query: What is acetic acid?

title: Acetic acid

text: Acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CHCOOH (also written as CHCOH or CHO). When undiluted, it is sometimes called "glacial acetic acid". Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a distinctive sour taste and pungent smell. In addition to household vinegar, it is mainly produced as a precursor to polyvinyl acetate and cellulose acetate. It is classified as a weak acid since it only partially dissociates in solution, but

title: Acetic acid

text: concentrated acetic acid is corrosive and can attack the skin. Acetic acid is the second simplest carboxylic acid (after formic acid). It consists of a methyl group attached to a carboxyl group. It is an important chemical reagent and industrial chemical, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group,

title: Acetic acid

text: 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 use is confined to a few niche applications. Acetic acid is a chemical reagent for the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small. The primary use of acetic acid is the production of vinyl acetate monomer (VAM). In 2008, this application was estimated

title: Acetic acid

text: to consume a third of the world's production of acetic acid. The reaction consists of ethylene and acetic acid with oxygen over a palladium catalyst, conducted in the gas phase. Vinyl acetate can be polymerised to polyvinyl acetate or other polymers, which are components in paints and adhesives. The major esters of acetic acid are commonly used as solvents for inks, paints and coatings. The esters include ethyl acetate, "n"-butyl acetate, isobutyl acetate, and propyl acetate. They are typically produced by catalyzed reaction from acetic acid and the corresponding alcohol: Most acetate esters, however, are produced from acetaldehyde using the

title: Acetic anhydride

text: vinyl acetate involved the intermediate ethylidene diacetate, the geminal diacetate obtained from acetaldehyde and acetic anhydride: Acetic anhydride dissolves in water to approximately 2.6% by weight. Aqueous solutions have limited stability because, like most acid anhydrides, acetic anhydride hydrolyses to give carboxylic acids. In this case, acetic acid is formed: As indicated by its organic chemistry, Acetic anhydride is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials, and is used in the manufacture of cigarette filters.

title: Acetic acid

text: acid solutions: Concentrated acetic acid can be ignited only with difficulty at standard temperature and pressure, but becomes a flammable risk in temperatures greater than , and can form explosive mixtures with air at higher temperatures (explosive limits: 5.4–16%). Acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CHCOOH (also written as CHCOH or CHO). When undiluted, it is sometimes called "glacial acetic acid". Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. Acetic acid has a

title: Acetic acid

text: be harmful to human reproduction. The product of the condensation of two molecules of acetic acid is acetic anhydride. The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give ketene at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride: Acetic anhydride is an acetylation agent. As such, its major application is for cellulose acetate, a synthetic textile also used for photographic film. Acetic anhydride is also a reagent for the production of

title: Acetic acid

text: acid acts both as a solvent and as a nucleophile to trap the rearranged carbocation. 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. It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as perchloric acid. Acetic acid injection into a tumor has been used to treat cancer since the 1800s. Acetic acid is used as part of cervical cancer

title: Acetic acid

text: by far the oldest and best-known application. Acetic acid undergoes the typical chemical reactions of a carboxylic acid. Upon treatment with a standard base, it converts to metal acetate and water. With strong bases (e.g., organolithium reagents), it can be doubly deprotonated to give LiCHCOLi. Reduction of acetic acid gives ethanol. The OH group is the main site of reaction, as illustrated by the conversion of acetic acid to acetyl chloride. Other substitution derivatives include acetic anhydride; this anhydride is produced by loss of water from two molecules of acetic acid. Esters of acetic acid can likewise be formed via

title: Acetic acid

text: can separate from the molecule by ionization: Because of this release of the proton (H), acetic acid has acidic character. Acetic acid is a weak monoprotic acid. In aqueous solution, it has a pK value of 4.76. Its conjugate base is acetate (CHCOO). A 1.0 M solution (about the concentration of domestic vinegar) has a pH of 2.4, indicating that merely 0.4% of the acetic acid molecules are dissociated. However, in very dilute (< 10 M) solution acetic acid is >90% dissociated. In solid acetic acid, the molecules form chains, individual molecules being interconnected by hydrogen bonds. In the vapour

