Ammonium acetate: Difference between revisions

|Verifiedfields=changed

|Watchedfields=changed

|verifiedrevid=444918095

|Name=Ammonium acetate

|ImageFile=Ammonium-acetate-2D.png

|ImageSize=200px

|ImageName=Ammonium acetate skeletal formula

|ImageFile1=Ammonium-acetate-3D-balls.png

|ImageSize1=200px

|ImageName1=Ball-and-stick model of ammonium acetate

|ImageFile2=Ammonium-acetate.JPG

|ImageSize2=200px

|ImageName2=Crystalline of ammonium acetate

|IUPACName=Ammonium ethanoate

|OtherNames=

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 631-61-8

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI=62947

| RTECS = AF3675000

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID=11925

| EC_number = 211-162-9

| PubChem=517165

| UNII_Ref = {{fdacite|correct|FDA}}

| UNNumber = 3077

| SMILES = O=C([O-])C.[N+H4]

|Section2={{Chembox Properties

| N=1 | H=7 | C=2 | O=2

| Appearance = White solid crystals, [[deliquescent]]

| Odor = Slightly acetic acid like

| Density = 1.17 g/cm³ (20 °C)<ref name=pphoic>{{cite book|last = Pradyot|first = Patnaik|year = 2003|title = Handbook of Inorganic Chemicals|publisher = The McGraw-Hill Companies, Inc.|isbn = 0-07-049439-8}}</ref><br> 1.073 g/cm³ (25 °C)

| SolubleOther = Soluble in [[ethanol|alcohol]], [[sulfur dioxide|SO₂]], [[acetone]], liquid [[ammonia]]<ref name=chemister />

| Solubility = 102 g/100 mL (0 °C)<br> 148 g/100 mL (4 °C)<ref name=pphoic /><br> 143 g/100 mL (20 °C)<br> 533 g/100 mL (80 °C)

| Solubility1 = 7.89 g/100 mL (15 °C)<ref name=tedia /><ref name=pphoic /><br> 131.24 g/100 g (94.2 °C)<ref name=chemister>{{Cite web|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=354|title=Ammonium acetate}}</ref>

| Solvent1 = methanol

| Solubility2 = 0.1 g/100 g<ref name=chemister />

| Solvent2 = dimethylformamide

| MeltingPtC = 113

| MeltingPt_ref =<ref>{{cite journal|last1=Davidson|first1=Arthur W.|last2=McAllister|first2=Walter H.|title=Solutions of Salts in Pure Acetic Acid. Ii. Solubilities of Acetates1|journal=Journal of the American Chemical Society|volume=52|issue=2|year=1930|pages=507–519|issn=0002-7863|doi=10.1021/ja01365a010}}</ref>

| BoilingPtC =

| BoilingPt_notes =

| pKa = 9.9

| pKb = 33

| Viscosity = 21

| MagSus = -41.1·10⁻⁶ cm³/mol

|Section3={{Chembox Structure

| CrystalStruct = [[Orthorhombic]]

|Section4={{Chembox Thermochemistry

| DeltaHf = −615 kJ/mol<ref name=chemister />

|Section7={{Chembox Hazards

| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/a5508.htm JT Baker]

| MainHazards = Irritant

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|303|316|320|333}}

| PPhrases = {{P-phrases|281|335}}

| GHS_ref = <ref name=tedia />

| NFPA-H = 1

| NFPA-F = 1

| NFPA-R = 1

| NFPA_ref = <ref name=tedia>{{cite web|url = http://reports.tedia.com/msds/M0009.pdf|title = Safety Data Sheet of Ammonium Acetate|date = 2011-08-12|website=tedia.com|publisher = Tedia Company Inc.|access-date = 2014-06-10}}</ref>

| FlashPtC = 136

| FlashPt_ref = <ref name=tedia />

| LD50 = 386 mg/kg (mice, intravenous)<ref name=chemister />

'''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.<ref name=Ullmann>{{Ullmann | author1 = Hosea Cheung | author2 = Robin S. Tanke | author3 = G. Paul Torrence | title = Acetic Acid | doi = 10.1002/14356007.a01_045.pub2}}</ref>

== History==

The synonym Spirit of Mindererus is named after R. Minderer, a physician from [[Augsburg]].<ref>{{Cite web |title=Spirit of Mindererus |url=https://www.thefreedictionary.com/Spirit+of+Mindererus |access-date=2023-06-07 |website=TheFreeDictionary.com}}</ref>

== Uses==

It is the main precursor to [[acetamide]]:<ref>{{ OrgSynth | author = Coleman, G. H. |author2=Alvarado, A. M. | title = Acetamide | volume = 3 | pages = 3 | collvol = 1 | collvolpages = 3 | year = 1923 | prep = cv1p0003 }}</ref>

:NH₄CH₃CO₂ → CH₃C(O)NH₂ + H₂O

It is also used as a diuretic.<ref name=Ullmann/>

===Buffer===

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 [[volatility (chemistry)|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.<ref>{{cite journal | year = 2008 | title = Preparation of single cells for imaging/profiling mass spectrometry| journal = J Am Soc Mass Spectrom | volume = 19 | pages = 1230–1236 | doi=10.1016/j.jasms.2008.05.006 | last1 = Berman | first1 = Elena S. F. | last2 = Fortson | first2 = Susan L. | last3 = Checchi | first3 = Kyle D. | last4 = Wu | first4 = Ligang | last5 = Felton | first5 = James S. | last6 = Kuang Jen | first6 = J. Wu | last7 = Kulp | first7 = Kristen S.| issue = 8| pmid = 18565760| doi-access = free }}</ref> It is also popular as a buffer for mobile phases for [[High-performance liquid chromatography|HPLC]] with [[Evaporative light scattering detector|ELSD]] and [[Charged aerosol detector|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.<ref>{{cite journal |last1=Konermann |first1=Lars |title=Addressing a Common Misconception: Ammonium Acetate as Neutral pH "Buffer" for Native Electrospray Mass Spectrometry |journal=American Society for Mass Spectrometry |date=2017 |volume=28 |issue=9 |pages=1827–1835 |doi=10.1007/s13361-017-1739-3 |pmid=28710594 |bibcode=2017JASMS..28.1827K |s2cid=25294943 |url=https://pubs.acs.org/doi/abs/10.1007/s13361-017-1739-3 |access-date=25 October 2022}}</ref>

===Other===

*a biodegradable de-icing agent.

*a catalyst in the [[Knoevenagel condensation]] and as a source of ammonia in the [[Reductive amination|Borch reaction]] in [[organic synthesis]].

*a protein precipitating reagent in [[dialysis (biochemistry)|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 ===

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.<ref>Australia New Zealand Food Standards Code {{cite web |url=http://www.comlaw.gov.au/Details/F2011C00827 |title=Standard 1.2.4 - Labelling of ingredients |access-date=2011-10-27}}</ref>

== Production ==

Ammonium acetate is produced by the neutralization of acetic acid with [[ammonium carbonate]] or by saturating glacial [[acetic acid]] with [[ammonia]].<ref>{{cite book|last=Brannt|first=William|title=A practical treatise on the manufacture of vinegar|year=1914|publisher=Henry Carey Baird & Co.|location=Lancaster, PA |pages=[https://archive.org/details/practicaltreatman00branrich/page/316 316]–317|url=https://archive.org/details/practicaltreatman00branrich}}</ref> Obtaining crystalline ammonium acetate is difficult on account of its hygroscopic nature.

== References ==

{{reflist}}

==External links==

{{Commons category|Ammonium acetate}}

{{clear}}

{{Acetates}}

{{Ammonium salts}}