Article
Licensed
Unlicensed
Requires Authentication
Thermal aging of 1-alkyl-3-methylimidazolium ionic liquids and its effect on dissolved cellulose
-
Falk Liebner
Published/Copyright:
January 14, 2010
Abstract
The thermal degradation products of 1-alkyl-3-methyl-imidazolium-type ionic liquids (e.g., BMIM, EMIM), which are commonly used in cellulose chemistry, were identified. Imidazole (5), N-methylimidazole (6), and N-alkylimidazoles (7, 8) are the main products. Moreover, dimeric substituted imidazoles (9–11) were found carrying a methylene bridge formed from the N-methyl structure. The former 1-alkyl group (butyl or ethyl) was not present in any of the dimeric compounds. The N-methylene intermediate (12) acts as a precursor for the substituted imidazoles linked by a methylene group. All thermal degradation products are bases and catalyze the previously described reaction between the reducing end of celluloses and 1-alkyl-3-imidazolium cations. To minimize this side reaction, ionic liquids have to be liberated from such basic compounds prior to application as cellulose solvents. In this regard, the usage of “recycled” (and unpurified) ionic liquids has to be treated with caution.
Keywords: aging; 1-butyl-3-methyl-imidazolium (BMIM); cellulose; cellulose dissolution; condensation; 1-ethyl-3-methyl-imidazolium (EMIM); ionic liquids; thermal degradation
Received: 2009-6-8
Accepted: 2009-10-8
Published Online: 2010-01-14
Published Online: 2010-01-14
Published in Print: 2010-02-01
©2010 by Walter de Gruyter Berlin New York
You are currently not able to access this content.
You are currently not able to access this content.
Articles in the same Issue
- Original Papers
- Recombinant manganese peroxidase (rMnP) from Pichia pastoris. Part 1: Kraft pulp delignification
- Recombinant manganese peroxidase (rMnP) from Pichia pastoris. Part 2: Application in TCF and ECF bleaching
- The role of hydroxyl and oxyl anion radicals in selectivity of oxygen delignification
- Thermal aging of 1-alkyl-3-methylimidazolium ionic liquids and its effect on dissolved cellulose
- Synchrotron X-ray fiber diffraction study on the thermal expansion behavior of cellulose crystals in tension wood of Japanese poplar in the low-temperature region
- Studies on the dehydrogenative polymerization of monolignol β-glycosides. Part 6: Monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides by GPC-PDA
- Reactivity of syringyl quinone methide intermediates in dehydrogenative polymerization. Part 2: pH effect in horseradish peroxidase-catalyzed polymerization of sinapyl alcohol
- Fractionation, analysis, and PCA modeling of properties of four technical lignins for prediction of their application potential in binders
- New model for predicting tensile strength and density of eucalyptus handsheets based on an activation parameter calculated from fiber distribution characteristics
- Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents
- Surface properties of extracts from cork black condensate
- Effect of helium DBD plasma treatment on the surface of wood samples
- Preparation of thermoplastic molding from steamed Japanese beech flour
- Alteration of the unsteady sorption behaviour of maple (Acer pseudoplatanus L.) and spruce (Picea abies (L.) Karst.) due to thermal modification
- Towards improved understanding of PEG-impregnated waterlogged archaeological wood: A model study on recent oak
- Determination of the change in appearance of lumber surfaces illuminated from various directions
- A study of water exchange in wood by means of 2D NMR relaxation correlation and exchange
- Measurement of surface growth stress in Eucalyptus nitens Maiden by splitting a log along its axis
- Obituary
- Dion Chen-Loung Chen (1930–2009)
- Meetings
- Meetings
Keywords for this article
aging;
1-butyl-3-methyl-imidazolium (BMIM);
cellulose;
cellulose dissolution;
condensation;
1-ethyl-3-methyl-imidazolium (EMIM);
ionic liquids;
thermal degradation
Articles in the same Issue
- Original Papers
- Recombinant manganese peroxidase (rMnP) from Pichia pastoris. Part 1: Kraft pulp delignification
- Recombinant manganese peroxidase (rMnP) from Pichia pastoris. Part 2: Application in TCF and ECF bleaching
- The role of hydroxyl and oxyl anion radicals in selectivity of oxygen delignification
- Thermal aging of 1-alkyl-3-methylimidazolium ionic liquids and its effect on dissolved cellulose
- Synchrotron X-ray fiber diffraction study on the thermal expansion behavior of cellulose crystals in tension wood of Japanese poplar in the low-temperature region
- Studies on the dehydrogenative polymerization of monolignol β-glycosides. Part 6: Monitoring of horseradish peroxidase-catalyzed polymerization of monolignol glycosides by GPC-PDA
- Reactivity of syringyl quinone methide intermediates in dehydrogenative polymerization. Part 2: pH effect in horseradish peroxidase-catalyzed polymerization of sinapyl alcohol
- Fractionation, analysis, and PCA modeling of properties of four technical lignins for prediction of their application potential in binders
- New model for predicting tensile strength and density of eucalyptus handsheets based on an activation parameter calculated from fiber distribution characteristics
- Extractives of the tropical wood wallaba (Eperua falcata Aubl.) as natural anti-swelling agents
- Surface properties of extracts from cork black condensate
- Effect of helium DBD plasma treatment on the surface of wood samples
- Preparation of thermoplastic molding from steamed Japanese beech flour
- Alteration of the unsteady sorption behaviour of maple (Acer pseudoplatanus L.) and spruce (Picea abies (L.) Karst.) due to thermal modification
- Towards improved understanding of PEG-impregnated waterlogged archaeological wood: A model study on recent oak
- Determination of the change in appearance of lumber surfaces illuminated from various directions
- A study of water exchange in wood by means of 2D NMR relaxation correlation and exchange
- Measurement of surface growth stress in Eucalyptus nitens Maiden by splitting a log along its axis
- Obituary
- Dion Chen-Loung Chen (1930–2009)
- Meetings
- Meetings
