Chemical Description

Sodium ethoxide is a white crystalline solid that is used as a strong base and as a reagent in organic synthesis.

Physical properties

White or yellowish powder; hygroscopic; darkens and decomposes on exposure to air; decomposes in water forming sodium hydroxide and ethanol; dissolves in absolute ethanol.

Preparation

Sodium ethoxide is prepared by reacting sodium with absolute ethanol: 2Na + 2C2H5OH → 2C2H5ONa + H2 Sodium in small quantities is added to absolute alcohol at 10°C. The temperature is raised to warming (to about 38°C). The mixture is cooled again and sodium and absolute alcohol are added gradually followed by careful warming. The process is repeated to obtain a sufficient yield of the p

Definition

ChEBI: An organic monosodium salt that has ethoxide as the counterion.

General Description

Sodium ethoxide is an alkoxide salt mainly used as a strong base in organic reactions such as deprotonation, dehydration and dehalogenation.

Hazard

As for caustic soda, ethanol. Sodium hydroxide is formed when sodium ethylate is exposed to moisture.

Flammability and Explosibility

Highlyflammable

Purification Methods

It is a hygroscopic powder which should be stored under N2 in a cool place. A likely impurity is EtOH which can be removed by warming at 60-80o under high vacuum. It is hydrolysed by H2O to yield NaOH and EtOH. Other impurities, if kept in air for long periods are NaOH and Na2CO3. In this case the powder cannot be used if these impurities affect the reactivity, and a fresh sample should be acquired [IR: Seubold J Org Chem 21 156 1956]. [Beilstein 1 H 311, 1 IV 1289.]