title: Acetic acid

text: Fischer esterification, and amides can be formed. When heated above , acetic acid decomposes to produce carbon dioxide and methane, or to produce ketene and water: Acetic acid is mildly corrosive to metals including iron, magnesium, and zinc, forming hydrogen gas and salts called acetates: Because aluminium forms a passivating acid-resistant film of aluminium oxide, aluminium tanks are used to transport acetic acid. Metal acetates can also be prepared from acetic acid and an appropriate base, as in the popular "baking soda + vinegar" reaction: A colour reaction for salts of acetic acid is iron(III) chloride solution, which results in

title: Acetic acid

text: it is central to the metabolism of carbohydrates and fats. Unlike longer-chain carboxylic acids (the fatty acids), acetic acid does not occur in natural triglycerides. However, the artificial triglyceride triacetin (glycerine triacetate) is a common food additive and is found in cosmetics and topical medicines. 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 acetic 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

title: Acetic acid

text: Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. Acetic acid has 349 kcal per 100 g. Vinegar is typically no less than 4% acetic acid by mass. Legal limits on acetic acid content vary by jurisdiction. Vinegar is used directly as a condiment, and in the pickling of vegetables and other foods. Table vinegar tends to be more diluted (4% to 8% acetic acid), while commercial food pickling employs solutions that are more concentrated. The proportion of acetic acid used worldwide as vinegar is not as large as commercial uses, but is

title: Acetic acid

text: heroin and other compounds. Glacial acetic acid is an excellent polar protic solvent, as noted above. It is frequently used as a solvent for recrystallization to purify organic compounds. Acetic acid is used as a solvent in the production of terephthalic acid (TPA), the raw material for polyethylene terephthalate (PET). In 2006, about 20% of acetic acid was used for TPA production. Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. For example, one stage in the commercial manufacture of synthetic camphor involves a Wagner-Meerwein rearrangement of camphene to isobornyl acetate; here acetic

title: Acetic acid

text: to trichloroacetic acid, and concluded with electrolytic reduction to acetic acid. By 1910, most glacial acetic acid was obtained from the pyroligneous liquor, a product of the distillation of wood. The acetic acid 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 time, Germany was producing 10,000 tons of glacial acetic acid, around 30% of which was used for the manufacture of indigo dye. Because both methanol and carbon monoxide are commodity raw materials, methanol carbonylation long appeared to be attractive precursors to acetic

title: Acetic acid

text: derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats. The global demand for acetic acid is about 6.5 million metric tons per year (Mt/a), of which approximately 1.5 Mt/a is met by recycling; the remainder is manufactured from methanol. Vinegar is mostly dilute acetic acid, often produced by fermentation and subsequent oxidation of ethanol. The trivial name "acetic acid" is the most commonly used and preferred IUPAC name. The systematic name "ethanoic acid", a valid IUPAC name, is constructed according to the substitutive

title: Acetic acid

text: nomenclature. The name "acetic acid" derives from "acetum", the Latin word for vinegar, and is related to the word acid itself. "Glacial acetic acid" 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 (the presence of 0.1% water lowers its melting point by 0.2 °C). A common symbol for acetic acid is "AcOH", where "Ac" is the pseudoelement symbol representing the acetyl group −C(=O)−; the conjugate base, acetate (), is thus represented as "AcO". (The "Ac" is not to be

title: Acetic acid bacteria

text: Acetic acid bacteria Acetic acid bacteria (AAB) are a group of Gram-negative bacteria which oxidize sugars or ethanol and produce acetic acid during fermentation. The acetic acid bacteria consist of 10 genera in the family "Acetobacteraceae". Several species of acetic acid bacteria are used in industry for production of certain foods and chemicals. All acetic acid bacteria are rod-shaped and obligate aerobes. Acetic acid bacteria are airborne and are ubiquitous in nature. They are actively present in environments where ethanol is being formed as a result of fermentation of sugars. They can be isolated from the nectar of flowers and

