Acetic acid

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Ace tic acid /əˈsiːtɪk/, systematically named e thanoic acid /ˌɛθəˈnoʊɪk/, is a colourless liquid organic compound w ith the chemical
Acetic acid
f ormula CH3COOH (also w ritten as CH3CO2H, C2H4O2, or HC2H3O2). When undiluted, it is sometimes called glacial acetic acid. Vinegar
is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart f rom w ater. Acetic acid has a
distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate
and cellulose acetate. It is classif ied as a w eak acid since it only partially dissociates in solution, but concentrated acetic acid is
corrosive and can attack the skin.

Acetic acid is the second simplest carboxylic acid (af ter f ormic acid). It consists of a methyl group attached to a carboxyl group. It is
an important chemical reagent and industrial chemical, used primarily in the production of cellulose acetate f or photographic f ilm,
polyvinyl acetate f or w ood glue, and synthetic f ibres and f abrics. In households, diluted acetic acid is of ten used in descaling
agents. In the f ood industry, acetic acid is controlled by the f ood additive code E260 as an acidity regulator and as a condiment. In
biochemistry, the acetyl group, derived f rom acetic acid, is f undamental to all f orms of lif e. When bound to coenzyme A, it is central to
the metabolism of carbohydrates and f ats.

The global demand f or acetic acid is about 6.5 million metric tons per year (Mt/a), of w hich approximately 1.5 Mt/a is met by recycling;
the remainder is manuf actured f rom methanol.[9] Vinegar is mostly dilute acetic acid, of ten produced by f ermentation and subsequent
oxidation of ethanol.

Contents [hide]
1 Nomenclature
2 Properties
2.1 Acidity
2.2 Structure
2.3 Solvent properties
2.4 Biochemistry
3 Production
3.1 Methanol carbonylation
3.2 Acetaldehyde oxidation
3.3 Ethylene oxidation
3.4 Oxidative fermentation
3.5 Anaerobic fermentation Names
4 Uses Pref erred IUPAC name
4.1 Vinyl acetate monomer Acetic acid[3]
4.2 Ester production Sy stematic IUPAC name
4.3 Acetic anhydride Ethanoic acid

4.4 Use as solvent Other names

Vinegar (when dilute); Hy drogen acetate;
4.5 Medical use
Methanecarboxy lic acid[1][2]
4.6 Foods
Identifiers
5 Reactions
CAS Number 64-19-7
5.1 Organic chemistry
3D model (JSmol) Interactiv e image
5.2 Reactions with inorganic compounds
3DMet B00009
5.3 Other derivatives Abbrev iations AcOH
6 History Beilstein 506007
6.1 Interstellar medium Ref erence
7 Health effects and safety ChEBI CHEBI:15366

8 See also ChEMBL ChEMBL539

9 References ChemSpider 171

10 External links DrugBank DB03166

ECHA Inf oCard 100.000.528
EC Number 200-580-7
Nomenclature [ edit ] E number E260 (preserv ativ es)
Gmelin Ref erence 1380
The trivial name acetic acid is the most commonly used and pref erred IUPAC name. The systematic name ethanoic acid, a valid
IUPHAR/BPS 1058
IUPAC name, is constructed according to the substitutive nomenclature.[10] The name acetic acid derives f rom acetum, the Latin w ord
KEGG D00010
f or vinegar, and is related to the w ord acid itself .
MeSH Acetic+acid
Glacial acetic acid is a name f or w ater-f ree (anhydrous) acetic acid. Similar to the German name Eisessig (ice vinegar), the name PubChem CID 176
comes f rom the ice-like crystals that f orm slightly below room temperature at 16.6 °C (61.9 °F) (the presence of 0.1% w ater low ers RTECS number AF1225000
its melting point by 0.2 °C).[11] UNII Q40Q9N063P

