Ammonium acetate

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Ammonium acetate
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Names
IUPAC name
Ammonium ethanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.149 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-162-9
PubChem CID
RTECS number
  • AF3675000
UNII
UN number 3077
  • InChI=1S/C2H4O2.H3N/c1-2(3)4;/h1H3,(H,3,4);1H3 Yes check.svgY
    Key: USFZMSVCRYTOJT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H4O2.H3N/c1-2(3)4;/h1H3,(H,3,4);1H3
    Key: USFZMSVCRYTOJT-UHFFFAOYAY
  • O=C([O-])C.[N+H4]
Properties
C2H7NO2
Molar mass 77.083 g·mol−1
AppearanceWhite 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) [2]
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 [3]
Solubility in methanol 7.89 g/100 mL (15 °C) [4] [1]
131.24 g/100 g (94.2 °C) [3]
Solubility in dimethylformamide 0.1 g/100 g [3]
Acidity (pKa)9.9
Basicity (pKb)33
-41.1·10−6 cm3/mol
Viscosity 21
Structure
Orthorhombic
Thermochemistry
−615 kJ/mol [3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling: [4]
GHS-pictogram-exclam.svg
Warning
H303, H316, H320, H333
P281, P335
NFPA 704 (fire diamond)
[4]
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
1
1
Flash point 136 °C (277 °F; 409 K) [4]
Lethal dose or concentration (LD, LC):
386 mg/kg (mice, intravenous) [3]
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

History

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

Uses

It is the main precursor to acetamide: [7]

NH4CH3CO2 → CH3C(O)NH2 + H2O

It is also used as a diuretic. [5]

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 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

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. [10]

Production

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.

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reverse reaction. On the other hand, a conjugate base is what remains after an acid has donated a proton during a chemical reaction. Hence, a conjugate base is a substance formed by the removal of a proton from an acid, as it can gain a hydrogen ion in the reverse reaction. Because some acids can give multiple protons, the conjugate base of an acid may itself be acidic.

<span class="mw-page-title-main">Ammonium</span> Polyatomic ion (NH₄, charge +1)

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2H
3O−
2. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3CO−
2, or CH
3COO−
.

<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.

<span class="mw-page-title-main">Fischer–Speier esterification</span>

Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer and Arthur Speier in 1895. Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to elimination. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give good to near quantitative yield of products. Commonly used catalysts for a Fischer esterification include sulfuric acid, p-toluenesulfonic acid, and Lewis acids such as scandium(III) triflate. For more valuable or sensitive substrates other, milder procedures such as Steglich esterification are used. The reaction is often carried out without a solvent or in a non-polar solvent to facilitate the Dean-Stark method. Typical reaction times vary from 1–10 hours at temperatures of 60-110 °C.

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral with the IMA symbol: Ace.

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Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

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

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

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

Ammonium sulfate (American English and international scientific usage; ammonium sulphate in British English); (NH4)2SO4, is an inorganic salt with a number of commercial uses. The most common use is as a soil fertilizer. It contains 21% nitrogen and 24% sulfur.

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.

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

Potassium citrate (also known as tripotassium citrate) is a potassium salt of citric acid with the molecular formula K3C6H5O7. It is a white, hygroscopic crystalline powder. It is odorless with a saline taste. It contains 38.28% potassium by mass. In the monohydrate form, it is highly hygroscopic and deliquescent.

In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is lysed by reacting with ammonia or an amine. The case where the reaction involves ammonia may be more specifically referred to as ammonolysis.

<span class="mw-page-title-main">Hexafluorosilicic acid</span> Octahedric silicon compound

Hexafluorosilicic acid is an inorganic compound with the chemical formula H
2SiF
6. Aqueous solutions of hexafluorosilicic acid consist of salts of the cation and hexafluorosilicate anion. These salts and their aqueous solutions are colorless.

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Ammonium heptamolybdate is the inorganic compound whose chemical formula is (NH4)6Mo7O24, normally encountered as the tetrahydrate. A dihydrate is also known. It is a colorless solid, often referred to as ammonium paramolybdate or simply as ammonium molybdate, although "ammonium molybdate" can also refer to ammonium orthomolybdate, (NH4)2MoO4, and several other compounds. It is one of the more common molybdenum compounds.

The deliming operation in leather processing is a drum/paddle or pit based operation where two main objectives are met:

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and trace elements.

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

Acetyl hypochlorite, also known as chlorine acetate, is a chemical compound with the formula CH3COOCl. It is a photosensitive colorless liquid that is a short lived intermediate in the Hunsdiecker reaction.

References

  1. 1 2 3 Pradyot, Patnaik (2003). Handbook of Inorganic Chemicals. The McGraw-Hill Companies, Inc. ISBN   0-07-049439-8.
  2. ↑ 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.
  3. 1 2 3 4 5 "Ammonium acetate".
  4. 1 2 3 4 "Safety Data Sheet of Ammonium Acetate" (PDF). tedia.com. Tedia Company Inc. 2011-08-12. Retrieved 2014-06-10.
  5. 1 2 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.
  6. ↑ "Spirit of Mindererus". TheFreeDictionary.com. Retrieved 2023-06-07.
  7. ↑ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses . 3: 3.; Collective Volume, 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.
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