title: Acetic acid

text: confused with the symbol for the element actinium; the context prevents confusion among organic chemists.) To better reflect its structure, acetic acid is often written as –C(O)OH, −C(=O)OH, COOH, and . In the context of acid-base reactions, the abbreviation "HAc" is sometimes used, where "Ac" in this case is a symbol for acetate (rather than acetyl). Acetate is the ion resulting from loss of from acetic acid. The name "acetate" can also refer to a salt containing this anion, or an ester of acetic acid. The hydrogen centre in the carboxyl group (−COOH) in carboxylic acids such as acetic acid

title: Acetic acid

text: 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 acid is not completely miscible, and its miscibility declines with longer n-alkanes. The solvent and miscibility properties of acetic acid make it a useful industrial chemical, for example, as a solvent in the production of dimethyl terephthalate. At physiological pHs, acetic acid is usually fully ionised to acetate. The acetyl group, formally derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A,

title: Acetic acid

text: it appears to serve as a mild antibacterial agent. Acetic acid 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 below. The biological route accounts for only about 10% of world production, but it remains important for the production of vinegar because many food purity laws require vinegar used in foods to be of biological origin. Other processes are methyl formate isomerization, conversion of syngas to acetic acid, and gas phase oxidation of ethylene and ethanol. Acetic acid is often

title: Acetic acid

text: photocatalytic oxidation technology for the selective oxidation of ethylene and ethane to acetic acid. Unlike traditional oxidation catalysts, the selective oxidation process will use UV light to produce acetic acid at ambient temperatures and pressure. For most of human history, acetic acid bacteria of the genus "Acetobacter" have made acetic acid, in the form of vinegar. 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. The overall chemical reaction facilitated by these bacteria is: A dilute alcohol solution inoculated with

title: Acetic acid

text: a deeply red colour that disappears after acidification. A more sensitive test uses lanthanum nitrate with iodine and ammonia to give a blue solution. Acetates when heated with arsenic trioxide form cacodyl oxide, which can be detected by its malodorous vapours. Organic or inorganic salts are produced from acetic acid. Some commercially significant derivatives: Halogenated acetic acids are produced from acetic acid. Some commercially significant derivatives: Amounts of acetic acid used in these other applications together account for another 5–10% of acetic acid use worldwide. Vinegar was known early in civilization as the natural result of exposure of beer and

title: Acetic acid

text: valuable, and the reaction conditions may be altered to produce more of them where needed. 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, the oxygen in air to produce acetic acid can oxidize acetaldehyde. Using modern catalysts, this reaction 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. Acetaldehyde may be prepared from

title: Acetic acid bacteria

text: cycle enzymes. Other genera, such as "Gluconobacter", do not oxidize ethanol, as they do not have a full set of Krebs cycle enzymes. As these bacteria produce acid, they are usually acid-tolerant, growing well below pH 5.0, although the pH optimum for growth is 5.4-6.3. One species of "Acetobacter", "Acetobacter xylinum", is able to synthesize cellulose, something normally done only by plants. Acetic acid bacteria Acetic acid bacteria (AAB) are a group of Gram-negative bacteria which oxidize sugars or ethanol and produce acetic acid during fermentation. The acetic acid bacteria consist of 10 genera in the family "Acetobacteraceae". Several species

title: Acetic acid

text: The two biggest producers of virgin acetic acid are Celanese and BP Chemicals. Other major producers include Millennium Chemicals, Sterling Chemicals, Samsung, Eastman, and Svensk Etanolkemi. 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 as an intermediate, and occurs in three steps. A catalyst, metal carbonyl, is needed for the carbonylation (step 2). Two related processes for the carbonylation of methanol: the rhodium-catalyzed Monsanto process, and the iridium-catalyzed Cativa process. The latter process is greener and more efficient and has

title: Acetic acid (medical use)

text: 25 USD. Acetic acid is more commonly used for external ear infections in the developing world than the developed. Acetic acid may be applied to the cervix to help detect cervical cancer during screening in many areas in the developing world. Acetic acid is applied to the cervix and if an area of white appears after about a minute the test is positive. Acetic acid (medical use) Acetic acid, which at low concentrations is known as vinegar, is used as a medication to treat a number of conditions. As an eardrop it is used to treat infections of the ear