A common symbol f or acetic acid is AcOH, w here Ac is the pseudoelement symbol representing the acetyl group CH3−C(=O)−; the UN number 2789

conjugate base, acetate (CH3COO−), is thus represented as AcO −.[12] (The Ac is not to be conf used w ith the symbol f or the element CompTox DTXSID5024394
Dashboard (EPA)
actinium; the context prevents conf usion among organic chemists). To better ref lect its structure, acetic acid is of ten w ritten as
InChI [show]
CH3–C(O)OH, CH3−C(=O)OH, CH3COOH, and CH3CO2H. In the context of acid-base reactions, the abbreviation HAc is sometimes
+
SMILES [show]
used,[13] w here Ac in this case is a symbol f or acetate (rather than acetyl). Acetate is the ion resulting f rom loss of H f rom acetic
Properties
acid. The name acetate can also ref er to a salt containing this anion, or an ester of acetic acid.[14] Chemical f ormula C 2H 4O2
Molar mass 60.052 g·mol−1
Properties [ edit ] Appearance Colourless liquid
Odor Heav ily v inegar-like
Acidity [ edit ] Density 1.049 g cm −3 (liquid); 1.27 g
cm −3 (solid)
The hydrogen centre in the carboxyl group (−COOH) in carboxylic acids such as acetic acid can separate f rom the molecule by
Melting point 16 to 17 °C; 61 to 62 °F;
ionization:
289 to 290 K
CH3COOH ⇌ CH3CO2− + H+
Because of this release of the proton (H+), acetic acid has acidic character. Acetic acid is a w eak monoprotic acid. In aqueous Boiling point 118 to 119 °C; 244 to
solution, it has a pKa value of 4.76.[15] Its conjugate base is acetate (CH3COO−). A 1.0 M solution (about the concentration of domestic 246 °F; 391 to 392 K

vinegar) has a pH of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated. [16] How ever, in very dilute (< 10−6 Solubility in water Miscible

M) solution acetic acid is >90% dissociated. log P -0.28[4]

Acidity (pKa) 4.756 (H 2O)[5]
12.6 (DMSO)[6]
Basicity (pKb) 9.24 (basicity of acetate
ion)
Conjugate base Acetate
Structure [ edit ] Magnetic -31.54·10−6 cm 3/mol
susceptibility (χ )
In solid acetic acid, the molecules f orm chains, individual molecules being interconnected by hydrogen bonds.[17] In the vapour at Ref ractiv e index 1.371 (VD = 18.19)
120 °C (248 °F), dimers can be detected. Dimers also occur in the liquid phase in dilute solutions in non-hydrogen-bonding solvents, (nD)

and a certain extent in pure acetic acid,[18] but are disrupted by hydrogen-bonding solvents. The dissociation enthalpy of the dimer is Viscosity 1.22 mPa s

estimated at 65.0–66.0 kJ/mol, and the dissociation entropy at 154–157 J mol−1 K−1.[19] Other carboxylic acids engage in similar Dipole moment 1.74 D

intermolecular hydrogen bonding interactions.[20] Thermochemistry

Heat capacity (C) 123.1 J K−1 mol−1
Solvent properties [ edit ] Std molar 158.0 J K−1 mol−1
entropy (So298)
Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and w ater. With a moderate relative static permittivity Std enthalpy of -483.88–483.16 kJ mol−1
(dielectric constant) of 6.2, it dissolves not only polar compounds such as inorganic salts and sugars, but also non-polar compounds f ormation
(ΔfH⦵298)
such as oils as w ell as polar solutes. It is miscible w ith polar and non-polar solvents such as w ater, chlorof orm, and hexane. With
Std enthalpy of -875.50–874.82 kJ mol−1
higher alkanes (starting w ith octane), acetic acid is not miscible at all compositions, and solubility of acetic acid in alkanes declines combustion
w ith longer n-alkanes.[21] The solvent and miscibility properties of acetic acid make it a usef ul industrial chemical, f or example, as a (ΔcH⦵298)
solvent in the production of dimethyl terephthalate.[9] Pharmacology
ATC code G01AD02 (WHO )
Biochemistry [ edit ] S02AA10 (WHO )
Hazards
At physiological pHs, acetic acid is usually f ully ionised to acetate.
Saf ety data sheet See: data page
The acetyl group, f ormally derived f rom acetic acid, is f undamental to all f orms of lif e. When bound to coenzyme A, it is central to the GHS pictograms
metabolism of carbohydrates and f ats. Unlike longer-chain carboxylic acids (the f atty acids), acetic acid does not occur in natural
triglycerides. How ever, the artif icial triglyceride triacetin (glycerine triacetate) is a common f ood additive and is f ound in cosmetics
GHS Signal word Danger
and topical medicines.[22]
GHS hazard H226, H314
Acetic acid is produced and excreted by acetic acid bacteria, notably the genus Acetob acter and Clostridium acetob utylicum. statements
These bacteria are f ound universally in f oodstuf f s, w ater, and soil, and acetic acid is produced naturally as f ruits and other f oods GHS P280, P305+351+338, P310
precautionary
spoil. Acetic acid is also a component of the vaginal lubrication of humans and other primates, w here it appears to serve as a mild statements
antibacterial agent.[23] NFPA 704
(f ire diamond) 2
Production [ edit ]
3 0

