Acetic acid
IUPAC name	Acetic acid, Ethanoic acid
Other names	Acetyl hydroxide (AcOH), Hydrogen acetate (HAc), Ethylic acid, Methanecarboxylic acid
Identifiers
CAS number	[64-19-7]
PubChem	176
InChI	1/C2H4O2/c1-2(3)4/h1H3, (H,3,4)/f/h3H
Properties
Molecular formula	CH3COOH
Molar mass	60. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 05 g/mol
Appearance	Colourless liquid or crystals
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 049 g·cm−3 (l) 1. Liquid is one of the principal States of matter. A liquid is a Fluid that has the particles loose and can freely form a distinct surface at the boundaries of 266 g·cm−3 (s)
Melting point	16. A solid' object is in the States of matter characterized by resistance to Deformation and changes of Volume. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C (289. 6 K, 61. 6 °F)
Boiling point	118. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 1 °C (391. 2 K, 244. 5 °F)
Solubility in water	Fully miscible
Acidity (pKa)	4. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Miscibility is a term commonly used in Chemistry that refers to the property of Liquids to mix in all proportions forming a Homogeneous Solution 76 at 25 °C
Viscosity	1. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 22 mPa·s at 25 °C
Structure
Dipole moment	1. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 74 D (gas)
Hazards
MSDS	External MSDS
NFPA 704	2 2 2
R-phrases	R10, R35
S-phrases	(S1/2), S23, S26, S45
Flash point	43 °C
Related compounds
Related carboxylic acid	formic acid, propionic acid, butyric acid
Related compounds	acetamide, ethyl acetate, acetyl chloride, acetic anhydride, acetonitrile, acetaldehyde, ethanol, thioacetic acid, acetylcholine, acetylcholinesterase
Supplementary data page
Structure and properties	n, εr, etc. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance and save the page --> This page provides supplementary chemical data on Acetic acid. Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. Propionic acid (systematically named propanoic acid) is a naturally-occurring Carboxylic acid with Chemical formula C[[Hydrogen H]]3CH2C Butyric acid (from Greek βούτυρος = butter) also known under the systematic name butanoic acid, is a Carboxylic acid with the structural Acetamide (or acetic acid amide or ethanamide) CH3CONH2 the Amide of Acetic acid, is a white crystalline solid in Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Acetyl chloride, also known as ethanoyl chloride, is an Acid chloride (also known as an Acyl chloride) derived from Acetic acid ( Ethanoic Acetic anhydride is the Chemical compound with the formula (CH3CO2O Acetonitrile (ACN is the Chemical compound with formula CH3CN Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO Thioacetic acid is an Organic compound with the Molecular formula CH3COSH The Chemical compound acetylcholine (often abbreviated ACh) is a Neurotransmitter in both the Peripheral nervous system (PNS and Central and save the page --> This page provides supplementary chemical data on Acetic acid. and save the page --> This page provides supplementary chemical data on Acetic acid. The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving vinegar its sour taste and pungent smell. and save the page --> This page provides supplementary chemical data on Acetic acid. and save the page --> This page provides supplementary chemical data on Acetic acid. Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. Vinegar is an acidic liquid processed from the Fermentation of Ethanol in a process that yields its key ingredient Acetic acid (also called ethanoic acid Its structural formula is represented as CH₃COOH. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Pure, water-free acetic acid (glacial acetic acid) is a colourless liquid that absorbs water from the environment (hygroscopy), and freezes below 16. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Liquid is one of the principal States of matter. A liquid is a Fluid that has the particles loose and can freely form a distinct surface at the boundaries of Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption 7 °C (62 °F) to a colourless crystalline solid. The Celsius Temperature scale was previously known as the centigrade scale. Fahrenheit is a temperature scale named after Daniel Gabriel Fahrenheit (1686–1736 a German Physicist who proposed it in 1724 In Materials science, a crystal is a Solid in which the constituent Atoms Molecules or Ions are packed in a regularly ordered repeating A solid' object is in the States of matter characterized by resistance to Deformation and changes of Volume. Acetic acid is corrosive, and its vapour causes irritation to the eyes, a dry and burning nose, sore throat and congestion to the lungs. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Corrosion means the breaking down of essential properties in a material due to Chemical reactions with its surroundings It is a weak acid because at standard temperature and pressure the dissociated acid exists in equilibrium with the undissociated form in aqueous solutions, in contrast to strong acids, which are fully dissociated. A weak acid is an Acid that does not completely donate all of its hydrogens when dissolved in water In Physical sciences standard conditions for temperature and pressure are Standard sets of conditions for experimental measurements to allow comparisons to be made Dissociation in Chemistry and Biochemistry is a general process in which ionic compounds ( complexes, Molecules, or Salts) separate In Chemistry, a solution is a Homogeneous Mixture composed of two or more substances A Strong acid is an Acid that Ionizes completely in an Aqueous solution (not in the case of Sulfuric acid as it is diprotic

Acetic acid is one of the simplest carboxylic acids (the second-simplest, next to formic acid). Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. It is an important chemical reagent and industrial chemical that is used in the production of polyethylene terephthalate mainly used in soft drink bottles; cellulose acetate, mainly for photographic film; and polyvinyl acetate for wood glue, as well as synthetic fibres and fabrics. A reagent or reactant is a substance or compound consumed during a Chemical reaction. Uses PET can be semi-rigid to rigid depending on its thickness and is very lightweight Cellulose acetate, first prepared in 1865 is the Acetate Ester of Cellulose. This article is mainly concerned with Still photography film For Motion picture film please see Film stock. Polyvinyl acetate ( PVA or PVAc) is a Rubbery Synthetic polymer. Glue or adhesive is a compound that adheres or bonds two items together In households diluted acetic acid is often used in descaling agents. A descaling agent, also known as descaling, anti-limestone, anti-limescale, anti-lime, or anti-scale, is a Solution to In the food industry acetic acid is used under the food additive code E260 as an acidity regulator. The food industry is the complex global collective of diverse Businesses that together supply much of the Food energy consumed by the World population. E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union. Acidity regulators, or pH control agents, are Food additives added to change or maintain PH ( Acidity or Basicity)

The global demand of acetic acid is around 6. 5 million tonnes per year (Mt/a), of which approximately 1. This article is about the tonne or metric ton For other tons see Ton. 5 Mt/a is met by recycling; the remainder is manufactured from petrochemical feedstocks or from biological sources. Petrochemicals are chemical products made from raw materials of Petroleum or other Hydrocarbon origin

Contents 1 Nomenclature 2 History 3 Chemical properties 3.1 Chemical reactions 3.2 Biochemistry 4 Production 4.1 Methanol carbonylation 4.2 Acetaldehyde oxidation 4.3 Ethylene oxidation 4.4 Oxidative fermentation 4.5 Anaerobic fermentation 5 Applications 5.1 Vinyl acetate monomer 5.2 Ester production 5.3 Acetic anhydride 5.4 Vinegar 5.5 Use as solvent 5.6 Other applications 6 Safety 7 See also 8 References 9 External links

