A Review of Chitin Solvents and Their Dissolution Mechanisms

Yi Zhong; Jie Cai; Li-Na Zhang

doi:10.1007/s10118-020-2459-x

Your Location：

Home >

Browse articles >

A Review of Chitin Solvents and Their Dissolution Mechanisms

REVIEW | Updated：2020-07-24

- A Review of Chitin Solvents and Their Dissolution Mechanisms
- Chinese Journal of Polymer Science Vol. 38, Issue 10, Pages: 1047-1060(2020)
- Affiliations：
  
  a.College of Chemistry & Molecule Sciences, Wuhan University, Wuhan 430072, China
  b.Hubei Engineering Center of Natural Polymer-based Medical Materials, Wuhan University, Wuhan 430072, China
  c.Research Institute of Shenzhen, Wuhan University, Shenzhen 518057, China
- Author bio：
  
  caijie@whu.edu.cn
- Funds：
- DOI：10.1007/s10118-020-2459-x
  CLC：
- Received：17 April 2020，
  
  Revised：2020-5-17，
  
  Accepted：18 May 2020，
  
  Online First：24 July 2020，
  
  Published：16 June 2020
- Accepted：
Scan QR Code
Zhong, Y.; Cai, J.; Zhang, L. N. A review of chitin solvents and their dissolution mechanisms. Chinese J. Polym. Sci. 2020, 38, 1047–1060

Yi Zhong, Jie Cai, Li-Na Zhang. A Review of Chitin Solvents and Their Dissolution Mechanisms[J]. Chinese Journal of Polymer Science, 2020, 38(10): 1047-1060.
Zhong, Y.; Cai, J.; Zhang, L. N. A review of chitin solvents and their dissolution mechanisms. Chinese J. Polym. Sci. 2020, 38, 1047–1060 DOI： 10.1007/s10118-020-2459-x.

Yi Zhong, Jie Cai, Li-Na Zhang. A Review of Chitin Solvents and Their Dissolution Mechanisms[J]. Chinese Journal of Polymer Science, 2020, 38(10): 1047-1060. DOI： 10.1007/s10118-020-2459-x.

摘要

Abstract

Chitin is an abundant natural nitrogen-containing biopolymer with great application potential in materials

environment

energy

and health. However

the structure characteristics and processing technologies have required intense research in related applications. In particular

there have been great efforts to developing solvents for chitin

and the results so far are quite encouraging. This review summarizes the main solvent systems used for chitin

namely the aqueous solvent systems (mineral acids

inorganic salt aqueous solutions

alkali aqueous solutions) and non-aqueous ones (LiCl-dimethylacetamide solvents

CaCl

·2H

O saturated methanol

ionic liquids

deep eutectic solvents

and protic organic solvents). The solvent properties

dissolution methods

and solution properties are discussed in detail. Special attention is paid to the dissolution mechanism in each system. This review can provide a reference for understanding the dissolution behavior of chitin and finding suitable solvents for it.

关键词

Keywords

references

Kumar, M. N. V. R. . A review of chitin and chitosan applications . React. Funct. Polym. , 2000 . 46 1 - 27 . DOI: 10.1016/S1381-5148(00)00038-9 http://doi.org/10.1016/S1381-5148(00)00038-9 .

Bartlett, D. H.; Azam, F. . Chitin, cholera, and competence . Science , 2005 . 310 1775 DOI: 10.1126/science.1122396 http://doi.org/10.1126/science.1122396 .

Nawawi, W. M. F. B. W.; Jones, M.; Murphy, R. J.; Lee, K. Y.; Kontturi, E.; Bismarck, A. . Nanomaterials derived from fungal sources-Is it the new type? . Biomacromolecules , 2020 . 21 30 - 55 . DOI: 10.1021/acs.biomac.9b01141 http://doi.org/10.1021/acs.biomac.9b01141 .

Food and Agriculture Organization of the United Nations. The state of world fisheries and aquaculture (FAO, 2018) . 2018 , https://apo.org.au/node/181941.

Crini, G. Historical landmarks in the discovery of chitin. In Sustainable agriculture reviews 35: chitin and chitosan: history, fundamentals and innovations , Crini, G.; Lichtfouse, E. Eds. Springer International Publishing, 2019 , DOI: 10.1007/978-3-030-16538-3_1.

Rudall, K. M. The chitin/protein complexes of insect cuticles. In Advances in insect physiololy . Beament, J. W. L.; Treherne, J. E.; Wigglesworth, V. B. Eds. Academic Press, 1963 , p.1.

Blackwell, J.; Gardner, K. H.; Kolpak, F. J.; Minke, R.; Claffey, W. B. Refinement of cellulose and chitin structures. In Fiber diffraction methods , American Chemical Society, 1980 , p.141.

Sikorski, P.; Hori, R.; Wada, M. . Revisit of α -chitin crystal structure using high resolution X-ray diffraction data . Biomacromolecules , 2009 . 10 1100 - 1105 . DOI: 10.1021/bm801251e http://doi.org/10.1021/bm801251e .