Acetic acid is produced industrially both synthetically and by bacterial f ermentation. About 75% of acetic acid made f or use in the
Flash point 40 °C (104 °F; 313 K)
chemical industry is made by the carbonylation of methanol, explained below .[9] The biological route accounts f or only about 10% of
Autoignition 427 °C (801 °F; 700 K)
w orld production, but it remains important f or the production of vinegar because many f ood purity law s require vinegar used in f oods temperature
to be of biological origin. Other processes are methyl f ormate isomerization, conversion of syngas to acetic acid, and gas phase Explosiv e limits 4–16%
oxidation of ethylene and ethanol.[24] Acetic acid is of ten a side product of dif f erent reactions, i.e. during heterogeneous catalytic Lethal dose or concentration (LD, LC):
acrylic acid synthesis [25][26][27] or f ermentative lactic acid production.[28] As of 2003–2005, total w orldw ide production of virgin acetic LD 50 (median 3.31 g kg−1, oral (rat)
dose)
acid[29] w as estimated at 5 Mt/a (million tonnes per year), approximately half of w hich w as produced in the United States. European
LC 50 (median 5620 ppm (mouse, 1 hr)
production w as approximately 1 Mt/a and declining, w hile Japanese production w as 0.7 Mt/a. Another 1.5 Mt w ere recycled each concentration) 16000 ppm (rat, 4 hr)[8]
year, bringing the total w orld market to 6.5 Mt/a.[30][31] Since then the global production has increased to 10.7 Mt/a (in 2010), and
NIOSH (US health exposure limits):
f urther; how ever, a slow ing in this increase in production is predicted.[32] The tw o biggest producers of virgin acetic acid are
PEL TWA 10 ppm (25 mg/m 3)[7]
Celanese and BP Chemicals. Other major producers include Millennium Chemicals, Sterling Chemicals, Samsung, Eastman, and (Permissible)
Svensk Etanolkemi.[33] REL TWA 10 ppm (25 mg/m 3) ST
(Recommended) 15 ppm (37 mg/m 3)[7]

Methanol carbonylation [ edit ] IDLH 50 ppm [7]

(Immediate
Most acetic acid is produced by methanol carbonylation. In this process, methanol and carbon monoxide react to produce acetic acid danger)

according to the equation: Related compounds

Related carboxy lic Formic acid
acids Propionic acid
Related Acetaldehy de
compounds
The process involves iodomethane as an intermediate, and occurs in three steps. A catalyst, metal carbonyl, is needed f or the Acetamide
carbonylation (step 2).[34] Acetic anhy dride
Acetonitrile
1. CH3OH + HI → CH3I + H2O Acety l chloride
2. CH3I + CO → CH3COI Ethanol
Ethy l acetate
3. CH3COI + H2O → CH3COOH + HI
Potassium acetate
Tw o related processes f or the carbonylation of methanol: the rhodium-catalyzed Monsanto process, and the iridium-catalyzed Cativa Sodium acetate
process. The latter process is greener and more ef f icient[35] and has largely supplanted the f ormer process, of ten in the same Thioacetic acid

