Chemical Properties
Clear colorless to yellow solution
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.
Uses
4-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 of scleroproteins.
Definition
ChEBI: N-methylmorpholine N-oxide is a morpholine N-oxide resulting from the oxidation of the amino group of N-methylmorpholine.
General Description
4-Methylmorpholine?
N-oxide is an organic compound used as a co-oxidant along with OsO
4 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
reaction suitability
reagent type: oxidant
Synthesis
A preparation method of N-methylmorpholine-N-oxide comprises the following steps: (1) adding the nano metal oxide into N-methyl morpholine (NMM) and mixing and stirring to uniformly mix the nano metal oxide with the NMM; (2) dropwise adding a hydrogen peroxide solution into a mixed solution of NMM and a catalyst; (3) raising the temperature to accelerate the reaction process; (4) and (4) filtering and distilling the solution prepared in the step (3) under reduced pressure to obtain the required NMMO solution. The method for preparing NMMO provided by the present disclosure has the advantages of a fast reaction rate, low reaction temperature, few byproducts, etc.
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.]
References
[1] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6498 - 6503
[2] Patent: EP1348692, 2003, A1. Location in patent: Page/Page column 6-7
[3] Journal of the American Chemical Society, 2003, vol. 125, # 10, p. 2868 - 2869
[4] Patent: EP1348692, 2003, A1. Location in patent: Page/Page column 7
[5] Patent: EP1348692, 2003, A1. Location in patent: Page/Page column 7