Nishiyama, Y.; Noishiki, Y.; Wada, M. . X-ray structure of anhydrous β -chitin at 1Å resolution . Macromolecules , 2011 . 44 950 - 957 . DOI: 10.1021/ma102240r http://doi.org/10.1021/ma102240r .

Sawada, D.; Nishiyama, Y.; Langan, P.; Forsyth, V. T.; Kimura, S.; Wada, M. . Direct determination of the hydrogen bonding arrangement in anhydrous β -chitin by neutron fiber diffraction . Biomacromolecules , 2012 . 13 288 - 291 . DOI: 10.1021/bm201512t http://doi.org/10.1021/bm201512t .

Krajewska, B. . Application of chitin- and chitosan-based materials for enzyme immobilizations: a review . Enzyme Microb. Technol. , 2004 . 35 126 - 139 . DOI: 10.1016/j.enzmictec.2003.12.013 http://doi.org/10.1016/j.enzmictec.2003.12.013 .

Jayakumar, R.; Menon, D.; Manzoor, K.; Nair, S. V.; Tamura, H. . Biomedical applications of chitin and chitosan based nanomaterials—a short review . Carbohydr. Polym. , 2010 . 82 227 - 232 . DOI: 10.1016/j.carbpol.2010.04.074 http://doi.org/10.1016/j.carbpol.2010.04.074 .

Kadokawa, J. I. . Ionic liquid as useful media for dissolution, derivatization, and nanomaterial processing of chitin . Green Sustain. Chem. , 2013 . 3 19 - 25 . .

Duan, B.; Huang, Y.; Lu, A.; Zhang, L. . Recent advances in chitin based materials constructed via physical methods . Prog. Polym. Sci. , 2018 . 82 1 - 33 . DOI: 10.1016/j.progpolymsci.2018.04.001 http://doi.org/10.1016/j.progpolymsci.2018.04.001 .

Zavgorodnya, O.; Shamshina, J. L.; Berton, P.; Rogers, R. D. Translational research from academia to industry: following the pathway of George Washington Carver. In Ionic liquids: current state and future directions , American Chemical Society, 2017 , p.1250.

Wu, S.; Duan, B.; Zeng, X.; Lu, A.; Xu, X.; Wang, Y.; Ye, Q.; Zhang, L. . Construction of blood compatible lysine-immobilized chitin/carbon nanotube microspheres and potential applications for blood purified therapy . J. Mater. Chem. B , 2017 . 5 2952 - 2963 . DOI: 10.1039/C7TB00101K http://doi.org/10.1039/C7TB00101K .

Shen, X.; Shamshina, J. L.; Berton, P.; Gurau, G.; Rogers, R. D. . Hydrogels based on cellulose and chitin: fabrication, properties, and applications . Green Chem. , 2016 . 18 53 - 75 . DOI: 10.1039/C5GC02396C http://doi.org/10.1039/C5GC02396C .

Shamshina, J. L.; Berton, P.; Rogers, R. D. . Advances in functional chitin materials: a review . ACS Sustain. Chem. Eng. , 2019 . 7 6444 - 6457 . DOI: 10.1021/acssuschemeng.8b06372 http://doi.org/10.1021/acssuschemeng.8b06372 .

Zhang, L.; Wang, J.; Yang, M.; Ke, N.; Zhang, B.; Wang, H.; Zheng, Q.; Xie, H. . Dissolution, materialization and derivatization of chitin and chitosan in ionic liquids . Sci. Sin. Chim. , 2019 . 49 1059 - 1072 . DOI: 10.1360/SSC-2019-0031 http://doi.org/10.1360/SSC-2019-0031 .

Wei, P.; Cai, J.; Zhang, L. . High-strength and tough crystalline polysaccharide-based materials . Chin. J. Chem. , 2020 . DOI: 10.1002/cjoc.202000036 DOI: 10.1002/cjoc.202000036 http://doi.org/10.1002/cjoc.202000036 .

Marchessault, R. H.; Morehead, F. F.; Walter, N. M. . Liquid crystal systems from fibrillar polysaccharides . Nature , 1959 . 184 632 - 633 . DOI: 10.1038/184632a0 http://doi.org/10.1038/184632a0 .

Fan, Y.; Saito, T.; Isogai, A. . Chitin nanocrystals prepared by TEMPO-mediated oxidation of α -chitin . Biomacromolecules , 2008 . 9 192 - 198 . DOI: 10.1021/bm700966g http://doi.org/10.1021/bm700966g .

Fan, Y.; Saito, T.; Isogai, A. . TEMPO-mediated oxidation of β -chitin to prepare individual nanofibrils . Carbohydr. Polym. , 2009 . 77 832 - 838 . DOI: 10.1016/j.carbpol.2009.03.008 http://doi.org/10.1016/j.carbpol.2009.03.008 .

Fan, Y.; Saito, T.; Isogai, A. . Individual chitin nano-whiskers prepared from partially deacetylated α -chitin by fibril surface cationization . Carbohydr. Polym. , 2010 . 79 1046 - 1051 . DOI: 10.1016/j.carbpol.2009.10.044 http://doi.org/10.1016/j.carbpol.2009.10.044 .

