関: carbinol、methanol、methyl alcohol

WordNet

a light volatile flammable poisonous liquid alcohol; used as an antifreeze and solvent and fuel and as a denaturant for ethyl alcohol (同)methyl_alcohol, wood_alcohol, wood_spirit
a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11

PrepTutorEJDIC

=methyl alcohol
ソジウム,ナトリウム(金属元素;化学記号はNa)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/05 14:34:17」(JST)

wiki en

Sodium methoxide is a chemical compound with the 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 CH
3OH → 2 CH
3ONa + H
2

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 can be contaminated with the hydroxide. The solid and especially solutions absorb carbon dioxide from the air, thus diminishing the effectiveness of the base.

In the solid form, sodium methoxide is polymeric, with a sheet-like arrays of Na⁺ centers, each bonded to four oxygen centers.^[1]

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.^[2]

Applications

Organic synthesis

Sodium methoxide is a routine base in organic chemistry, applicable to the synthesis of numerous compounds, ranging from pharmaceuticals to agrichemicals.^[2] As a base, it is employed in dehydrohalogenations and various condensations.^[3] It is also a nucleophile for the production of methyl ethers.^[4]

Industrial applications

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.

Safety

Sodium methoxide is highly caustic, and the hydrolysis gives methanol, which is toxic and volatile.

NFPA 704

The ratings for this substance vary widely.

Rating	4 3 3	4 3 2	3 3 2	2 3 2	2 2 2
Source	State of Connecticut^[5]	DuPont^[6]	Pharmco AAPR^[7]	ScienceLab^[8](Both ratings on same sheet)

References

^ E. Weiss (1964). "Die Kristallstruktur des Natriummethylats" [The Crystal Structure of Sodium Methylate]. Zeitschrift für Anorganische und Allgemeine Chemie (in German) 332 (3–4): 197–203. doi:10.1002/zaac.19643320311.
^ ^a ^b Y. El-Kattan, J. McAtee, B. Bessieres (2006). "Sodium Methoxide". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rs089m.pub2.
^ O. E. Curtis, Jr., J. M. Sandri, R. E. Crocker, H. Hart (1958), "Dicyclopropyl ketone", Org. Synth. 38: 19, doi:10.15227/orgsyn.038.0019 ; Coll. Vol. 4: 278
^ F. Reverdin (1927), "3,5-Dinitroanisole", Org. Synth. 7: 28, doi:10.15227/orgsyn.007.0028 ; Coll. Vol. 1: 219
^ "The Code Officials Perspective".
^ "DuPont Material Safety Data Sheet".
^ "Pharmco AAPR Material Safety Data Sheet".
^ "ScienceLab Material Safety Data Sheet".

UpToDate Contents

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English Journal

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Schmid M1, Guihéneuf F2, Stengel DB3.
Food chemistry.Food Chem.2016 Oct 1;208:161-8. doi: 10.1016/j.foodchem.2016.03.123. Epub 2016 Apr 1.
This study evaluated the impact of different food- and non-food grade extraction solvents on yield and fatty acid composition of the lipid extracts of two seaweed species (Palmaria palmata and Laminaria digitata). The application of chloroform/methanol and three different food grade solvents (ethano
PMID 27132836

Simultaneous analysis of eight vitamin E isomers in Moringa oleifera Lam. leaves by ultra performance convergence chromatography.

Qi N1, Gong X2, Feng C3, Wang X4, Xu Y5, Lin L6.
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A new method for simultaneous determination of eight vitamin E isomers including α-, β-, γ-, and δ-tocopherol and α-, β-, γ-, and δ-tocotrienol by ultra-performance convergence chromatography (UPC(2)) equipped with a diode array detector was reported. They were separated on a BEH 2-EP column
PMID 27080892

Optimization extraction conditions for improving phenolic content and antioxidant activity in Berberis asiatica fruits using response surface methodology (RSM).

Belwal T1, Dhyani P1, Bhatt ID2, Rawal RS1, Pande V3.
Food chemistry.Food Chem.2016 Sep 15;207:115-24. doi: 10.1016/j.foodchem.2016.03.081. Epub 2016 Mar 23.
This study for the first time designed to optimize the extraction of phenolic compounds and antioxidant potential of Berberis asiatica fruits using response surface methodology (RSM). Solvent selection was done based on the preliminary experiments and a five-factors-three-level, Central Composite De
PMID 27080887

Japanese Journal

Optimization and Kinetic Studies on Biodiesel Production from Kusum (<i>Schleichera triguga</i>) Oil Using Response Surface Methodology

Journal of Oleo Science 64(9), 987-997, 2015
NAID 130005096011

Synthesis of 1,6'-Bi- and 1,6':3,6-Terazulenes from 1-Pyridyl- and 1,3-Di(pyridyl)azulenes by the Ziegler-Hafner Method

Chemistry letters 42(6), 638-640, 2013-06-05
NAID 10031176034

Synthesis of Linoleoyl Ethanolamide

Journal of Oleo Science 62(6), 427-433, 2013
NAID 130004436059

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★リンクテーブル★

リンク元	「ナトリウムメトキシド」「carbinol」

「ナトリウムメトキシド」

Sodium methoxide
	IUPAC name sodium methoxide
	Other names sodium methylate
Identifiers
CAS number	124-41-4
PubChem	10942334
ChemSpider	29033
UNII	IG663U5EMC
Jmol-3D images	Image 1
	SMILES [Na+].[O-]C ;
	InChI InChI=1S/CH3O.Na/c1-2;/h1H3;/q-1;+1 ; Key: WQDUMFSSJAZKTM-UHFFFAOYSA-N InChI=1/CH3O.Na/c1-2;/h1H3;/q-1;+1; Key: WQDUMFSSJAZKTM-UHFFFAOYAC ;
Properties
Molecular formula	CH3NaO
Molar mass	54.02
Appearance	white solid
Melting point	127 ºC
Boiling point	>300 °C
Solubility	soluble in ethanol, methanol, fats, esters; insoluble in hydrocarbons
Structure
Crystal structure	hexagonal
Hazards
EU classification	Harmful (Xn), Corrosive (C)
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references

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英: sodium methoxide
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「carbinol」

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カルビノール

関: methanol、methyl alcohol、sodium methoxide

[1] E. Weiss (1964). "Die Kristallstruktur des Natriummethylats" [The Crystal Structure of Sodium Methylate]. Zeitschrift für Anorganische und Allgemeine Chemie (in German) 332 (3–4): 197–203. doi:10.1002/zaac.19643320311.

[eEROS-2] Y. El-Kattan, J. McAtee, B. Bessieres (2006). "Sodium Methoxide". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rs089m.pub2.

[3] O. E. Curtis, Jr., J. M. Sandri, R. E. Crocker, H. Hart (1958), "Dicyclopropyl ketone", Org. Synth. 38: 19, doi:10.15227/orgsyn.038.0019 ; Coll. Vol. 4: 278

[4] F. Reverdin (1927), "3,5-Dinitroanisole", Org. Synth. 7: 28, doi:10.15227/orgsyn.007.0028 ; Coll. Vol. 1: 219

[5] "The Code Officials Perspective".

[6] "DuPont Material Safety Data Sheet".

[7] "Pharmco AAPR Material Safety Data Sheet".

[8] "ScienceLab Material Safety Data Sheet".

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sodium methoxide