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化学进展 2013, Vol. 25 Issue (05): 832-837 DOI: 10.7536/PC120947 前一篇   后一篇

• 综述与评论 •

甲壳素和壳聚糖在离子液体中的溶解与改性

孙璠1, 徐民2, 李克让1, 张帅1, 刘蒲*1   

  1. 1. 郑州大学化学与分子工程学院 郑州 450001;
    2. 安阳市质量技术监督检验测试中心 安阳 455001
  • 收稿日期:2012-09-01 修回日期:2012-12-01 出版日期:2013-05-24 发布日期:2013-04-15
  • 通讯作者: 刘蒲 E-mail:liupu@zzu.edu.cn
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Dissolution and Chemical Modification of Chitin and Chitosan in Ionic Liquids

Sun Fan1, Xu Min2, Li Kerang1, Zhang Shuai1, Liu Pu*1   

  1. 1. The College of Chemistry and Molecular Engineering,Zhengzhou University,Zhengzhou 450001, China;
    2. Anyang Quality Technical Director Examination Test Center, Anyang 455001, China
  • Received:2012-09-01 Revised:2012-12-01 Online:2013-05-24 Published:2013-04-15

甲壳素及壳聚糖作为生物大分子材料难溶于诸多溶剂,从而限制了其应用和修饰改性。因此,研究与开发良好的溶剂体系具有重要意义。本文首先对甲壳素及壳聚糖在各种离子液体中的溶解性能和溶解机理进行了详细综述,其次概述了甲壳素与壳聚糖在离子液体介质中进行修饰的化学反应研究(如:水解作用、酰基化反应和接枝共聚反应等),最后提出离子液体作为一类可回收循环使用的良好溶解介质将会对甲壳素及壳聚糖的实际应用和修饰改性提供更好的媒介,并拓宽甲壳素及壳聚糖的研究与应用领域。

关键词： 甲壳素, 壳聚糖, 离子液体, 溶解, 化学改性

Chitin and chitosan, as the biological macromolecular materials, are hardly soluble in many traditional solvents. This behavior limits their wide application and chemical modification. Therefore, it will be of great importance to research and develop the better solvent system. In this paper, the dissolution performance and dissolving mechanism of chitin or chitosan in ionic liquids are reviewed in the first place. Secondly, the chemical modifications of chitin or chitosan in ionic liquids (such as hydrolysis, acylation, graft copolymerization and so on) are summarized. Ionic liquid, as a kind of the recycled fine solvent, will provide a better media for the effective application and chemical modification of chitin or chitosan. Based on the ionic liquid solvent, the research and application of chitin or chitosan will be broaden. Contents
1 Introduction
2 The dissolution of chitin or chitosan in ionic liquid
2.1 The dissolution of chitin or chitosan in the imidazole-based ionic liquid
2.2 The dissolution of chitin or chitosan in other ionic liquid
3 The chemical reaction of chitin or chitosan in ionic liquid
3.1 The degradation of chitin or chitosan in ionic liquid
3.2 The acylation of chitin or chitosan in ionic liquid
3.3 The graft copolymerization of chitin or chitosan in ionic liquid
3.4 The other reaction of chitin or chitosan in ionic liquid
4 Outlook

Key words: chitin, chitosan, ionic liquids, dissolution, chemical modification

中图分类号: 

