Methyl Morpholine Oxide
Methyl Morpholine Oxide
Methyl Morpholine Oxide is used as a solvent for paints, varnishes, lacquers, printing ink, and pharmaceuticals, among other applications
Methyl Morpholine Oxide is also used as a reagent in synthetic organic chemistry and commercially for the swelling and dissolution of cellulose.
Methyl Morpholine 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 Methyl Morpholine Oxide:
Painting (Pigments, Binders, and Biocides)
Plastic Composites Manufacturing
Textiles (Fiber & Fabric Manufacturing)
Working with Glues and Adhesives
Methyl Morpholine Oxide is a solvent for cellulose to produce fiber. N-methylmorpholine oxide a heterocyclic amine oxide and morpholine derivative
The process of Methyl Morpholine Oxide is considered to be the most environmentally friendly method of producing regenerated cellulose fibers on a commercial scale.
The use of Methyl Morpholine 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 Methyl Morpholine 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: N-methylmorpholine 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
Methyl Morpholine Oxide, monohydrate
CAS names
Morpholine, 4-methyl-, 4-oxide
IUPAC names
Methyl Morpholine Oxide monohydrate
4-methyl-morpholine, 4-oxide
Methyl Morpholine Oxide
N-methylmorpholine 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, Methyl Morpholine Oxide is the only such compound known that has the ability to solvate cellulose for downstream utilization in fiber production.
Methyl Morpholine Oxide is an integral component of the Lyocell process used for such previously mentioned purposes.
The highly polar nature of Methyl Morpholine Oxide provides an excellent solvent for disruption of the extensive hydrogen-bonded network formed by carbohydrate polymers.
Methyl Morpholine 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
Methyl Morpholine 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.
Methyl Morpholine Oxide is known to change the highly crystalline structure of cellulose after its dissolution and regeneration
Methyl Morpholine 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
Methyl Morpholine 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
Methyl Morpholine 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 Methyl Morpholine Oxide:
Non-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
Pure Methyl Morpholine Oxide is a solid at ambient temperatures, so solutions are made at elevated temperature with addition of some water.
Methyl Morpholine 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.
Methyl Morpholine Oxide is commercially supplied both as a monohydrate C5H11NO2·H2O and as the anhydrous compound.
Methyl Morpholine Oxide monohydrate is used as a solvent for cellulose in the lyocell process to produce cellulose fibers.
Methyl Morpholine Oxide is available commercially also as the monohydrate; it has a melting point of 70 °C, and is stable under normal conditions.
Methyl Morpholine Oxide is soluble in polar solvents, especially water.
Methyl Morpholine Oxide displays characteristic reactivity with various transition metals, which undergo oxidation with this reagent.
As a result, Methyl Morpholine Oxide is a preferred stoichiometric oxidant for transition metal-catalyzed oxidations.
USES OF Methyl Morpholine Oxide
Liquid Methyl Morpholine Oxide is a colorless, flammable organic liquid. It has a strong odor similar to gasoline.
The Methyl Morpholine 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 Methyl Morpholine Oxide is a crystalline solid and is also known as morpholine.
Solid Methyl Morpholine Oxide is used in the synthesis of 4-Methylmorpholine 4-oxide (NMMO) which has applications in pharmaceuticals, research chemicals, pesticides, etc.
Methyl Morpholine Oxide monohydrate is used as a solvent in the lyocell process to produce lyocell fiber.
Methyl Morpholine 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 Methyl Morpholine 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.
Methyl Morpholine 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 Methyl Morpholine 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 Methyl Morpholine 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 Methyl Morpholine Oxide
Methyl Morpholine 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
Methyl Morpholine Oxide, as an N-oxide, is an oxidant.
Methyl Morpholine 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 Methyl Morpholine 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.
PRODUCTION OF 4-Methylmorpholine 4-oxide
PATENT NO: US5216154A
SUMMARY OF THE INVENTION
It has been surprisingly discovered in accordance with the present invention that when N-methylmorpholine is reacted with aqueous hydrogen peroxide in an atmosphere of carbon dioxide in the absence of other additive materials, there is a substantially quantitative conversion of the N-methylmorpholine to Methyl Morpholine Oxide and the product will contain less than about 25 parts per billion of nitrosamine contaminants
WHAT IS LYOCELL PROCESS?
NMMO PROCESS= 4-Methylmorpholine 4-oxide PROCESS
One of the main alternatives for the production of cellulose fibres is the NMMO process (N-methyl-morpholine-N-oxide), also called the Lyocell process, developed since the 1960s and commercialized in 1992 by Courtaulds in Mobile, Alabama, USA.
Earlier the research team of Franks and Varga, which was involved in studies on the manufacture of cellulose fibres based on amines, found that aqueous solutions of NMMO have excellent cellulose-dissolving properties and cellulose can be recovered from these solutions in the form of fibres by dilution with water.
The NMMO process consists of three steps:
1.Production of homogeneous solution from cellulose pulp, NMMO and water, e.g. cellulose pulp with concentration of 13 wt% is dissolved in the Methyl Morpholine Oxide (67 wt%) containing approximately 20 wt% of water. The water is removed during dissolving.
