Boiling Point Of Acetic Acid

Colorless and faint organic acrid institute in vinegar

"Acetic" redirects hither. Not to exist confused with Ascetic.

Acetic acrid

Names
Preferred IUPAC name Acetic acid[iii]
Systematic IUPAC proper noun Ethanoic acid
Other names Vinegar (when dilute); Hydrogen acetate; Methanecarboxylic acid[1] [2]
Identifiers
CAS Number	64-19-7 Y
3D model (JSmol)	Interactive image
3DMet	B00009
Abbreviations	AcOH
Beilstein Reference	506007
ChEBI	CHEBI:15366 Y
ChEMBL	ChEMBL539 Y
ChemSpider	171 Y
DrugBank	DB03166 Y
ECHA InfoCard	100.000.528
EC Number	200-580-seven
E number	E260 (preservatives)
Gmelin Reference	1380
IUPHAR/BPS	1058
KEGG	C00033 D00010 Y
MeSH	Acetic+acrid
PubChem CID	176
RTECS number	AF1225000
UNII	Q40Q9N063P Y
UN number	2789
CompTox Dashboard (EPA)	DTXSID5024394
InChI InChI=1S/C2H4O2/c1-2(three)four/h1H3,(H,3,four) Y Cardinal: QTBSBXVTEAMEQO-UHFFFAOYSA-N Y
SMILES CC(O)=O
Backdrop
Chemical formula	CH3COOH
Tooth mass	threescore.052 thousand·mol−1
Appearance	Colourless liquid
Olfactory property	Heavily vinegar-like
Density	1.049 g/cm3 (liquid); ane.27 g/cm3 (solid)
Melting indicate	sixteen to 17 °C; 61 to 62 °F; 289 to 290 K
Humid point	118 to 119 °C; 244 to 246 °F; 391 to 392 Chiliad
Solubility in water	Miscible
log P	-0.28[iv]
Vapor pressure	11.6mmHg (20 °C)[v]
Acerbity (pThousand a)	4.756
Conjugate base of operations	Acetate
Magnetic susceptibility (χ)	-31.54·10−half-dozen cm3/mol
Refractive alphabetize (n D)	i.371 (VD = xviii.19)
Viscosity	i.22 mPa s
Dipole moment	ane.74 D
Thermochemistry
Heat capacity (C)	123.1 J K−1 mol−1
Std molar entropy (South ⦵ 298)	158.0 J 1000−1 mol−1
Std enthalpy of formation (Δf H ⦵ 298)	-483.88–483.16 kJ/mol
Std enthalpy of combustion (Δc H ⦵ 298)	-875.50–874.82 kJ/mol
Pharmacology
ATC code	G01AD02 (WHO) S02AA10 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Gamble statements	H226, H314
Precautionary statements	P280, P305+P351+P338, P310
NFPA 704 (burn diamond)	3 2 0
Flash point	twoscore °C (104 °F; 313 G)
Autoignition temperature	427 °C (801 °F; 700 K)
Explosive limits	4–xvi%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	3.31 g kg−1, oral (rat)
LC50 (median concentration)	5620 ppm (mouse, 1 hr) 16000 ppm (rat, 4 hr)[7]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA ten ppm (25 mg/mthree)[6]
REL (Recommended)	TWA ten ppm (25 mg/kthree) ST 15 ppm (37 mg/m3)[vi]
IDLH (Firsthand danger)	50 ppm[6]
Related compounds
Related carboxylic acids	Formic acid Propionic acid
Related compounds	Acetaldehyde Acetamide Acerb anhydride Acetonitrile Acetyl chloride Ethanol Ethyl acetate Potassium acetate Sodium acetate Thioacetic acrid
Supplementary data page
Acetic acid (data page)
Except where otherwise noted, information are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Nverify (what is Y Due north  ?) Infobox references

Chemic chemical compound

Acetic acrid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula CH_iiiCOOH (also written as CH_threeCO₂H, C₂H_ivO₂ , or HC_twoH₃O₂ ). Vinegar is at to the lowest degree 4% acetic acid past book, making acetic acid the main component of vinegar apart from water and other trace elements.