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[1] Bartlett D H, Azam F. Science, 2005, 310: 1775-1777
[2] Pavinatto F J, Caseli L, Oliveira O N. Biomacromol., 2010, 11: 1897-1908
[3] Dong W, Han B Q, Feng Y L, Song F L, Chang J, Jiang H P, Tang Y Y, Liu W S. Biomacromol., 2010, 11: 1527-1533
[4] Gaharwar K A, Schexnailder J P, Qu J, Wu C H, Schmidt G. ACS Appl. Mater. Interfaces, 2010, 2(11): 3119-3127
[5] Zhou D, Zhang L N, Zhou J P, Guo S L. Water Res., 2004, 38: 2643-2650
[6] Davila-Rodriguez J L, Escobar-Barrios V A, Shirai K, Rangel-Mendez J R. J. Fluorine Chem., 2009, 130: 718-726
[7] Yao H T, Li C K, Chou R H, Liu J H, Yang H T, Chiang M T. J. Agric. Food Chem., 2010, 58(8): 5187-5193
[8] Liu X F, Zhi X N, Liu Y F, Sun Z, Shen J. J. Agric. Food Chem., 2012, 60(13): 3471-3476
[9] Ramos V M, Rodriguez N M, Rodriguez M S, Heras A, Agullo E. Carbohydr. Res., 2003, 51: 425-429
[10] Singla A K, Chawla M. J. Pharm. Pharmacol., 2001, 53: 1047-1067
[11] Sato T, Ishii T, Okahata Y. Biomaterials, 2001, 22: 2075-2080
[12] Suh J K, Matthew H W. Biomaterials, 2000, 21: 2589-2598
[13] Brondani D, Dupont J, Spinelli A, Vieira I C. Sens. Actuators, B: Chem., 2011, 138: 236-243
[14] Wang Y C, Lin M C, Wang D M, Hsieh H. Biomaterials, 2003, 24: 1047-1057
[15] Krajewska B. Enzyme Microb. Technol., 2004, 35: 126-139
[16] Pillai C K S, Paul W, Sharma C P. Prog. Polym. Sci., 2009, 34(7): 641-678
[17] Aslak E, Stine N N, Arnljot E, Kjell M V. Biomacromol, 2004, 5(5): 2048-2054
[18] Martin P, Gerard C. Carbohydr. Polym., 2002, 50(4): 363-370
[19] Paulechka Y U, Kabo G J, Blokhin A V, Vydrov O A, Magee J W, Frenkel M. J. Chem. Eng. Data, 2003, 48: 457-462
[20] Kabo G J, Blokhin A V, Paulechka Y U, Kabo A, Shymanovich M P, Magee J W. Chem. Eng. Data, 2004, 49: 453-461
[21] Domanska U, Bogel-yukasik R. J. Phys. Chem. B, 2005, 109: 12124-12132
[22] Ngo H L, LeCompte K, Hargens L, McEwen A B. Thermochim. Acta, 2000, 357: 97-102
[23] 张锁江(Zhang S J), 吕兴梅(Lv X M). 离子液体: 从基础研究到工业应用(Ionic Liquids: From Basic Research to Industry Application). 北京: 科学出版社(Beijing: Beijing Scientific Press), 2006. 60-83
[24] Swatloski R P, Spear S K, Holbrey J D, Rogers R D. J. Am. Chem. Soc., 2002, 124(18): 4974-4975
[25] He Y, Li Z, Simone P, Lodge T P. J. Am. Chem. Soc., 2006, 128: 2745-2750
[26] Zhou Y, Antonietti M. J. Am. Chem. Soc., 2003, 125: 14960-14961
[27] Yoshio M, Mukai T, Ohno H, Kato T. J. Am. Chem. Soc., 2004, 126: 994-995
[28] Miao W, Chan T H. Acc. Chem. Res., 2006, 39: 897-908
[29] Xie H, Zhang S, Li S. Green Chem., 2006, 8: 630-633
[30] Mantz R A, Fox D M, Green J M, Fylstra P A, de long H C, Trulore P C. Z. Naturforsch. A: Phys. Sci., 2007, 62(5/6): 275-280
[31] Wu Y, Sasaki T, Irie S, Sakurai K. Polymer, 2008, 49: 2321-2327
