Synthesis of Cellulose Tricarbonates in 1-Butyl-3-methylimidazolium Chloride/Pyridine

被引:31
作者
Elschner, Thomas [1 ]
Koetteritzsch, Manuela [1 ]
Heinze, Thomas [1 ]
机构
[1] Univ Jena, Ctr Excellence Polysaccharide Res, Inst Organ Chem & Macromol Chem, D-07743 Jena, Germany
关键词
carbonates; cellulose; ionic liquids; NMR; polysaccharides; IONIC LIQUIDS; CARBONATES;
D O I
10.1002/mabi.201300345
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Cellulose phenyl tricarbonates could be synthesized by a novel and fast procedure applying 1-butyl-3-methylimidazolium chloride/pyridine as reaction medium. Even cellulose phenyl carbonates with high degree of substitution are accessible at low molar ratio very efficiently. The reagent phenyl chloroformate is inert in the mixture, which is different from the solvent N,N-dimethylacetamide/LiCl that is usually applied. The products were characterized in detail by two-dimensional NMR- and FTIR-spectroscopy, elemental analysis, and size-exclusion chromatography. This class of cellulose derivatives is a very important intermediate for the design of structures based on cellulose by nucleophilc attack on the carbonyl group.
引用
收藏
页码:161 / 165
页数:5
相关论文
共 17 条
[1]   Ionic liquids - media for unique phosphorus chemistry [J].
Amigues, E ;
Hardacre, C ;
Keane, G ;
Migaud, M ;
O'Neill, M .
CHEMICAL COMMUNICATIONS, 2006, (01) :72-74
[2]   PREPARATION OF CELLULOSE CARBONATE [J].
BARKER, SA ;
TUN, HC ;
DOSS, SH ;
GRAY, CJ ;
KENNEDY, JF .
CARBOHYDRATE RESEARCH, 1971, 17 (02) :471-&
[3]  
CHAVES MS, 1985, MAKROMOL CHEM, V186, P17
[4]   Reactivity of ionic liquids [J].
Chowdhury, Shahana ;
Mohan, Ram S. ;
Scott, Janet L. .
TETRAHEDRON, 2007, 63 (11) :2363-2389
[5]   ADVANTAGES OF FLUOROFORMATES AS CARBOALKOXYLATING REAGENTS FOR POLAR REACTANTS [J].
DANG, VA ;
OLOFSON, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1851-1854
[6]   Synthesis and aminolysis of polysaccharide carbonates [J].
Elschner, Thomas ;
Ganske, Kristin ;
Heinze, Thomas .
CELLULOSE, 2013, 20 (01) :339-353
[7]  
FO SC, 2011, BIOMACROMOLECULES, V12, P1956
[8]   Ionic Liquids - Promising but Challenging Solvents for Homogeneous Derivatization of Cellulose [J].
Gericke, Martin ;
Fardim, Pedro ;
Heinze, Thomas .
MOLECULES, 2012, 17 (06) :7458-7502
[9]   Studies on the tosylation of cellulose in mixtures of ionic liquids and a co-solvent [J].
Gericke, Martin ;
Schaller, Jens ;
Liebert, Tim ;
Fardim, Pedro ;
Meister, Frank ;
Heinze, Thomas .
CARBOHYDRATE POLYMERS, 2012, 89 (02) :526-536
[10]   Synthesis and properties of cellulose carbonate derivatives [J].
Hayashi, S .
KOBUNSHI RONBUNSHU, 2002, 59 (01) :1-7