf071692e
6. Abe, M.; Fukaya, Y.; Ohno, H. Extraction of polysaccharides from bran with phosphonate or phosphinate-derived ionic liquids under short mixing time and low temperature Green Chem. 2010, 12, 1274-1280 10.1039/c003976d
7. Phillips, D. M.; Drummy, L. F.; Conrady, D. G.; Fox, D. M.; Naik, R. R.; Stone, M. O.; Trulove, P. C.; Long, H. C. D.; Mantz, R. A. Dissolution and Regeneration of Bombyx mori Silk Fibroin Using Ionic Liquids J. Am. Chem. Soc. 2004, 126, 14350-14351 10.1021/ja046079f
8. 2 Green Chem. 2006, 8, 630-633 10.1039/b517297g
9. Qin, Y.; Lu, X.; Sun, N.; Rogers, R. D. Dissolution or extraction of crustacean shells using ionic liquids to obtain high molecular weight purified chitin and direct production of chitin films and fibers Green Chem. 2010, 12, 968-971 10.1039/c003583a
10. Xu, A.; Wang, J.; Wang, H. Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems Green Chem. 2010, 12, 268-275 10.1039/B916882F
11. Sikorski, P.; Hori, R.; Wada, M. Revisit of α-Chitin Crystal Structure Using High Resolution X-ray Diffraction Data Biomacromolecules 2009, 10, 1100-1105 10.1021/bm801251e
12. Crowhurst, L.; Mawdsley, P. R.; Perez-Arlandis, J. M.; Salter, P. A.; Welton, T. Solvent-solute interactions in ionic liquids Phys. Chem. Chem. Phys. 2003, 5, 2790-2794 10.1039/B303095D
13. Ohno, H.; Fukaya, Y. Task Specific Ionic Liquids for Cellulose Technology Chem. Lett. 2009, 38, 2-7 10.1246/cl.2009.2
14. Brandt, A.; Grasvik, J.; Hallett, J. P.; Welton, T. Deconstruction of lignocellulosic biomass with ionic liquids Green Chem. 2013, 15, 550-583 10.1039/c2gc36364j
15. Abe, M.; Ohno, H. Solubilization of Biomass Components with Ionic Liquids Toward Biomass Energy Conversions. In Production of Biofuels and Chemicals with Ionic Liquids; Fang, Z.; Smith, R. L. J.; Qi, X., Eds.; Springer Science + Business Media B.V.: Dordrecht, 2013; Chapter 2, pp 29-59.
16. Mazza, M.; Catana, D. A.; Garcia, C. V.; Cecutti, C. Influence of water on the dissolution of cellulose in selected ionic liquids Cellulose 2009, 16, 207-215 10.1007/s10570-008-9257-x
17. Abe, M.; Fukaya, Y.; Ohno, H. Fast and facile dissolution of cellulose with tetrabutylphosphonium hydroxide containing 40 wt% water Chem. Commun. 2012, 48, 1808-1810 10.1039/c2cc16203b
18. Abe, M.; Kuroda, K.; Sato, D.; Kunimura, H.; Ohno, H. Effects of polarity, hydrophobicity, and density of ionic liquids on cellulose solubility Phys. Chem. Chem. Phys. 2015, 17, 32276-32282 10.1039/C5CP05808B
19. Shigemasa, Y.; Matsuura, H.; Sashiwa, H.; Saimoto, H. Evaluation of different absorbance ratios from infrared spectroscopy for analyzing the degree of deacetylation in chitin Int. J. Biol. Macromol. 1996, 18, 237-242 10.1016/0141-8130(95)01079-3
20. Noishiki, Y.; Nishiyama, Y.; Wada, M.; Kuga, S. Inclusion complex of β-chitin and aliphatic amines Biomacromolecules 2005, 6, 2362-2364 10.1021/bm0500446
21. Moorjani, M. N.; Achutha, V.; Khasim, D. I. Parameters affecting the viscosity of chitosan from prawn waste J. Food Sci. Technol. 1975, 12, 187-189
22. Abe, M.; Kuroda, K.; Ohno, H. Maintenance-Free Cellulose Solvents Based on Onium Hydroxides ACS Sustainable Chem. Eng. 2015, 3 (8) 1771-1776 10.1021/acssuschemeng.5b00303
23. Abe, M.; Yamada, T.; Ohno, H. Dissolution of wet wood biomass without heating RSC Adv. 2014, 4, 17136-17140 10.1039/C4RA01038H
24. Abe, M.; Yamanaka, S.; Yamada, H.; Yamada, T.; Ohno, H. Almost complete dissolution of woody biomass with tetra-n-butylphosphonium hydroxide aqueous solution at 60 °C Green Chem. 2015, 17, 4432-4438 10.1039/C5GC00646E
25. Hyväkkö, U.; King, A. W. T.; Kilpeläinen, I. Extraction of wheat straw with aqueous tetra-n-butylphosphonium hydroxide BioResources 2013, 9, 1565-1577 10.15376/biores.9.1.1565-1577