Ammonium formate

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Ammonium formate
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Names
IUPAC name
Ammonium formate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.959 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • BQ6650000
UNII
  • InChI=1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3 Yes check.svgY
    Key: VZTDIZULWFCMLS-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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 solventsSoluble in liquid ammonia, alcohol, diethyl ether [2]
Thermochemistry
−556.18 kJ/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [1]
Warning
H315, H319, H335 [1]
P261, P305+P351+P338 [1]
NFPA 704 (fire 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

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 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.

Related Research Articles

<span class="mw-page-title-main">Ammonia</span> Chemical compound (NH3)

Ammonia is an inorganic compound of nitrogen and hydrogen with the formula NH3. A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous waste, particularly among aquatic organisms, and it contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to 45 percent of the world's food and fertilizers. Around 70% of ammonia is used to make fertilisers in various forms and composition, such as urea and Diammonium phosphate. Ammonia in pure form is also applied directly into the soil.

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline; see Category:Amines for a list of amines. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

Urea, also known as carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

<span class="mw-page-title-main">Formic acid</span> Simplest carboxylic acid (HCOOH)

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

<span class="mw-page-title-main">Ammonium bicarbonate</span> Chemical compound

Ammonium bicarbonate is an inorganic compound with formula (NH4)HCO3. The compound has many names, reflecting its long history. Chemically speaking, it is the bicarbonate salt of the ammonium ion. It is a colourless solid that degrades readily to carbon dioxide, water and ammonia.

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.

<span class="mw-page-title-main">Ammonium carbonate</span> Chemical used as leavening agent and smelling salt

Ammonium carbonate is a salt with the chemical formula (NH4)2CO3. Since it readily degrades to gaseous ammonia and carbon dioxide upon heating, it is used as a leavening agent and also as smelling salt. It is also known as baker's ammonia and was a predecessor to the more modern leavening agents baking soda and baking powder. It is a component of what was formerly known as sal volatile and salt of hartshorn, and produces a pungent smell when baked.

<span class="mw-page-title-main">Formamide</span> Chemical compound

Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.

Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.

Adams' catalyst, also known as platinum dioxide, is usually represented as platinum(IV) oxide hydrate, PtO2•H2O. It is a catalyst for hydrogenation and hydrogenolysis in organic synthesis. This dark brown powder is commercially available. The oxide itself is not an active catalyst, but it becomes active after exposure to hydrogen whereupon it converts to platinum black, which is responsible for reactions.

Palladium on carbon, often referred to as Pd/C, is a form of palladium used as a catalyst. The metal is supported on activated carbon to maximize its surface area and activity.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

The Leuckart reaction is the chemical reaction that converts aldehydes or ketones to amines by reductive amination in the presence of heat. The reaction, named after Rudolf Leuckart, uses either ammonium formate or formamide as the nitrogen donor and reducing agent. It requires high temperatures, usually between 120 and 130 °C; for the formamide variant, the temperature can be greater than 165 °C.

<span class="mw-page-title-main">Benzylamine</span> Chemical compound

Benzylamine is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). It consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. This colorless water-soluble liquid is a common precursor in organic chemistry and used in the industrial production of many pharmaceuticals. The hydrochloride salt was used to treat motion sickness on the Mercury-Atlas 6 mission in which NASA astronaut John Glenn became the first American to orbit the Earth.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

<span class="mw-page-title-main">1-Phenylethylamine</span> Chemical compound

1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. Classified as a primary amine, this colorless liquid is often used in chiral resolutions. Like benzylamine, it is relatively basic and forms stable ammonium salts and imines.

<span class="mw-page-title-main">Ammonium cyanide</span> Chemical compound

Ammonium cyanide is an unstable inorganic compound with the formula NH4CN.

<span class="mw-page-title-main">Ammonium thiocyanate</span> Chemical compound

Ammonium thiocyanate is an inorganic compound with the formula NH4SCN. It is the salt of the ammonium cation and the thiocyanate anion.

<span class="mw-page-title-main">Ammonium carbamate</span> Chemical compound

Ammonium carbamate is a chemical compound with the formula [NH4][H2NCO2] consisting of ammonium cation NH+4 and carbamate anion NH2COO. It is a white solid that is extremely soluble in water, less so in alcohol. Ammonium carbamate can be formed by the reaction of ammonia NH3 with carbon dioxide CO2, and will slowly decompose to those gases at ordinary temperatures and pressures. It is an intermediate in the industrial synthesis of urea (NH2)2CO, an important fertilizer.

<span class="mw-page-title-main">Formetorex</span> Chemical compound

Formetorex (INN), also known as formetamide or N-formylamphetamine, is a substituted amphetamine described as an anorectic which does not appear to have ever been marketed.

References

  1. 1 2 3 4 Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
  2. 1 2 3 4 "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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