Ammonium Acetate - Wikipedia

Ammonium acetate

Names
IUPAC name Ammonium ethanoate
Identifiers
CAS Number	631-61-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:62947 N
ChemSpider	11925 Y
ECHA InfoCard	100.010.149
EC Number	211-162-9
PubChem CID	517165
RTECS number	AF3675000
UNII	RRE756S6Q2 Y
UN number	3077
CompTox Dashboard (EPA)	DTXSID5023873
InChI InChI=1S/C2H4O2.H3N/c1-2(3)4;/h1H3,(H,3,4);1H3 YKey: USFZMSVCRYTOJT-UHFFFAOYSA-N Y InChI=1/C2H4O2.H3N/c1-2(3)4;/h1H3,(H,3,4);1H3Key: USFZMSVCRYTOJT-UHFFFAOYAY
SMILES O=C([O-])C.[N+H4]
Properties
Chemical formula	C2H7NO2
Molar mass	77.083 g·mol−1
Appearance	White solid crystals, deliquescent
Odor	Slightly acetic acid like
Density	1.17 g/cm3 (20 °C)[1] 1.073 g/cm3 (25 °C)
Melting point	113 °C (235 °F; 386 K)[4]
Solubility in water	102 g/100 mL (0 °C) 148 g/100 mL (4 °C)[1] 143 g/100 mL (20 °C) 533 g/100 mL (80 °C)
Solubility	Soluble in alcohol, SO2, acetone, liquid ammonia[2]
Solubility in methanol	7.89 g/100 mL (15 °C)[3][1] 131.24 g/100 g (94.2 °C)[2]
Solubility in dimethylformamide	0.1 g/100 g[2]
Acidity (pKa)	9.9
Basicity (pKb)	33
Magnetic susceptibility (χ)	-41.1·10−6 cm3/mol
Viscosity	21
Structure
Crystal structure	Orthorhombic
Thermochemistry
Std enthalpy offormation (ΔfH⦵298)	−615 kJ/mol[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
GHS labelling:[3]
Pictograms
Signal word	Warning
Hazard statements	H303, H316, H320, H333
Precautionary statements	P281, P335
NFPA 704 (fire diamond)	[3] 1 1 1
Flash point	136 °C (277 °F; 409 K)[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	386 mg/kg (mice, intravenous)[2]
Safety data sheet (SDS)	JT Baker
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Ammonium acetate, also known as spirit of Mindererus in aqueous solution, is a chemical compound with the formula NH4CH3CO2. It is a white, hygroscopic solid and can be derived from the reaction of ammonia and acetic acid. It is available commercially.[5]

History

[edit]

The synonym Spirit of Mindererus is named after R. Minderer, a physician from Augsburg.[6]

Uses

[edit]

It is the main precursor to acetamide:[7]

NH4CH3CO2 → CH3C(O)NH2 + H2O

It is also used as a diuretic.[5]

Buffer

[edit]

As the salt of a weak acid and a weak base, ammonium acetate is often used with acetic acid to create a buffer solution. Ammonium acetate is volatile at low pressures. Because of this, it has been used to replace cell buffers that contain non-volatile salts in preparing samples for mass spectrometry.[8] It is also popular as a buffer for mobile phases for HPLC with ELSD and CAD-based detection for this reason. Other volatile salts that have been used for this include ammonium formate.

When dissolving ammonium acetate in pure water, the resulting solution typically has a pH of 7, because the equal amounts of acetate and ammonium neutralize each other. However, ammonium acetate is a dual component buffer system, which buffers around pH 4.75 ± 1 (acetate) and pH 9.25 ± 1 (ammonium), but it has no significant buffer capacity at pH 7, contrary to common misconception.[9]

Other

[edit]