[32] Yamazaki S, Takegawa A, Kaneko Y, Kadokawa J, Yamagata M, Ishikawa M. Electrochem. Commun., 2009, 11: 68-70
[33] Prasad K, Murakami M, Kaneko Y, Nakamura Y, Takada A, Kadokawa J I. Int. J. Biol. Macromol., 2009, 45: 221-225
[34] Wang W T, Zhu J, Wang X L, Huang Y, Wang Y Z. J. Macromol. Sci. Part B: Phys., 2010, 49: 528-541
[35] 段先泉(Duan X Q), 徐纪纲(Xu J G), 何北海(He B H), 李军荣(Li J R), 程春祖(Chen C Z). 化工新材料(New Chemical Materials), 2011, 39(4): 56-63
[36] 朱庆松(Zhu Q S), 韩小进(Han X J), 程春祖(Cheng C Z), 武长城(Wu C C). 高分子学报(Acta Polymerica Sinica), 2011, 10: 1173-1179
[37] Chen Q T, Xu A L, Zhi Y, Wang J J, Shang S J. Green Chem., 2011, 13(2): 3446-3452
[38] Xiao W J, Chen Q, Wu Y, Wu T H, Dai L Z. Carbohydr. Polym., 2011, 83: 233-238
[39] Dawsey T R, Mccormick C L. Macromol. Sci. Rev. Macromol. Chem. Phys., 1990, 30: 405-440
[40] 周雅文(Zhou Y W), 邓宇(Deng Y), 尚海萍(Shang H P). 造纸化学品(Paper Chemicals), 2009, 28(11): 40-43
[41] 陶海霞(Tao H X), 廖芳丽(Liao F L), 车剑锋(Che J F). 广州化工(Guangzhou Chemical Industry), 2009, 37(9): 126-127
[42] Qin Y, Lu X M, Sun N, Rogers R D. Green Chem., 2010, 12(6): 968-969
[43] Tatsuya S, Takeshi K, Kazuya Y, Kadokawa J I. Int. J. Biol. Macromol., 2012, 50: 861-864
[44] 熊玉兵(Xiong Y B), 王泽(Wang Z), 王荣民(Wang R M), 吴称意(Wu C Y), 王鸿(Wang H). CN 101503530A, 2009
[45] Singh P K, Bhattacharya B, Nagarale R K, Kim K M, Rhee H W. Synth. Met., 2010, 160: 139-142
[46] 臧洪俊(Zang H J), 杨芳Yang F), 王清凯(Wang Q K), 程博闻(Chen B W), 宋俊(Song J). CN 102168232 A, 2011
[47] 杨海静(Yang H J), 魏立刚(Wei L G), 李坤兰(Li K L), 马英冲(Ma Y C), 王少军(Wang S J), 安庆大(An Q D), 平清伟(Ping Q W), 余加佑(Yu J Y). 高分子材料科学与工程(Polymer Materials Science and Engineering), 2011, 27(6): 154-157
[48] Park T J, Jung Y J, Choi S W, Park H, Kim H, Kim E, Lee S H, Kim J H. Macromol. Res., 2011, 19(3): 213-215
[49] Stefanescu C, Daly W H, Negulescu I I. Carbohydr. Polym., 2012, 87(1): 435-443
[50] 梁升(Liang S), 纪欢欢(Ji H H), 李露(Li L), 于世涛(Yu S T), 刘福胜(Liu F S), 解从霞(Xie C X). 高分子材料科学与工程(Polymer Materials Science and Engineering), 2010, 26(2): 70-72
[51] Li L, Yuan B, Liu W, Yu S T, Xie C X, Liu F S, Shan L J. J. Polym. Enivron., 2012, 20: 388-394
[52] Li L, Yuan B, Liu S W, Yu S T, Xie C X, Liu F S, Liang S, Guo X Y. J. Appl. Polym. Sci., 2012, 123: 3772-3780
[53] Li L, Yuan B, Liu W, Yu S T, Xie C X, Liu F S, Guo X Y, Pei L J, Zhang B Q. Mater. Chem., 2012, 22(17): 8585-8593
[54] Ma B M, Zhang M, He C J, Sun J F. Carbohydr. Polym., 2012, 88(1): 347-351
[55] Biskup R C, Rokita B, Lotfy S, Ulanski P, Rosiak J M. Carbohydr. Polym., 2005, 60(2): 175-184
[56] Terbojevich M, Cosani A, Muzzarelli R A A. Carbohydr. Polym., 1996, 29(1): 63-68
[57] Zhang H, Neau S H. Biomater., 2002, 23(13): 2761-2766