Acetic acid is the second simplest carboxylic acid (after formic acid). Information technology is an of import chemical reagent and industrial chemical, used primarily in the product of cellulose acetate for photographic picture show, polyvinyl acetate for wood glue, and synthetic fibres and fabrics. In households, diluted acetic acrid is often used in descaling agents. In the food manufacture, acetic acrid is controlled by the food additive code E260 as an acidity regulator and every bit a additive. In biochemistry, the acetyl group, derived from acetic acid, is cardinal to all forms of life. When bound to coenzyme A, it is cardinal to the metabolism of carbohydrates and fats.

The global demand for acetic acrid is about 6.5 million metric tons per twelvemonth (t/a), of which approximately 1.5 t/a is met by recycling; the rest is manufactured from methanol.^[8] Vinegar is mostly dilute acetic acrid, often produced by fermentation and subsequent oxidation of ethanol.

Classification [edit]

The trivial name "acerb acid" is the most normally used and preferred IUPAC name. The systematic name "ethanoic acrid", a valid IUPAC proper noun, is synthetic according to the substitutive nomenclature.^[9] The proper noun "acetic acrid" derives from "acetum", the Latin word for vinegar, and is related to the discussion "acid" itself.

"Glacial acetic acrid" is a name for water-free (anhydrous) acetic acid. Similar to the German name "Eisessig" ("ice vinegar"), the name comes from the ice-like crystals that form slightly below room temperature at sixteen.6 °C (61.9 °F) (the presence of 0.ane% water lowers its melting point past 0.2 °C).^[10]

A common symbol for acetic acrid is AcOH, where Ac is the pseudoelement symbol representing the acetyl group CH₃−C(=O)−; the conjugate base, acetate (CH₃COO⁻ ), is thus represented every bit AcO⁻ .^[11] (The symbol Ac for the acetyl functional group is not to be dislocated with the symbol Air conditioning for the element actinium; the context prevents confusion among organic chemists). To amend reflect its structure, acerb acid is oft written equally CH_three−C(O)OH, CH₃−C(=O)OH, CH₃COOH, and CH₃CO₂H. In the context of acid–base reactions, the abbreviation HAc is sometimes used,^[12] where Ac in this instance is a symbol for acetate (rather than acetyl). Acetate is the ion resulting from loss of H⁺ from acerb acrid. The name "acetate" can also refer to a salt containing this anion, or an ester of acetic acid.^[13]

Properties [edit]

Acidity [edit]

The hydrogen heart in the carboxyl group (−COOH) in carboxylic acids such as acetic acrid can separate from the molecule past ionization:

CH₃COOH ⇌ CH₃CO − ii + H⁺

Because of this release of the proton (H⁺ ), acetic acid has acidic character. Acetic acrid is a weak monoprotic acid. In aqueous solution, it has a pK_a value of 4.76.^[xiv] Its conjugate base is acetate (CH₃COO⁻ ). A 1.0 M solution (virtually the concentration of domestic vinegar) has a pH of 2.4, indicating that but 0.4% of the acetic acid molecules are dissociated.^[15] Even so, in very dilute (< 10⁻⁶ M) solution acerb acrid is >ninety% dissociated.

Cyclic dimer of acetic acid; dashed green lines correspond hydrogen bonds

Structure [edit]

In solid acetic acid, the molecules class chains, individual molecules being interconnected by hydrogen bonds.^[16] In the vapour at 120 °C (248 °F), dimers can exist detected. Dimers too occur in the liquid phase in dilute solutions in non-hydrogen-bonding solvents, and a certain extent in pure acetic acid,^[17] simply are disrupted by hydrogen-bonding solvents. The dissociation enthalpy of the dimer is estimated at 65.0–66.0 kJ/mol, and the dissociation entropy at 154–157 J mol^−one M⁻¹.^[18] Other carboxylic acids engage in similar intermolecular hydrogen bonding interactions.^[19]

Solvent backdrop [edit]

Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and h2o. With a relative static permittivity (dielectric constant) of 6.ii, it dissolves non only polar compounds such as inorganic salts and sugars, but also non-polar compounds such as oils as well as polar solutes. It is miscible with polar and non-polar solvents such as water, chloroform, and hexane. With higher alkanes (starting with octane), acetic acrid is not miscible at all compositions, and solubility of acerb acid in alkanes declines with longer n-alkanes.^[20] The solvent and miscibility backdrop of acerb acid make it a useful industrial chemical, for example, equally a solvent in the production of dimethyl terephthalate.^[8]

Biochemistry [edit]

At physiological pHs, acetic acid is usually fully ionised to acetate.