• a biodegradable de-icing agent.
• a catalyst in the Knoevenagel condensation and as a source of ammonia in the Borch reaction in organic synthesis.
• a protein precipitating reagent in dialysis to remove contaminants via diffusion.
• a reagent in agricultural chemistry for determination of soil CEC (cation exchange capacity) and determination of available potassium in soil wherein the ammonium ion acts as a replacement cation for potassium.
• part of Calley's method for lead artifact conservation

Food additive

[edit]

Ammonium acetate is also used as a food additive as an acidity regulator; INS number 264. It is approved for usage in Australia and New Zealand.[10]

Production

[edit]

Ammonium acetate is produced by the neutralization of acetic acid with ammonium carbonate or by saturating glacial acetic acid with ammonia.[11] Obtaining crystalline ammonium acetate is difficult on account of its hygroscopic nature.

References

[edit]

1. ^ a b c Pradyot, Patnaik (2003). Handbook of Inorganic Chemicals. The McGraw-Hill Companies, Inc. ISBN 0-07-049439-8.
2. ^ a b c d e "Ammonium acetate".
3. ^ a b c d "Safety Data Sheet of Ammonium Acetate" (PDF). tedia.com. Tedia Company Inc. 2011-08-12. Retrieved 2014-06-10.
4. ^ Davidson, Arthur W.; McAllister, Walter H. (1930). "Solutions of Salts in Pure Acetic Acid. Ii. Solubilities of Acetates1". Journal of the American Chemical Society. 52 (2): 507–519. doi:10.1021/ja01365a010. ISSN 0002-7863.
5. ^ a b Hosea Cheung; Robin S. Tanke; G. Paul Torrence. "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2. ISBN 978-3527306732.
6. ^ "Spirit of Mindererus". TheFreeDictionary.com. Retrieved 2023-06-07.
7. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses. 3: 3; Collected Volumes, vol. 1, p. 3.
8. ^ Berman, Elena S. F.; Fortson, Susan L.; Checchi, Kyle D.; Wu, Ligang; Felton, James S.; Kuang Jen, J. Wu; Kulp, Kristen S. (2008). "Preparation of single cells for imaging/profiling mass spectrometry". J Am Soc Mass Spectrom. 19 (8): 1230–1236. doi:10.1016/j.jasms.2008.05.006. PMID 18565760.
9. ^ Konermann, Lars (2017). "Addressing a Common Misconception: Ammonium Acetate as Neutral pH "Buffer" for Native Electrospray Mass Spectrometry". American Society for Mass Spectrometry. 28 (9): 1827–1835. Bibcode:2017JASMS..28.1827K. doi:10.1007/s13361-017-1739-3. PMID 28710594. S2CID 25294943. Retrieved 25 October 2022.
10. ^ Australia New Zealand Food Standards Code "Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
11. ^ Brannt, William (1914). A practical treatise on the manufacture of vinegar. Lancaster, PA: Henry Carey Baird & Co. pp. 316–317.

External links

[edit] Wikimedia Commons has media related to Ammonium acetate.

