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
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.959 Edit this at Wikidata
RTECS number
  • BQ6650000
UNII
  • InChI=1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3 checkY
    Key: VZTDIZULWFCMLS-UHFFFAOYSA-N checkY
  • InChI=1/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3
    Key: VZTDIZULWFCMLS-UHFFFAOYAT
  • O=CO.N
  • C(=O)O.N
Properties
CH5NO2
Molar mass 63.056 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]
(grams per 100g of water)102g(0 °C)
142.7 g (20 °C)
202.4 g (40 °C)
516 g (80 °C)[2]
Solubility in other solvents Soluble in liquid ammonia, alcohol, diethyl ether[2]
Thermochemistry
Std enthalpy of
formation
(ΔfH⦵298)
 −556.18 kJ/mol
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Warning
H315, H319, H335[1]
P261, P305+P351+P338[1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Lethal dose or concentration (LD, LC):
410 mg/kg (mice, intravenous)[2]
Safety data sheet (SDS) JT Baker MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ammonium formate, NH4HCO2, is the

crystalline solid
.

Reductive amination

Acetone can be transformed into isopropylamine as follows:[citation needed]

CH3C(O)CH3 + 2 HCO2− +NH4 → (CH3)2CHNHCHO + 2 H2O + NH3 + CO2
(CH3)2CHNHCHO + H2O → (CH3)2CHNH2 + HCO2H

Uses

Pure ammonium formate decomposes into

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, formaldehyde to methanol, and nitro compounds to amines.[3][4] Activated single bonds to heteroatoms can also be replaced by hydrogens (hydrogenolysis).

Ammonium formate can be used for

ketones (Leuckart reaction), by the following reaction:[5]

Ammonium formate can be used as a mobile phase additive in

liquid chromatography-mass spectrometry (LC/MS). The pKa
values of formic acid and the ammonium ion are 3.8 and 9.2, respectively.

Reactions

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

  1. ^ a b c d Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
  2. ^ a b c d "Ammonium formate".
  3. hdl:2027.42/25034
    .
  4. ISBN 978-0-471-72091-1
    .
  5. PMID 18909189
    .

External links

Media related to Ammonium formate at Wikimedia Commons

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