The acetyl grouping, formally derived from acerb acid, is fundamental to all forms of life. When bound to coenzyme A, information technology is central to the metabolism of carbohydrates and fats. Different longer-chain carboxylic acids (the fatty acids), acetic acid does not occur in natural triglycerides. Nonetheless, the artificial triglyceride triacetin (glycerine triacetate) is a mutual nutrient condiment and is plant in cosmetics and topical medicines.^[21]

Acetic acid is produced and excreted by acetic acid bacteria, notably the genus Acetobacter and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil, and acerb acid is produced naturally as fruits and other foods spoil. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where information technology appears to serve as a balmy antibacterial agent.^[22]

Product [edit]

Purification and concentration institute for acerb acid in 1884

Acerb acrid is produced industrially both synthetically and by bacterial fermentation. About 75% of acetic acid made for use in the chemical industry is made by the carbonylation of methanol, explained beneath.^[viii] The biological route accounts for just about x% of world production, but it remains important for the production of vinegar considering many food purity laws crave vinegar used in foods to exist of biological origin. Other processes are methyl formate isomerization, conversion of syngas to acetic acrid, and gas phase oxidation of ethylene and ethanol.^[23] Acetic acid is often a side product of dissimilar reactions, e.g. during heterogeneous catalytic acrylic acid synthesis^{[24] [25] [26]} or fermentative lactic acid production.^[27] Acetic acrid can be purified via fractional freezing using an ice bath. The water and other impurities volition remain liquid while the acetic acid volition precipitate out. As of 2003–2005, total worldwide production of virgin acetic acid^[28] was estimated at v Mt/a (million tonnes per twelvemonth), approximately one-half of which was produced in the United states. European production was approximately ane Mt/a and declining, while Japanese production was 0.7 Mt/a. Some other one.5 Mt were recycled each year, bringing the full globe market to 6.5 Mt/a.^{[29] [xxx]} Since then the global product has increased to 10.7 Mt/a (in 2010), and further; however, a slowing in this increase in production is predicted.^[31] The ii biggest producers of virgin acerb acid are Celanese and BP Chemicals. Other major producers include Millennium Chemicals, Sterling Chemicals, Samsung, Eastman, and Svensk Etanolkemi.^[32]

Methanol carbonylation [edit]

Most acetic acid is produced by methanol carbonylation. In this process, methanol and carbon monoxide react to produce acetic acid according to the equation:

The process involves iodomethane equally an intermediate, and occurs in three steps. A catalyst, metal carbonyl, is needed for the carbonylation (step 2).^[33]

1. CH_threeOH + HI → CH_iiiI + H_twoO
2. CH_iiiI + CO → CH_iiiCOI
3. CH_threeCOI + H_twoO → CH_iiiCOOH + HI

Ii related processes exist for the carbonylation of methanol: the rhodium-catalyzed Monsanto process, and the iridium-catalyzed Cativa process. The latter process is greener and more efficient^[34] and has largely supplanted the former procedure, often in the same production plants. Catalytic amounts of h2o are used in both processes, but the Cativa process requires less, so the water-gas shift reaction is suppressed, and fewer by-products are formed.

By altering the process conditions, acerb anhydride may likewise be produced on the same plant using the rhodium catalysts.^[35]

Acetaldehyde oxidation [edit]

Prior to the commercialization of the Monsanto process, most acetic acid was produced past oxidation of acetaldehyde. This remains the second-most-important manufacturing method, although it is usually not competitive with the carbonylation of methanol. The acetaldehyde can exist produced by hydration of acetylene. This was the ascendant technology in the early 1900s.^[36]

Light naphtha components are readily oxidized by oxygen or even air to give peroxides, which decompose to produce acerb acrid according to the chemical equation, illustrated with butane:

two C_ivH₁₀ + 5 O_ii → iv CH₃CO_twoH + ii H_twoO

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

The typical reaction is conducted at temperatures and pressures designed to exist as hot as possible while notwithstanding keeping the butane a liquid. Typical reaction atmospheric condition are 150 °C (302 °F) and 55 atm.^[37] Side-products may as well form, including butanone, ethyl acetate, formic acid, and propionic acrid. These side-products are as well commercially valuable, and the reaction weather may be altered to produce more of them where needed. Withal, the separation of acetic acrid from these by-products adds to the cost of the procedure.^[38]

Under similar atmospheric condition and using similar catalysts as are used for butane oxidation, the oxygen in air to produce acetic acrid can oxidize acetaldehyde.^[38]

2 CH₃CHO + O₂ → 2 CH₃CO_iiH

Using modern catalysts, this reaction tin can have an acetic acid yield greater than 95%. The major side-products are ethyl acetate, formic acid, and formaldehyde, all of which have lower boiling points than acetic acid and are readily separated by distillation.^[38]

Ethylene oxidation [edit]

Acetaldehyde may exist prepared from ethylene via the Wacker process, and so oxidised equally above.