v t e Acetyl halides and salts of the acetate ion

AcOH He LiOAc Be(OAc)2Be4O(OAc)6 B(OAc)3B2O(OAc)4 AcOAcROAc NH4OAc AcOOH FAcFOAc Ne NaOAcNaH(OAc)2 Mg(OAc)2 Al(OAc)3ALSOLAl(OAc)2OHAl(OH)2OAcAl2SO4(OAc)4 Si P S ClAcClOAc Ar KOAc Ca(OAc)2 Sc(OAc)3 Ti(OAc)4 VO(OAc)3 Cr(OAc)2Cr(OAc)3 Mn(OAc)2Mn(OAc)3 Fe(OAc)2Fe(OAc)3 Co(OAc)2 Ni(OAc)2 CuOAcCu(OAc)2 Zn(OAc)2 Ga(OAc)3 Ge As(OAc)3 Se BrAcBrOAc Kr RbOAc Sr(OAc)2 Y(OAc)3 Zr(OAc)4 Nb Mo(OAc)2 Tc Ru2(OAc)4ClRu(OAc)3 Rh2(OAc)4 Pd(OAc)2 AgOAc Cd(OAc)2 In(OAc)3 Sn(OAc)2Sn(OAc)4 Sb(OAc)3 Te IAcIOAcI(OAc)3 Xe CsOAc Ba(OAc)2 * Lu(OAc)3 Hf Ta W Re Os Ir Pt(OAc)2 Au(OAc)3 Hg2(OAc)2Hg(OAc)2 TlOAcTl(OAc)3 Pb(OAc)2Pb(OAc)4 Bi(OAc)3 Po At Rn Fr Ra ** Lr Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og   * La(OAc)3 Ce(OAc)3 Pr(OAc)3 Nd(OAc)3 Pm Sm(OAc)3 Eu(OAc)3 Gd(OAc)3 Tb(OAc)3 Dy(OAc)3 Ho(OAc)3 Er(OAc)3 Tm(OAc)3 Yb(OAc)3 ** Ac(OAc)3 Th(OAc)4 Pa UO2(OAc)2 Np Pu Am Cm Bk Cf Es Fm Md No

v t e Ammonium salts
Inorganic salts	monatomic anions NH4F (NH4)2S NH4Cl (NH4)2Se NH4Br NH4I oxyanions NH4NO2 NH4NO3 (NH4)2CO3 (NH4)4UO2(CO3)2 (NH4)HCO3 NH4H2AsO4 NH4OCN (NH4)3PO4 (NH4)2HPO4 (NH4)H2PO4 (NH4PO4)n(OH)2 NH4NaHPO4 (NH4)2SO3 (NH4)2SO4 (NH4)Al(SO4)2·12H2O (NH4)2Fe(SO4)2·6H2O NH4Fe(SO4)2·12H2O NH4SO3NH2 (NH4)HSO4 (NH4)2S2O8 (NH4)2S2O3 NH4ClO3 NH4ClO4 NH4VO3 (NH4)2CrO4 (NH4)2Cr2O7 NH4MnO4 (NH4)3AsO4 NH4BrO4 (NH4)2MoO4 (NH4)6Mo7O24 (NH4)3Mo12PO40 NH4IO3 (NH4)2Ce(NO3)6 (NH4)8Ce2(SO4)8·4H2O (NH4)10H2W12O42·4H2O NH4ReO4 other anions NH4BF4 NH4N3 NH4CN NH4[Au(CN)2] (NH4)HF2 (NH4)2SeBr6 (NH4)3AlF6 NH4SbF6 NH4AsF6 (NH4)3CrF6 (NH4)3FeF6 (NH4)3GaF6 (NH4)2GeF6 (NH4)3InF6 NH4NbF6 (NH4)2PtF6 (NH4)2ReF6 (NH4)2SnF6 NH4TaF6 (NH4)2UF6 (NH4)3VF6 (NH4)SiF6 (NH4)HS NH4SCN (NH4)2ZnCl4 (NH4)2MoS4 NH4I3 (NH4)2PtBr6 (NH4)2SnBr6 (NH4)2TeCl6 (NH4)2IrCl6 (NH4)2OsCl6 (NH4)2PtCl6 (NH4)2ReCl6 (NH4)2PdCl6 (NH4)2PbCl6 (NH4)3RhCl6 (NH4)2SeCl6 (NH4)2SnCl6 (NH4)4[Fe(CN)6]
Organic salts	Aluminon Ammonium acetate Ammonium adipate Ammonium benzoate Ammonium bituminosulfonate Ammonium carbamate Ammonium citrate Ammonium diethyl dithiophosphate Ammonium ferric citrate Ammonium formate Ammonium fumarate Ammonium glutamate Ammonium lactate Ammonium lauryl sulfate Ammonium malate Ammonium nonanoate Ammonium oxalate Ammonium picrate Ammonium perfluorononanoate Ammonium propionate Ammonium thioglycolate Cupferron Ferric ammonium oxalate Murexide