:Ammonium formate
{{chembox
| Watchedfields = changed
| verifiedrevid = 448768519
| ImageFile = Ammonium-formate-2D.png
| ImageSize = 160px
| ImageName = Skeletal formula of ammonium formate
| ImageFile1 = Ammonium-formate-3D-balls.png
| ImageSize1 = 160px
| ImageName1 = Ball-and-stick model of ammonium formate
| ImageFile2 = Ammonium-formate-xtal-packing-a-3x3x3-3D-sf.png
| IUPACName = Ammonium formate
| OtherNames =
|Section1={{Chembox Identifiers
| InChI = 1/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3
| InChIKey = VZTDIZULWFCMLS-UHFFFAOYAT
| SMILES1 = C(=O)O.N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VZTDIZULWFCMLS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 540-69-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3801F9644E
| PubChem = 2723923
| RTECS = BQ6650000
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=10442
| SMILES = O=CO.N
}}
|Section2={{Chembox Properties
| N=1 | H=5 | C=1 | O=2
| Appearance = White monoclinic crystals, deliquescent
| Odor = Slightly ammoniac
| MeltingPtC = 116
| BoilingPtC = 180
| BoilingPt_notes =
decomposes{{Cite web|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=1071|title = Ammonium formate}}
| Solubility = (grams per 100g of water)102g(0 °C)
142.7 g (20 °C)
202.4 g (40 °C)
516 g (80 °C)
| SolubleOther = Soluble in liquid ammonia, ethanol, diethyl ether
| Solvent = other solvents
| pKa =
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −556.18 kJ/mol
}}
|Section4={{Chembox Hazards
| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/f6018.htm JT Baker MSDS]
| GHSPictograms = {{GHS07}}{{Sigma-Aldrich|aldrich|id=516961|name=Ammonium formate|accessdate=2014-06-10}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 1
| LD50 = 410 mg/kg (mice, intravenous)
}}
}}
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|date=May 2015}}
: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.{{ cite journal | journal = Tetrahedron Lett. | volume = 25 | issue = 32 | year = 1984 | pages = 3415–3418 | title = A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent | first1 = Siya | last1 = Ram | first2 = Richard E. | last2 = Ehrenkaufer | doi = 10.1016/S0040-4039(01)91034-2 | hdl = 2027.42/25034 | hdl-access = free }}{{cite book | first1 = Michael B. | last1 = Smith | first2 = Jerry | last2 = March | title = March's Advanced Organic Chemistry | publisher = John Wiley & Sons | year = 2007 | edition=6th | isbn = 978-0-471-72091-1 | page = 1816 }} 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:{{cite journal|last = Alexander|first = Elliot|author2=Ruth Bowman Wildman |title = Studies on the Mechanism of the Leuckart Reaction|journal = Journal of the American Chemical Society|year = 1948|volume = 70|issue = 3|pages = 1187–1189|doi = 10.1021/ja01183a091|pmid = 18909189}}
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
{{reflist}}
External links
{{Commons category inline|Ammonium formate}}
{{Ammonium salts}}