The chemistry of side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process)

Progress in Polymer Science (Oxford)

Volumn 26, Issue 9, 2001, Pages 1763-1837

  Rosenau, Thomas ^a   Potthast, Antje ^a   Sixta, Herbert ^b   Kosma, Paul ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b LENZING AG   (Austria)

Author keywords

Cellulose; Cellulosic fibers; Decomposition; Heterolytic processes; Homolytic processes; Lyocell; N Methylmorpholine N oxide; Thermal degradation

Indexed keywords

BYPRODUCTS; CATALYSTS; DISSOLUTION; HYDRATES; PYROLYSIS; SOLVENTS; STABILIZERS (AGENTS);

CHEMICAL STABILIZERS;

CELLULOSE;

CELLULOSE FIBERS;

EID: 0035505474     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0079-6700(01)00023-5     Document Type: Review

References (203)

1. Quellung und Lösen von Cellulose im Aminoxid-Wasser-System
2. The phase behavior of the quasiternary system N-methylmorpholine-N-oxide, water and cellulose
3. Lenzing Lyocell
4. Production of porous celluslose beads on a laboratory scale
5. Structural aspects of new cellulose fibers and films from NMMO-solution
6. Lyocell products with functional properties
7. Manufacture of ceramic hollow membranes and filaments according to the Lyocell-process
8. Lyocell products with built-in functional properties
9. Lenzing-Lyocell - Die wichtigsten unterschiede zu den anderen cellulosischen Fasern
10. Lyocell - An ecological alternative
11. Biodegradation of N-methylmorpholine-N-oxide
12. Oriented cellulose films and fibers from a mesophase system
13. The structural format of cellulose fibers from amine oxide solutions
14. Courtaulds Tencel fibre in Apparel Fabrics
15. Cellulosic filament yarn from the NMMO process
16. Studies on the wet fibrillation of lyocell fibers
17. Lyocell fibers. Alternatives for reducing fibrillation
18. Fibrillation - Problem or chance?
19. Fibrillation propensity of lyocell and the influence of reactive dyeings
20. Methods for reducing the tendency of Lyocell fibers to fibrillate
21. Influence of the physical process parameters on the structure formation of Lyocell fibers
22. The influence of air-gap conditions on the structure formation of Lyocell fibers
23. Finishing of Lyocell
24. Finishing of Lyocell
25. Finishing of Lyocell. Part 1-3
26. Finishing of Lyocell. Part 1-3
27. Finishing of Lyocell. Part 1-3
28. Investigations on the structure of regenerated cellulose fibers
29. Recent results with Lyocell fibers in textiles
30. Lyocell. A fiber with a great future
31. Nonwovens applications of Lyocell fibers
32. Polythermal study of the heat of dissolution of cellulose in N-methylmorpholine N-oxide
33. Thermal stability of cellulose in methylmorpholine N-oxide-based systems
34. 2O solution system
35. Particle analysis by laser diffraction. Application and restrictions in the Lyocell process
36. Dielectric absorption and molecular mechanisms of the initial stages of cellulose dissolution in N-methylmorpholine N-oxide
37. Specific features of cellulose dissolution in tertiary amine oxides
38. Role of water during dissolution of cellulose in N-methylmorpholine N-oxide
39. Ab initio investigations of hydrogen bonding in aliphatic N-oxide-water systems
40. Quantum-chemical study of interaction of cellulose with N-methylmorpholine N-oxide
41. Characteristics of the interaction of cellulose with N-methylmorpholine-N-oxide
42. Hydrogen bonding. Part 45
43. Barriers to rotation of bridging bonds of cellulose molecule in its interaction with N-methylmorpholine N-oxide
44. Effect of donor-acceptor interactions on solubility of cellulose in methylmorpholine N-oxide-based systems
45. Solution of cellulose in aprotic mixed solvents. 2. Effect of the physical structure of the cellulose on the dissolution process
46. On the mechanism of cellulose dissolution in nonaqueous solvents, especially in O-basic systems
47. Investigation of the dissolution of cellulose in binary aprotic systems. 1. Solubility and decrease in degree of polymerization of a textile pulp in binary systems with N-methylmorpholine N-oxide as one component
48. Rheology of cellulosic N-methylmorpholine oxide monohydrate solutions
49. Rheology of cellulosic and lignocellulosic N-methylmorpholine N-oxide solutions
50. Rheological behavior of cellulose/monohydrate of N-methylmorpholine N-oxide solutions. Part 1. Liquid state
51. Rheology of concentrated N-methylmorpholine N-oxide cellulose solutions
52. Cellulose-NMMO solutions and their flow properties
53. Investigation of the state of solution of cellulose in solvent mixtures with N-methylmorpholine-N-oxide
54. Supramolecular structure of moderately concentrated solutions of cellulose in amine N-oxides
55. In situ X-ray scattering investigations of solutions of cellulose in N-methylmorpholine N-oxide during shear flow
56. X-ray study of intracrystallite swelling of cellulose in N-methylmorpholine N-oxide solutions
57. Swelling and dissolution of cellulose in amine oxide/water systems
