- Sodium methoxide
Sodium methoxide Identifiers CAS number PubChem ChemSpider UNII Jmol-3D images Image 1 Properties Molecular formula CH3NaO Molar mass 54.02 Appearance white solid Melting point
Hazards MSDS Oxford MSDS EU classification Harmful (Xn), Corrosive (C) (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Sodium methoxide is a chemical compound, with formula CH3ONa. This colourless solid, which is formed by the deprotonation of methanol, is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base.
Preparation and structure
Sodium methoxide is prepared by carefully treating methanol with sodium :
- 2 Na + 2 CH3OH → 2 CH3ONa + H2
The reaction is so exothermic that ignition is possible. The resulting solution, which is colorless, is often used as a source of sodium methoxide, but the pure material can be isolated by evaporation followed by heating to remove residual methanol. The solid hydrolyzes in water to give sodium hydroxide, and commercial samples are significantly contaminated with the hydroxide. The solid and especially solutions absorb carbon dioxide from the air, thus diminishing the effectiveness of the base.
The structure, and hence its basicity, of sodium methoxide in solution depends on the solvent. It is significantly stronger base in DMSO where it is more fully ionized and free of hydrogen bonding.
Sodium methoxide is a routine base in organic chemistry, applicable to the synthesis of numerous compounds, ranging from pharmaceuticals to agrichemicals. As a base, it is employed in dehydrohalogenations and aldol condensations. It is also a nucleophile for the production of methyl ethers. 
Sodium methoxide is used as an initiator of anionic addition polymerization with ethylene oxide, forming a polyether with high molecular weight. Biodiesel is prepared from vegetable oils and animal fats, that is, fatty acid triglycerides, by transesterification with methanol to give fatty acid methyl esters (FAMEs). This transformation is catalyzed by sodium methoxide.
- ^ E. Weiss, “Die Kristallstruktur des Natriummethylats” Zeitschrift fur Anorganische und Allgemeine Chemie 1964, volume 332, p. 197-203. doi:10.1002/zaac.19643320311
- ^ a b Y. El-Kattan, J. McAtee, B. Bessieres “Sodium Methoxide” in Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, 2006, New York. doi:10.1002/047084289X.rs089m.pub2. Article Online Posting Date: September 15, 2006.
- ^ Frederic Reverdin, "3,5-Dinitroanisolel", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0219 ; Coll. Vol. 1: 219
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sodium methoxide — natrio metilatas statusas T sritis chemija formulė CH₃ONa atitikmenys: angl. sodium methylate; sodium methoxide rus. метилат натрия; метоксид натрия ryšiai: sinonimas – natrio metoksidas … Chemijos terminų aiškinamasis žodynas
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Methoxide — Methoxides are organic salts and the simplest alkoxides. Sodium methoxide and potassium hydroxide have widespread use, though other variants such as lithium hydroxide, rubidium methoxide, caesium methoxide, and francium methoxide exist as well.… … Wikipedia
sodium — /soh dee euhm/, n. 1. Chem. a soft, silver white, metallic element that oxidizes rapidly in moist air, occurring in nature only in the combined state, and used in the synthesis of sodium peroxide, sodium cyanide, and tetraethyllead: a necessary… … Universalium
sodium borohydride — noun : a hygroscopic crystalline compound NaBH4 that is flammable but remarkably stable in air and decomposes readily in water only above room temperature or in the presence of acid to yield hydrogen and sodium metaborate, that is made in various … Useful english dictionary
methoxide — (ˈ)meth+ noun Etymology: meth + oxide : a binary compound of methoxyl; especially : a base formed from methanol by replacement of the hydroxyl hydrogen with a metal sodium methoxide NaOCH3 * * * /meth ok suyd, sid/, n. Chem. methylate (def. 1).… … Useful english dictionary
sodium methylate — Chem. a white, free flowing, flammable powder, CH3ONa, decomposed by water to sodium hydroxide and methyl alcohol: used chiefly in organic synthesis. Also called sodium methoxide. * * * … Universalium
sodium methylate — natrio metilatas statusas T sritis chemija formulė CH₃ONa atitikmenys: angl. sodium methylate; sodium methoxide rus. метилат натрия; метоксид натрия ryšiai: sinonimas – natrio metoksidas … Chemijos terminų aiškinamasis žodynas
sodium methylate — Chem. a white, free flowing, flammable powder, CH3ONa, decomposed by water to sodium hydroxide and methyl alcohol: used chiefly in organic synthesis. Also called sodium methoxide … Useful english dictionary
Méthanolate de sodium — Général Nom IUPAC méthanolate de sodium Synonymes m … Wikipédia en Français