You, J.; Zhu, L.; Wang, Z.; Zong, L.; Li, M.; Wu, X.; Li, C. . Liquid exfoliated chitin nanofibrils for re-dispersibility and hybridization of two-dimensional nanomaterials . Chem. Eng. J. , 2018 . 344 498 - 505 . DOI: 10.1016/j.cej.2018.03.121 http://doi.org/10.1016/j.cej.2018.03.121 .

Kurita, K. . Controlled functionalization of the polysaccharide chitin . Prog. Polym. Sci. , 2001 . 26 1921 - 1971 . DOI: 10.1016/S0079-6700(01)00007-7 http://doi.org/10.1016/S0079-6700(01)00007-7 .

Zhong, C.; Cooper, A.; Kapetanovic, A.; Fang, Z.; Zhang, M.; Rolandi, M. . A facile bottom-up route to self-assembled biogenic chitin nanofibers . Soft Matter , 2010 . 6 5298 - 5301 . DOI: 10.1039/c0sm00450b http://doi.org/10.1039/c0sm00450b .

You, J.; Li, M.; Ding, B.; Wu, X.; Li, C. . Crab chitin-based 2D soft nanomaterials for fully biobased electric devices . Adv. Mater. , 2017 . 29 1606895 DOI: 10.1002/adma.201606895 http://doi.org/10.1002/adma.201606895 .

Duan, B.; Chang, C.; Ding, B.; Cai, J.; Xu, M.; Feng, S.; Ren, J.; Shi, X.; Du, Y.; Zhang, L. . High strength films with gas-barrier fabricated from chitin solution dissolved at low temperature . J. Mater. Chem. A , 2013 . 1 1867 - 1874 . DOI: 10.1039/C2TA00068G http://doi.org/10.1039/C2TA00068G .

King, C.; Shamshina, J. L.; Gurau, G.; Berton, P.; Khan, N. F. A. F.; Rogers, R. D. . A platform for more sustainable chitin films from an ionic liquid process . Green Chem. , 2017 . 19 117 - 126 . DOI: 10.1039/C6GC02201D http://doi.org/10.1039/C6GC02201D .

Huang, J. C.; Zhong, Y.; Zhang, L. N.; Cai, J. . Extremely strong and transparent chitin films: a high-efficiency, energy-saving, and "green" route using an aqueous KOH/urea solution . Adv. Funct. Mater. , 2017 . 27 1701100 DOI: 10.1002/adfm.201701100 http://doi.org/10.1002/adfm.201701100 .

Zhu, K.; Shi, S.; Cao, Y.; Lu, A.; Hu, J.; Zhang, L. . Robust chitin films with good biocompatibility and breathable properties . Carbohydr. Polym. , 2019 . 212 361 - 367 . DOI: 10.1016/j.carbpol.2019.02.054 http://doi.org/10.1016/j.carbpol.2019.02.054 .

Huang, Y.; Zhong, Z.; Duan, B.; Zhang, L.; Yang, Z.; Wang, Y.; Ye, Q. . Novel fibers fabricated directly from chitin solution and their application as wound dressing . J. Mater. Chem. B , 2014 . 2 3427 - 3432 . DOI: 10.1039/c4tb00098f http://doi.org/10.1039/c4tb00098f .

Zhu, K.; Tu, H.; Yang, P.; Qiu, C.; Zhang, D.; Lu, A.; Luo, L.; Chen, F.; Liu, X.; Chen, L.; Fu, Q.; Zhang, L. . Mechanically strong chitin fibers with nanofibril structure, biocompatibility, and biodegradability . Chem. Mater. , 2019 . 31 2078 - 2087 . DOI: 10.1021/acs.chemmater.8b05183 http://doi.org/10.1021/acs.chemmater.8b05183 .

Chang, C.; Chen, S.; Zhang, L. . Novel hydrogels prepared via direct dissolution of chitin at low temperature: structure and biocompatibility . J. Mater. Chem. , 2011 . 21 3865 - 3871 . DOI: 10.1039/c0jm03075a http://doi.org/10.1039/c0jm03075a .

Xu, D. D.; Huang, J. C.; Zhao, D.; Ding, B. B.; Zhang, L. N.; Cai, J. . High-flexibility, high-toughness double-cross-linked chitin hydrogels by sequential chemical and physical cross-linkings . Adv. Mater. , 2016 . 28 5844 - 5849 . DOI: 10.1002/adma.201600448 http://doi.org/10.1002/adma.201600448 .

Duan, B.; Zheng, X.; Xia, Z.; Fan, X.; Guo, L.; Liu, J.; Wang, Y.; Ye, Q.; Zhang, L. . Highly biocompatible nanofibrous microspheres self-assembled from chitin in NaOH/urea aqueous solution as cell carriers . Angew. Chem. Int. Ed. , 2015 . 54 5152 - 5156 . DOI: 10.1002/anie.201412129 http://doi.org/10.1002/anie.201412129 .