Nomenclature

The trivial name acetic acid is the most commonly used and officially preferred name by the IUPAC. In Chemistry and Zoology, a trivial name (also a Common name or vernacular name) is a non- Systematic name. The International Union of Pure and Applied Chemistry ( IUPAC) (aɪjuːpæk or ay-yoo-pec) is an international Non-governmental organization This name derives from acetum, the Latin word for vinegar, and is related to the word acid itself. Latin ( lingua Latīna, laˈtiːna is an Italic language, historically spoken in Latium and Ancient Rome. The synonym ethanoic acid is a systematic name that is used in introductions to chemical nomenclature. The IUPAC nomenclature of organic chemistry is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied

Glacial acetic acid is a trivial name for water-free acetic acid. Similar to the German name Eisessig (literally, ice-vinegar), the name comes from the ice-like crystals that form slightly below room temperature at 16. The German language (de ''Deutsch'') is a West Germanic language and one of the world's major languages. 7 °C (about 62 °F).

The most common and official abbreviation for acetic acid is AcOH or HOAc where Ac stands for the acetyl group CH₃−C(=O)−;. In Organic chemistry, acetyl (ethanoyl is a Functional group, the Acyl of Acetic acid, with Chemical formula - C[[Oxygen In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions In the context of acid-base reactions the abbreviation HAc is often used where Ac instead stands for the acetate anion (CH₃COO⁻), although this use is regarded by many as misleading. An acetate, or ethanoate, is either a salt or Ester of Acetic acid. An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge In either case, the Ac is not to be confused with the abbreviation for the chemical element actinium. A chemical element is a type of Atom that is distinguished by its Atomic number; that is by the number of Protons in its nucleus. Actinium (ækˈtɪniəm is a radioactive Chemical element with the symbol Ac and Atomic number 89 which was discovered in 1899, the earliest

Acetic acid has the empirical formula CH₂O and the molecular formula C₂H₄O₂ or HC₂H₃O₂ (to emphasize the role of the 'active' hydrogen in forming the salt sodium acetate). A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes ^[1] To better reflect its structure, acetic acid is often written as CH₃-CO₂-H, CH₃COOH, CH₃CO₂H, or HOCOCH₃. The ion resulting from loss of H⁺ from acetic acid is the acetate anion. An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge The proton ( Greek πρῶτον / proton "first" is a Subatomic particle with an Electric charge of one positive The name acetate can also refer to a salt containing this anion, or an ester of acetic acid. Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least

History

Vinegar was known, early in civilization, as the natural result of air exposure of beer and wine, as acetic acid-producing bacteria are present throughout the world. Vinegar is an acidic liquid processed from the Fermentation of Ethanol in a process that yields its key ingredient Acetic acid (also called ethanoic acid Beer is the world's oldest and most widely consumed Alcoholic beverage and the third most popular drink overall after water and tea Wine is an Alcoholic beverage made from the fermentation of Grape juice

The use of acetic acid in alchemy extends into the third century BC, when the Greek philosopher Theophrastos 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. Alchemy a part of the Occult Tradition is both a philosophy and a practice with an ultimately unknown aim involving the improvement of the alchemist as well as the making of Greece (Ελλάδα transliterated: Elláda, historically, Ellás,) officially the Hellenic Republic (Ελληνική Δημοκρατία Theophrastus ( Greek:; 371 – c 287 BC a Greek native of Eressos in Lesbos, was the successor of Aristotle in the Peripatetic For the drug referred to as "pigment" see Black tar heroin. Lead carbonate, is the chemical compound PbCO3 It is prepared industrially from Lead(II acetate and Carbon dioxide. Verdigris is the common name for the Green coating or Patina formed when Copper, Brass or Bronze is weathered and exposed to Copper (ˈkɒpɚ is a Chemical element with the symbol Cu (cuprum and Atomic number 29 Copper(II acetate, also referred to as cupric acetate, is the Chemical compound with the formula Cu (OAc2 where AcO- Ancient Romans boiled soured wine in lead pots to produce a highly sweet syrup called sapa. Rome ( Roma ˈroma Roma is the capital city of Italy and Lazio, and is Italy's largest and most populous city with more than 2 Sapa was rich in lead acetate, a sweet substance also called sugar of lead or sugar of Saturn, which contributed to lead poisoning among the Roman aristocracy. Lead(II acetate is a Chemical compound, a white crystalline substance with a Sweetish taste Saturn ( Latin: Saturnus) was a major Roman God of agriculture and harvest Lead poisoning (also known as saturnism, plumbism, or painter's colic) is a medical condition caused by increased levels of the metal Lead in

In the 8th century, the Muslim alchemist Jabir Ibn Hayyan (Geber) was the first to concentrate acetic acid from vinegar through distillation. For the 12th century astronomer see Jabir ibn Aflah. For the anonymous 14th century Spanish alchemist see Pseudo-Geber. Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture In the Renaissance, glacial acetic acid was prepared through the dry distillation of metal acetates. The Renaissance (from French Renaissance, meaning "rebirth" Italian: Rinascimento, from re- "again" and nascere Dry distillation is the Heating of Solid materials to produce Liquid or Gaseous products (which may condense into solids The 16th century German alchemist Andreas Libavius described such a procedure, and he compared the glacial acetic acid produced by this means to vinegar. Germany, officially the Federal Republic of Germany ( ˈbʊndəsʁepuˌbliːk ˈdɔʏtʃlant is a Country in Central Europe. Andreas Libavius (1555 &ndash July 25, 1616) was a German doctor and Chemist. The presence of water in vinegar has such a profound effect on acetic acid's properties that for centuries chemists believed that glacial acetic acid and the acid found in vinegar were two different substances. The French chemist Pierre Adet proved them to be identical. Pierre-Auguste Adet was a French scientist politician and diplomat born in Nevers on 17 May 1763.

