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CAS Number : 7529-22-8
EC Number : 231-391-8
Chemical formula : C5H11NO2
Molar mass : 117.15 g/mol
Melting point : 180 to 184 °C
ECHA InfoCard : 100.028.538
PubChem CID : 82029
ChemSpider : 74032
N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.
N-Methylmorpholine N-oxide (more correctly 4-methylmorpholine 4-oxide), NMO or NMMO is an organic compound.
This heterocyclic amine oxide and morpholine derivative is used in organic chemistry as a co-oxidant and sacrificial catalyst in oxidation reactions for instance in osmium tetroxide oxidations and the Sharpless asymmetric dihydroxylation or oxidations with TPAP.
N-methylmorpholine N-oxide is commercially supplied both as a 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 of N-methylmorpholine N-oxide
Solvent of cellulose
N-methylmorpholine N-oxide is used as a solvent in the lyocell process to produce lyocell fiber.
N-methylmorpholine N-oxide dissolves cellulose to form a solution called dope, and the cellulose is reprecipitated in a water bath to produce a fiber.
The process is similar but not analogous to the viscose process.
In the viscose process, cellulose is made soluble by conversion to its xanthate derivatives.
With N-methylmorpholine N-oxide, cellulose is not derivatized but dissolves to give a homogeneous polymer solution.
The resulting fiber is similar to viscose; this was observed, for example, for Valonia cellulose microfibrils.
Dilution with water causes the cellulose to reprecipitate, i.e. the solvation of cellulose with N-methylmorpholine N-oxide is a water sensitive process.
Cellulose remains insoluble to most solvents since it has a strong and highly structured intermolecular hydrogen bonding network, which resists common solvents.
N-methylmorpholine N-oxide is able to break the hydrogen bonding network that keeps cellulose insoluble to water and other solvents.
Similar solubility has been obtained in a few solvents, particularly a mix of lithium chloride in dimethyl acetamide and some hydrophilic ionic liquids.
Dissolution of scleroproteins
Another use of N-methylmorpholine N-oxide is in the dissolution of scleroprotein .
This dissolution occurs in the crystal areas which are more homogeneous and contain glycine and alanine residues with a small number of other residues.
How N-methylmorpholine N-oxide dissolves these proteins is scarcely studied.
Other studies, however, have been done in similar amide systems (i.e. hexapeptide).
The hydrogen bonds of the amides can be broken by N-methylmorpholine N-oxide.
Oxidant of N-methylmorpholine N-oxide
N-methylmorpholine N-oxide, as an N-oxide, is an oxidant.
N-methylmorpholine N-oxide is generally used in stoichiometric amounts as a secondary oxidant (a cooxidant) to regenerate a primary (catalytic) oxidant after the latter has been reduced by the substrate.
Vicinal syn-dihydroxylation reactions for example, would, in theory, require stoichiometric amounts of toxic, volatile and expensive osmium tetroxide, but if continuously regenerated with N-methylmorpholine N-oxide, the amount required can be reduced to catalytic quantities.
Use and Manufacturing of N-methylmorpholine N-oxide
Used as a reagent in synthetic organic chemistry and commercially for swelling and dissolution of cellulose; Used as an intermediate, to make flexible and rigid polyurethane foams, as a solvent in synthetic fiber production, and in industrial and professional coatings, adhesives, and sealants
Industry Uses of N-methylmorpholine N-oxide
-Hydraulic fluids
-Intermediate
-Other (specify)
General Manufacturing Information
Industry Processing Sectors
-All Other Basic Organic Chemical Manufacturing
-Organic Fiber Manufacturing
-Utilities
N-methylmorpholine N-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis.
In recent studies, N-methylmorpholine N-oxide has been used as a catalyst in silylcyanation of aldehydes and ketones.
Lyocell, a regenerated cellulose fiber, can be prepared using N-methylmorpholine N-oxide in an eco-friendly manner.
Application of N-methylmorpholine N-oxide
Non-metallic catalyst for the cyanosilylation of ketones.
Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
N-methylmorpholine N-oxide is available commercially as the monohydrate; it has a melting point of 70 °C, and is stable under normal conditions.
N-methylmorpholine N-oxide is soluble in polar solvents, especially water.
N-methylmorpholine N-oxide displays characteristic reactivity with various transition metals, which undergo oxidation with this reagent.
Because of this, N-methylmorpholine N-oxide is a preferred stoichiometric oxidant for transition metal-catalyzed oxidations.
The options to use N-methylmorpholine N-oxide and its hydrated forms in cellulose and material chemistry are very diverse, rendering the compound—if used correctly—a highly valuable chemical with many potential applications in dissolving, activating and modifying cellulosic substrates.
This applies to large-scale industrial use in lyocell processing, pilot-scale biorefineries, and small-scale lab work in research.
N-methylmorpholine N-oxide is an activated cellulose product.
N-methylmorpholine N-oxide is used for the treatment of autoimmune diseases and can be used as a reagent to synthesize fatty acid esters.
This drug has been shown to have low water permeability, meaning it does not readily diffuse through membranes, which may be due to its high hydrochloric acid content.
N-methylmorpholine N-oxide is a metabolite of Morpholine (M723725).
N-Methylmorpholine N-Oxide is commonly used to dissolve cellulose as well as in the dissolution of scleroproteins.
N-methylmorpholine-N-oxide (NMO) in acetonitrile solution will oxidise activated primary halides to aldehydes and secondary halides to ketones in good yields at room temperature.
N-methylmorpholine-N-oxide is prepared by reacting the azeotrope of methylmorpholine and water with an aqueous solution of hydrogen peroxide.
The reaction solution product is thereupon concentrated to the desired content in N-methylmorpholine-N-oxide.
N-methylmorpholine-N-oxide is used as a solvent to prepare cellulose fibers.
N-methylmorpholine-N-oxide is an oxidant and involved in the catalytic OsO4 oxidation of olefins to cis-1,2-diols.
N-methylmorpholine-N-oxide is also involved in ruthenium catalyzed oxidation of alcohols to aldehydes and ketones.
N-methylmorpholine-N-oxide is a common industrial solvent used in the production of cellulose fibers.
Currently, N-methylmorpholine-N-oxide is the only such compound known that has the ability to solvate cellulose for downstream utilization in fiber production .
N-methylmorpholine-N-oxide is an integral component of the Lyocell process used for such previously mentioned purposes .
The highly polar nature of N-methylmorpholine-N-oxide provides an excellent solvent for disruption of the extensive hydrogen-bonded network formed by carbohydrate polymers .
N-methylmorpholine-N-oxide has also been shown to be useful in the production of biofuels; pretreatment of cellulosic biomass such as sugarcane with the compound was shown to increase the degree of downstream enzymatic hydrolysis for improved yields following fermentation.
N-methylmorpholine-N-oxide is an organic compound.
This heterocyclic amine oxide and morpholine derivative is used in organic chemistry as a co-oxidant and sacrificial catalyst in oxidation reactions for instance in osmium tetroxide oxidations and the Sharpless asymmetric dihydroxylation or oxidations with TPAP.
N-methylmorpholine-N-oxide is commercially supplied both as a monohydrate C5H11NO2.H2O and as the anhydrous compound.
N-methylmorpholine-N-oxide is used as a solvent for Lyocell manufacturing.
FIRST AID MEASURES of N-methylmorpholine N-oxide
SWALLOWED :
IF SWALLOWED, REFER FOR MEDICAL ATTENTION, WHERE POSSIBLE, WITHOUT DELAY.
For advice, contact a Poisons
Information Centre or a doctor.
Urgent hospital treatment is likely to be needed.
In the mean time, qualified first-aid personnel should treat the patient following observation and employing supportive measures as indicated by the patient's condition.
EYE :
If this product comes in contact with the eyes:
Wash out immediately with fresh running water.
Ensure complete irrigation of the eye by keeping eyelids apart and away from eye and moving the eyelids by occasionally lifting the upper and lower lids.
Seek medical attention without delay; if pain persists or recurs seek medical attention.