title: Acetic acid

text: bacteria may be represented as: These acetogenic bacteria produce acetic acid from one-carbon compounds, including methanol, carbon monoxide, or a mixture of carbon dioxide and hydrogen: This ability of "Clostridium" to metabolize sugars directly, or to produce acetic acid from less costly inputs, suggests that these bacteria could produce acetic acid more efficiently than ethanol-oxidizers like "Acetobacter". However, "Clostridium" bacteria are less acid-tolerant than "Acetobacter". Even the most acid-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, it remains more

title: Acetic acid

text: B2 North molecular cloud (also known as the Sgr B2 Large Molecule Heimat source). Acetic acid has the distinction of being the first molecule discovered in the interstellar medium using solely radio interferometers; in all previous ISM molecular discoveries made in the millimetre and centimetre wavelength regimes, single dish radio telescopes were at least partly responsible for the detections. Concentrated acetic acid is corrosive to skin. These burns or blisters may not appear until hours after exposure. Prolonged inhalation exposure (eight hours) to acetic acid vapours at 10 ppm can produce some irritation of eyes, nose, and throat; at 100

title: Acetic acid

text: Roman aristocracy. 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 acetic acid's properties that for centuries chemists believed that glacial acetic acid and the acid found in vinegar were two different substances. French chemist Pierre Adet proved them identical. In 1845 German chemist Hermann Kolbe synthesised acetic acid from inorganic compounds for the first time. This reaction sequence consisted of chlorination of carbon disulfide to carbon tetrachloride, followed by pyrolysis to tetrachloroethylene and aqueous chlorination

title: Methylene cyclopropyl acetic acid

text: Methylene cyclopropyl acetic acid Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian digestion after ingestion of hypoglycin. Methylene cyclopropyl acetic acid (MCPA) is a compound found in lychee ("Litchi chinensis") seeds. It is also a metabolite in mammalian digestion after ingestion of hypoglycin, a rare and potentially toxic amino acid, chemically related to the common amino acid lysine. Hypoglycin is found in the unripe ackee fruit in Africa. Dihydrosterculic acid is the major carbocyclic fatty acid in the seed oils of "Litchi chinensis". It is a cyclopropene fatty acid; these have

title: Acetic acid

text: screening in many areas in the developing world. The acid is applied to the cervix and if an area of white appears after about a minute the test is positive. Acetic acid is an effective antiseptic when used as a 1% solution, with broad spectrum of activity against streptococci, staphylococci, pseudomonas, enterococci and others. It may be used to treat skin infections caused by pseudomonas strains resistant to typical antibiotics. While diluted acetic acid is used in iontophoresis, no high quality evidence supports this treatment for rotator cuff disease. As a treatment for otitis externa, it is on the World

title: Acetic acid

text: most vinegar is made in submerged tank culture, first described in 1949 by Otto Hromatka and Heinrich Ebner. 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-hour fed-batch process. Species of anaerobic bacteria, including members of the genus "Clostridium" or "Acetobacterium" can convert sugars to acetic acid directly without creating ethanol as an intermediate. The overall chemical reaction conducted by these

title: Acetic acid

text: became the dominant method of acetic acid production (see Monsanto process). In the late 1990s, the chemicals company BP Chemicals commercialised the Cativa catalyst ([Ir(CO)I]), which is promoted by iridium for greater efficiency. This iridium-catalyzed Cativa process is greener and more efficient and has largely supplanted the Monsanto process, often in the same production plants. Interstellar acetic acid was discovered in 1996 by a team led by David Mehringer using the former Berkeley-Illinois-Maryland Association array at the Hat Creek Radio Observatory and the former Millimeter Array located at the Owens Valley Radio Observatory. It was first detected in the Sagittarius

title: Acetic acid

text: at , dimers can be detected. Dimers also occur in the liquid phase in dilute solutions in non-hydrogen-bonding solvents, and a certain extent in pure acetic acid, 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 K. Other carboxylic acids engage in similar intermolecular hydrogen bonding interactions. Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water. With a moderate relative static permittivity (dielectric constant) of 6.2, it dissolves not only polar compounds such as inorganic salts and sugars, but

title: Acetic acid

text: Tishchenko reaction. In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers, and wood stains. First, glycol monoethers are produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing processes, where it is used as a resist solvent). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to

