Confirmation of the Presence of Formaldehyde and N-(Methylene)morpholinium Cations as Reactive Species in the Cellulose/NMMO/Water System by Trapping Reactions
-
A. Potthast
Summary
The presence of formaldehyde (4) in solutions of cellulose in N-methylmorpholine-N-oxide (NMMO, 1) has been shown by trapping formaldehyde as dimedone adduct 8 in a two-phase system. o-Dichlorobenzene was used as an inert solvent to extract the trapping product as soon as it had formed.
Morpholine is a degradation product of NMMO and is always present in systems containing NMMO. Formaldehyde can react with morpholine to form an intermediate carbenium-iminium ion, N-(methylene) morpholinium (6). The occurrence of 6 in the system cellulose/NMMO was demonstrated by trapping this intermediate in a Mannich type reaction with 2-acetonaphthone (9). Both formaldehyde and N-(methylene)morpholinium cations are highly reactive species readily undergoing further reactions with nucleophiles. These processes might contribute to the observed discoloration of the reaction mixture, and might also be responsible for the decomposition of NMMO that is inducible by carbenium-iminium ions.
Copyright © 2000 by Walter de Gruyter GmbH & Co. KG
Articles in the same Issue
- Identification of Indoor Rot Fungi by Taxon-Specific Priming Polymerase Chain Reaction
- Characteristics of Spruce [Picea abies (L.) Karst] Latewood Formed under Abnormally Low Temperatures
- The Chemical Nature of Kiln Brown Stain in Radiata Pine
- Microdistribution of Some Copper and Zinc Containing Waterborne and Organic Solvent Wood Preservatives in Spruce Wood Cell Walls
- X-Ray Diffraction as an Analytical Method in Wood Preservatives
- Modifications of Hybrid Walnut (Juglans nigra 23 x Juglans regia) Wood Colour and Phenolic Composition Under Various Steaming Conditions
- Incorporation of 13C-Labeled Coniferyl Alcohol into Developing Ginkgo biloba L. Lignin Revealed by Analytical Pyrolysis and CuO Oxidation in Combination with Isotope Ratio Monitoring-Gas Chromatography-Mass Spectrometry
- Atomic Force Microscopy (AFM) Investigation of Langmuir-Blodgett (LB) Films of Sugar Cane Bagasse Lignin
- Comparison of Acetic Acid Lignin with Milled Wood and Alkaline Lignins from Wheat Straw
- Monitoring of Lignin and Hemicelluloses in Spent Cooking Liquor during Kraft Delignification
- Preparation of Wood with Thermoplastic Properties, Part 1. Classical Synthesis
- Preparation of Wood with Thermoplastic Properties, Part 2. Simplified Technologies
- The Effect of Hydrostatic Pressure on Physical Properties and Microstructure of Spruce and Cherry
- Application of Liquefied Wood to a New Resin System—Synthesis and Properties of Liquefied Wood/Epoxy Resins
- Lab-Scale Synthesis of Isotopically Labeled Formaldehyde for the Production of Formaldehyde-Based Wood Adhesives
- Confirmation of the Presence of Formaldehyde and N-(Methylene)morpholinium Cations as Reactive Species in the Cellulose/NMMO/Water System by Trapping Reactions
- Compressive Creep of Wood under High Temperature Steam
- Literature Reports
Articles in the same Issue
- Identification of Indoor Rot Fungi by Taxon-Specific Priming Polymerase Chain Reaction
- Characteristics of Spruce [Picea abies (L.) Karst] Latewood Formed under Abnormally Low Temperatures
- The Chemical Nature of Kiln Brown Stain in Radiata Pine
- Microdistribution of Some Copper and Zinc Containing Waterborne and Organic Solvent Wood Preservatives in Spruce Wood Cell Walls
- X-Ray Diffraction as an Analytical Method in Wood Preservatives
- Modifications of Hybrid Walnut (Juglans nigra 23 x Juglans regia) Wood Colour and Phenolic Composition Under Various Steaming Conditions
- Incorporation of 13C-Labeled Coniferyl Alcohol into Developing Ginkgo biloba L. Lignin Revealed by Analytical Pyrolysis and CuO Oxidation in Combination with Isotope Ratio Monitoring-Gas Chromatography-Mass Spectrometry
- Atomic Force Microscopy (AFM) Investigation of Langmuir-Blodgett (LB) Films of Sugar Cane Bagasse Lignin
- Comparison of Acetic Acid Lignin with Milled Wood and Alkaline Lignins from Wheat Straw
- Monitoring of Lignin and Hemicelluloses in Spent Cooking Liquor during Kraft Delignification
- Preparation of Wood with Thermoplastic Properties, Part 1. Classical Synthesis
- Preparation of Wood with Thermoplastic Properties, Part 2. Simplified Technologies
- The Effect of Hydrostatic Pressure on Physical Properties and Microstructure of Spruce and Cherry
- Application of Liquefied Wood to a New Resin System—Synthesis and Properties of Liquefied Wood/Epoxy Resins
- Lab-Scale Synthesis of Isotopically Labeled Formaldehyde for the Production of Formaldehyde-Based Wood Adhesives
- Confirmation of the Presence of Formaldehyde and N-(Methylene)morpholinium Cations as Reactive Species in the Cellulose/NMMO/Water System by Trapping Reactions
- Compressive Creep of Wood under High Temperature Steam
- Literature Reports