In 1847 the German chemist Hermann Kolbe synthesized acetic acid from inorganic materials for the first time. Adolph Wilhelm Hermann Kolbe ( September 27, 1818 &ndash November 25, 1884) was a German Chemist. In Chemistry, chemical synthesis is purposeful execution of Chemical reactions in order to get a product, or several products Inorganic chemistry is the branch of Chemistry concerned with the properties and behavior of Inorganic compounds This field covers all Chemical compounds This reaction sequence consisted of chlorination of carbon disulfide to carbon tetrachloride, followed by pyrolysis to tetrachloroethylene and aqueous chlorination to trichloroacetic acid, and concluded with electrolytic reduction to acetic acid. Chlorination is the process of adding the element Chlorine to Water as a method of Water purification to make it fit for human consumption as Carbon tetrachloride, also known by many other names (see Table is the Organic compound with the formula CCl4 Pyrolysis is the Chemical decomposition of organic materials by heating in the absence of Oxygen or any other reagents except possibly Steam Tetrachloroethylene, also known under its systematic name tetrachloroethene and as perchloroethylene, perchloroethene, perc, and PCE Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of Acetic acid in which the three Hydrogen atoms of the Methyl In chemistry and manufacturing electrolysis is a method of separating chemically bonded elements and compounds by passing an Electric current Organic reductions or organic oxidations or organic redox reactions are Redox reactions that take place with Organic compounds In Organic ^[2]

By 1910 most glacial acetic acid was obtained from the "pyroligneous liquor" from distillation of wood. The acetic acid was isolated from this by treatment with milk of lime, and the resultant calcium acetate was then acidified with sulfuric acid to recover acetic acid. Calcium hydroxide, traditionally called slaked lime, hydrated lime, or pickling lime, is a Chemical compound with the chemical formula The Chemical compound calcium acetate is the Calcium salt of Acetic acid. Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. At this time Germany was producing 10,000 tons of glacial acetic acid, around 30% of which was used for the manufacture of indigo dye. Units of mass There are three similar units of Mass called the ton: Long ton (simply ton in countries such as the United Indigo dye is Dye with a distinctive blue color (see Indigo) The chemical compound that constitutes the indigo dye is called indigotin ^[3][4]

Chemical properties

The hydrogen (H) atom in the carboxyl group (−COOH) in carboxylic acids such as acetic acid can be given off as an H⁺ ion (proton), giving them their acidic character. Carboxyl group or CO2H is a Functional group present in Amino acids and Carboxylic acids Its structure is composed of one carbon atom attached Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H The proton ( Greek πρῶτον / proton "first" is a Subatomic particle with an Electric charge of one positive Acetic acid is a weak, effectively monoprotic acid in aqueous solution, with a pK_a value of 4. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are 8. Its conjugate base is acetate (CH₃COO⁻). Within the Brønsted - Lowry ( protonic) theory of acids and bases, a conjugate acid is the acid member HX of a pair of two compounds that transform An acetate, or ethanoate, is either a salt or Ester of Acetic acid. A 1. 0 M solution (about the concentration of domestic vinegar) has a pH of 2. In Chemistry, concentration is the measure of how much of a given substance there is mixed with another substance 4, indicating that merely 0. 4% of the acetic acid molecules are dissociated.

The crystal structure of acetic acid shows that the molecules pair up into dimers connected by hydrogen bonds. A dimer is a Chemical or Biological entity consisting of two subunits called Monomers which are held together by either Intramolecular forces A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen ^[5] The dimers can also be detected in the vapour at 120 °C. They also occur in the liquid phase in dilute solutions in non-hydrogen-bonding solvents, and a certain extent in pure acetic acid,^[6] but 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^–1 K^–1. ^[7] This dimerization behaviour is shared by other lower carboxylic acids.

Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water. Liquid is one of the principal States of matter. A liquid is a Fluid that has the particles loose and can freely form a distinct surface at the boundaries of Hydrophile, from the Greek (hydros "water" and φιλια (philia "friendship" refers to a physical property of a Molecule "Polar molecule" and "Non-polar" redirect here In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen Water is a common Chemical substance that is essential for the survival of all known forms of Life. With a moderate dielectric constant of 6. Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test 2, it can dissolve not only polar compounds such as inorganic salts and sugars, but also non-polar compounds such as oils and elements such as sulfur and iodine. Sugar is a class of edible Crystalline substances mainly Sucrose, Lactose, and Fructose. A chemical element is a type of Atom that is distinguished by its Atomic number; that is by the number of Protons in its nucleus. Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 Iodine (ˈaɪədaɪn ˈaɪədɪn or /ˈaɪədiːn/ from ιώδης iodes "violet" is a Chemical element that has the symbol I and Atomic It readily mixes with other polar and non-polar solvents such as water, chloroform, and hexane. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Chloroform, also known as trichloromethane and methyl trichloride, is a Chemical compound with formula C[[Hydrogen H]] Cl Hexane is an Alkane Hydrocarbon with the Chemical formula CH3(CH24CH3 or C6H14 This dissolving property and miscibility of acetic acid makes it a widely used industrial chemical. Miscibility is a term commonly used in Chemistry that refers to the property of Liquids to mix in all proportions forming a Homogeneous Solution

Chemical reactions

Acetic acid is corrosive to metals including iron, magnesium, and zinc, forming hydrogen gas and metal salts called acetates. Corrosion means the breaking down of essential properties in a material due to Chemical reactions with its surroundings The M acro E xpansion T emplate A ttribute L anguage complements TAL, providing macros which allow the reuse of code across Iron (ˈаɪɚn is a Chemical element with the symbol Fe (ferrum and Atomic number 26 Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 Atomic weight 24 Zinc (ˈzɪŋk from Zink is a Metallic Chemical element with the symbol Zn and Atomic number 30 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 An acetate, or ethanoate, is either a salt or Ester of Acetic acid. Aluminium, when exposed to oxygen, forms a thin layer of aluminium oxide on its surface which is relatively resistant, so that aluminium tanks can be used to transport acetic acid. WikipediaNaming Metal acetates can also be prepared from acetic acid and an appropriate base, as in the popular "baking soda + vinegar" reaction. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Sodium bicarbonate or sodium hydrogen carbonate is the Chemical compound with the formula NaHCO3 With the notable exception of chromium(II) acetate, almost all acetates are soluble in water. Chromium(II acetate, better known as chromous acetate is the compound Cr2(CH3CO24(H2O2

Mg(s) + 2 CH₃COOH(aq) → (CH₃COO)₂Mg(aq) + H₂(g)

NaHCO₃(s) + CH₃COOH(aq) → CH₃COONa(aq) + CO₂(g) + H₂O(l)