Removal of contact lenses after an eye injury should only be undertaken by skilled personnel.
SKIN :
If skin contact occurs:
Immediately remove all contaminated clothing, including footwear.
Flush skin and hair with running water (and soap if available).
Seek medical attention in event of irritation.
INHALED :
If fumes or combustion products are inhaled remove from contaminated area.
Lay patient down. Keep warm and rested.
Prostheses such as false teeth, which may block airway, should be removed, where possible, prior to initiating first aid procedures.
Apply artificial respiration if not breathing, preferably with a demand valve resuscitator, bag-valve mask device, or pocket mask as trained.
Perform CPR if necessary.
Substance identity
EC / List no.: 231-391-8
CAS no.: 7529-22-8
Mol. formula: C5H11NO2
Hazard classification & labelling of N-methylmorpholine-N-oxide
According to the classification provided by companies to ECHA in REACH registrations this substance is a flammable solid, may intensify fire (oxidiser) and is suspected of damaging fertility or the unborn child.
About N-methylmorpholine-N-oxide
N-methylmorpholine-N-oxide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
N-methylmorpholine-N-oxide is used in formulation or re-packing and at industrial sites.
Consumer Uses of N-methylmorpholine-N-oxide
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life of N-methylmorpholine-N-oxide
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers of N-methylmorpholine-N-oxide
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
ECHA has no public registered data on the types of manufacture using this substance.
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Formulation or re-packing of N-methylmorpholine-N-oxide
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
Release to the environment of N-methylmorpholine-N-oxide can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites of N-methylmorpholine-N-oxide
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
N-methylmorpholine-N-oxide is used for the manufacture of: chemicals and textile, leather or fur.
Release to the environment of N-methylmorpholine-N-oxide can occur from industrial use: in processing aids at industrial sites and as an intermediate step in further manufacturing of another substance (use of intermediates).
Manufacture of N-methylmorpholine-N-oxide
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Synonyms:
4-methylmorpholine 4-oxide monohydrate
4-methylmorpholine 4-oxide, monohydrate
Morpholine, 4-methyl-, 4-oxide
4-methylmorpholine 4-oxide! !monohydrate!
4-methyl-4lambda5-morpholin-4-one
4-methyl-morpholine, 4-oxide
4-Methylmorpholine 4-oxide
1644045-05-5
7529-22-8
4-Methylmorpholine N-oxide
7529-22-8
4-Methylmorpholine 4-oxide
N-Methylmorpholine oxide
N-Methylmorpholine N-oxide
Morpholine, 4-methyl-, 4-oxide
4-methyl-4-oxidomorpholin-4-ium
Methyl morpholine oxide
N-Methylmorpholine-N-oxide
4-Methylmorpholine-4-oxide
NMO
NMMO
4-Methylmorpholine Oxide
4-methylmorpholine-N-oxide
N-Methylmorpholine 4-oxide
MFCD00005947
ARC64PKJ0F
CHEBI:52093
4-methylmorpholin-4-ium-4-olate
NSC73198
NSC-73198
NSC-82153
Morpholine, 4-oxide
NMO solution