In more recent times, chemical company Showa Denko, which opened an ethylene oxidation constitute in Ōita, Nihon, in 1997, commercialised a cheaper single-stage conversion of ethylene to acetic acid.^[39] The procedure is catalyzed by a palladium metal catalyst supported on a heteropoly acid such as silicotungstic acid. A similar process uses the same metal catalyst on silicotungstic acrid and silica:^[40]

C_iiH_four + O₂ → CH₃CO₂H

It is thought to be competitive with methanol carbonylation for smaller plants (100–250 kt/a), depending on the local price of ethylene. The approach volition be based on utilizing a novel selective photocatalytic oxidation technology for the selective oxidation of ethylene and ethane to acetic acrid. Different traditional oxidation catalysts, the selective oxidation procedure will utilise UV calorie-free to produce acerb acid at ambient temperatures and pressure.

Oxidative fermentation [edit]

For most of human history, acetic acid leaner of the genus Acetobacter accept fabricated acetic acid, in the grade of vinegar. Given sufficient oxygen, these bacteria can produce vinegar from a diverseness of alcoholic foodstuffs. Commonly used feeds include apple cider, wine, and fermented grain, malt, rice, or tater mashes. The overall chemical reaction facilitated past these bacteria is:

C₂H₅OH + O_ii → CH_iiiCOOH + H₂O

A dilute alcohol solution inoculated with Acetobacter and kept in a warm, airy place will become vinegar over the class of a few months. Industrial vinegar-making methods advance this process past improving the supply of oxygen to the bacteria.^[41]

The first batches of vinegar produced past fermentation probably followed errors in the winemaking procedure. If must is fermented at too loftier a temperature, acetobacter will overwhelm the yeast naturally occurring on the grapes. As the demand for vinegar for culinary, medical, and sanitary purposes increased, vintners quickly learned to use other organic materials to produce vinegar in the hot summer months before the grapes were ripe and ready for processing into wine. This method was slow, still, and not e'er successful, every bit the vintners did non sympathize the procedure.^[42]

I of the start modern commercial processes was the "fast method" or "German language method", first practised in Frg in 1823. In this process, fermentation takes place in a tower packed with wood shavings or charcoal. The alcohol-containing feed is trickled into the top of the tower, and fresh air supplied from the bottom by either natural or forced convection. The improved air supply in this process cut the time to gear up vinegar from months to weeks.^[43]

Present, nearly vinegar is made in submerged tank civilisation, first described in 1949 past Otto Hromatka and Heinrich Ebner.^[44] In this method, alcohol is fermented 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% acerb acid tin can be prepared in only 24 hours in batch process, even 20% in threescore-hour fed-batch process.^[42]

Anaerobic fermentation [edit]

Species of anaerobic bacteria, including members of the genus Clostridium or Acetobacterium tin can catechumen sugars to acetic acrid directly without creating ethanol as an intermediate. The overall chemical reaction conducted by these bacteria may be represented as:

C_half-dozenH₁₂O₆ → iii CH₃COOH

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

2 CO_two + 4 H₂ → CH₃COOH + 2 H₂O

This power of Clostridium to metabolize sugars directly, or to produce acetic acrid from less plush inputs, suggests that these bacteria could produce acetic acid more efficiently than ethanol-oxidizers similar Acetobacter. However, Clostridium bacteria are less acid-tolerant than Acetobacter. Even the nearly acrid-tolerant Clostridium strains can produce vinegar in concentrations of only a few per cent, compared to Acetobacter strains that can produce vinegar in concentrations up to 20%. At present, information technology remains more cost-effective to produce vinegar using Acetobacter, rather than using Clostridium and concentrating it. As a result, although acetogenic bacteria have been known since 1940, their industrial employ is confined to a few niche applications.^[45]

Uses [edit]

Acetic acid is a chemical reagent for the product of chemical compounds. The largest unmarried use of acetic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester product. The volume of acetic acid used in vinegar is comparatively small.^{[8] [30]}