58. The influence of activation on the solution state of cellulose dissolved in N-methylmorpholine-N-oxide-monohydrate
59. Investigations on structures in the system cellulose/N-methylmorpholine N-oxide monohydrate by means of light scattering measurements
60. The dipole moment of amine oxides
61. The relative basicities of trialkylamine and trialkylamine oxides in benzene and water
62. Preparation and basicities of N,N-diethyl and N,N-dimethylaniline oxides
63. Quantitative Bestimmung verschiedener B-Funktionen in organischen Borverbindungen durch Oxydation mit Trimethylamin-N-oxyd
64. Crystalline anhydrous trimethylamine N-oxide
65. The conformational analysis of saturated heterocycles. Part XXXVIII. N-Alkylpiperidine and N-alkylmorpholine N-oxides
66. Cellulose organic solvents. I. The structure of anhydrous N-methylmorpholine-N-oxide and N-methylmorpholine-N-oxide monohydrate
67. Cellulose organic solvents II
68. Alkaloid N-oxides
69. Synthetic utility of amine N-oxides
70. Ready oxidation of halides to aldehydes using trimethylamine N-oxide in dimethylsulfoxide
71. Ruthenium catalyzed oxidation of alcohols to aldehydes and ketones by amine-N-oxides
72. Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols
73. Osmium tetraoxide cis hydroxylation of unsaturated substrates
74. 4 oxidation of olefins to cis-l,2-glycols using tertiary amine oxides as the oxidant
75. Selective oxidation of organoboranes with anhydrous trimethylamine N-oxide
76. 9
77. 17]
78. Cellulose organic solvents. III. The structure of N-methylmorpholine-N-oxide-trans-1,2-cyclohexanediol complex
79. Untersuchungen zur Auflösung und Verformung von Cellulose in N-methylmorpholin-N-oxid
80. Polymer solutions
81. Molding and spinning compositions based on cellulose with a low content of low-molecular-weight degradation products
82. New decarbonylation reactions of carbonylruthenium(II) complexes
83. Vorsicht bei der Darstellung von Trimethylaminoxyd
84. The degradation of and stabilization of cellulose dissolved in N-methylmorpholine-N-oxide (NMMO)
85. Probleme der schwefelkohlenstofffreien Verformung von Zellulose zu textilen Zellulosefäden mittels N-Methylmorpholin-N-oxids
86. Untersuchungen an Lösungen von Cellulose in N-Methylmorpholine-N-oxid (MMNO)
87. Critical questions on the future of NMMO technology
88. The chemistry of side reactions and byproduct formation in the system NMMO/water/cellulose
89. Chemistry of the cellulose/NMMO/water system: Heterolytic reactions
90. Chemistry of the cellulose/NMMO/water system: Homolytic reactions
91. Kinetics and preparation of amine oxides
92. Potentiometric titration of long chain amine oxides using alkyl halide to remove tertiary amine interference
93. Reinigung und Rückgewinnung sowie Methoden der quantitativen Bestimmung von N-Methylmorpholin-N-oxid
94. Titanometric determination of the N-oxide group in pyridine-N-oxide and related compounds
95. Microdetermination of the amine oxide group in organic compounds by reduction with titanium(III)
96. Ozonation of wastewater containing N-methylmorpholine-N-oxide
97. Separation of morpholine and some of its metabolites by high-performance liquid chromatography
98. Liquid chromatographic determination of morpholine and its thermal breakdown products in steam-water cycles at nuclear power plants
99. Application of a fused-silica column to the determination of very volatile amines by gas-solid chromatography
100. Determination of morpholine and N-methylmorpholine formed as degradation products in cellulose fiber production by capillary isotachophoresis
101. Separation of morpholine, N-methylmorpholine and N-methylmorpholine-N-oxide by indirect UV absorption capillary electrophoresis
102. Thermal reactions of N-methylmorpholine-N-oxide (NMMO): A general method for separation and quantification of N-methylmorpholine-N-oxide and its main degradation products N-methylmorpholine and morpholine by capillary electrophoresis (CE)
103. A general method for the quantification of NMMO and its main degradation products by capillary electrophoresis
104. Investigations of the acyclic forms of reducing sugars and Amadori products by FTIR spectroscopy
105. The reaction kinetics of the formation of isovaleraldehyde, 2-acetyl-1-pyrroline, di(H)di(OH)-6-methylpyranone, phenylacetaldehyde, 5-methyl-2-phenyl-hexenal, and 2-acetylfuran in model systems
106. A study of the behavior of Maillard reaction products analyzed by solid-phase microextraction - Gas chromatography - Mass selective detection
107. Separation and partial characterization of Maillard reaction products by capillary zone electrophoresis
108. Heterolytic reactions in the system NMMO/cellulose/water
109. The oxidation product from α-tocopherol and potassium ferricyanide and its reaction with ascorbic and hydrochloric acids
110. Optical resolution of the α-tocopherol spiro dimer and demonstration of its fluxional nature
111. Über die chemie des vitamins E. Die Struktur des kaliumferricyanid-oxidationsproduktes von α-Tocopherol