Duan, B.; Gao, X.; Yao, X.; Fang, Y.; Huang, L.; Zhou, J.; Zhang, L. . Unique elastic N-doped carbon nanofibrous microspheres with hierarchical porosity derived from renewable chitin for high rate supercapacitors . Nano Energy , 2016 . 27 482 - 491 . DOI: 10.1016/j.nanoen.2016.07.034 http://doi.org/10.1016/j.nanoen.2016.07.034 .

Duan, B.; Shou, K.; Su, X.; Niu, Y.; Zheng, G.; Huang, Y.; Yu, A.; Zhang, Y.; Xia, H.; Zhang, L. . Hierarchical microspheres constructed from chitin nanofibers penetrated hydroxyapatite crystals for bone regeneration . Biomacromolecules , 2017 . 18 2080 - 2089 . DOI: 10.1021/acs.biomac.7b00408 http://doi.org/10.1021/acs.biomac.7b00408 .

Duan, B.; Gao, H.; He, M.; Zhang, L. . Hydrophobic modification on surface of chitin sponges for highly effective separation of oil . ACS Appl. Mater. Interfaces , 2014 . 6 19933 - 19942 . DOI: 10.1021/am505414y http://doi.org/10.1021/am505414y .

Knecht, E.; Hibbert, E. . Some observations relating to chitin . J. Soc. Dyers Colour. , 1926 . 42 343 - 345 . .

Clark, G. L.; Smith, A. F. . X-ray diffraction studies of chitin, chitosan, and derivatives . J. Phys. Chem. , 1936 . 40 863 - 879 . DOI: 10.1021/j150376a001 http://doi.org/10.1021/j150376a001 .

Meyer, K. H.; Wehrli, H. . Comparaison chimique de la chitine et de la cellulose . Helv. Chim. Acta , 1937 . 20 353 - 362 . DOI: 10.1002/hlca.19370200156 http://doi.org/10.1002/hlca.19370200156 .

Hackman, R. H. . Studies on chitin V. The action of mineral acids on chitin . Aust. J. Biol. Sci. , 1962 . 15 526 - 537 . .

Nagasawa, K.; Tohira, Y.; Inoue, Y.; Tanoura, N. . Reaction between carbohydrates and sulfuric acid: Part I. Depolymerization and sulfation of polysaccharides by sulfuric acid . Carbohydr. Res. , 1971 . 18 95 - 102 . DOI: 10.1016/S0008-6215(00)80261-X http://doi.org/10.1016/S0008-6215(00)80261-X .

Vincendon, M. . Regenerated chitin from phosphoric acid solutions . Carbohydr. Polym. , 1997 . 32 233 - 237 . DOI: 10.1016/S0144-8617(97)00005-2 http://doi.org/10.1016/S0144-8617(97)00005-2 .

Wu, T.; Wang, G.; Gao, C.; Chen, Z.; Feng, L.; Wang, P.; Zeng, X.; Wu, Z. . Phosphoric acid-based preparing of chitin nanofibers and nanospheres . Cellulose , 2016 . 23 477 - 491 . DOI: 10.1007/s10570-015-0829-2 http://doi.org/10.1007/s10570-015-0829-2 .

von Weimarn, P. P. . Conversion of fibroin, chitin, casein, and similar substances into the ropy-plastic state and colloidal solution . Ind. Eng. Chem. , 1927 . 19 109 - 110 . DOI: 10.1021/ie50205a034 http://doi.org/10.1021/ie50205a034 .

von Weimarn, P. P. . Zur dispersoidchemie von cellulose . Kolloidzeitschrift , 1912 . 11 41 - 47 . .

Gagnaire, D.; Saintgermain, J.; Vincendon, M. . NMR studies of chitin and chitin derivatives . Macromol. Chem. Phys. , 1982 . 183 593 - 601 . DOI: 10.1002/macp.1982.021830309 http://doi.org/10.1002/macp.1982.021830309 .

Musatova, G. N.; Mogilevskii, E. M.; Ginzberg, M. A.; Arkhangelskii, D. N. . The dissolution temperature of cellulose xanthate . Fibre Chem. , 1972 . 2 451 - 453 . DOI: 10.1007/BF00581007 http://doi.org/10.1007/BF00581007 .

Noguchi, J.; Wada, O.; Seo, H.; Tokura, S.; Nishi, N. . Chitin and chitosan-cellulose fibres . Kobunshi Kagaku , 1973 . 30 320 - 326 . DOI: 10.1295/koron1944.30.320 http://doi.org/10.1295/koron1944.30.320 .

Sannan, T.; Kurita, K.; Iwakura, Y. . Studies on chitin, 1. Solubility change by alkaline treatment and film casting . Makromo. Chem. , 1975 . 176 1191 - 1195 . DOI: 10.1002/macp.1975.021760426 http://doi.org/10.1002/macp.1975.021760426 .

Einbu, A.; Naess, S. N.; Elgsaeter, A.; Vårum, K. M. . Solution properties of chitin in alkali . Biomacromolecules , 2004 . 5 2048 - 2054 . DOI: 10.1021/bm049710d http://doi.org/10.1021/bm049710d .

