Sodium Ethoxide

Sodium ethoxide is the organic compound with the formula C2H5ONa. It is a colourless solid that dissolves in polar solvents. It is commonly used as a strong base. Its molecular weight is 68.05 and at melting point of 260 degree C it decomposes. Its specific gravity is 1.1 and is stable under ordinary conditions.

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Detailed Description for Sodium Ethoxide

Sodium ethoxide is the organic compound with the formula C2H5ONa. It is a colourless solid that dissolves in polar solvents. It is usually used as a strong base. It is typically prepared in a solution with ethanol. It is available commercially and as a solution in ethanol. It is simply prepared in the laboratory by treating sodium metal with absolute ethanol.

2 C2H5OH + 2 Na 2 C2H5ONa + H2

 

An alternative, cheaper route involves the reaction of sodium hydroxide with anhydrous ethanol. This reaction will suffer from incomplete conversion to the alkoxide, but for less stringent applications, full conversion is insignificant. The salt product is purified by precipitation in a solution of anhydrous acetone.

PHYSICAL AND CHEMICAL PROPERTIES 

PHYSICAL STATE

white to yellow powder

MELTING POINT 260 C (Decomposes)
BOILING POINT

 

SPECIFIC GRAVITY 1.1
SOLUBILITY IN WATER Reacts violently (miscible with methanol and ethanol)
pH

 

VAPOR DENSITY  
AUTOIGNITION

 

NFPA RATINGS Health: 3; Flammability: 2; Reactivity: 2

REFRACTIVE INDEX

 

FLASH POINT

32 C

STABILITY Stable underordinary conditions

 

Item

Indicator

Appearance

Light yellow viscous liquid

Content(Total alkali)

17.5%-21.0%

Sodium ethoxide(NaOCH3)

16.0%-21.0%

Sodium hydroxide(NaOH)

≤0.5%

Sodium carbonate(Na2CO3)

≤0.1%

Water(H2O)

≤0.2%

 

Uses:

Sodium ethoxide is commonly used in the Claisen condensation and malonic ester synthesis. Sodium ethoxide may either deprotonate the α-position of an ester molecule, forming an enolate, or the ester molecule may undergo a nucleophilic substitution called transesterification. If the starting material is an ethyl ester, trans-esterification is irrelevant since the product is identical to the starting material. In practice, the alcohol/alkoxide solvating mixture must match the alkoxy components of the reacting esters to minimize the number of different products.

Many alkoxides are prepared by salt metathesis from sodium ethoxide.

PHYSICAL AND CHEMICAL PROPERTIES 

APPEARANCE

white to yellow powder

MELTING POINT

260 degree C (Decomposes)

BOILING POINT

 

SPECIFIC GRAVITY

1.1

SOLUBILITY IN WATER

Reacts violently (miscible with methanol and ethanol)

pH

 

VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATING

Health: 3, Flammability: 2, Reactivity: 2

REFRACTIVE INDEX

 

FLASH POINT

32 degree C

STABILITY

Stable under ordinary conditions

 

Item

Indicator

Appearance

Light yellow viscous liquid

Content(Total alkali)

17.5%-21.0%

Sodium ethoxide(NaOCH3)

16.0%-21.0%

Sodium hydroxide(NaOH)

≤0.5%

Sodium carbonate(Na2CO3)

≤0.1%

Water(H2O)

≤0.2%

 

Uses:

Sodium ethoxide is generally used in the Claisen condensation and also in malonic ester synthesis. It either deprotonate the α-position of an ester molecule, forming an enolate or the ester molecule may undertake a nucleophilic substitution called transesterification. If the preliminary material is an ethyl ester, trans-esterification is irrelevant since the product is matching to the preliminary material. In practice, the alcohol or alkoxide solvating mixture should match the alkoxy components of the reacting esters to reduce the number of different products.

Many alkoxides are prepared by salt metathesis from sodium ethoxide.


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