Ammonium formate

Description

Ammonium formate, NH₄HCO₂, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.

Description

Ammonium formate (NH4HCO2) can effectively function as a hydrogen transfer agent in the presence of Pd/C for the reduction of alkenes.

Chemical properties

colourless crystals

Physical properties

White monoclinic deliquescent crystals or granules; density 1.280 g/cm³; melts at 116°C; highly soluble in water (102 g/100 g at 0°C), solubility rapidly increasing with temperature (i.e., 531 g/100 g at 80°C); soluble in liquid ammonia, alcohol and ether.

The Uses of Ammonium formate

Ammonium formate is widely used in various organic reactions like Leuckart reaction which involves the reductive amination of aldehydes and ketones. It serves as a buffer in high performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC/MS). It finds application in palladium on carbon (Pd/C) reduction of functional groups. For example, reduction of alkenes to alkanes and formaldehyde to methanol. It is also used to prepare formic acid insitu as well as used to store formic acid by making it as an ammonium salt.

The Uses of Ammonium formate

A 250 mL flask was charged with the SM (3.7 g, 19 mmol), ammonium formate (14 g, 190 mmol), and Pd/C (8.6%, 0.32 g) in MeOH (150 mL). After all the ammonium formate was dissolved, the reaction flask was evacuated and flushed with N2. The reaction mixture was stirred under inert atmosphere (N2) at RT overnight. The mixture was filtered through celite, concentrated in vacuo, diluted with 2M NaOH (ca pH 10), and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), and concentrated to provide the crude product which was taken forward without further purification. [3.1 g, 83%, 85:15 α:β]

The Uses of Ammonium formate

In chemical analysis, especially to ppt base metals from salts of the "noble" metals.

The Uses of Ammonium formate

Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry. Formic acid can also be obtained by reacting ammonium formate with a dilute acid, and since ammonium formate is also produced from formic acid, it can serve as a way of storing formic acid.
Ammonium formate can also be used in palladium on carbon (Pd / C) reduction of functional groups. In the presence of Pd / C, ammonium formate decomposes to hydrogen, carbon dioxide, and ammonia.
Ammonium formate can be used for reductive amination of aldehydes and ketones (Leuckart reaction)
Ammonium formate can be used as a buffer in high performance liquid chromatography (HPLC), and is suitable for use with liquid chromatography/mass spectrometry (LC/MS). .

What are the applications of Application

Ammonium formate is a buffer component for glycosaminoglycan purification

What are the applications of Application

Ammonium formate solution is 10 M, a buffer component for purification of glycosaminoglycans

Definition

ChEBI: The ammonium salt of formic acid.

Reactions

When heated, ammonium formate eliminates water, forming formamide. Upon further heating it forms to HCN and H₂O. A side reaction of this is the decomposition of formamide to CO and NH₃.

General Description

White solid with a weak odor of ammonia. Sinks and mixes slowly with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

Salts, basic, such as Ammonium formate, are generally soluble in water. The resulting solutions contain moderate concentrations of hydroxide ions and have pH's greater than 7.0. They react as bases to neutralize acids. These neutralizations generate heat, but less or far less than is generated by neutralization of the bases in reactivity group 10 (Bases) and the neutralization of amines. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Health Hazard

Inhalation causes irritation of nose and throat. Ingestion irritates mouth and stomach. Contact with eyes or skin causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Toxic and irritating ammonia and formic acid gases may form in fire.

Flammability and Explosibility

Not classified

Safety Profile

Moderately toxic by ingestion andintravenous routes. When heated to decomposition itemits toxic fumes of NOx and NH3.

Purification Methods

Heat the solid in NH3 vapour and dry it in a vacuum till the NH3 odour is faint (note that it can evaporate completely in a vacuum). Recrystallise it from absolute EtOH and then keep it in a desiccator over 99% H2SO4 in vacuo. It is very hygroscopic. It exists in two forms, stable needles and less stable plates. It also forms acid salts, i.e. HCO2NH4.3HCO2H and HCO2NH4.HCO2H. [Kensall & Adler J Am Chem Soc 43 1473 1921, Beilstein 2 IV 18.]