2.The fibre forming process – the solution is filtered and passed through spinnerets to make the filaments, which are spun into water.
3. Recovery of NMMO from the regenerating and washing bath – NMMO solvent is recovered from this aqueous solution to 99.5% and reused.
The technology of cellulose fibres based on NMMO as a direct solvent of cellulose.
It has been found that dissolution of cellulose in NMMO depends on the temperature and the content of water in the system
The NMMO technology is fully ecological and environmentally friendly, with no effluents or gases emitted to the atmosphere.
Lyocell fibres are characterized by high crystallinity, high orientation, low lateral hold between fibres, relatively large pore volume and high tenacity ranging from 35 to 42 cN/tex.
They are an excellent raw material for the manufacture of clothing, technical textiles and sanitary products
Despite many advantages, the NMMO process has not replaced the viscose process up to now.
The main reason is the fibrillation of fibres manufactured by this method, which occurs with stress along the fibre axis in the wet state, imposing limitations on the use of the method in textile manufacture.
However, such a tendency to fibrillation can be utilized in the technical textiles sector for manufacture of non-wovens, filters and special papers.
Fibrillation improves filtration efficiency, air permeability, tear strength and opacity.
Although fibrillation could be used for creating attractive effects in the production of textiles, there is still a challenge to the product manufacturers to eliminate this problem.
Many research centres try to modify Lyocell fibres to eliminate their susceptibility to fibrillation.
Modifications include enzymatic treatment, alkali and urea treatment and cross-linking.
Urea and Alkali treatment of NMMO-type woven fabrics
While the untreated fabrics show no fibrillation, by increasing the concentration of urea or alkali a very slight formation of microfibrils can be identified for both treatments.
Due to cross-linking, Courtaulds, Lenzing AG and Akzo-Nobel developed a Tencel A100 fibre with fibrillation reduced to a minimum.
Modification of the Lyocell-type fibres was also conducted by the Thuringian Institute of Textile and Plastics Research in Rudolstadt (Germany), resulting in production of fibres with bactericidal properties under the trade name Alceru Silver.
The Man-made Fibres Department at the Technical University of Łódz (Poland) studied the possibility of reducing the susceptibility of the fibres to fibrillation by modification of the fibre structure during the spinning process.
Modification was based on incorporating cationic, anionic or non-ionic surface-active modifiers into the spinning solution or the coagulating bath.
Additionally, a low molecular weight polyethylene or high molecular weight poly(ethylene oxide) was also added to the spinning solution.
The fibres obtained were characterized by different mechanical characteristics, moisture absorption and susceptibility to fibrillation, as well as a wide range of porosity
The Methyl Morpholine Oxide (NMMO) Process of Producing Regenerated Fibers
Regenerated Cellulose Fibers
Narendra Reddy & Yiqi Yang
Chapter
First Online: 25 October 2014
Abstract
The NMMO process is considered to be the most environmentally friendly method of producing regenerated cellulose fibers on a commercial scale.
Regenerated cellulose fibers generally called “lyocell” (Lenzing) and also available in trade names such as “New Cell” (Akzo Nobel) and “Tencel” (Courtaulds) are regenerated cellulose fibers that are commercially available and are claimed to have considerable advantages over the traditional regenerated cellulose fibers produced through the viscose or cuprammonium process.
Schematics of the steps involved in the dissolution, production, and regeneration of the fibers are shown in Figs. 18.1 and 18.2.
It has been well documented that the properties of the fibers produced using the NMMO process can be varied to a large extent by controlling the spinning parameters such as type of solvent, extrusion speed, air gap distance, coagulation conditions, etc. [00Dre, 01Fin].
Similarly, post-fiber treatments such as solvent exchange during precipitation from methanol to water or posttreatment with hot water and aqueous NaOH changes the crystallinity, fibrillar structure, and therefore fiber properties [01Fin].
Changes in the tensile properties and fibrillation of the fibers with varying air gap distance and conditions in the air gap are given in Table 18.1.
As seen in the table, elongation and fibrillation index are affected by the spinning conditions to a greater extent than the tenacity or modulus because of the changes in the orientation and crystallinity of the fibers.
Similar changes in fiber properties were observed when the concentration of cellulose or % water in the solution was changed as seen in Table 18.2.
Lower concentration of cellulose will allow the fibers to relax leading to lower tensile properties but less fibrillation [96Mor1].
Morphologically, fibers obtained through the NMMO process have a circular cross section compared to the irregular cross section seen in conventional viscose-type fibers.
Cite this chapter
Reddy, N., Yang, Y. (2015). The Methyl Morpholine Oxide (NMMO) Process of Producing Regenerated Fibers. In: Innovative Biofibers from Renewable Resources. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45136-6_18
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DOI
https://doi.org/10.1007/978-3-662-45136-6_18
Original Research
Open Access
Published: 15 September 2021
On the role of Methyl Morpholine Oxide (NMMO) in the generation of elemental transition metal precipitates in cellulosic materials
Thomas Rosenau, Antje Potthast, Hubert Hettegger, Markus Bacher, Martina Opietnik, Thomas Röder & Immanuel Adorjan
Cellulose volume 28, pages10143–10161 (2021)Cite this article
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Abstract
Several literature reports describe the role of aqueous solutions of Methyl Morpholine Oxide monohydrate (NMMO) as a suitable medium for the generation of transition metal (nano)particles in or on cellulosic materials and further elaborate its role as a co-reactant of the transition metal salts that are reduced to the elemental metal.