Feng, F.; Liu, Y.; Hu, K. . Influence of alkali-freezing treatment on the solid state structure of chitin . Carbohydr. Res. , 2004 . 339 2321 - 2324 . DOI: 10.1016/j.carres.2004.06.017 http://doi.org/10.1016/j.carres.2004.06.017 .

Cai, J.; Zhang, L. . Rapid dissolution of cellulose in LiOH/Urea and NaOH/Urea aqueous solutions . Macromol. Biosci. , 2005 . 5 539 - 548 . DOI: 10.1002/mabi.200400222 http://doi.org/10.1002/mabi.200400222 .

Cai, J.; Zhang, L. . Unique gelation behavior of cellulose in NaOH/Urea aqueous solution . Biomacromolecules , 2006 . 7 183 - 189 . DOI: 10.1021/bm0505585 http://doi.org/10.1021/bm0505585 .

Cai, J.; Zhang, L.; Zhou, J.; Qi, H.; Chen, H.; Kondo, T.; Chen, X.; Chu, B. . Multifilament fibers based on dissolution of cellulose in NaOH/urea aqueous solution: structure and properties . Adv. Mater. , 2007 . 19 821 - 825 . DOI: 10.1002/adma.200601521 http://doi.org/10.1002/adma.200601521 .

Cai, J.; Zhang, L.; Liu, S. L.; Liu, Y. T.; Xu, X. J.; Chen, X. M.; Chu, B.; Guo, X. L.; Xu, J.; Cheng, H.; Han, C. C.; Kuga, S. . Dynamic self-assembly induced rapid dissolution of cellulose at low temperatures . Macromolecules , 2008 . 41 9345 - 9351 . DOI: 10.1021/ma801110g http://doi.org/10.1021/ma801110g .

Hu, X.; Du, Y.; Tang, Y.; Wang, Q.; Feng, T.; Yang, J.; Kennedy, J. F. . Solubility and property of chitin in NaOH/urea aqueous solution . Carbohydr. Polym. , 2007 . 70 451 - 458 . DOI: 10.1016/j.carbpol.2007.05.002 http://doi.org/10.1016/j.carbpol.2007.05.002 .

Ding, B.; Cai, J.; Huang, J.; Zhang, L.; Chen, Y.; Shi, X.; Du, Y.; Kuga, S. . Facile preparation of robust and biocompatible chitin aerogels . J. Mater. Chem. , 2012 . 22 5801 - 5809 . DOI: 10.1039/c2jm16032c http://doi.org/10.1039/c2jm16032c .

Cai, J.; Huang, J. C.; Zhang, L. N. 2013 , ZL 201310034088.4.

Huang, J. Rapid dissolution of chitin in potassium hydroxide/urea aqueous solution under low temperature, and preparation and characterization of novel materials . Doctoral thesis, Wuhan University, Hubei, China, 2017 .

Ding, B.; Zhao, D.; Song, J.; Gao, H.; Xu, D.; Xu, M.; Cao, X.; Zhang, L.; Cai, J. . Light weight, mechanically strong and biocompatible α -chitin aerogels from different aqueous alkali hydroxide/urea solutions . Sci. China Chem. , 2016 . 59 1405 - 1414 . DOI: 10.1007/s11426-016-0205-5 http://doi.org/10.1007/s11426-016-0205-5 .

Xu, H.; Fang, Z.; Tian, W.; Wang, Y.; Ye, Q.; Zhang, L.; Cai, J. . Green fabrication of amphiphilic quaternized β -chitin derivatives with excellent biocompatibility and antibacterial activities for wound healing . Adv. Mater. , 2018 . 30 1801100 DOI: 10.1002/adma.201801100 http://doi.org/10.1002/adma.201801100 .

Cai, J.; Zhang, L. N. Method for continuously preparing chitin/chitosan solutions with different deacetylation degrees. 2017 , CN201711023349A.

Fang, Y.; Duan, B.; Lu, A.; Liu, M.; Liu, H.; Xu, X.; Zhang, L. . Intermolecular interaction and the extended wormlike chain conformation of chitin in NaOH/urea aqueous solution . Biomacromolecules , 2015 . 16 1410 - 1417 . DOI: 10.1021/acs.biomac.5b00195 http://doi.org/10.1021/acs.biomac.5b00195 .

Fang, Y.; Zhang, R.; Duan, B.; Liu, M.; Lu, A.; Zhang, L. . Recyclable universal solvents for chitin to chitosan with various degrees of acetylation and construction of robust hydrogels . ACS Sustain. Chem. Eng. , 2017 . 5 2725 - 2733 . DOI: 10.1021/acssuschemeng.6b03055 http://doi.org/10.1021/acssuschemeng.6b03055 .

Ru, G.; Luo, H.; Liang, X.; Wang, L.; Liu, C.; Feng, J. . Quantitative NMR investigation on the low-temperature dissolution mechanism of chitin in NaOH/urea aqueous solution . Cellulose , 2015 . 22 2221 - 2229 . DOI: 10.1007/s10570-015-0667-2 http://doi.org/10.1007/s10570-015-0667-2 .

Austin, P. R. Chitin solution. 1977 , US4059457A.

