Ammonium formate

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Ammonium formate
Skeletal formula of ammonium formate
Ball-and-stick model of ammonium formate
Ammonium-formate-xtal-packing-a-3x3x3-3D-sf.png
Names
IUPAC name
Ammonium formate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.959 Edit this at Wikidata
RTECS number
  • BQ6650000
UNII
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
fH298)
−556.18 kJ/mol
Hazards
Safety data sheet JT Baker MSDS
GHS pictograms GHS07: Harmful[1]
GHS Signal word Warning
GHS hazard statements
H315, H319, H335[1]
P261, P305+351+338[1]
NFPA 704 (fire diamond)
2
1
1
Lethal dose or concentration (LD, LC):
LD50 (median dose)
410 mg/kg (mice, intravenous)[2]
Except where otherwise noted, 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.

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 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]

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[]

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. ^ Jump up to: a b c d Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
  2. ^ Jump up to: a b c d http://chemister.ru/Database/properties-en.php?dbid=1&id=1071
  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: 1187–1189. doi:10.1021/ja01183a091.

External links[]

Media related to Ammonium formate at Wikimedia Commons

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