Acetic acid undergoes the typical chemical reactions of a carboxylic acid, such as producing water and a metal ethanoate when reacting with alkalis, producing a metal ethanoate when reacted with a metal, and producing a metal ethanoate, water and carbon dioxide when reacting with carbonates and hydrogencarbonates. Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 Atomic weight 24 A solid' object is in the States of matter characterized by resistance to Deformation and changes of Volume. Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 This page is about the physical properties of gas as a state of matter Sodium bicarbonate or sodium hydrogen carbonate is the Chemical compound with the formula NaHCO3 Sodium acetate, (also sodium ethanoate) is the Sodium salt of Acetic acid. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as Liquid is one of the principal States of matter. A liquid is a Fluid that has the particles loose and can freely form a distinct surface at the boundaries of A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H An acetate, or ethanoate, is either a salt or Ester of Acetic acid. In Chemistry, an alkali (from Arabic: Al-Qaly القلي القالي) is a basic, ionic salt of an Alkali metal Water is a common Chemical substance that is essential for the survival of all known forms of Life. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single In Chemistry, a carbonate is a salt or Ester of Carbonic acid. In Inorganic chemistry, bicarbonate ( IUPAC -recommended nomenclature hydrogencarbonate) is an intermediate form in the Deprotonation Most notable of all its reactions is the formation of ethanol by reduction, and formation of derivatives such as acetyl chloride via nucleophilic acyl substitution. Acetyl chloride, also known as ethanoyl chloride, is an Acid chloride (also known as an Acyl chloride) derived from Acetic acid ( Ethanoic Nucleophilic acyl substitution describes the Substitution reaction involving Nucleophiles and Acyl compounds Other substitution derivatives include acetic anhydride; this anhydride is produced by loss of water from two molecules of acetic acid. Acetic anhydride is the Chemical compound with the formula (CH3CO2O In Chemistry, an anhydride is a compound that can be considered as derived from another compound by subtracting the molecules of water. A condensation reaction is a Chemical reaction in which two Molecules or moieties ( Functional groups) combine to form one single molecule together with Esters of acetic acid can likewise be formed via Fischer esterification, and amides can also be formed. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Fischer esterification or Fischer-Speier esterification is a special type of Esterification and the process of forming an Ester by Refluxing a In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized When heated above 440 °C, acetic acid decomposes to produce carbon dioxide and methane, or to produce ketene and water. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Methane is a Chemical compound with the molecular formula. It is the simplest Alkane, and the principal component of Natural gas. A ketene is an Organic compound of the form R2C=C=O Hermann Staudinger pioneered the research of ketenes

Acetic acid can be detected by its characteristic smell! A colour reaction for salts of acetic acid is iron(III) chloride solution, which results in a deeply red colour that disappears after acidification. In Chemistry, a color reaction is a Chemical reaction that is used to transform colorless Chemical compounds into colored derivatives which can Iron chloride redirects here For Iron(II chloride see Iron(II chloride. Acetates when heated with arsenic trioxide form cacodyl oxide, which can be detected by its malodorous vapours. Arsenic trioxide is the most important commercial compound of Arsenic, and the main starting material for arsenic chemistry Cacodyl oxide is a Chemical compound of the formula 2O This Organoarsenic compound is primarily of historical significance as it is sometimes

Biochemistry

The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. In Organic chemistry, acetyl (ethanoyl is a Functional group, the Acyl of Acetic acid, with Chemical formula - C[[Oxygen In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions When bound to coenzyme A it is central to the metabolism of carbohydrates and fats. Coenzyme A ( CoA, CoASH, or HSCoA) is a Coenzyme, notable for its role in the synthesis and oxidation of Fatty acids Metabolism is the set of Chemical reactions that occur in living Organisms in order to maintain Life. Carbohydrates (from ' Hydrates of Carbon ' or saccharides ( Greek σάκχαρον meaning " Sugar " are the most Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. pH is the measure of the acidity or alkalinity of a Solution. Unlike longer-chain carboxylic acids (the fatty acids), acetic acid does not occur in natural triglycerides. In Chemistry, especially Biochemistry, a fatty acid is a Carboxylic acid often with a long unbranched Aliphatic tail ( chain) which (more properly known as, TAG or triacylglyceride) is Glyceride in which the Glycerol is Esterified with three Fatty acids It is the However, the artificial triglyceride triacetin (glycerin triacetate) is a common food additive, and is found in cosmetics and topical medicines. The Triglyceride 123-triacetoxypropane is more generally known as triacetin and glycerin triacetate.

Acetic acid is produced and excreted by certain bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The Bacteria ( singular: bacterium) are a large group of unicellular Microorganisms Typically a few Micrometres in length bacteria have Acetobacter is a genus of Acetic acid bacteria characterized by the ability to convert alcohol ( Ethanol) to Acetic acid in the presence Clostridium acetobutylicum, included in the genus Clostridium, is a commercially valuable Bacterium. These bacteria are found universally in foodstuffs, water, and soil, and acetic acid is produced naturally as fruits and other foods spoil. Food is any substance usually composed primarily of Carbohydrates Fats water and/or Proteins that can be eaten or drunk by an Water is a common Chemical substance that is essential for the survival of all known forms of Life. Soil, often typeset as SOiL, is a four piece rock band from Chicago Illinois United States founded by Shaun Glass Tom Schofield Tim King and Adam Zadel Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent. Vaginal lubrication is the naturally produced lubricating fluid that reduces friction during Sexual intercourse. Human beings, humans or man (Origin 1590–1600 L homō man OL hemō the earthly one (see Humus A primate is a member of the biological order Primates ( Latin: "prime first rank" the group that contains Lemurs the Aye-aye Antiseptics (from Greek αντί - anti, '"against" + σηπτικός - septikos, "putrefactive" are antimicrobial ^[8]

Production

Acetic acid is produced both synthetically and by bacterial fermentation. Fermentation is the process of deriving energy from the oxidation of organic compounds such as carbohydrates using an endogenous electron acceptor which is Today, the biological route accounts for only about 10% of world production, but it remains important for vinegar production, as the world food purity laws stipulate that vinegar used in foods must be of biological origin. About 75% of acetic acid made for use in the chemical industry is made by methanol carbonylation, explained below. Alternative methods account for the rest. ^[9]

Total worldwide production of virgin acetic acid is estimated at 5 Mt/a (million tonnes per year), approximately half of which is produced in the United States. The United States of America —commonly referred to as the European production stands at approximately 1 Mt/a and is declining, and 0. 7 Mt/a is produced in Japan. For a topic outline on this subject see List of basic Japan topics. Another 1. 5 Mt are recycled each year, bringing the total world market to 6. 5 Mt/a. ^[10][11] The two biggest producers of virgin acetic acid are Celanese and BP Chemicals. Celanese ( is a large American chemical company based in Dallas, Texas. BP plc, previously known as British Petroleum, is the third largest global Energy company, a multinational oil company (" Oil major Other major producers include Millennium Chemicals, Sterling Chemicals, Samsung, Eastman, and Svensk Etanolkemi. Millennium Inorganic Chemicals is a Hunt Valley MD based chemical company Sterling Chemicals is a chemicals producer located in Houston Texas. The Samsung Group ( Korean:, Samsung Guerup) is South Korea 's largest company or Chaebol and the world's largest conglomerate Eastman Chemical Company is a United States based Chemical company, engaged in the manufacture and sale of chemicals plastics and fibers The company Svensk Etanolkemi AB, or Sekab is a major Nordic producer of Ethanol, ethanol Derivatives such as Acetic acid and Ethyl acetate

Methanol carbonylation

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

CH₃OH + CO → CH₃COOH

The process involves iodomethane as an intermediate, and occurs in three steps. Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. Iodomethane, commonly called Methyl iodide and commonly abbreviated "MeI" is the Chemical compound with the formula CH3I A catalyst, usually a metal complex, is needed for the carbonylation (step 2). Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst The term complex in Chemistry is usually used to describe molecules or ensembles formed by the combination of Ligands and metal Ions.