production plants. Catalytic amounts of w ater are used in both processes, but the Cativa process requires less, so the w ater-gas Supplementary data page
shif t reaction is suppressed, and f ew er by-products are f ormed. Structure and Ref ractiv e index (n),
properties Dielectric constant (εr), etc.
By altering the process conditions, acetic anhydride may also be produced on the same plant using the rhodium catalysts.[36]
Thermody namic Phase behav iour
data solid–liquid–gas
Acetaldehyde oxidation [ edit ]
Spectral data UV, IR, NMR, MS
Prior to the commercialization of the Monsanto process, most acetic acid w as produced by oxidation of acetaldehyde. This remains Except where otherwise noted, data are giv en
the second-most-important manuf acturing method, although it is usually not competitive w ith the carbonylation of methanol. The f or materials in their standard state (at 25 °C
[77 °F], 100 kPa).
acetaldehyde can be produced by hydration of acetylene. This w as the dominant technology in the early 1900s.[37]
v erif y (what is ?)
Light naphtha components are readily oxidized by oxygen or even air to give peroxides, w hich decompose to produce acetic acid Inf obox ref erences
according to the chemical equation, illustrated w ith butane:

2 C4H10 + 5 O2 → 4 CH3CO2H + 2 H2O

Such oxidations require metal catalyst, such as the naphthenate salts of manganese, cobalt, and chromium.

The typical reaction is conducted at temperatures and pressures designed to be as hot as possible w hile still keeping the butane a liquid. Typical
reaction conditions are 150 °C (302 °F) and 55 atm.[38] Side-products may also f orm, including butanone, ethyl acetate, f ormic acid, and propionic
acid. These side-products are also commercially valuable, and the reaction conditions may be altered to produce more of them w here needed.
How ever, the separation of acetic acid f rom these by-products adds to the cost of the process. [39]

Under similar conditions and using similar catalysts as are used f or butane oxidation, the oxygen in air to produce acetic acid can oxidize
acetaldehyde.[39]

2 CH3CHO + O2 → 2 CH3CO2H
Acetic acid cry stals
Using modern catalysts, this reaction can have an acetic acid yield greater than 95%. The major side-products are ethyl acetate, f ormic acid, and
f ormaldehyde, all of w hich have low er boiling points than acetic acid and are readily separated by distillation.[39]

Ethylene oxidation [ edit ]

Acetaldehyde may be prepared f rom ethylene via the Wacker process, and then oxidised as above.

In more recent times, chemical company Show a Denko, w hich opened an ethylene oxidation plant in Ōita, Japan, in 1997, commercialised Cy clic dimer of acetic acid;
dashed green lines represent
a cheaper single-stage conversion of ethylene to acetic acid.[40] The process is catalyzed by a palladium metal catalyst supported on a
hy drogen bonds
heteropoly acid such as silicotungstic acid. Similar process use the same metal catalyst on silicotungstic acid and silica: [41]

C2H4 + O2 → CH3CO2H

It is thought to be competitive w ith methanol carbonylation f or smaller plants (100–250 kt/a), depending on the local price of ethylene. The
approach w ill be based on utilizing a novel selective photocatalytic oxidation technology f or the selective oxidation of ethylene and ethane
to acetic acid. Unlike traditional oxidation catalysts, the selective oxidation process w ill use UV light to produce acetic acid at ambient
temperatures and pressure.

Oxidative fermentation [ edit ]

For most of human history, acetic acid bacteria of the genus Acetob acter have made acetic acid, in the f orm of vinegar. Given suf f icient
oxygen, these bacteria can produce vinegar f rom a variety of alcoholic f oodstuf f s. Commonly used f eeds include apple cider, w ine, and
f ermented grain, malt, rice, or potato mashes. The overall chemical reaction f acilitated by these bacteria is:

C2H5OH + O2 → CH3COOH + H2O

A dilute alcohol solution inoculated w ith Acetob acter and kept in a w arm, airy place w ill become vinegar over the course of a f ew months.
Industrial vinegar-making methods accelerate this process by improving the supply of oxygen to the bacteria.[42] Purif ication and concentration plant
f or acetic acid in 1884
The f irst batches of vinegar produced by f ermentation probably f ollow ed errors in the w inemaking process. If must is f ermented at too
high a temperature, acetobacter w ill overw helm the yeast naturally occurring on the grapes. As the demand f or vinegar f or culinary,
medical, and sanitary purposes increased, vintners quickly learned to use other organic materials to produce vinegar in the hot summer months bef ore the grapes w ere ripe and
ready f or processing into w ine. This method w as slow , how ever, and not alw ays successf ul, as the vintners did not understand the process. [43]