Vinyl acetate monomer [edit]

The primary utilise of acerb acrid is the production of vinyl acetate monomer (VAM). In 2008, this awarding was estimated to eat a third of the world'southward production of acerb acrid.^[viii] The reaction consists of ethylene and acetic acid with oxygen over a palladium catalyst, conducted in the gas stage.^[46]

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

Vinyl acetate can exist polymerised to polyvinyl acetate or other polymers, which are components in paints and adhesives.^[46]

Ester production [edit]

The major esters of acerb acid are commonly used equally solvents for inks, paints and coatings. The esters include ethyl acetate, northward-butyl acetate, isobutyl acetate, and propyl acetate. They are typically produced by catalyzed reaction from acetic acid and the corresponding alcohol:

CH₃COO−H + HO−R → CH_threeCOO−R + H_twoO, R = general alkyl group

For example, acetic acrid and ethanol gives ethyl acetate and water.

CH₃COO−H + HO−CH₂CH_iii → CH₃COO−CH₂CH₃ + H₂O

Near acetate esters, even so, are produced from acetaldehyde using the Tishchenko reaction. In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers, and wood stains. Starting time, glycol monoethers are produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid. The iii major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more than commonly known as PGMEA in semiconductor manufacturing processes, where it is used equally a resist solvent). This application consumes about 15% to xx% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human being reproduction.^[thirty]

Acerb anhydride [edit]

The product of the condensation of 2 molecules of acetic acrid is acetic anhydride. The worldwide production of acerb anhydride is a major awarding, and uses approximately 25% to thirty% of the global production of acerb acid. The principal process involves aridity of acerb acid to requite ketene at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride:^[47]

CH_iiiCO₂H → CH₂=C=O + H₂O

CH₃CO_iiH + CH₂=C=O → (CH_iiiCO)₂O

Acetic anhydride is an acetylation agent. As such, its major application is for cellulose acetate, a constructed textile also used for photographic film. Acerb anhydride is as well a reagent for the production of heroin and other compounds.^[47]

Use as solvent [edit]

Glacial acetic acid is an excellent polar protic solvent, as noted above. It is often used as a solvent for recrystallization to purify organic compounds. Acerb acid is used as a solvent in the production of terephthalic acrid (TPA), the raw cloth for polyethylene terephthalate (PET). In 2006, about twenty% of acetic acrid was used for TPA product.^[thirty]

Acetic acrid is oft used as a solvent for reactions involving carbocations, such every bit Friedel-Crafts alkylation. For example, ane phase in the commercial manufacture of synthetic camphor involves a Wagner-Meerwein rearrangement of camphene to isobornyl acetate; here acetic acid acts both every bit a solvent and as a nucleophile to trap the rearranged carbocation.^[48]

Glacial acetic acid is used in belittling chemistry for the estimation of weakly element of group i substances such as organic amides. Glacial acetic acid is a much weaker base than water, so the amide behaves equally 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.^[49]

Medical employ [edit]

Acetic acid injection into a tumor has been used to treat cancer since the 1800s.^{[50] [51]}

Acetic acid is used as office of cervical cancer screening in many areas in the developing world.^[52] The acid is applied to the cervix and if an expanse of white appears subsequently nigh a minute the test is positive.^[52]

Acetic acid is an effective antiseptic when used as a 1% solution, with broad spectrum of action against streptococci, staphylococci, pseudomonas, enterococci and others.^{[53] [54] [55]} It may be used to treat peel infections caused by pseudomonas strains resistant to typical antibiotics.^[56]

While diluted acetic acid is used in iontophoresis, no high quality testify supports this treatment for rotator cuff disease.^{[57] [58]}

As a handling for otitis externa, information technology is on the World Health Organization's Listing of Essential Medicines.^{[59] [60]}

Foods [edit]

Acetic acid has 349 kcal (one,460 kJ) per 100 yard.^[61] Vinegar is typically no less than 4% acetic acid by mass.^{[62] [63] [64]} Legal limits on acerb acrid content vary by jurisdiction. Vinegar is used direct as a condiment, and in the pickling of vegetables and other foods. Tabular array vinegar tends to exist more than diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more than concentrated. The proportion of acerb acid used worldwide as vinegar is not as large as commercial uses, but is by far the oldest and best-known awarding.^[65]

Reactions [edit]

Organic chemical science [edit]