However, this would assign NMMO the role of a reductant, which is in contradiction of its obvious oxidative nature.
In the present study, the exemplary cases of silver, gold, and platinum salts as the precursors of the respective metal (nano)particles in aqueous NMMO/cellulose mixtures were investigated. Naturally, NMMO did not act as a reducing agent in any case—this role was taken over by the frequently used NMMO stabilizer propyl gallate, or by cellulose itself, into which carbonyl and carboxyl groups were introduced.
Also, hypochlorite—produced intermediately from chloride ions and subsequently undergoing disproportionation into chloride and chlorate—or transient N-methylene(morpholinium) ions generated from NMMO, which are in turn oxidized to formyl morpholide, can act as the corresponding reductants while the metal ions are reduced, depending on the reaction conditions.
Apart from providing interesting mechanistic insights, the study points to the importance of a precise description of the composition of the chemical systems used, as well as the importance of seemingly inert auxiliaries, which turned out to be essential co-reactants in the metal (nano)particle generation.
The Methyl Morpholine Oxide (NMMO) Process of Producing Regenerated Fibers
October 2015
DOI:10.1007/978-3-662-45136-6_18
In book: Innovative Biofibers from Renewable Resources (pp.65-71)
Authors:
Narendra Reddy
Center for Incubation, Innovation, Research and Consultancy
Yang Yiqi
Yangtze University
The NMMO process is considered to be the most environmentally friendly method of producing regenerated cellulose fibers on a commercial scale.
Regenerated cellulose fibers generally called “lyocell” (Lenzing) and also available in trade names such as “New Cell” (Akzo Nobel) and “Tencel” (Courtaulds) are regenerated cellulose fibers that are commercially available and are claimed to have considerable advantages over the traditional regenerated cellulose fibers produced through the viscose or cuprammonium process.
Schematics of the steps involved in the dissolution, production, and regeneration of the fibers are shown in Figs. 18.1 and 18.2.
It has been well documented that the properties of the fibers produced using the NMMO process can be varied to a large extent by controlling the spinning parameters such as type of solvent, extrusion speed, air gap distance, coagulation conditions, etc. [00Dre, 01Fin]. Similarly, post-fiber treatments such as solvent exchange during precipitation from methanol to water or posttreatment with hot water and aqueous NaOH changes the crystallinity, fibrillar structure, and therefore fiber properties [01Fin].
Changes in the tensile properties and fibrillation of the fibers with varying air gap distance and conditions in the air gap are given in Table 18.1.
As seen in the table, elongation and fibrillation index are affected by the spinning conditions to a greater extent than the tenacity or modulus because of the changes in the orientation and crystallinity of the fibers.
Similar changes in fiber properties were observed when the concentration of cellulose or % water in the solution was changed as seen in Table 18.2.
Lower concentration of cellulose will allow the fibers to relax leading to lower tensile properties but less fibrillation [96Mor1].
Morphologically, fibers obtained through the NMMO process have a circular cross section compared to the irregular cross section seen in conventional viscose-type fibers.
Synonyms:
4- methyl morpholine 4-oxide monohydrate
4- methyl morpholine N-oxide
4- methyl-4-oxidomorpholin-4-ium
4- methylmorpholine 4-oxide
4- methylmorpholine 4-oxide monohydrate
4- methylmorpholine 4-oxide, monohydrate
4- methylmorpholine N-oxide
N- methylmorpholine oxide
4- methylmorpholine-4-oxide
morpholine, 4-methyl-, 4-oxide
4-Methylmorpholine N-oxide Chemical Properties,Uses,Production
Chemical Properties
Clear colorless to yellow solution
Uses
4-Methylmorpholine N-Oxide is a metabolite of Morpholine (M723725). 4-Methylmorpholine 4-oxide is commonly used to dissolve cellulose as well as in the dissolution of of scleroproteins.
Uses
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.
Uses
Non-metallic catalyst for the cyanosilylation of ketones. Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.
General Description
4-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. Lyocell, a regenerated cellulose fiber, can be prepared using 4-methylmorpholine?N-oxide in an eco-friendly manner.
Flammability and Explosibility
Flammable
Purification Methods
When the oxide is dried for 2-3hours at high vacuum, it dehydrates. Add MeOH to the oxide and distil off the solvent under vacuum until the temperature is ca 95o. Then add Me2CO at reflux and cool to 20o. The crystals are filtered off, washed with Me2CO and dried. The degree of hydration may vary and may be important for the desired reactions. [van Rheenan et al. Tetrahedron Lett 1973 1076, Schneider & Hanze US Pat 2 769 823; see also Sharpless et al. Tetrahedron Lett 2503 1976.]