Kinetic and chemical studies on the isomerization of monosaccharides in N-methylmorpholine-N-oxide (NMMO) under Lyocell conditions

被引:21
作者
Adorjan, I [1 ]
Sjöberg, J [1 ]
Rosenau, T [1 ]
Hofinger, A [1 ]
Kosma, P [1 ]
机构
[1] Univ Nat Resources & Applied Life Sci, BOKU, Dept Chem, Christian Doppler Lab Heterogene Katalyse, A-1190 Vienna, Austria
关键词
capillary electrophoresis; isomerization; degradation; NMMO; monosaccharides; aldoses;
D O I
10.1016/j.carres.2004.06.004
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
The Lyocell process is a modern and environmentally fully compatible industrial fiber-making technology. Cellulosic pulp is dissolved without chemical derivatization in a melt of N-methylmorpholine-N-oxide monohydrate (NMMO). In the present work, the reactions of monosaccharides under Lyocell conditions were investigated in detail, using capillary zone electrophoresis as the analytical technique to clarify the composition of reaction mixtures and to follow the kinetics. Under Lyocell conditions, xylose and glucose undergo two competitive reactions: rapid conversion to nonreducing products, and complete isomerization involving the whole carbohydrate backbone, via ketose intermediates. Sugar acids are present in minor amounts only, as demonstrated by employing isotopically labeled material for NMR techniques. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1899 / 1906
页数:8
相关论文
共 17 条
[1]  
ADORJAN I, UNPUB CELLULOSE
[2]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 :27-66
[3]  
DEBRUIJN JM, 1987, RECL TRAV CHIM PAY B, V106, P35
[4]   ENOLIZATION AND ISOMERIZATION OF MONOSACCHARIDES IN AQUEOUS, ALKALINE-SOLUTION [J].
DEWIT, G ;
KIEBOOM, APG ;
VANBEKKUM, H .
CARBOHYDRATE RESEARCH, 1979, 74 (SEP) :157-175
[5]   Carbon exchange in hot alkaline degradation of glucose [J].
Ellis, AV ;
Wilson, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8469-8474
[7]   HYDROXIDE-CATALYZED ISOMERIZATION OF [1-C-13] D-MANNOSE - EVIDENCE FOR THE INVOLVEMENT OF 3,4-ENEDIOLS [J].
KINGMORRIS, MJ ;
SERIANNI, AS .
CARBOHYDRATE RESEARCH, 1986, 154 :29-36
[8]   C-13 NMR-STUDIES OF [1-C-13]ALDOSES - EMPIRICAL RULES CORRELATING PYRANOSE RING CONFIGURATION AND CONFORMATION WITH C-13 CHEMICAL-SHIFTS AND C-13-C-13 SPIN COUPLINGS [J].
KINGMORRIS, MJ ;
SERIANNI, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3501-3508
[9]   Degradation of cellulose under alkaline conditions [J].
Knill, CJ ;
Kennedy, JF .
CARBOHYDRATE POLYMERS, 2003, 51 (03) :281-300
[10]   The chemistry of side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process) [J].
Rosenau, T ;
Potthast, A ;
Sixta, H ;
Kosma, P .
PROGRESS IN POLYMER SCIENCE, 2001, 26 (09) :1763-1837