One of the f irst modern commercial processes w as the "f ast method" or "German method", f irst practised in Germany in 1823. In this process, f ermentation takes place in a
tow er packed w ith w ood shavings or charcoal. The alcohol-containing f eed is trickled into the top of the tow er, and f resh air supplied f rom the bottom by either natural or f orced
convection. The improved air supply in this process cut the time to prepare vinegar f rom months to w eeks. [44]

Now adays, most vinegar is made in submerged tank culture, f irst described in 1949 by Otto Hromatka and Heinrich Ebner.[45] In this method, alcohol is f ermented to vinegar in a
continuously stirred tank, and oxygen is supplied by bubbling air through the solution. Using modern applications of this method, vinegar of 15% acetic acid can be prepared in
only 24 hours in batch process, even 20% in 60-hour f ed-batch process.[43]

Anaerobic fermentation [ edit ]

Species of anaerobic bacteria, including members of the genus Clostridium or Acetob acterium can convert sugars to acetic acid directly w ithout creating ethanol as an
intermediate. The overall chemical reaction conducted by these bacteria may be represented as:

C6H12O6 → 3 CH3COOH

These acetogenic bacteria produce acetic acid f rom one-carbon compounds, including methanol, carbon monoxide, or a mixture of carbon dioxide and hydrogen:

2 CO2 + 4 H2 → CH3COOH + 2 H2O

This ability of Clostridium to metabolize sugars directly, or to produce acetic acid f rom less costly inputs, suggests that these bacteria could produce acetic acid more ef f iciently
than ethanol-oxidizers like Acetob acter. How ever, Clostridium bacteria are less acid-tolerant than Acetob acter. Even the most acid-tolerant Clostridium strains can produce
vinegar in concentrations of only a f ew per cent, compared to Acetob acter strains that can produce vinegar in concentrations up to 20%. At present, it remains more cost-
ef f ective to produce vinegar using Acetob acter, rather than using Clostridium and concentrating it. As a result, although acetogenic bacteria have been know n since 1940, their
industrial use is conf ined to a f ew niche applications.[46]

Uses [ edit ]

Acetic acid is a chemical reagent f or the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate monomer, closely f ollow ed
by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small. [9][31]

Vinyl acetate monomer [ edit ]

The primary use of acetic acid is the production of vinyl acetate monomer (VAM). In 2008, this application w as estimated to consume a third of the w orld's production of acetic
acid.[9] The reaction consists of ethylene and acetic acid w ith oxygen over a palladium catalyst, conducted in the gas phase.[47]

2 H3C−COOH + 2 C2H4 + O2 → 2 H3C−CO−O−CH=CH2 + 2 H2O

Vinyl acetate can be polymerised to polyvinyl acetate or other polymers, w hich are components in paints and adhesives.[47]

Ester production [ edit ]

The major esters of acetic acid are commonly used as solvents f or inks, paints and coatings. The esters include ethyl acetate, n-butyl acetate, isobutyl acetate, and propyl
acetate. They are typically produced by catalyzed reaction f rom acetic acid and the corresponding alcohol:

H3C−COOH + HO−R → H3C−CO−O−R + H2O, (R = a general alkyl group)

Most acetate esters, how ever, are produced f rom acetaldehyde using the Tishchenko reaction. In addition, ether acetates are used as solvents f or nitrocellulose, acrylic
lacquers, varnish removers, and w ood stains. First, glycol monoethers are produced f rom ethylene oxide or propylene oxide w ith alcohol, w hich are then esterif ied w ith acetic
acid. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate
(PMA, more commonly know n as PGMEA in semiconductor manuf acturing processes, w here it is used as a resist solvent). This application consumes about 15% to 20% of
w orldw ide acetic acid. Ether acetates, f or example EEA, have been show n to be harmf ul to human reproduction. [31]

Acetic anhydride [ edit ]

The product of the condensation of tw o molecules of acetic acid is acetic anhydride. The w orldw ide production of acetic anhydride is a major application, and uses
approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give ketene at 700–750 °C. Ketene is thereaf ter
reacted w ith acetic acid to obtain the anhydride:[48]