112. Chemical reactions in the system cellulose/NMMO/water
113. Redox and acidity properties of alkyl- and arylamine radical cations and the corresponding aminyl radicals
114. Amine radical cations: An electron spin resonance study of cations generated by radiolysis
115. Radical cations of trialkylamines: ESR spectra and structures
116. Trapping reactions as analytical tools to study the system NMMO/cellulose (Lyocell process)
117. A concise synthesis of N-(trideuteromethyl)morpholine-N-oxide monohydrate
118. Iron-catalyzed dealkylation of trimethylamine oxide
119. Redox and acidity properties of 4-substituted aniline radical cations in water
120. Kinetics of base-catalyzed cleavage of glycosidic linkages
121. 2O system; Degradation aspects
122. An experimental approach to spinning new cellulose fibers with N-methylmorpholine-oxide as a solvent
123. Ersatz von an Stickstoff gebundenen Wasserstoffatomen durch die Methylgruppe mit Hülfe von Formaldehyd
124. The action of formaldehyde on amines and amino acids
125. Rheological and other properties of cellulose solution in N-methylmorpholine-N-oxide
126. Detoxication mechanisms. III. The scope and mechanism of the iron-catalyzed dealkylation of tertiary amine oxide
127. Oxidativ bedingte Abbaureaktionen in NMMO-Celluloselösungen
128. Copper-induced synthesis of iminiums: Trimethylamine oxidation or amine N-oxide conversion
129. 2/ acetic acid system in acetonitrile
130. Decarboxylation oxydante des acides carboxyliques aliphatiques par un systeme cuivre(I)/oxygene
131. Behavior of wood polysaccharides during oxygen-alkali delignification
132. Behaviour of pulp polysaccharides during oxygen alkali delignification
133. The chemistry of alkaline degradation of cellulose and oxidized celluloses
134. The chemistry of alkaline degradation of cellulose and oxidized celluloses
135. Neuere Methoden der präparativen organischen Chemie. Die Verwendung von Pyridin-N-oxyden zur Gewinnung von substituierten Pyridinen
136. Selective reduction of the N-O bond in N-oxides and in nitrones by sodium hydrogen telluride
137. Synthetic methods and reactions; 87. Deoxygenation of pyridine N-oxides with trimethyl(ethyl)amine-sulfur dioxide complexes
138. Chemoselective deoxygenation of nitrones and N-oxides with tetrathiomolybdate
139. Selective deoxygenation of amine N-oxides using borohydride exchange resin-copper sulfate in methanol
140. Recent Japanese work on the chemistry of pyridine 1-oxide and related compounds
141. A new method for deoxygenation of tertiary amine N-oxides with acetic formic anhydride
142. Deoxygenation of amine oxides by in situ-generated formic pivalic anhydride
143. Die Acylierung der N,N-Dimethyl-arylamin-oxyde; Der Mechanismus der Polonovski Reaktion
144. Notiz über einige weitere Entmethylierungen der N,N-Dimethyl-arylamine über das N-oxyd
145. Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids
146. Modified Polonovski reaction, a versatile synthetic tool
147. Compounds of trialkylamine oxides with sulfur dioxide and trioxide
148. Synthetic methods and reactions; 88. Sulfuryl chloride fluoride, a convenient reagent for the preparation of amides from carboxylic acids and primary amines under mild conditions
149. The Polonovski transformation of (+)-napharidine. A study of the stereochemistry and utility in synthesis
150. Indoloquinolizidine N-oxides and Polonovski rearrangement
151. Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation
152. Instabilities in the system NMMO/water/cellulose (Lyocell process) caused by Polonowski type reactions
153. Use of formaldehyde for making wheat straw cellulose pulp
154. Confirmation of the presence of formaldehyde and N-(methylene)morpholinium cations as reactive species in the cellulose/NMMO/water system by trapping reactions
155. 13C NMR studies of the adducts
156. Periodate oxidation of cellulose by homogeneous reaction
157. Dyeable cross-linked cellulose from low formaldehyde and non-formaldehyde finishing systems
158. Chemical crosslinking of hydroxypropyl cellulose and chitosan blends
159. Eine Synthese von β-Ketonbasen
160. Advances in the chemistry of Mannich bases
161. Further advances in the chemistry of Mannich bases
162. Advances in the chemistry of β-aminoketones
163. Synthesis of chiral 4-alkyl 4-hydroxy cyclopentenones via a diastereo-selective tandem aza-Cope/Mannich cyclization reaction from aldehydo-sugars
164. Aminoalkylation of electron-rich compounds using performed iminium salts derived from aldehydes other than formaldehyde
165. Autocatalytic decomposition of N-methylmorpholine-N-oxide induced by Mannich intermediates
166. Side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process)
167. Dimethyl-methylen-immonium-jodid
168. Thermal decomposition of amine oxides to olefins and dialkylhydroxylamines
169. Olefines from amines: The Hofmann elimination and amine oxide pyrolysis
170. Amine oxides. VII. The thermal decomposition of the N-oxides of N-methylazacycloalkanes
171. Spin trapping: ESR parameters of spin adducts