Ammonium formate

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

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
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
−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 diamond
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 ?)
Infobox references

Reductive amination

Acetone can be transformed into isopropylamine as follows:

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

Uses

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, 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 reductive amination of aldehydes and ketones (Leuckart reaction), by the following reaction:[5]

Ammonium formate can be used as a mobile phase additive 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

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. Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
  2. "Ammonium formate".
  3. Ram, Siya; Ehrenkaufer, Richard E. (1984). "A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent". Tetrahedron Lett. 25 (32): 3415–3418. doi:10.1016/S0040-4039(01)91034-2. hdl:2027.42/25034.
  4. Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 1816. ISBN 978-0-471-72091-1.
  5. Alexander, Elliot; Ruth Bowman Wildman (1948). "Studies on the Mechanism of the Leuckart Reaction". Journal of the American Chemical Society. 70 (3): 1187–1189. doi:10.1021/ja01183a091. PMID 18909189.

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