CH3CO2H → CH2=C=O + H2O

CH3CO2H + CH2=C=O → (CH3CO) 2O

Acetic anhydride is an acetylation agent. As such, its major application is f or cellulose acetate, a synthetic textile also used f or photographic f ilm. Acetic anhydride is also a
reagent f or the production of heroin and other compounds.[48]

Use as solvent [ edit ]

Glacial acetic acid is an excellent polar protic solvent, as noted above. It is f requently used as a solvent f or recrystallization to purif y organic compounds. Acetic acid is used as
a solvent in the production of terephthalic acid (TPA), the raw material f or polyethylene terephthalate (PET). In 2006, about 20% of acetic acid w as used f or TPA production. [31]

Acetic acid is of ten used as a solvent f or reactions involving carbocations, such as Friedel-Craf ts alkylation. For example, one stage in the commercial manuf acture of synthetic
camphor involves a Wagner-Meerw ein rearrangement of camphene to isobornyl acetate; here acetic acid acts both as a solvent and as a nucleophile to trap the rearranged
carbocation.[49]

Glacial acetic acid is used in analytical chemistry f or the estimation of w eakly alkaline substances such as organic amides. Glacial acetic acid is a much w eaker base than w ater,
so the amide behaves as a strong base in this medium. It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as perchloric acid.[50]

Medical use [ edit ]

Main article: Acetic acid (medical use)

Acetic acid injection into a tumor has been used to treat cancer since the 1800s. [51][52]

Acetic acid is used as part of cervical cancer screening in many areas in the developing w orld.[53] The acid is applied to the cervix and if an area of w hite appears af ter about a
minute the test is positive.[53]

Acetic acid is an ef f ective antiseptic w hen used as a 1% solution, w ith broad spectrum of activity against streptococci, staphylococci, pseudomonas, enterococci and others.
[54][55][56] It may be used to treat skin inf ections caused by pseudomonas strains resistant to typical antibiotics. [57]

While diluted acetic acid is used in iontophoresis, no high quality evidence supports this treatment f or rotator cuf f disease. [58][59]

As a treatment f or otitis externa, it is on the World Health Organization's List of Essential Medicines, the saf est and most ef f ective medicines needed in a health system.[60]

Foods [ edit ]
Main article: Vinegar

Acetic acid has 349 kcal per 100 g.[61] Vinegar is typically no less than 4% acetic acid by mass.[62][63][64] Legal limits on acetic acid content vary by jurisdiction. Vinegar is used
directly as a condiment, and in the pickling of vegetables and other f oods. Table vinegar tends to be more diluted (4% to 8% acetic acid), w hile commercial f ood pickling employs
solutions that are more concentrated. The proportion of acetic acid used w orldw ide as vinegar is not as large as commercial uses, but is by f ar the oldest and best-know n
application.[65]

Reactions [ edit ]

Organic chemistry [ edit ]

acetyl acetic ethanol

chloride acid (i) LiAlH4,
SOCl 2 ether
+
(ii) H3O

Two ty pical organic reactions of acetic acid

Acetic acid undergoes the typical chemical reactions of a carboxylic acid. Upon treatment w ith a standard base, it converts to metal acetate and w ater. With strong bases (e.g.,
organolithium reagents), it can be doubly deprotonated to give LiCH2CO2Li. Reduction of acetic acid gives ethanol. The OH group is the main site of reaction, as illustrated by the
conversion of acetic acid to acetyl chloride. Other substitution derivatives include acetic anhydride; this anhydride is produced by loss of w ater f rom tw o molecules of acetic
acid. Esters of acetic acid can likew ise be f ormed via Fischer esterif ication, and amides can be f ormed. When heated above 440 °C (824 °F), acetic acid decomposes to produce
carbon dioxide and methane, or to produce ketene and w ater:[66][67][68]

CH3COOH → CH4 + CO2

CH3COOH → CH2CO + H2O

Reactions with inorganic compounds [ edit ]

Acetic acid is mildly corrosive to metals including iron, magnesium, and zinc, f orming hydrogen gas and salts called acetates:

Mg + 2 CH3COOH → (CH3COO) 2Mg + H2

Because aluminium f orms a passivating acid-resistant f ilm of aluminium oxide, aluminium tanks are used to transport acetic acid. Metal acetates can also be prepared f rom acetic
acid and an appropriate base, as in the popular "baking soda + vinegar" reaction:

NaHCO3 + CH3COOH → CH3COONa + CO2 + H2O

A colour reaction f or salts of acetic acid is iron(III) chloride solution, w hich results in a deeply red colour that disappears af ter acidif ication. [69] A more sensitive test uses
lanthanum nitrate w ith iodine and ammonia to give a blue solution.[70] Acetates w hen heated w ith arsenic trioxide f orm cacodyl oxide, w hich can be detected by its malodorous
vapours.[71]

Other derivatives [ edit ]

Organic or inorganic salts are produced f rom acetic acid. Some commercially signif icant derivatives:

Sodium acetate, used in the textile industry and as a f ood preservative (E262).
Copper(II) acetate, used as a pigment and a f ungicide.
Aluminium acetate and iron(II) acetate—used as mordants f or dyes.
Palladium(II) acetate, used as a catalyst f or organic coupling reactions such as the Heck reaction.

Halogenated acetic acids are produced f rom acetic acid. Some commercially signif icant derivatives:

Chloroacetic acid (monochloroacetic acid, MCA), dichloroacetic acid (considered a by-product), and trichloroacetic acid. MCA is used in the manuf acture of indigo dye.
Bromoacetic acid, w hich is esterif ied to produce the reagent ethyl bromoacetate.
Trif luoroacetic acid, w hich is a common reagent in organic synthesis.

Amounts of acetic acid used in these other applications together account f or another 5–10% of acetic acid use w orldw ide. [31]

History [ edit ]

Vinegar w as know n early in civilization as the natural result of exposure of beer and w ine to air, because acetic acid-producing bacteria are present globally. The use of acetic
acid in alchemy extends into the 3rd century BC, w hen the Greek philosopher Theophrastus described how vinegar acted on metals to produce pigments usef ul in art, including
white lead (lead carbonate) and verdigris, a green mixture of copper salts including copper(II) acetate. Ancient Romans boiled soured w ine to produce a highly sw eet syrup
called sapa. Sapa that w as produced in lead pots w as rich in lead acetate, a sw eet substance also called sugar of lead or sugar of Saturn, w hich contributed to lead poisoning
among the Roman aristocracy.[72]

In the 16th-century German alchemist Andreas Libavius described the production of acetone f rom the dry distillation of lead acetate, ketonic decarboxylation. The presence of
w ater in vinegar has such a prof ound ef f ect on acetic acid's properties that f or centuries chemists believed that glacial acetic acid and the acid f ound in vinegar w ere tw o
dif f erent substances. French chemist Pierre Adet proved them identical.[72][73]

In 1845 German chemist Hermann Kolbe synthesised acetic acid f rom inorganic compounds f or the f irst time. This reaction sequence consisted of
chlorination of carbon disulf ide to carbon tetrachloride, f ollow ed by pyrolysis to tetrachloroethylene and aqueous chlorination to trichloroacetic
acid, and concluded w ith electrolytic reduction to acetic acid.[74]

By 1910, most glacial acetic acid w as obtained f rom the pyroligneous liquor, a product of the distillation of w ood. The acetic acid w as isolated by
treatment w ith milk of lime, and the resulting calcium acetate w as then acidif ied w ith sulf uric acid to recover acetic acid. At that time, Germany
w as producing 10,000 tons of glacial acetic acid, around 30% of w hich w as used f or the manuf acture of indigo dye.[72][75]

Because both methanol and carbon monoxide are commodity raw materials, methanol carbonylation long appeared to be attractive precursors to
acetic acid. Henri Dreyf us at British Celanese developed a methanol carbonylation pilot plant as early as 1925.[76] How ever, a lack of practical
materials that could contain the corrosive reaction mixture at the high pressures needed (200 atm or more) discouraged commercialization of
these routes. The f irst commercial methanol carbonylation process, w hich used a cobalt catalyst, w as developed by German chemical company
Cry stallised acetic acid.
BASF in 1963. In 1968, a rhodium-based catalyst (cis−[Rh(CO) 2I2]−) w as discovered that could operate ef f iciently at low er pressure w ith almost
no by-products. US chemical company Monsanto Company built the f irst plant using this catalyst in 1970, and rhodium-catalyzed methanol
carbonylation became the dominant method of acetic acid production (see Monsanto process). In the late 1990s, the chemicals company BP Chemicals commercialised the Cativa
catalyst ([Ir(CO) 2I2]−), w hich is promoted by iridium[77] f or greater ef f iciency. This iridium-catalyzed Cativa process is greener and more ef f icient[35] and has largely supplanted the
Monsanto process, of ten in the same production plants.