(1) CH₃OH + HI → CH₃I + H₂O

(2) CH₃I + CO → CH₃COI

(3) CH₃COI + H₂O → CH₃COOH + HI

By altering the process conditions, acetic anhydride may also be produced on the same plant. Acetic anhydride is the Chemical compound with the formula (CH3CO2O Because both methanol and carbon monoxide are commodity raw materials, methanol carbonylation long appeared to be an attractive method for acetic acid production. Henry Drefyus at British Celanese developed a methanol carbonylation pilot plant as early as 1925. Celanese ( is a large American chemical company based in Dallas, Texas. ^[12] However, 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. Pressure (symbol 'p' is the force per unit Area applied to an object in a direction perpendicular to the surface The Standard atmosphere is an international reference pressure defined as 101325 Pa and formerly used as unit of Pressure (symbol atm The first commercial methanol carbonylation process, which used a cobalt catalyst, was developed by German chemical company BASF in 1963. Cobalt (ˈkoʊbɒlt is a hard lustrous silver-grey Metal, a Chemical element with symbol Co. BASF SE () is a German chemical company and the largest chemical company in the world In 1968, a rhodium-based catalyst (cis−[Rh(CO)₂I₂]⁻) was discovered that could operate efficiently at lower pressure with almost no by-products. Rh redirects here For other uses see Rh (disambiguation Rhodium (ˈroʊdiəm is a Chemical element with the symbol The first plant using this catalyst was built by US chemical company Monsanto in 1970, and rhodium-catalysed methanol carbonylation became the dominant method of acetic acid production (see Monsanto process). The Monsanto Company ( is a multinational Agricultural biotechnology Corporation. The Monsanto process is an important method for the manufacture of Acetic acid. In the late 1990s, the chemicals company BP Chemicals commercialized the Cativa catalyst ([Ir(CO)₂I₂]⁻), which is promoted by ruthenium. BP plc, previously known as British Petroleum, is the third largest global Energy company, a multinational oil company (" Oil major The Cativa process is a method for the production of Acetic acid by the Carbonylation of Methanol. Ruthenium (ruːˈθiːniəm is a Chemical element that has the symbol Ru and Atomic number 44 This iridium-catalysed process is greener and more efficient^[13] and has largely supplanted the Monsanto process, often in the same production plants. Iridium (ɪˈrɪdiəm is a Chemical element that has the symbol Ir and Atomic number 77 Green chemistry, also called sustainable chemistry is a chemical philosophy encouraging the design of products and processes that reduce or eliminate the use and generation of hazardous

Acetaldehyde oxidation

Prior to the commercialization of the Monsanto process, most acetic acid was produced by oxidation of acetaldehyde. Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO This remains the second most important manufacturing method, although it is uncompetitive with methanol carbonylation. The acetaldehyde may be produced via oxidation of butane or light naphtha, or by hydration of ethylene. Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state

When butane or light naphtha is heated with air in the presence of various metal ions, including those of manganese, cobalt and chromium; peroxides form and then decompose to produce acetic acid according to the chemical equation

2 C₄H₁₀ + 5 O₂ → 4 CH₃COOH + 2 H₂O

Typically, the reaction is run at a combination of temperature and pressure designed to be as hot as possible while still keeping the butane a liquid. Butane, also called n -butane, is the unbranched Alkane with four Carbon Atoms CH3CH2CH2CH3 Naphtha normally refers to a number of different flammable liquid mixtures of hydrocarbons i An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Manganese (ˈmæŋgəniːz is a Chemical element, designated by the symbol Mn. Cobalt (ˈkoʊbɒlt is a hard lustrous silver-grey Metal, a Chemical element with symbol Co. Chromium (ˈkroʊmiəm is a Chemical element which has the symbol Cr and Atomic number 24 Organic peroxides are Organic compounds containing the Peroxide Functional group (ROOR' A chemical equation is a symbolic representation of a Chemical reaction. Temperature is a physical property of a system that underlies the common notions of hot and cold something that is hotter generally has the greater temperature Typical reaction conditions are 150 °C and 55 atm. Side products may also form, including butanone, ethyl acetate, formic acid, and propionic acid. Butanone is a manufactured organic chemical. It is a colorless liquid with a sharp sweet butterscotch odor reminiscent of Acetone. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. Propionic acid (systematically named propanoic acid) is a naturally-occurring Carboxylic acid with Chemical formula C[[Hydrogen H]]3CH2C These side products are also commercially valuable, and the reaction conditions may be altered to produce more of them if this is economically useful. However, the separation of acetic acid from these by-products adds to the cost of the process.

Under similar conditions and using similar catalysts as are used for butane oxidation, acetaldehyde can be oxidized by the oxygen in air to produce acetic acid

2 CH₃CHO + O₂ → 2 CH₃COOH

Using modern catalysts, this reaction can have an acetic acid yield greater than 95%. Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Temperature and layers The temperature of the Earth's atmosphere varies with altitude the mathematical relationship between temperature and altitude varies among five 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. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. Formaldehyde is a Chemical compound with the formula H2CO It is the simplest Aldehyde —an organic compound containing a terminal Carbonyl The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture ^[14]

Ethylene oxidation

Acetaldehyde may be prepared from ethylene via the Wacker process, and then oxidized as above. Structure This Hydrocarbon has four Hydrogen Atoms bound to a pair of Carbon atoms that are connected by a Double bond. The Wacker process or the Hoechst-Wacker process (named after the chemical companies of the same name originally referred to the oxidation of Ethylene to Acetaldehyde More recently a cheaper single-stage conversion of ethylene to acetic acid was commercialized by chemical company Showa Denko, which opened an ethylene oxidation plant in Ōita, Japan, in 1997. is a Japanese chemical engineering firm History Prior to World War II it was a part of the Mori group of companies as. WikipediaWikiProject Japanese prefectures for guidelines --> is a prefecture of Japan located on Kyūshū Island. For a topic outline on this subject see List of basic Japan topics. ^[15] The process is catalysed by a palladium metal catalyst supported on a heteropoly acid such as tungstosilicic acid. Palladium (pronounced \pəˈleɪdiəm\ is a rare and lustrous silvery-white metal that was discovered in 1803 by William Hyde Wollaston, who named it palladium after the A heteropoly acid is a class of Acid made up of a particular combination of Hydrogen and Oxygen with certain Metals and Non-metals Tungstosilicic acid is the most commonly encountered Heteropoly acid. It is thought to be competitive with methanol carbonylation for smaller plants (100–250 kt/a), depending on the local price of ethylene.

