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.
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.
^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.
^Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 1816. ISBN978-0-471-72091-1.
^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.
External links
Media related to Ammonium formate at Wikimedia Commons
May 14, 2023
ammonium, formate, nh4hco2, ammonium, salt, formic, acid, colorless, hygroscopic, crystalline, solid, namesiupac, name, identifierscas, number, model, jsmol, interactive, imageinteractive, imagechemspider, 10442, yecha, infocard, 959pubchem, 2723923rtecs, numb. Ammonium formate NH4HCO2 is the ammonium salt of formic acid It is a colorless hygroscopic crystalline solid Ammonium formate NamesIUPAC name Ammonium formateIdentifiersCAS Number 540 69 2 Y3D model JSmol Interactive imageInteractive imageChemSpider 10442 YECHA InfoCard 100 007 959PubChem CID 2723923RTECS number BQ6650000UNII 3801F9644E YCompTox Dashboard EPA DTXSID6029624InChI InChI 1S CH2O2 H3N c2 1 3 h1H H 2 3 1H3 YKey VZTDIZULWFCMLS UHFFFAOYSA N YInChI 1 CH2O2 H3N c2 1 3 h1H H 2 3 1H3Key VZTDIZULWFCMLS UHFFFAOYATSMILES O CO NC O O NPropertiesChemical formula C H 5N O 2Molar mass 63 056 g mol 1Appearance White monoclinic crystals deliquescentOdor Slightly ammoniacDensity 1 26 g cm3 1 Melting point 116 C 241 F 389 K Boiling point 180 C 356 F 453 K decomposes 2 Solubility in water 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 ThermochemistryStd enthalpy offormation DfH 298 556 18 kJ molHazardsGHS labelling Pictograms 1 Signal word WarningHazard statements H315 H319 H335 1 Precautionary statements P261 P305 P351 P338 1 NFPA 704 fire diamond 211Lethal dose or concentration LD LC LD50 median dose 410 mg kg mice intravenous 2 Safety data sheet SDS JT Baker MSDSExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Reductive amination 2 Uses 3 Reactions 4 References 5 External linksReductive amination EditAcetone 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 HCO2HUses EditPure 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 EditWhen 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 Edit a b c d Sigma Aldrich Co Ammonium formate Retrieved on 2014 06 10 a b c d Ammonium formate 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 Smith Michael B March Jerry 2007 March s Advanced Organic Chemistry 6th ed John Wiley amp Sons p 1816 ISBN 978 0 471 72091 1 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 External links Edit Media related to Ammonium formate at Wikimedia Commons Retrieved from https en wikipedia org w index php title Ammonium formate amp oldid 1122048287, wikipedia, wiki, book, books, library,