Two typical organic reactions of acetic acid

Acetic acid undergoes the typical chemic reactions of a carboxylic acid. Upon handling with a standard base of operations, it converts to metal acetate and h2o. With potent bases (e.g., organolithium reagents), information technology tin be doubly deprotonated to requite LiCH₂COOLi. Reduction of acetic acid gives ethanol. The OH group is the master site of reaction, equally illustrated by the conversion of acetic acid to acetyl chloride. Other substitution derivatives include acetic anhydride; this anhydride is produced past loss of water from two molecules of acetic acid. Esters of acetic acrid tin also be formed via Fischer esterification, and amides tin exist formed. When heated above 440 °C (824 °F), acetic acid decomposes to produce carbon dioxide and methyl hydride, or to produce ketene and h2o:^{[66] [67] [68]}

CH₃COOH → CH₄ + CO_ii

CH₃COOH → CH₂=C=O + H₂O

Reactions with inorganic compounds [edit]

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

Mg + 2 CH₃COOH → (CH_iiiCOO)₂Mg + H_two

Because aluminium forms a passivating acrid-resistant film of aluminium oxide, aluminium tanks are used to send acetic acrid. Metallic acetates can as well be prepared from acetic acrid and an appropriate base, as in the popular "baking soda + vinegar" reaction giving off sodium acetate:

NaHCO₃ + CH_threeCOOH → CH₃COONa + CO₂ + H_iiO

A colour reaction for salts of acetic acid is atomic number 26(III) chloride solution, which results in a securely red colour that disappears after acidification.^[69] A more than sensitive test uses lanthanum nitrate with iodine and ammonia to give a blue solution.^[70] Acetates when heated with arsenic trioxide grade cacodyl oxide, which can be detected by its malodorous vapours.^[71]

Other derivatives [edit]

Organic or inorganic salts are produced from acetic acrid. Some commercially significant derivatives:

• Sodium acetate, used in the textile industry and as a nutrient preservative (E262).
• Copper(2) acetate, used as a pigment and a fungicide.
• Aluminium acetate and fe(II) acetate—used as mordants for dyes.
• Palladium(II) acetate, used every bit a catalyst for organic coupling reactions such as the Heck reaction.

Halogenated acerb acids are produced from acetic acid. Some commercially meaning derivatives:

• Chloroacetic acrid (monochloroacetic acrid, MCA), dichloroacetic acid (considered a by-product), and trichloroacetic acid. MCA is used in the manufacture of indigo dye.
• Bromoacetic acrid, which is esterified to produce the reagent ethyl bromoacetate.
• Trifluoroacetic acid, which is a common reagent in organic synthesis.

Amounts of acetic acrid used in these other applications together account for some other v–10% of acetic acid use worldwide.^[30]

History [edit]

Vinegar was known early in civilization as the natural result of exposure of beer and wine to air, because acetic acrid-producing bacteria are present globally. The use of acerb acrid in abracadabra extends into the 3rd century BC, when the Greek philosopher Theophrastus described how vinegar acted on metals to produce pigments useful in art, including white lead (lead carbonate) and verdigris, a green mixture of copper salts including copper(II) acetate. Ancient Romans boiled soured vino to produce a highly sweet syrup called sapa. Sapa that was produced in lead pots was rich in atomic number 82 acetate, a sweet substance also called carbohydrate of lead or carbohydrate of Saturn, which contributed to lead poisoning among the Roman elite.^[72]

In the 16th-century German alchemist Andreas Libavius described the production of acetone from the dry distillation of lead acetate, ketonic decarboxylation. The presence of water in vinegar has such a profound effect on acerb acid's properties that for centuries chemists believed that glacial acerb acid and the acid found in vinegar were two different substances. French pharmacist Pierre Adet proved them identical.^{[72] [73]}

Crystallised acetic acrid.