NSC 73198
NSC 82153
EINECS 231-391-8
UNII-ARC64PKJ0F
4-methylmorpholine 4-oxide, monohydrate
N-Methyl morpholine N-oxide
4-methyl morpholine N-oxide
4-methyl-4-oxido-morpholin-4-ium
4-methylmorpholine-4-oxide solution
n-methylmorpholineoxide
methylmorpholine N-oxide
methylmorpholine-N-oxide
4-Methylmorpholine-oxide
N-methylmorpholin-N-oxid
4methylmorpholine N-oxide
4methylmorpholine-N oxide
4methylmorpholine-N-oxide
N-methyl morpholine oxide
N-methyl morpholine-oxide
N-methyl-morpholine oxide
4-methyl morpholine oxide
N-methylmopholine N-oxide
N-methylmorphline N-oxide
N-methylmorpholin-N-oxide
N-methymorpholine N-oxide
4-methylmopholine N-oxide
4-methylmorpholin-N-oxide
4-Methylmorpholine4-oxide
4-methymorpholine N-oxide
DSSTox_CID_9287
4-methylmorpholin-4-oxide
N-methyimorpholine N-oxide
4-methylmorpholine N oxide
4-methylmorpholine-N oxide
EC 231-391-8
N-methyl morpholin-N-oxide
4-methy-morpholine-N-oxide
4-methyl morpholin N-oxide
4-methylnnorpholine N-oxide
SCHEMBL1845
N-methyl morpholine-N-oxide
N-methyl-morpholine N-oxide
N-methyl-morpholine-N-oxide
4-methyl morpholine-N-oxide
4-methyl-morpholine N-oxide
4-methyl-morpholine-N-oxide
4-methylmorpholine-N- oxide
DSSTox_RID_78750
NCIOpen2_000398
NCIOpen2_000960
4-methyl morpholine-4-oxide
4-methyl-morpholine 4-oxide
4-methyl-morpholine-4-oxide
DSSTox_GSID_29287
4-methyl-morpholine-N- oxide
CHEMBL3184330
DTXSID3029287
LFTLOKWAGJYHHR-UHFFFAOYSA-
ZINC157080
4-Methylmorpholine N-oxide, 97%
NSC82153
Tox21_200479
c1367
AKOS009159059
METHYL MORPHOLINE OXIDE [INCI]
4-methyl-4-oxidanidyl-morpholin-4-ium
N-METHYLMORPHOLINE N-OXIDE [MI]
NCGC00248649-01
NCGC00258033-01
BP-30197
4-Methyl-1,4.lambda.~5~-oxazinan-4-ol
CAS-7529-22-8
CS-0016218
M0981
M2192
EN300-37514
D71257
A840005
Q416248
W-104395
4-Methylmorpholine N-oxide solution, 50 wt. % in H2O
4-Methylmorpholine N-oxide, 50 wt.% solution in water
4-methylmorpholine n-oxide (50% in water, ca. 4.8mol/l)
4-Methylmorpholine N-oxide solution, technical, ~50% in H2O
Morpholine N-oxide, polymer-bound, 50-100 mesh, extent of labeling: 2.0-3.0 mmol/g loading, 1 % cross-linked with divinylbenzene
231-391-8 [EINECS]
4-Methylmorpholin-4-oxid [German] [ACD/IUPAC Name]
4-Methylmorpholine 4-oxide [ACD/IUPAC Name]
4-Methylmorpholine N-oxide
4-Méthylmorpholine-4-oxyde [French]
4-Oxyde de 4-méthylmorpholine [French] [ACD/IUPAC Name]
507437 [Beilstein]
7529-22-8 [RN]
ARC64PKJ0F
Methyl morpholine oxide
MFCD00005947 [MDL number]
Morpholine, 4-methyl-, 4-oxide [ACD/Index Name]
N-Methylmorpholine 4-oxide
N-methylmorpholine N-oxide
N-Methylmorpholine oxide
N-methylmorpholine-N-oxide [Wiki]
NMO
N-óxido de N-metilmorfolina [Portuguese]
231-391-8MFCD00005947
4-hydroxy-4-methylmorpholin-4-ium [ACD/IUPAC Name]
4-Methyl-1,4λ5-oxazinan-4-ol
4-methyl-4-oxidomorpholin-4-ium
4-Methyl-4-oxido-morpholin-4-ium
4-methylmorpholin-4-ium-4-olate
4-methylmorpholin-4-ol
4-Methylmorpholine N-oxidemissing
4-METHYLMORPHOLINE OXIDE
4-Methylmorpholine-4-oxide
4-methylmorpholinen-oxide
4-Methylmorpholine-N-oxide
4-Methyl-morpholine-N-oxide
MFCD00149388 [MDL number]
morpholine, 4-methyl-, 4-oxide
N-methylmorpholine-N'-oxide
N-methyl-morpholine-N-oxide
UNII:ARC64PKJ0F
UNII-ARC64PKJ0F
