N-Methylmorpholine N-oxide

N-Methylmorpholine N-oxide
Identifiers
CAS Number	7529-22-8 ;
3D model ( JSmol)	Interactive image;
ChEBI	CHEBI:52093 ;
ChemSpider	74032 ;
ECHA InfoCard	100.028.538
PubChem CID	82029;
UNII	ARC64PKJ0F ;
CompTox Dashboard (EPA)	DTXSID3029287 ;
	InChI InChI=1S/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3 Key: LFTLOKWAGJYHHR-UHFFFAOYSA-N ; InChI=1/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3 Key: LFTLOKWAGJYHHR-UHFFFAOYAV;
	SMILES C[N+]1(CCOCC1)[O-];
Properties
Chemical formula	C5H11NO2
Molar mass	117.15 g/mol
Melting point	180 to 184 °C (356 to 363 °F; 453 to 457 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

N-Methylmorpholine N-oxide (more correctly 4-methylmorpholine 4-oxide), NMO or NMMO is an

monohydrate C₅H₁₁NO₂·H₂O and as the anhydrous compound. The monohydrate is used as a solvent for cellulose in the lyocell process to produce cellulose fibers

.

Uses

Solvent of cellulose

NMMO monohydrate is used as a solvent in the lyocell process to produce lyocell fiber.

Valonia cellulose microfibrils. Dilution with water causes the cellulose to reprecipitate, i.e. the solvation of cellulose with NMMO is a water sensitive process.^[3]

Cellulose remains insoluble in most solvents because it has a strong and highly structured intermolecular hydrogen bonding network, which resists common solvents. NMMO breaks the hydrogen bonding network that keeps cellulose insoluble in water and other solvents. Similar solubility has been obtained in a few solvents, particularly a mix of

dimethyl acetamide and some hydrophilic ionic liquids

.

Dissolution of scleroproteins

Another use of NMMO is in the dissolution of

hexapeptide). The hydrogen bonds of the amides can be broken by NMMO.^[4]

Oxidant

NMO, as an

catalytic

quantities.

References

doi:10.1002/047084289X.rm216.pub2

doi:10.1002/14356007.a05_375.pub2

^ Noé, Pierre, and Henri Chanzy "Swelling of Valonia cellulose microfibrils in amine oxide systems." Canadian Journal of Chemistry Volume 86 issue 6 pages 520-524(2008). retrieved via EBSCO, Advanced Placement Source. 11 Nov. 2009.

^ E. S. Sashina, N. P. Novoselov, S. V.Toroshekova, V. E. Petrenko, "Quantum-chemical study of the mechanism of dissolution of scleroproteins in N-methylmorpholine N-oxide." Russian Journal of General Chemistry volume78 issue 1 pages 139-145 (2008). retrieved via EBSCO, Advanced Placement Source. 11 Nov. 2009.

^ Preparation of 3H-Pyrrolo[2,3-c]isoquinolines and 3H-Pyrrolo[2,3-c][2,6]- and 3H-Pyrrolo[2,3-c][1,7]-naphthyridines U. Narasimha Rao, Xuemei Han and Edward R. Biehl Arkivoc 2002 (x) 61-66 online article

Retrieved from "https://en.wikipedia.org/w/index.php?title=N-Methylmorpholine_N-oxide&oldid=1157851888"

[1] doi:10.1002/047084289X.rm216.pub2

[2] doi:10.1002/14356007.a05_375.pub2

[3] Noé, Pierre, and Henri Chanzy "Swelling of Valonia cellulose microfibrils in amine oxide systems." Canadian Journal of Chemistry Volume 86 issue 6 pages 520-524(2008). retrieved via EBSCO, Advanced Placement Source. 11 Nov. 2009.

[Sashina_2008-4] E. S. Sashina, N. P. Novoselov, S. V.Toroshekova, V. E. Petrenko, "Quantum-chemical study of the mechanism of dissolution of scleroproteins in N-methylmorpholine N-oxide." Russian Journal of General Chemistry volume78 issue 1 pages 139-145 (2008). retrieved via EBSCO, Advanced Placement Source. 11 Nov. 2009.

[5] Preparation of 3H-Pyrrolo[2,3-c]isoquinolines and 3H-Pyrrolo[2,3-c][2,6]- and 3H-Pyrrolo[2,3-c][1,7]-naphthyridines U. Narasimha Rao, Xuemei Han and Edward R. Biehl Arkivoc 2002 (x) 61-66 online article

[3]

[4]

[5]