Oxidative fermentation

For most of human history, acetic acid, in the form of vinegar, has been made by acetic acid bacteria of the genus Acetobacter. Acetic acid bacteria are bacteria that derive their energy from the Oxidation of Ethanol to Acetic acid during respiration. Acetobacter is a genus of Acetic acid bacteria characterized by the ability to convert alcohol ( Ethanol) to Acetic acid in the presence Given sufficient oxygen, these bacteria can produce vinegar from a variety of alcoholic foodstuffs. Commonly used feeds include apple cider, wine, and fermented grain, malt, rice, or potato mashes. For the non-alcoholic beverage commonly known in the US as "cider" see Apple cider. Wine is an Alcoholic beverage made from the fermentation of Grape juice Malting is a process applied to Cereal grains in which the grains are made to Germinate by soaking in water and are then quickly halted from germinating further Rice is a Cereal foodstuff which forms an important part of the diet of many people worldwide and as such it is a staple food for many The potato is a Starchy Tuberous crop Vegetable from the perennial Solanum tuberosum of the Solanaceae The overall chemical reaction facilitated by these bacteria is:

C₂H₅OH + O₂ → CH₃COOH + H₂O

A dilute alcohol solution inoculated with Acetobacter and kept in a warm, airy place will become vinegar over the course of a few months. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Water is a common Chemical substance that is essential for the survival of all known forms of Life. Industrial vinegar-making methods accelerate this process by improving the supply of oxygen to the bacteria. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the

The first batches of vinegar produced by fermentation probably followed errors in the winemaking process. Winemaking, or vinification, is the production of Wine, starting with selection of the Grapes and ending with bottling the finished wine If must is fermented at too high a temperature, acetobacter will overwhelm the yeast naturally occurring on the grapes. MUST may refer to Militära underrättelse- och säkerhetstjänsten, the Swedish Military Intelligence and Security Service Misr University Yeasts are a growth form of eukaryotic Microorganisms classified in the kingdom Fungi, with about 1500 Species currently described For the Tokyo University supercomputer see Gravity Pipe. GRAPE, or GRA phics P rogramming E nvironment is 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, however, and not always successful, as the vintners did not understand the process.

One of the first modern commercial processes was the "fast method" or "German method", first practised in Germany in 1823. In this process, fermentation takes place in a tower packed with wood shavings or charcoal. Charcoal' is the blackish residue consisting of impure Carbon obtained by removing water and other volatile constituents from Animal and Vegetation 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. Temperature and layers The temperature of the Earth's atmosphere varies with altitude the mathematical relationship between temperature and altitude varies among five Convection in the most general terms refers to the movement of molecules within Fluids (i The improved air supply in this process cut the time to prepare vinegar from months to weeks.

Most vinegar today is made in submerged tank culture, first described in 1949 by Otto Hromatka and Heinrich Ebner. A microbiological culture, AKA microbial culture, is a method of multiplying microbial organisms by letting them reproduce in predetermined culture media under controlled laboratory 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% acetic acid can be prepared in only 24 hours in batch process, even 20% in 60 h fed-batch process.

Anaerobic fermentation

Species of anaerobic bacteria, including members of the genus Clostridium, can convert sugars to acetic acid directly, without using ethanol as an intermediate. An anaerobic organism is any Organism that does not require Oxygen for growth and may even die in its presence Clostridium is a Genus of Gram-positive bacteria belonging to the Firmicutes. The overall chemical reaction conducted by these bacteria may be represented as:

C₆H₁₂O₆ → 3 CH₃COOH

More interestingly from the point of view of an industrial chemist, these acetogenic bacteria can produce acetic acid from 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 utilize sugars directly, or to produce acetic acid from less costly inputs, means that these bacteria could potentially produce acetic acid more efficiently than ethanol-oxidizers like Acetobacter. The term acetogen refers to a bacterium that generates Acetate as a product of Anaerobic respiration. Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas. Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 However, Clostridium bacteria are less acid-tolerant than Acetobacter. Even the most acid-tolerant Clostridium strains can produce vinegar of only a few per cent acetic acid, compared to Acetobacter strains that can produce vinegar of up to 20% acetic acid. At present, it remains more cost-effective to produce vinegar using Acetobacter than to produce it using Clostridium and then concentrating it. As a result, although acetogenic bacteria have been known since 1940, their industrial use remains confined to a few niche applications.

Applications

Acetic acid is a chemical reagent for the production of chemical compounds. A reagent or reactant is a substance or compound consumed during a Chemical reaction. The largest single use of acetic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester production. A monomer (from Greek mono "one" and meros "part" is a small Molecule that may become chemically bonded to other The volume of acetic acid used in vinegar is comparatively small.

Vinyl acetate monomer

The major use of acetic acid is for the production of vinyl acetate monomer (VAM). Vinyl acetate is an Organic compound with the formula CH3COOCH=CH2 This application consumes approximately 40% to 45% of the world's production of acetic acid. The reaction is of ethylene and acetic acid with oxygen over a palladium catalyst. Structure This Hydrocarbon has four Hydrogen Atoms bound to a pair of Carbon atoms that are connected by a Double bond. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Palladium (pronounced \pəˈleɪdiəm\ is a rare and lustrous silvery-white metal that was discovered in 1803 by William Hyde Wollaston, who named it palladium after the Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst

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

Vinyl acetate can be polymerized to polyvinyl acetate or to other polymers, which are applied in paints and adhesives. Polyvinyl acetate ( PVA or PVAc) is a Rubbery Synthetic polymer. A polymer is a large Molecule ( Macromolecule) composed of repeating Structural units typically connected by Covalent Chemical bonds Paint is any Liquid, liquifiable or mastic composition which after application to a substrate in a thin layer is converted to an opaque Solid Glue or adhesive is a compound that adheres or bonds two items together

Ester production

The major esters of acetic acid are commonly used solvents for inks, paints and coatings. Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least An ink is a Liquid containing various Pigments and/or Dyes used for coloring a surface to produce an Image, text, or Paint is any Liquid, liquifiable or mastic composition which after application to a substrate in a thin layer is converted to an opaque Solid Coating is a Covering that is applied to an object The aim of applying coatings is to improve surface properties of a bulk material usually referred to as a substrate The esters include ethyl acetate, n-butyl acetate, isobutyl acetate, and propyl acetate. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 n -Butyl acetate, also known as butyl ethanoate, is an Organic compound commonly used as a Solvent in the production of Lacquers The Chemical compound isobutyl acetate, with systematic name 2-methylpropyl ethanoate, is a common solvent The Chemical compound propyl acetate, also known as propyl ethanoate, is a common Solvent. They are typically produced by catalysed reaction from acetic acid and the corresponding alcohol. Catalysis is the process in which the rate of a Chemical reaction is increased by means of a Chemical substance known as a catalyst In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon  : H₃C-COOH + HO-R → H₃C-CO-O-R + H₂O, where R = a general alkyl group

Most acetate esters, however, are produced from acetaldehyde using the Tishchenko reaction. An alkyl is a Univalent radical consisting of Carbon and Hydrogen atoms arranged in a chain Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula C[[Hydrogen H]]3CH O or MeCHO The Tishchenko reaction is a Chemical reaction that involves Disproportionation of an Aldehyde lacking a hydrogen atom in the alpha position in the presence Additionally, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers and wood stains. Nitrocellulose (also cellulose nitrate, flash paper) is a highly flammable compound formed by Nitrating Cellulose through exposure to Acrylic paint is fast-drying Paint containing pigment suspended in an acrylic polymer Emulsion. Varnish is a transparent, hard protective finish or film primarily used in Wood finishing but also for other materials First glycol monoethers are produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid. Propylene oxide is a highly toxic flammable Chemical compound. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human reproduction.

