Crystallization of cellulose with N‐methylmorpholine N‐oxide: A new method of texturing cellulose

Chanzy, H.; Dubé, M.; Marchessault, R. H.

doi:10.1002/pol.1979.130170408

Cited by 103 publications

(48 citation statements)

References 7 publications

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“…During the course of this work the solubility of EXWL in N-methylmorpholine N-oxide (MMNO), a new solvent for cellulosic materials (35,36) was tested. The patent literature (36) vaguely specifies MMNO as a solvent for lignin as well as cellulose.…”

Section: Solubility Of Exwlmentioning

confidence: 99%

Characterization of aspen exploded wood lignin

Marchessault¹,

Coulombe²,

Morikawa³

et al. 1982

Can. J. Chem.

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114

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Exploded wood lignin (EXWL) was extracted from moist steam hydrolysed aspen (Populustremuloides) wood using methanol. The lignin was examined by elemental analysis, gel permeation chromatography, infrared spectroscopy, proton and 13C nmr. The observed nmr spectra were compared with those of aspen milled wood lignin (MWL). Typical composition of the material is C9H9.2O2.7(OCH3)1.1 Assignment of all the signals in the nmr spectrum led to the conclusion that the explosion process causes cleavage of the β-aryl-ether bond. The weight average molecular weight was found to be 1700–1900 and the polydispersity 2.6. The finely divided exploded wood was soluble in 90% methanol/water mixtures to well beyond 20% by weight at room temperature.

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Section: Solubility Of Exwlmentioning

confidence: 99%

Characterization of aspen exploded wood lignin

Marchessault¹,

Coulombe²,

Morikawa³

et al. 1982

Can. J. Chem.

Self Cite

114

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“…La N-methyl morpholine N-oxyde est connue I pour son pouvoir solvant vis a vis de la cellulose (1). Une bonne connaissance des interactions entre I l'eau et cette base est une premiere approche de 1 1'Ctude de ce phenomtne complexe.…”

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Étude, par spectroscopie de vibration, de deux solvants de la cellulose: La N-méthyl morpholine N-oxyde et son monohydrate

Maï¹,

Herzog-Cance²,

Potier³

et al. 1982

Can. J. Chem.

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The ir and Raman spectra of N-methyl morpholine N-oxide and its monohydrate have been investigated in the frequency range 4000–50 cm−1. For these two compounds, classified among the best cellulose solvents, there exists only the conformer where NO and CH3 groups are respectively in axial and equatorial positions. For anhydrous N-methyl morpholine N-oxide, the dipole–dipole interaction is characterized by a strong line at 75 cm−1 in the Raman spectra.The molecules can be divided into two parts: a hydrophobic part (O(CH2)2) not active in the cellulose dissolution, and a hydrophilic part, which is able to stabilize a chain of water molecules and reveals the importance of the pyramidal environment of water molecules in the monohydrate.

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“…Furthermore, the biochemical relevance of dissolved compounds in water is an important aspect of current research on protein stability and biomolecular recognition. Tertiary aliphatic Noxides are remarkable species in these respects: Some are known as good cosolvents with water for dissolving cellulose fibers, [1][2][3][4][5][6] increasing the reactivity of the swollen cellulose material for further derivatization in pollution-free industrial fiber processing. For instance, N-methylmorpholine-N-oxide (NMMO) in water dissolves cellulose, whereas N,N,N-trimethylamine-N-oxide (TMAO) does not.…”

Section: Introductionmentioning

confidence: 99%

“…21,22 In this work, a force field for two prototypical N-oxides, TMAO and NMMO, is developed and tested for its capability to reproduce experimental data. It is intended to be balanced in the sense of satisfying several requirements: (1) The functional form and the parameters should be compatible with common water models and biopolymer force fields such as CHARMM [23][24][25] for proteins and extensions for carbohydrates; 26 (2) the force field should be as simple as possible to avoid overly expensive computations for simulating the solvent, yet account for intramolecular flexibility; (3) certain terms in the force field that represent topologically similar units should be attributed identical, i.e., transferable parameters guiding future parametrization of other N-oxide species; (4) it should be applicable for a range of different situations such as various concentrations. Because experimental information about N-oxide systems is very limited, the parametrization relies mainly on quantum-chemical calculations.…”

Section: Introductionmentioning

confidence: 99%

Binary Phases of Aliphatic N-Oxides and Water: Force Field Development and Molecular Dynamics Simulation

et al. 2003

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Aliphatic N-oxides as cosolvents with water play an important role in stabilizing and destabilizing the structure of biopolymers such as cellulose and proteins. To allow for detailed microscopic investigations, an empirical force field to be used in molecular simulations is developed for two N-oxide species, N,N,N-trimethylamine-N-oxide (TMAO) and N-methylmorpholine-N-oxide (NMMO). The intra-and intermolecular force field is parametrized mainly on the basis of quantum-chemical calculations and is tested against available experimental spectroscopic, crystallographic, and liquid state data. Special emphasis is put on the identification of transferable potential terms in order to guide future parametrization of other species. By construction, the force field is compatible with widely used potential functions for proteins and carbohydrates. With the resulting parameter set, molecular dynamics simulations are carried out on binary mixtures of water and N-oxides, revealing structural features and the influence of intramolecular N-oxide flexibility. Limitations and possible extensions of the presented models are also discussed.

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Crystallization of cellulose with N‐methylmorpholine N‐oxide: A new method of texturing cellulose

Cited by 103 publications

References 7 publications

Characterization of aspen exploded wood lignin

Characterization of aspen exploded wood lignin

Étude, par spectroscopie de vibration, de deux solvants de la cellulose: La N-méthyl morpholine N-oxyde et son monohydrate

Binary Phases of Aliphatic N-Oxides and Water: Force Field Development and Molecular Dynamics Simulation

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