N-METHYLMORPHOLINE N-OXIDE
N-Methylmorpholine N-oxide
N-Methylmorpholine N-oxide is used as a solvent for paints, varnishes, lacquers, printing ink, and pharmaceuticals, among other applications
N-Methylmorpholine N-oxide is also used as a reagent in synthetic organic chemistry and commercially for the swelling and dissolution of cellulose.
N-Methylmorpholine N-oxide is employed 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
Application Areas of N-Methylmorpholine N-oxide:
Painting (Pigments, Binders, and Biocides)
Plastic Composites Manufacturing
Textiles (Fiber & Fabric Manufacturing)
Working with Glues and Adhesives
N-Methylmorpholine N-oxide is a solvent for cellulose to produce fiber. N-Methylmorpholine N-oxide is a heterocyclic amine oxide and morpholine derivative
The process of N-Methylmorpholine N-oxide is considered to be the most environmentally friendly method of producing regenerated cellulose fibers on a commercial scale.
The use of N-methylmorpholine-N-oxide in the manufacture of cellulosic products according to the lyocell technology, mostly fibers, is well established on an industrial scale.
While more dilute aqueous solutions of N-methylmorpholine-N-oxide have a swelling effect on cellulosic pulp, the respective monohydrate is able to dissolve cellulose at elevated temperatures above 80 °C so that a spinnable dope is obtained
CAS Number: 7529-22-8
CAS no.: 7529-22-8
EC / List no.: 231-391-8
Synonyms: 4-methylmorpholine 4-oxide, NMO, NMMO
Properties
Chemical formula: C5H11NO2
Mol. formula: C5H11NO2
Molar mass: 117.15 g/mol
Melting point: 180 to 184 °C
Substance names and other identifiers
4-methylmorpholine 4-oxide, monohydrate
CAS names
Morpholine, 4-methyl-, 4-oxide
IUPAC names
4-methylmorpholine 4-oxide monohydrate
4-methyl-morpholine, 4-oxide
4-Methylmorpholine 4-oxide
4-methylmorpholine 4-oxide, monohydrate
N-methylmorpholine oxide
Other identifiers
1644045-05-5
Deleted CAS number
7529-22-8
The precipitation in aqueous media of cellulose from solutions in Nmethylmorpholine N-oxide (NMMO) hydrates is an important stage in the process of manufacturing of fibres, films and other cellulose objects
N-Methylmorpholine-N-oxide (MMO) 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 a cellulose solvent that is used industrially for the spinning of cellulosic fibers (the Lyocell process).
Recently, it has been shown that when NMMO is used for pretreatment, there is a great improvement in biofuel production from lignocellulosic materials.
N-methylmorpholine-N-oxide is known to change the highly crystalline structure of cellulose after its dissolution and regeneration
N-methylmorpholine-N-oxide (NMMO) hydrates are direct solvents for cellulose, used commercially in the preparation of homogenous cellulose-NMMO-water solutions (dope) for making mainly fibres (Lyocell process).
The production of the cellulose objects by the NMMO process passes through the step of regeneration of the spun or extruded dope in a coagulation bath
N-Methylmorpholine-N-oxide is capable of dissolving cellulose without any further addition of chemicals. The solution can be used to produce cellulosic staple fibres by pressing it through spinning jets into an aqueous spinning bath
N-Methylmorpholine-N-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis. In recent studies, it has been used as a catalyst in silylcyanation of aldehydes and ketones.[1] Lyocell, a regenerated cellulose fiber, can be prepared using 4-methylmorpholine N-oxide in an eco-friendly manner.
Special Applications of N-Methylmorpholine-N-oxide:
Non-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
Pure N-Methylmorpholine N-oxide is a solid at ambient temperatures, so solutions are made at elevated temperature with addition of some water.
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.
N-Methylmorpholine N-oxide monohydrate is used as a solvent for cellulose in the lyocell process to produce cellulose fibers.
N-Methylmorpholine-N-Oxide is available commercially also 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.
As a result, N-Methylmorpholine-N-Oxide is a preferred stoichiometric oxidant for transition metal-catalyzed oxidations.
USES OF N-Methylmorpholine N-oxide
Liquid N-Methylmorpholine N-oxide is a colorless, flammable organic liquid. It has a strong odor similar to gasoline.
The N-Methylmorpholine N-oxide is used in the production of pesticides and as an intermediate for manufacturing several industrial chemicals such as solvents, plasticizers, fertilizers, and insecticides among others.
Applications : pharmaceuticals (as an intermediate), agriculture (as pesticide & fertilizer), and chemical synthesis (for producing other chemicals) among others.
Solid:
Solid N-Methylmorpholine N-oxide is a crystalline solid and is also known as morpholine.
Solid N-Methylmorpholine N-oxide is used in the synthesis of N-Methylmorpholine N-oxide (NMMO) which has applications in pharmaceuticals, research chemicals, pesticides, etc.
N-Methylmorpholine N-oxide monohydrate is used as a solvent in the lyocell process to produce lyocell fiber.
N-Methylmorpholine N-oxide monohydrate 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 NMMO 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 (found in animal tissue).
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
N-Methylmorpholine-N-oxide or NMO 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. NMO is commercially supplied both as a monohydrate C5H11NO2.H2O and as the anhydrous compound. NMO is used as a solvent for Lyocell manufacturing.
Oxidant
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 would 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.
N-methyl morpholine – N-oxide (NMO or NMMO) is an organic compound with the molecular formula C5H11NO2.
At room temperature, it is in forms of crystalline solid or liquid, which is non-toxic, slightly alkaline, soluble in water, ethanol, etc., strong hygroscopicity, and each molecule can be combined with more than one crystal water, has a strong solubility of cellulose.
Such heterocyclic amine oxides and morpholine derivatives are used as co-oxidants and sacrificed catalysts for oxidation reactions in organic chemistry, such as osmium oxide and asymmetric dihydroxylation or oxidation with TPAP.
NMMO is commercially available in the form of monohydrate C5H11NO2·H2O and anhydrous compounds.
In Lyocell production of cellulose fibers, monohydrate is used as a solvent for cellulose.
SYNONYMS:
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
4-Methylmorpholine N-oxide acts as a non-metallic catalyst for the cyanosilylation of ketones.
It is also employed as a co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids. It serves as a solvent in the Lyocell process to produce tencel fiber. Further, it is used in the preparation of aldehydes from primary alcohols in the presence of tetrapropylammonium perruthenate.