Acetic anhydride

The condensation product of two molecules of acetic acid is acetic anhydride. A condensation reaction is a Chemical reaction in which two Molecules or moieties ( Functional groups) combine to form one single molecule together with Acetic anhydride is the Chemical compound with the formula (CH3CO2O The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. Acetic anhydride may be produced directly by methanol carbonylation bypassing the acid, and Cativa plants can be adapted for anhydride production. The Cativa process is a method for the production of Acetic acid by the Carbonylation of Methanol.

Acetic anhydride is a strong acetylation agent. Acetylation (or in IUPAC nomenclature ethanoylation) describes a reaction that introduces an Acetyl Functional group into an Organic compound As such, its major application is for cellulose acetate, a synthetic textile also used for photographic film. Cellulose acetate, first prepared in 1865 is the Acetate Ester of Cellulose. A textile is a flexible material comprised of a network of natural or artificial Fibres often referred to as thread or Yarn. This article is mainly concerned with Still photography film For Motion picture film please see Film stock. Acetic anhydride is also a reagent for the production of aspirin, heroin, and other compounds. Aspirin, or acetylsalicylic acid (ASA (əˌsɛtɨlsælɨˌsɪlɨk ˈæsɨd is a Salicylate drug, often used as an Analgesic to relieve Heroin ( INN: diacetylmorphine, BAN: diamorphine) is a semi-synthetic opioid synthesized from Morphine, a derivative

Vinegar

In the form of vinegar, acetic acid solutions (typically 5% to 18% acetic acid, with the percentage usually calculated by mass) are used directly as a condiment, and also in the pickling of vegetables and other foodstuffs. Vinegar is an acidic liquid processed from the Fermentation of Ethanol in a process that yields its key ingredient Acetic acid (also called ethanoic acid A condiment is a prepared edible substance or Mixture, often preserved or fermented (usually a liquid that is added in relatively small Pickling, also known as brining or corning, is the process of preserving Food by Anaerobic fermentation in Brine (a solution Table vinegar tends to be more diluted (5% to 8% acetic acid), while commercial food pickling generally employs more concentrated solutions. The amount of acetic acid used as vinegar on a worldwide scale is not large, but historically, this is by far the oldest and most well-known application.

Use as solvent

Glacial acetic acid is an excellent polar protic solvent, as noted above. In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen Acetic acid, also known as ethanoic acid, is an organic chemical compound, giving Vinegar its sour taste It is frequently used as a solvent for recrystallization to purify organic compounds. Recrystallization (see also Crystallization) is a physical process that has meanings in Chemistry, Metallurgy and Geology. Pure molten acetic acid is used as a solvent in the production of terephthalic acid (TPA), the raw material for polyethylene terephthalate (PET). A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Terephthalic acid is one Isomer of the three Phthalic acids. It finds important use as a Commodity chemical, principally as a starting compound Uses PET can be semi-rigid to rigid depending on its thickness and is very lightweight Although currently accounting for 5%–10% of acetic acid use worldwide, this specific application is expected to grow significantly in the next decade, as PET production increases.

Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. A carbocation (ˌkɑrboʊˈkætaɪɒn is an Ion with a positively-charged Carbon Atom. The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. For example, one stage in the commercial manufacture of synthetic camphor involves a Wagner-Meerwein rearrangement of camphene to isobornyl acetate; here acetic acid acts both as a solvent and as a nucleophile to trap the rearranged carbocation. } Camphor is a waxy white or transparent solid with a strong aromatic odor A Wagner-Meerwein rearrangement is a class of Carbocation 12-rearrangement reactions in which a Hydrogen, Alkyl or Aryl In Chemistry, a nucleophile (literally nucleus lover as in nucleus and phile) is a Reagent that forms a Chemical bond to A rearrangement reaction is a broad class of Organic reactions where the carbon skeleton of a Molecule is rearranged to give a Structural isomer of the original Acetic acid is the solvent of choice when reducing an aryl nitro-group to an aniline using palladium-on-carbon. Redox (shorthand for reduction-oxidation reaction describes all Chemical reactions in which atoms have their Oxidation number ( Oxidation state In the context of organic molecules aryl refers to any Functional group or Substituent derived from a Simple aromatic ring, may it be Phenyl Nitro compounds are Organic compounds that contain one or more nitro Functional groups (-2 Aniline, phenylamine or aminobenzene is an Organic compound with the formula C6H7N Palladium on carbon, often referred to as Pd/C, is a form of Palladium used for Catalysis.

Glacial acetic acid is used in analytical chemistry for the estimation of weakly alkaline substances such as organic amides. Glacial acetic acid is a much weaker base than water, so the amide behaves as a strong base in this medium. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as perchloric acid. Perchloric acid, HClO4 is an Oxoacid of Chlorine and is a colorless liquid soluble in water.

Other applications

Dilute solutions of acetic acids are also used for their mild acidity. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Examples in the household environment include the use in a stop bath during the development of photographic films, and in descaling agents to remove limescale from taps and kettles. The household is the basic unit of analysis in many Social, Microeconomic and Government models Stop bath is the second of three chemical baths usually used in processing traditional black-and-white Photographic films plates and paper. A descaling agent, also known as descaling, anti-limestone, anti-limescale, anti-lime, or anti-scale, is a Solution to Limescale is the hard off-white chalky deposit found in kettles hot-water boilers and the inside of inadequately maintained hot-water central heating systems The acidity is also used for treating the sting of the box jellyfish by disabling the stinging cells of the jellyfish, preventing serious injury or death if applied immediately, and for treating outer ear infections in people in preparations such as Vosol. Box jellyfish are invertebrates belonging to the class Cubozoa, named for their Cube -shaped medusae. Otitis externa ("swimmer's ear" is an Inflammation of the outer Ear and ear canal Vosol is an Antiseptic used to treat Otitis externa, a problem of the Ear canal. Equivalently, acetic acid is used as a spray-on preservative for livestock silage, to discourage bacterial and fungal growth. A preservative is a natural or synthetic chemical that is added to products such as foods pharmaceuticals paints biological samples wood etc For the Christian Alternative band please see Silage (band Silage is fermented, high-moisture Fodder that can A fungus (ˈfʌŋgəs is a eukaryotic Organism that is a member of the kingdom Fungi (ˈfʌndʒaɪ Glacial acetic acid is also used as a wart and verruca remover. A wart (also known as verruca) is generally a small rough Tumor, typically on hands and feet but often other locations that can resemble a Cauliflower A plantar wart (also verruca plantaris or commonly known as verruca) is a Wart caused by the Human papillomavirus (HPV occurring on the