Poirier, M.; Charlet, G. . Chitin fractionation and characterization in N , N -dimethylacetamide/lithium chloride solvent system . Carbohydr. Polym. , 2002 . 50 363 - 370 . DOI: 10.1016/S0144-8617(02)00040-1 http://doi.org/10.1016/S0144-8617(02)00040-1 .

Germain, J. S.; Vincendon, M. . 1 H, 13 C and 7 Li nuclear magnetic resonance study of the lithium chloride- N , N -dimethylacetamide system . Org. Magn. Reson. , 1983 . 21 371 - 375 . DOI: 10.1002/omr.1270210607 http://doi.org/10.1002/omr.1270210607 .

Vincendon, M. . 1 H NMR study of the chitin dissolution mechanism . Makromo. Chem. , 1985 . 186 1787 - 1795 . DOI: 10.1002/macp.1985.021860907 http://doi.org/10.1002/macp.1985.021860907 .

de Vasconcelos, C. L.; Bezerril, P. M.; Pereira, M. R.; Ginani, M. F.; Fonseca, J. L. C. . Viscosity-temperature behavior of chitin solutions using lithium chloride/DMA as solvent . Carbohydr. Res. , 2011 . 346 614 - 618 . DOI: 10.1016/j.carres.2010.12.016 http://doi.org/10.1016/j.carres.2010.12.016 .

Austin, P. R.; Brine, C. J.; Castle, J. E.; Zikakis, J. P. . Chitin: new facets of research . Science , 1981 . 212 749 DOI: 10.1126/science.7221561 http://doi.org/10.1126/science.7221561 .

Okuda, H.; Takeuchi, T.; Senoh, H.; Arito, H.; Matsushima, T. . Developmental toxicity induced by inhalation exposure of pregnant rats to N , N -dimethylacetamide . J. Occup. Health , 2006 . 48 154 DOI: 10.1539/joh.48.154 http://doi.org/10.1539/joh.48.154 .

Gitlin, M. . Lithium side effects and toxicity: prevalence and management strategies . Int. J. Bipolar Disord. , 2016 . 4 27 DOI: 10.1186/s40345-016-0068-y http://doi.org/10.1186/s40345-016-0068-y .

Tokura, S.; Nishi, N.; Takahashi, K.; Shirai, A.; Uraki, Y. . Novel drug delivery system by chitin derivative . Macromol. Symp. , 1995 . 99 201 - 208 . DOI: 10.1002/masy.19950990121 http://doi.org/10.1002/masy.19950990121 .

Tokura, S.; Nishimura, S. I.; Sakairi, N.; Nishi, N. . Biological activities of biodegradable polysaccharide . Macromol. Symp. , 1996 . 101 389 - 396 . DOI: 10.1002/masy.19961010144 http://doi.org/10.1002/masy.19961010144 .

Tamura, H.; Nagahama, H.; Tokura, S. . Preparation of chitin hydrogel under mild conditions . Cellulose , 2006 . 13 357 - 364 . DOI: 10.1007/s10570-006-9058-z http://doi.org/10.1007/s10570-006-9058-z .

Nagahama, H.; Higuchi, T.; Jayakumar, R.; Furuike, T.; Tamura, H. . XRD studies of β -chitin from squid pen with calcium solvent . Int. J. Biol. Macromol. , 2008 . 42 309 - 313 . DOI: 10.1016/j.ijbiomac.2007.10.011 http://doi.org/10.1016/j.ijbiomac.2007.10.011 .

Sun, B. . Study on the mechanism of Nylon 6,6 dissolving process using CaCl 2 /MeOH as the solvent . Chinese J. Polym. Sci. , 1994 . 12 57 - 65 . .

Hattori, M.; Saito, M.; Okajima, K.; Kamide, K. . Molecular characterization of nylon 6,6 and its dissolved state in mixture of calcium chloride and methanol . Polym. J. , 1995 . 27 631 - 644 . DOI: 10.1295/polymj.27.631 http://doi.org/10.1295/polymj.27.631 .

Wasserscheid, P.; Keim, W. . Ionic liquids—new “solutions” for transition metal catalysis . Angew. Chem. Int. Ed. , 2000 . 39 3772 - 3789 . DOI: 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5 http://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5 .

Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. . Dissolution of cellose with ionic liquids . J. Am. Chem. Soc. , 2002 . 124 4974 - 4975 . DOI: 10.1021/ja025790m http://doi.org/10.1021/ja025790m .

Reichert, W. M.; Swatloski, R. P.; Rogers, R. D. In The 222 nd ACS National Meeting , Chicago, IL, 2001 .

Reichert, W. M.; Swatloski, R. P.; Rogers, R. D. In The 221 st ACS National Meeting , San Diego, CA, 2001 .

Spear, S. K.; Swatloski, R. P.; Rogers, R. D. In The 221 st ACS National Meeting , San Diego, CA, 2001 .

Shamshina, J. L. . Chitin in ionic liquids: historical insights into the polymer's dissolution and isolation a review . Green Chem. , 2019 . 21 3974 - 3993 . DOI: 10.1039/C9GC01830A http://doi.org/10.1039/C9GC01830A .