title: Acetic acid

text: wine to air, because acetic acid-producing bacteria are present globally. The use of acetic acid in alchemy 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 wine to produce a highly sweet syrup called "sapa". Sapa that was produced in lead pots was rich in lead acetate, a sweet substance also called "sugar of lead" or "sugar of Saturn", which contributed to lead poisoning among the

title: Acetic acid

text: ethylene via the Wacker process, and then oxidised as above. In more recent times, chemical company Showa Denko, which opened an ethylene oxidation plant in Ōita, Japan, in 1997, commercialised a cheaper single-stage conversion of ethylene to acetic acid. The process is catalyzed by a palladium metal catalyst supported on a heteropoly acid such as silicotungstic acid. Similar process use the same metal catalyst on silicotungstic acid and silica: 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 will be based on utilizing a novel selective

title: Acetic acid bacteria

text: from damaged fruit. Other good sources are fresh apple cider and unpasteurized beer that has not been filter sterilized. In these liquids, they grow as a surface film due to their aerobic nature and active motility. Fruit flies or vinegar eels are considered as a common vector in propagating acetic acid bacteria. The growth of "Acetobacter" in wine can be suppressed through effective sanitation, by complete exclusion of air from wine in storage, and by the use of moderate amounts of sulfur dioxide in the wine as a preservative. Vinegar is produced when acetic acid bacteria act on alcoholic beverages

title: Acetic acid

text: largely supplanted the former process, often in the same production plants. Catalytic amounts of water 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, acetic anhydride may also be produced on the same plant using the rhodium catalysts. Prior to the commercialization of the Monsanto process, most acetic acid was produced by 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 be produced by hydration of acetylene.

title: Acetic acid

text: This was the dominant technology in the early 1900s. Light naphtha components are readily oxidized by oxygen or even air to give peroxides, which decompose to produce acetic acid according to the chemical equation, illustrated with butane: Such oxidations require metal catalyst, such as the naphthenate salts of manganese, cobalt, and chromium. The typical reaction is conducted at temperatures and pressures designed to be as hot as possible while still keeping the butane a liquid. Typical reaction conditions are and 55 atm. Side-products may also form, including butanone, ethyl acetate, formic acid, and propionic acid. These side-products are also commercially

title: Acetic acid

text: a side product of different reactions, i.e. during heterogeneous catalytic acrylic acid synthesis or fermentative lactic acid production. As of 2003–2005, total worldwide production of virgin acetic acid was estimated at 5 Mt/a (million tonnes per year), approximately half of which was produced in the United States. European production was approximately 1 Mt/a and declining, while Japanese production was 0.7 Mt/a. Another 1.5 Mt were recycled each year, bringing the total world market to 6.5 Mt/a. Since then the global production has increased to 10.7 Mt/a (in 2010), and further; however, a slowing in this increase in production is predicted.

title: Acetic acid (medical use)

text: Acetic acid (medical use) Acetic acid, which at low concentrations is known as vinegar, is used as a medication to treat a number of conditions. As an eardrop it is used to treat infections of the ear canal. It may be used with an ear wick. As a liquid it is used to flush the bladder in those who have a urinary catheter in an attempt to prevent infection or blockage. As a gel it may be used to adjust the pH of the vagina. It may also be applied to the cervix to help detect cervical cancer during screening.

title: Acetic acid (medical use)

text: Side effects may include burning at the site of application. Allergic reactions may rarely occur. Use is not recommended in the ear in people who have a hole in the eardrum. It works against both bacterial and fungal causes of external ear infections. Acetic acid has been used medically since the time of Ancient Egypt. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Acetic acid is available as a generic medication. In the United States a course of treatment with the ear preparation costs less than

title: Indole-3-acetic acid

text: Indole-3-acetic acid Indole-3-acetic acid (IAA, 3-IAA) is the most common, naturally occurring, plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents. IAA is predominantly produced in cells of the apex (bud) and very young leaves of a plant. Plants can synthesize IAA by several independent biosynthetic pathways. Four of them start from tryptophan, but there is also a biosynthetic pathway independent of