Organic or inorganic salts are produced from acetic acid, including:

• Sodium acetate, used in the textile industry and as a food preservative (E262). Sodium acetate, (also sodium ethanoate) is the Sodium salt of Acetic acid. A textile is a flexible material comprised of a network of natural or artificial Fibres often referred to as thread or Yarn. A preservative is a natural or synthetic chemical that is added to products such as foods pharmaceuticals paints biological samples wood etc E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union.
• Copper(II) acetate, used as a pigment and a fungicide. Copper(II acetate, also referred to as cupric acetate, is the Chemical compound with the formula Cu (OAc2 where AcO- For the drug referred to as "pigment" see Black tar heroin. Fungicides are Chemical compounds or biological organisms used to kill or inhibit fungi or fungal spores
• Aluminium acetate and iron(II) acetate—used as mordants for dyes. Aluminium acetates are the Aluminium Salts of Acetic acid. Three such salts exist neutral aluminium triacetate, Al(C2H3O23 Iron(II acetate is an off-white or light brown solid ionic compound of Iron. A mordant is a substance used to set Dyes on fabrics by forming an insoluble compound with the dye A dye can generally be described as a Colored substance that has an affinity to the substrate to which it is being applied
• Palladium(II) acetate, used as a catalyst for organic coupling reactions such as the Heck reaction. Palladium(II acetate is a Chemical compound of Palladium described by the formula Pd(O2CCH32 or Pd(OAc2 The Heck reaction (also called the Mizoroki-Heck reaction) is the Chemical reaction of an unsaturated Halide (or Triflate) with an Alkene
• Silver acetate, used as a pesticide. Silver acetate (AgC2H3O2 is a Photosensitive, white crystalline substance commonly used as a Pesticide. A pesticide is a substance or mixture of substances used to kill a pest.

Substituted acetic acids produced include:

• Monochloroacetic acid (MCA), dichloroacetic acid (considered a by-product), and trichloroacetic acid. Chloroacetic acid is the Chemical compound with the formula ClCH2CO2H Trichloroacetic acid (also known as trichloroethanoic acid) is an analogue of Acetic acid in which the three Hydrogen atoms of the Methyl MCA is used in the manufacture of indigo dye. Indigo dye is Dye with a distinctive blue color (see Indigo) The chemical compound that constitutes the indigo dye is called indigotin
• Bromoacetic acid, which is esterified to produce the reagent ethyl bromoacetate. Ethyl 2-bromoacetate is the Chemical compound with the formula CH2BrCO2C2H5
• Trifluoroacetic acid, which is a common reagent in organic synthesis. Trifluoroacetic acid (TFA is the Chemical compound with the formula CF3CO2H Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic

Amounts of acetic acid used in these other applications together (apart from TPA) account for another 5%–10% of acetic acid use worldwide. These applications are, however, not expected to grow as much as TPA production.

Safety

Concentrated acetic acid is corrosive and must therefore be handled with appropriate care, since it can cause skin burns, permanent eye damage, and irritation to the mucous membranes. Corrosion means the breaking down of essential properties in a material due to Chemical reactions with its surroundings These burns or blisters may not appear until hours after exposure. Latex gloves offer no protection, so specially resistant gloves, such as those made of nitrile rubber, should be worn when handling the compound. LaTeX (ˈleɪtɛ Nitrile rubber or Buna-N, is a Synthetic rubber Copolymer of Acrylonitrile (ACN and Butadiene. Concentrated acetic acid can be ignited with difficulty in the laboratory. It becomes a flammable risk if the ambient temperature exceeds 39 °C (102 °F), and can form explosive mixtures with air above this temperature (explosive limits: 5. 4%–16%).

The hazards of solutions of acetic acid depend on the concentration. The following table lists the EU classification of acetic acid solutions:

Concentration by weight	Molarity	Classification	R-Phrases
10%–25%	1. Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling In Chemistry, concentration is the measure of how much of a given substance there is mixed with another substance R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous 67–4. 16 mol/L	Irritant (Xi)	R36/38
25%–90%	4. R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous 16–14. 99 mol/L	Corrosive (C)	R34
>90%	>14. R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous 99 mol/L	Corrosive (C)	R10, R35

Solutions at more than 25% acetic acid are handled in a fume hood because of the pungent, corrosive vapour. R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous Dilute acetic acid, in the form of vinegar, is harmless. However, ingestion of stronger solutions is dangerous to human and animal life. It can cause severe damage to the digestive system, and a potentially lethal change in the acidity of the blood. Digestion is the breaking down of chemicals in the body into a form that can be absorbed Blood is a specialized Bodily fluid that delivers necessary substances to the body's cells ��such as nutrients and oxygen—and transports Waste products

Due to incompatibilities, it is recommended to keep acetic acid away from chromic acid, ethylene glycol, nitric acid, perchloric acid, permanganates, peroxides and hydroxyls. Chromic acid generally refers to a collection of compounds generated by the acidification of solutions containing Chromate and Dichromate anions or the Ethylene glycol ( monoethylene glycol ( MEG) 12-ethanediol, IUPAC name: ethane-12-diol) is an Alcohol with two -OH Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and Perchloric acid, HClO4 is an Oxoacid of Chlorine and is a colorless liquid soluble in water. A peroxide is a compound containing an Oxygen -oxygen single bond. Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond.

See also

• Common chemicals, where to purchase common chemicals used in experiments
• Carboxylic acid, compounds containing the -COOH group
• Fatty acid, straight-chain carboxylic acids
• Acetate anion, CH₃COO⁻, abbreviated AcO⁻
• Acetyl group, the CH₃-CO– group, abbreviated Ac
• Acetyl-coenzyme A, an important acetyl-carrier in cells

References

External links

• CID 176 from PubChem
• Computational Chemistry Wiki
• International Chemical Safety Card 0363
• Safety data in condensed form
• Acetic acid MSDS (Material Safety Data Sheet)
• National Pollutant Inventory - Acetic acid fact sheet
• NIOSH Pocket Guide to Chemical Hazards
• 29 CFR 1910.1000, Table Z-1 (US Permissible exposure limits)
• Celanese, major acetic acid producer
• Usage of acetic acid in Organic Syntheses
• Acetic acid pH and titration - freeware for data analysis, simulation and distribution diagram generation

PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component

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