In 1845 German language chemist Hermann Kolbe synthesised acetic acid from inorganic compounds for the kickoff time. This reaction sequence consisted of chlorination of carbon disulfide to carbon tetrachloride, followed past pyrolysis to tetrachloroethylene and aqueous chlorination to trichloroacetic acid, and concluded with electrolytic reduction to acerb acid.^[74]

Past 1910, near glacial acetic acid was obtained from the pyroligneous liquor, a product of the distillation of wood. The acetic acrid was isolated by treatment with milk of lime, and the resulting calcium acetate was then acidified with sulfuric acid to recover acetic acid. At that fourth dimension, Germany was producing ten,000 tons of glacial acetic acid, effectually xxx% of which was used for the manufacture 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 Dreyfus at British Celanese developed a methanol carbonylation airplane pilot plant equally early on equally 1925.^[76] However, a lack of applied materials that could contain the corrosive reaction mixture at the loftier pressures needed (200 atm or more than) discouraged commercialization of these routes. The showtime commercial methanol carbonylation process, which used a cobalt goad, was developed by German chemic company BASF in 1963. In 1968, a rhodium-based catalyst (cis−[Rh(CO)₂I₂]⁻ ) was discovered that could operate efficiently at lower force per unit area with about no by-products. The states chemical company Monsanto Company built the starting time plant using this catalyst in 1970, and rhodium-catalyzed methanol carbonylation became the ascendant method of acetic acrid production (see Monsanto procedure). In the late 1990s, the chemicals company BP Chemicals commercialised the Cativa catalyst ([Ir(CO)_twoI₂]⁻ ), which is promoted past iridium^[77] for greater efficiency. This iridium-catalyzed Cativa process is greener and more efficient^[34] and has largely supplanted the Monsanto process, oft in the same production plants.

Interstellar medium [edit]

Interstellar acetic acid was discovered in 1996 by a team led by David Mehringer^[78] using the quondam Berkeley-Illinois-Maryland Clan array at the Chapeau Creek Radio Observatory and the former Millimeter Array located at the Owens Valley Radio Observatory. Information technology was first detected in the Sagittarius B2 North molecular cloud (besides known every bit the Sgr B2 Big Molecule Heimat source). Acetic acrid has the stardom of being the starting time molecule discovered in the interstellar medium using solely radio interferometers; in all previous ISM molecular discoveries made in the millimetre and centimetre wavelength regimes, unmarried dish radio telescopes were at to the lowest degree partly responsible for the detections.^[78]

Health furnishings and safety [edit]

Concentrated acerb acid is corrosive to skin.^{[79] [lxxx]} These burns or blisters may non appear until hours after exposure.

Prolonged inhalation exposure (viii hours) to acetic acid vapours at ten ppm can produce some irritation of eyes, nose, and throat; at 100 ppm marked lung irritation and possible impairment to lungs, optics, and skin may effect. Vapour concentrations of 1,000 ppm crusade marked irritation of eyes, olfactory organ and upper respiratory tract and cannot exist tolerated. These predictions were based on animal experiments and industrial exposure.

In 12 workers exposed for two or more years to acerb 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 than is intolerable to most persons and results in intensive lacrimation and irritation of the eyes, nose, and pharynx, with pharyngeal oedema and chronic bronchitis. Unacclimatised humans experience extreme eye and nasal irritation at concentrations in excess of 25 ppm, and conjunctivitis from concentrations below x ppm has been reported. In a study of 5 workers exposed for vii to 12 years to concentrations of 80 to 200 ppm at peaks, the principal findings were blackening and hyperkeratosis of the skin of the easily, conjunctivitis (but no corneal harm), 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 following table lists the EU classification of acetic acid solutions:^{[82] [ citation needed ]}

Concentration by weight	Molarity	GHS pictograms	H-Phrases
10–25%	1.67–4.xvi mol/L		H315
25–90%	4.16–14.99 mol/Fifty		H314
>90%	>fourteen.99 mol/L		H226, H314

Concentrated acetic acid tin can be ignited only with difficulty at standard temperature and pressure, merely becomes a combustible hazard in temperatures greater than 39 °C (102 °F), and can form explosive mixtures with air at college temperatures (explosive limits: v.4–xvi%).

See also [edit]

• Acetic acid (data page)
• Acids in vino

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External links [edit]

Wait upwards acetic in Wiktionary, the free dictionary.

• International Chemical Rubber Carte du jour 0363
• National Pollutant Inventory – Acetic acrid fact sail
• NIOSH Pocket Guide to Chemic Hazards
• Method for sampling and analysis
• 29 CFR 1910.1000, Table Z-one (US Permissible exposure limits)
• ChemSub Online: Acetic acid
• Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of acerb acid
• Acetic acid spring to proteins in the PDB
• Swedish Chemicals Agency. Data sheet – Acetic Acid
• Process Menstruum sheet of Acetic acid Product past the Carbonylation of Methanol

Boiling Point Of Acetic Acid,

Source: https://en.wikipedia.org/wiki/Acetic_acid

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