Sodium ethanolate

Structural formula
General
Surname	Sodium ethanolate
other names	Sodium ethylate; Sodium ethoxide;
Molecular formula	C 2 H 5 NaO
Brief description	colorless to yellowish odorless hygroscopic powder
External identifiers / databases
EC number	205-487-5
ECHA InfoCard	100,004,989
PubChem	2723922
Wikidata	Q412779
properties
Molar mass	68.05 g · mol -1
Physical state	firmly
density	0.868 g cm −3
Melting point	260 ° C (with exclusion of oxygen)
solubility	Decomposes in water
safety instructions
H and P phrases	H: 228-251-314
	EUH: 014
	P: 210-235 + 410-280-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338
Toxicological data	598 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sodium ethanolate is a whitish to yellowish amorphous, hygroscopic powder with the empirical formula C ₂ H ₅ NaO from the group of alcoholates and is mostly used as a strong base.
Sodium ethanolate should not be confused with sodium methoxide ( empirical formula CH ₃ NaO).

Extraction and presentation

Sodium ethanolate is formed when ethanol reacts with sodium , releasing hydrogen:

{\ displaystyle \ mathrm {2 \ CH_ {3} CH_ {2} OH + 2 \ Na \ longrightarrow 2 \ CH_ {3} CH_ {2} ONa + H_ {2}}}

properties

Sodium ethanolate reacts violently with water, forming caustic soda and ethanol :

{\ displaystyle \ mathrm {CH_ {3} CH_ {2} ONa + H_ {2} O \ longrightarrow CH_ {3} CH_ {2} OH + NaOH (aq)}}

Violent reactions also occur with acids and some metals . When reacting with acids, the ethanolation is protonated to ethanol and the sodium salt is formed. Even water is sufficient as an acid .

At 30–50 ° C, sodium ethanolate ignites by itself in air.

use

Sodium ethoxide is used for the synthesis of numerous chemical compounds (e.g. as a catalyst in a Michael addition or as a reaction product for the formation of an ethyl ether according to the Williamson ether synthesis .) Esters are formed with carboxylic acid chlorides . It is also used for the production of metal oxide particles, ceramics, siloxanes and phosphates .

safety instructions

The caustic soda that is created with water, on damp skin or mucous membranes, makes the product extremely corrosive. There is a particular risk to the eyes (corneal damage) and the respiratory tract if dust is formed. The alcohol vapors produced when larger quantities decompose have an anesthetic effect and irritate the eyes, the nasal and throat mucous membranes. Sodium ethanolate also has a strong corrosive effect on dry skin, because the ethanolate is a significantly stronger base than sodium hydroxide solution and also more hydrophobic than this, so that it can more easily penetrate into more hydrophobic tissue and cause burns there.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on sodium ethoxide in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on sodium ethanolate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Entry on sodium ethoxide. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on sodium ethoxide in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.004.989-2] Entry on sodium ethanolate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[3] Entry on sodium ethoxide. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.