Ammonium formate

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Ammonium formate
Ammonium-formate-2D.png
Ball-and-stick model of the ammonium cation Ball-and-stick model of the formate anion
Identifiers
CAS number 540-69-2 YesY
PubChem 2723923
ChemSpider 10442 YesY
RTECS number BQ6650000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula NH4HCO2
Molar mass 63.0559 g/mol
Appearance white monoclinic crystals
deliquescent
Density 1.280 g/cm3
Melting point 116 °C
Boiling point decomposes
Solubility in water 102 g/100 mL (0 °C)
143 g/100 mL (20 °C)
531 g/100 mL (80 °C)
Solubility soluble in liquid ammonia, alcohol and diethyl ether
Hazards
MSDS JT Baker MSDS
GHS pictograms GHS-pictogram-exclam.svg[1]
GHS hazard statements H315, H319, H335[1]
GHS precautionary statements P261, P305+351+338[1]
R-phrases R36/37/38
S-phrases S26, S36
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
LD50 2250 mg/kg, oral (mouse)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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

Uses[edit]

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. This hydrogen gas is adsorbed onto the surface of the palladium metal, where it can react with various functional groups. For example, alkenes can be reduced to alkanes, or formaldehyde to methanol. Activated single bonds to heteroatoms can also be replaced by hydrogens (hydrogenolysis).

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). The pKa values of formic acid and the ammonium ion are 3.8 and 9.2, respectively.

Reactions[edit]

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.

References[edit]

  1. ^ a b c Sigma-Aldrich Co., Ammonium formate. Retrieved on 2013-07-20.