Ammonium formate

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Ammonium formate
Skeletal formula of ammonium formate
Ball-and-stick model of ammonium formate
Names
IUPAC name
Ammonium formate
Identifiers
540-69-2 YesY
ChemSpider 10442 YesY
Jmol-3D images Image
Image
PubChem 2723923
RTECS number BQ6650000
Properties
CH5NO2
Molar mass 63.06 g·mol−1
Appearance White monoclinic crystals, deliquescent
Odor Slightly ammoniac
Density 1.26 g/cm3[1]
Melting point 116 °C (241 °F; 389 K)
Boiling point 180 °C (356 °F; 453 K)
decomposes[2]
102 g/100 mL (0 °C)
142.7 g/100 mL (20 °C)
202.4 g/100 mL (40 °C)
516 g/100 mL (80 °C)[2]
Solubility in other solvents Soluble in liquid ammonia, alcohol, diethyl ether[2]
Thermochemistry
−556.18 kJ/mol
Hazards
MSDS JT Baker MSDS
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[1]
GHS signal word Warning
H315, H319, H335[1]
P261, P305+351+338[1]
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
410 mg/kg (mice, intravenous)[2]
Except where noted otherwise, data is 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), by the following reaction:[3]

The Leuckart reaction scheme-.svg

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 hydrogen cyanide (HCN) and water. A side reaction of this is the decomposition of formamide to carbon monoxide (CO) and ammonia.

References[edit]

  1. ^ a b c d Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
  2. ^ a b c d http://chemister.ru/Database/properties-en.php?dbid=1&id=1071
  3. ^ Alexander, Elliot; Ruth Bowman Wildman (1948). "Studies on the Mechanism of the Leuckart Reaction". Journal of the American Chemical Society 70: 1187–1189. doi:10.1021/ja01183a091. 

External links[edit]

Media related to Ammonium formate at Wikimedia Commons