Xie, H.; Zhang, S.; Li, S. . Chitin and chitosan dissolved in ionic liquids as reversible sorbents of CO 2 . Green Chem. , 2006 . 8 630 - 633 . DOI: 10.1039/b517297g http://doi.org/10.1039/b517297g .

Wu, Y.; Sasaki, T.; Irie, S.; Sakurai, K. . A novel biomass-ionic liquid platform for the utilization of native chitin . Polymer , 2008 . 49 2321 - 2327 . DOI: 10.1016/j.polymer.2008.03.027 http://doi.org/10.1016/j.polymer.2008.03.027 .

Prasad, K.; Murakami, M.; Kaneko, Y.; Takada, A.; Nakamura, Y.; Kadokawa, J. . Weak gel of chitin with ionic liquid, 1-allyl-3-methylimidazolium bromide . Int. J. Biol. Macromol. , 2009 . 45 221 - 225 . DOI: 10.1016/j.ijbiomac.2009.05.004 http://doi.org/10.1016/j.ijbiomac.2009.05.004 .

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 . DOI: 10.1039/c003583a http://doi.org/10.1039/c003583a .

Rogers R. D. 2019 , Application Number US2019/0040209A1.

Wang, W. T.; Zhu, J.; Wang, X. L.; Huang, Y.; Wang, Y. Z. . Dissolution behavior of chitin in ionic liquids . J. Maromol. Sci. B , 2010 . 49 528 - 541 . DOI: 10.1080/00222341003595634 http://doi.org/10.1080/00222341003595634 .

Taft, R. W.; Kamlet, M. J. . The solvatochromic comparison method. 2. The α -scale of solvent hydrogen-bond donor (HBD) acidities . J. Am. Chem. Soc. , 1976 . 98 2886 - 2894 . DOI: 10.1021/ja00426a036 http://doi.org/10.1021/ja00426a036 .

Kamlet, M. J.; Taft, R. W. . The solvatochromic comparison method. I. The β -scale of solvent hydrogen-bond acceptor (HBA) basicities . J. Am. Chem. Soc. , 1976 . 98 377 - 383 . DOI: 10.1021/ja00418a009 http://doi.org/10.1021/ja00418a009 .

Yokoyama, T.; Taft, R. W.; Kamlet, M. J. . The solvatochromic comparison method. 3. Hydrogen bonding by some 2-nitroaniline derivatives . J. Am. Chem. Soc. , 1976 . 98 3233 - 3237 . DOI: 10.1021/ja00427a030 http://doi.org/10.1021/ja00427a030 .

Kamlet, M. J.; Abboud, J. L.; Taft, R. W. . The solvatochromic comparison method. 6. The π * scale of solvent polarities . J. Am. Chem. Soc. , 1977 . 99 6027 - 6038 . DOI: 10.1021/ja00460a031 http://doi.org/10.1021/ja00460a031 .

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 . DOI: 10.1039/B303095D http://doi.org/10.1039/B303095D .

Shimo, M.; Abe, M.; Ohno, H. . Functional comparison of polar ionic liquids and onium hydroxides for chitin dissolution and deacetylation to chitosan . ACS Sustain. Chem. Eng. , 2016 . 4 3722 - 3727 . DOI: 10.1021/acssuschemeng.6b00368 http://doi.org/10.1021/acssuschemeng.6b00368 .

Uto, T.; Idenoue, S.; Yamamoto, K.; Kadokawa, J. I. . Understanding dissolution process of chitin crystal in ionic liquids: theoretical study . Phys. Chem. Chem. Phys. , 2018 . 20 20669 - 20677 . DOI: 10.1039/C8CP02749H http://doi.org/10.1039/C8CP02749H .

Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Silva, Pereira C. . Ionic liquids: a pathway to environmental acceptability . Chem. Soc. Rev. , 2011 . 40 1383 - 1403 . DOI: 10.1039/C004968A http://doi.org/10.1039/C004968A .

Swatloski, R. P.; Holbrey, J. D.; Rogers, R. D. . Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate . Green Chem. , 2003 . 5 361 - 363 . DOI: 10.1039/b304400a http://doi.org/10.1039/b304400a .

Smiglak, M.; Reichert, W. M.; Holbrey, J. D.; Wilkes, J. S.; Sun, L.; Thrasher, J. S.; Kirichenko, K.; Singh, S.; Katritzky, A. R.; Rogers, R. D. . Combustible ionic liquids by design: is laboratory safety another ionic liquid myth? . Chem. Commun. , 2006 . 2554 - 2556 . DOI: 10.1039/b602086k http://doi.org/10.1039/b602086k .

Ostadjoo, S.; Berton, P.; Shamshina, J. L.; Rogers, R. D. . Scaling-up ionic liquid-based technologies: how much do we care about their toxicity? Prima facie information on 1-ethyl-3-methylimidazolium acetate . Toxicol. Sci. , 2017 . 161 249 - 265 . .

Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. K.; Tambyrajah, V. . Novel solvent properties of choline chloride/urea mixtures . Chem. Commun. , 2003 . 70 - 71 . DOI: 10.1039/b210714g http://doi.org/10.1039/b210714g .

