Ammonium cyanide
Encyclopedia
Ammonium cyanide is an unstable inorganic compound
Inorganic compound
Inorganic compounds have traditionally been considered to be of inanimate, non-biological origin. In contrast, organic compounds have an explicit biological origin. However, over the past century, the classification of inorganic vs organic compounds has become less important to scientists,...

 with the formula NH4CN.

Uses

Ammonium cyanide is generally used in organic synthesis. Being unstable, it is not shipped or sold commercially.

Preparation

Ammonium cyanide is prepared in solution by bubbling hydrogen cyanide into aqueous ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...

 at a low temperature
HCN + NH3(aq) → NH4CN(aq)


It may be prepared by the reaction of calcium cyanide
Calcium cyanide
Calcium cyanide is an inorganic compound with the formula Ca2. It is the calcium salt of hydrogen cyanide. At normal conditions, it appears as colorless crystals or white powder with characteristic odor of bitter almonds . Like other similar cyanides it is very toxic...

 and ammonium carbonate
Ammonium carbonate
Ammonium carbonate is a commercial salt with the chemical formula 2CO3. It is used when crushed as a smelling salt. It can be crushed when needed in order to revive someone who has fainted...

:
Ca(CN)2 + (NH4)2CO3 → 2 NH4CN + CaCO3

In dry state, ammonium cyanide is made by heating a mixture of potassium cyanide
Potassium cyanide
Potassium cyanide is an inorganic compound with the formula KCN. This colorless crystalline compound, similar in appearance to sugar, is highly soluble in water. Most KCN is used in gold mining, organic synthesis, and electroplating. Smaller applications include jewelry for chemical gilding and...

 or potassium ferrocyanide
Potassium ferrocyanide
Potassium ferrocyanide is the inorganic compound with formula K4[Fe6]•3H2O. It is the potassium salt of the coordination complex [Fe6]4-. This salt forms lemon-yellow monoclinic crystals.-Synthesis:...

 with ammonium chloride
Ammonium chloride
Ammonium chloride NH4Cl is an inorganic compound with the formula NH4Cl. It is a white crystalline salt that is highly soluble in water. Solutions of ammonium chloride are mildly acidic. Sal ammoniac is a name of natural, mineralogical form of ammonium chloride...

 and condensing the vapours into ammonium cyanide crystals:
KCN + NH4Cl → NH4CN + KCl

Reactions

Ammonium cyanide decomposes to ammonia and hydrogen cyanide; often forming a black polymer of hydrogen cyanide:
NH4CN → NH3 + HCN


It undergoes double decomposition reactions in solution with a number of metal salts. It reacts with glyoxal
Glyoxal
Glyoxal is an organic compound with the formula OCHCHO. This yellow colored liquid is the smallest dialdehyde . Its tautomer acetylenediol is unstable.-Production:...

 producting glycine
Glycine
Glycine is an organic compound with the formula NH2CH2COOH. Having a hydrogen substituent as its 'side chain', glycine is the smallest of the 20 amino acids commonly found in proteins. Its codons are GGU, GGC, GGA, GGG cf. the genetic code.Glycine is a colourless, sweet-tasting crystalline solid...

 (aminoacetic acid):
NH4CN + (CHO)2 → NH2CH2COOH + HCN


Reactions with ketones yield aminonitriles:
NH4CN + CH3COCH3 → NH2CH2CH2CH2CN + H2O

Toxicity

The solid or its solution is highly toxic. Ingestion can cause death. Exposure to the solid can be harmful as it decomposes to highly toxic hydrogen cyanide and ammonia.

Chemical Analysis

Elemental composition: H 9.15%, C 27.23%, N 63.55%.

Ammonium cyanide may be analyzed by heating the salt and trapping the decomposed products. hydrogen cyanide and ammonia in water at low temperatures. The aqueous solution is analyzed for cyanide ion by silver nitrate
Silver nitrate
Silver nitrate is an inorganic compound with chemical formula . This compound is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides...

 titrimetric method or an ionselective
electrode method; and ammonia is measured by titration
Titration
Titration, also known as titrimetry, is a common laboratory method of quantitative chemical analysis that is used to determine the unknown concentration of an identified analyte. Because volume measurements play a key role in titration, it is also known as volumetric analysis. A reagent, called the...

or electrode technique.
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