[58] Varum K M, Ottoy M H, Smidsord O. Carbohydr. Polym., 2001, 46(1): 89-98
[59] Rege P R, Block L H. Carbohydr. Res., 1999, 321(3/4): 235-245
[60] Allan G G, Peyron M. Carbohydrate Res., 1995, 277(2): 257-272
[61] Tanioka S, Matsul Y, Icie I, Tanigawa T. Biosci. Biotechnol. Biochem., 1996, 60(12): 2001-2004
[62] 赵宗保(Zhao Z B), 张泽会(Zhang Z H), 李昌志(Li C Z). CN 101723989 A, 2010
[63] 吴廷华(Wu T H), 肖文军(Xiao W J), 陈沁(Chen Q). CN 102134615 A, 2011
[64] 胡燚(Hu Y), 黄和(Huang H), 贾儒(Jia R). CN 102276663A, 2011
[65] Seddon K, Stark A, Torres M. Pure. Appl. Chem., 2000, 72(12): 2275-2287
[66] Chen Q, Xiao W J, Zhou L J, Wu T H, Wu Y. Polym. Degrad. Stab., 2012, 97(1): 49-53
[67] 单永奎(Shan Y K), 单冲冲(Shan C C), 赵新华(Zhao X H), 王平(Wang P), 张新华(Zhang X H). CN 101481427 A, 2009
[68] 单丽娟(Shan L J), 刘仕伟(Liu S W), 李露(Li L), 于世涛(Yu S T), 刘福胜(Liu F S), 解从霞(Xie C X). 高校化学工程学报(Journal of Chemical Engineering of Chinese Universities), 2010, 24(6): 981-984
[69] Jenkins D W, Hudson S M. J. Polym. Sci. Part A: Polym. Chem., 2001, 39: 4174-4181
[70] Mine S B, Izawa H, Kaneko Y, Dadokawa J. Carbohydr. Res., 2009, 344: 2263-2265
[71] 梁升(Liang S), 纪欢欢(Ji H H), 李露(Li L), 于世涛(Yu S T), 刘福胜(Liu F S), 解从霞(Xie C X). 高校化学工程学报(Journal of Chemical Engineering of Chinese Universities), 2009, 23(5): 901-905
[72] 梁升(Liang S), 纪欢欢(Ji H H), 李露(Li L), 于世涛(Yu S T), 刘福胜(Liu F S), 解从霞(Xie C X). 精细化工(Fine Chemicals), 2009, 26(4): 391-394
[73] 梁升(Liang S), 纪欢欢(Ji H H), 李露(Li L), 于世涛(Yu S T), 刘福胜(Liu F S), 解从霞(Xie C X). 青岛科技大学学报(自然科学报)(Journal of Qingdao University of Science & Technology), 2010, 31(2): 129-132
[74] 张惠欣(Zhang H X), 葛丽环(Ge L H), 尹静(Yi J), 周宏勇(Zhou H Y), 冯磊(Feng L). 化学研究与应用(Chemical Research and Application), 2012, 23(12): 1595-1598
[75] Stefanescu C, Daly W, Negulescu I. Polym. Prepr., 2008, 49(2): 793-794
[76] Stefanescu C, Daly W, Negulescu I. Polym. Prepr., 2009, 50(1): 143-144
[77] Stefanescu C, Daly W, Negulescu I. Polym. Prepr., 2009, 50(2): 551-552
[78] Stefanescu C, Daly W, Negulescu I. Polym. Prepr., 2010, 51(1): 391-392
[79] 韩小进(Han X J), 程春祖(Cheng C Z), 朱庆松(Zhu Q S), 武长城(Wu C C). 化工学报(Acta Chemical Sinica), 2010, 61(11): 3020-3024
[80] 韩小进(Han X J), 程春祖(Cheng C Z), 朱庆松(Zhu Q S), 武长城(Wu C C). 高分子材料科学与工程(Polymer Materials Science and Engineering), 2011, 27(1): 20-23
[81] 韩小进(Han X J), 程春祖(Cheng C Z), 朱庆松(Zhu Q S), 武长城(Wu C C). 化工学报(Acta Chemical Sinica), 2011, 62(7): 2055-2060
[82] Hua D B, Jiang J L, Kuang L J, Jiang J, Zheng W, Liang H J. Macromol., 2011, 44(6): 1298-1230
[83] 徐德增(Xu D Z), 门秀龙(Men X L), 唐玲俊(Tang L J), 苏丹(Su D), 郭静(Guo J). 合成纤维工业(China Synthetic Fiber Industry), 2011, 34(2): 7-10
[84] Chen A N, Liu Z P, Akbulut M. Chem. Commun., 2011, 47(8): 2312-1214
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