Interstellar medium [ edit ]

Interstellar acetic acid w as discovered in 1996 by a team led by David Mehringer [78] using the f ormer Berkeley-Illinois-Maryland Association array at the Hat Creek Radio
Observatory and the f ormer Millimeter Array located at the Ow ens Valley Radio Observatory. It w as f irst detected in the Sagittarius B2 North molecular cloud (also know n as the
Sgr B2 Large Molecule Heimat source). Acetic acid has the distinction of being the f irst molecule discovered in the interstellar medium using solely radio interf erometers; in all
previous ISM molecular discoveries made in the millimetre and centimetre w avelength regimes, single dish radio telescopes w ere at least partly responsible f or the detections. [78]

Health effects and safety [ edit ]

Concentrated acetic acid is corrosive to skin.[79][80] These burns or blisters may not appear until hours af ter exposure.

Prolonged inhalation exposure (eight hours) to acetic acid vapours at 10 ppm can produce some irritation of eyes, nose, and throat; at 100 ppm marked lung irritation and possible
damage to lungs, eyes, and skin may result. Vapour concentrations of 1,000 ppm cause marked irritation of eyes, nose and upper respiratory tract and cannot be tolerated.
These predictions w ere based on animal experiments and industrial exposure.

In 12 w orkers exposed f or tw o or more years to acetic acid airborne average concentration of 51 ppm (estimated), produced symptoms of conjunctive irritation, upper
respiratory tract irritation, and hyperkeratotic dermatitis. Exposure to 50 ppm or more is intolerable to most persons and results in intensive lacrimation and irritation of the eyes,
nose, and throat, w ith pharyngeal oedema and chronic bronchitis. Unacclimatised humans experience extreme eye and nasal irritation at concentrations in excess of 25 ppm,
and conjunctivitis f rom concentrations below 10 ppm has been reported. In a study of f ive w orkers exposed f or seven to 12 years to concentrations of 80 to 200 ppm at peaks,
the principal f indings w ere blackening and hyperkeratosis of the skin of the hands, conjunctivitis (but no corneal damage), bronchitis and pharyngitis, and erosion of the exposed
teeth (incisors and canines).[81]

The hazards of solutions of acetic acid depend on the concentration. The f ollow ing table lists the EU classif ication of acetic acid solutions:[82]

Conce ntration
M olarity Clas s ification R-Phras e s
by w e ight

10–25% 1.67–4.16 mol/L Irritant (Xi) R36/38

25–90% 4.16–14.99 mol/L Corrosive (C) R34

>90% >14.99 mol/L Corrosive (C) Flammable (F) R10, R35

Concentrated acetic acid can be ignited only w ith dif f iculty at standard temperature and pressure, but becomes a f lammable risk in temperatures greater than 39 °C (102 °F), and
can f orm explosive mixtures w ith air at higher temperatures (explosive limits: 5.4–16%).
See also [ edit ]

Acetic acid (data page)

Acetyl group, the CH3-CO– group
Acids in w ine
Acetate

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External links [ edit ]

International Chemical Saf ety Card 0363

National Pollutant Inventory – Acetic acid f act sheet
NIOSH Pocket Guide to Chemical Hazards
Method f or sampling and analysis
29 CFR 1910.1000, Table Z-1 (US Permissible exposure limits)
ChemSub Online: Acetic acid
Calculation of vapor pressure , liquid density , dynamic liquid viscosity , surf ace tension of acetic acid
Acetic acid bound to proteins in the PDB
Sw edish Chemicals Agency. Inf ormation sheet – Acetic Acid
Process Flow sheet of Acetic acid Production by the Carbonylation of Methanol