Abbott, A. P.; Boothby, D.; Capper, G.; Davies, D. L.; Rasheed, R. K. . Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids . J. Am. Chem. Soc. , 2004 . 126 9142 - 9147 . DOI: 10.1021/ja048266j http://doi.org/10.1021/ja048266j .

Francisco, M.; van, den Bruinhorst A.; Kroon, M. C. . New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing . Green Chem. , 2012 . 14 2153 - 2157 . DOI: 10.1039/c2gc35660k http://doi.org/10.1039/c2gc35660k .

Silva, L. P.; Araújo, C. F.; Abranches, D. O.; Melle-Franco, M.; Martins, M. A. R.; Nolasco, M. M.; Ribeiro-Claro, P. J. A.; Pinho, S. P.; Coutinho, J. A. P. . What a difference a methyl group makes – probing choline-urea molecular interactions through urea structure modification . Phys. Chem. Chem. Phys. , 2019 . 21 18278 - 18289 . DOI: 10.1039/C9CP03552D http://doi.org/10.1039/C9CP03552D .

Ashworth, C. R.; Matthews, R. P.; Welton, T.; Hunt, P. A. . Doubly ionic hydrogen bond interactions within the choline chloride-urea deep eutectic solvent . Phys. Chem. Chem. Phys. , 2016 . 18 18145 - 18160 . DOI: 10.1039/C6CP02815B http://doi.org/10.1039/C6CP02815B .

Sharma, M.; Mukesh, C.; Mondal, D.; Prasad, K. . Dissolution of α -chitin in deep eutectic solvents . RSC Adv. , 2013 . 3 18149 - 18155 . DOI: 10.1039/c3ra43404d http://doi.org/10.1039/c3ra43404d .

Mukesh, C.; Mondal, D.; Sharma, M.; Prasad, K. . Choline chloride-thiourea, a deep eutectic solvent for the production of chitin nanofibers . Carbohydr. Polym. , 2014 . 103 466 - 471 . DOI: 10.1016/j.carbpol.2013.12.082 http://doi.org/10.1016/j.carbpol.2013.12.082 .

Idenoue, S.; Yamamoto, K.; Kadokawa, J. I. . Dissolution of chitin in deep eutectic solvents composed of imidazolium ionic liquids and thiourea . ChemEngineering , 2019 . 3 90 DOI: 10.3390/chemengineering3040090 http://doi.org/10.3390/chemengineering3040090 .

Shuklov, I. A.; Dubrovina, N. V.; Boerner, A. . Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis . ChemInform , 2007 . 19 2925 - 2943 . DOI: 10.1055/s-2007-983902 http://doi.org/10.1055/s-2007-983902 .

Tokura, S.; Nishi, N.; Noguchi, J. . Studies on chitin. III. Preparation of chitin fibers . Polym. J. , 1979 . 11 781 - 786 . DOI: 10.1295/polymj.11.781 http://doi.org/10.1295/polymj.11.781 .

Austin, P. R. Chitin solutions and purification of chitin. In Methods enzymol . Academic Press, 1988 , 161 .

Buffington, L. A.; Stevens, E. S. . Far-ultraviolet circular dichroism of solutions, gels, and films of chitins . J. Am. Chem. Soc. , 1979 . 101 5159 - 5162 . DOI: 10.1021/ja00512a008 http://doi.org/10.1021/ja00512a008 .

Min, B. M.; Lee, S. W.; Lim, J. N.; You, Y.; Lee, T. S.; Kang, P. H.; Park, W. H. . Chitin and chitosan nanofibers: electrospinning of chitin and deacetylation of chitin nanofibers . Polymer , 2004 . 45 7137 - 7142 . DOI: 10.1016/j.polymer.2004.08.048 http://doi.org/10.1016/j.polymer.2004.08.048 .

Views

188

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Squaramide-directed Cooperative One-dimensional Assembly in Telechelic Polydimethylsiloxane for Hierarchical Network Formation

Regulation of Microphase Separation in Bio-based Thermoplastic Polyurethanes Driven by Hard Segment Content

Hydrogen Bonding in Gel Polymer Electrolyte Enables High Performance High-mass-loading Silicon Anode

Anti-biofouling Hydrogels: Surface Hydration, Classification, and Biomedical Applications

Polarity-regulated Nano-silica Steering Carbon Black Network Evolution and Reconfiguration in Conductive Silicone Elastomers: Experimental and Molecular Simulations

Related Author

Yu-Hong Zhang

Jian-Fei Ma

Hao-Bo Wei

Jie Wang

Feng Wang

De-Xian Yin

Yu-Qiong Hu

Ya-Nan Cheng

Related Institution

School of Chemistry and Pharmaceutical Engineering, Jilin University of Chemical Technology

Department of Polymer Science and Engineering, University of Science and Technology of China

State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology

School of Materials Science and Engineering, State Key Laboratory of Advanced Materials for Intelligent Sensing, Tianjin University

School of Energy (National Industry-Education Platform for Energy Storage), Tianjin University

⁰