title: Acetic acid

text: oedema and chronic bronchitis. Unacclimatised humans experience extreme eye and nasal irritation at concentrations in excess of 25 ppm, and conjunctivitis from concentrations below 10 ppm has been reported. In a study of five workers exposed for seven to 12 years to concentrations of 80 to 200 ppm at peaks, the principal findings were blackening and hyperkeratosis of the skin of the hands, conjunctivitis (but no corneal damage), bronchitis and pharyngitis, and erosion of the exposed teeth (incisors and canines). The hazards of solutions of acetic acid depend on the concentration. The following table lists the EU classification of acetic

title: Indole-3-acetic acid

text: activation and poly(adp-ribose) polymerases cleavage. In 2002 it had been hypothesized that IAA coupled with horseradish peroxidase (HRP) could be used in targeted cancer therapy. Radical-IAA molecules would attach to cells marked by HRP and HRP reactive cells would be selectively killed. In 2010 in vitro experiments proved this concept of IAA as an immunotoxin when used in preclinical studies of targeted cancer therapy, as it induced apoptosis in bladder and in hematological malignancies. Indole-3-acetic acid Indole-3-acetic acid (IAA, 3-IAA) is the most common, naturally occurring, plant hormone of the auxin class. It is the best known of the auxins,

title: Methylene cyclopropyl acetic acid

text: stemming from intense vomiting, to delirium and coma, and finally seizures and death. The symptoms stemming from lychee poisoning are near identical, both being caused by MCPA, with lychee seeds also containing methylenecyclopropyl glycine (MCPG), a homologue of Hypoglycin A. In 2014, numerous children died in Bihar (the largest producer of lychees in India) after consuming lychees. The vast majority of the fatalities were undernourished children who ate unripened lychees, their preexisting low blood sugar detrimentally amplifying the effects. Methylene cyclopropyl acetic acid Methylene cyclopropyl acetic acid (MCPA) is found in lychee seeds and also a toxic metabolite in mammalian

title: Acetic acid bacteria

text: such as wine. They are used to perform specific oxidation reactions through processes called “oxidative fermentations”, that creates vinegar as a byproduct. In the biotechnological industry, these bacterias' oxidation mechanism is exploited to produce a number of compounds such as l-ascorbic acid, dihydroxyacetone, gluconic acid, and cellulose. Besides food industry, some acetic acid bacterias are used as biocatalysts for the industrial production of compounds. They are used as the important biocatalysts for the development of eco-friendly fermentation processes as an alternative to the chemical synthesis. Some genera, such as "Acetobacter", can oxidize ethanol to carbon dioxide and water using Krebs

title: Acetic anhydride

text: water, alcohol foam or carbon dioxide are preferred for fire suppression. The vapour of acetic anhydride is harmful. Acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CHCO)O. Commonly abbreviated AcO, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air. Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. The pi system linkage through the central oxygen

title: Methylene cyclopropyl acetic acid

text: been found in many plants of the order Malvales (Sterculiaceae, Malvaceae, Bombaceae and Tiliaceae), in up to 60% of seed oil content, depending on the species but also in leaves, roots and shoots. They are accompanied by small amounts of their cyclopropanoid analogues, i.e. cyclopropyl acetic acid. Any organic compound with an amine and a carboxylic acid functional group is considered an amino acid. There are 22 proteinogenic amino acids, twenty found in the standard genetic code and two (selenocysteine and pyrrolysine) that can be added by a special translation mechanism. They are incorporated into proteins through translation. Non-proteinogenic amino

title: Acetic acid

text: ppm marked lung irritation and possible damage to lungs, eyes, and skin may result. Vapour concentrations of 1,000 ppm cause marked irritation of eyes, nose and upper respiratory tract and cannot be tolerated. These predictions were based on animal experiments and industrial exposure. In 12 workers exposed for two or more years to acetic acid airborne average concentration of 51 ppm (estimated), produced symptoms of conjunctive irritation, upper respiratory tract irritation, and hyperkeratotic dermatitis. Exposure to 50 ppm or more is intolerable to most persons and results in intensive lacrimation and irritation of the eyes, nose, and throat, with pharyngeal

title: Acetic anhydride

text: Acetic anhydride is produced by carbonylation of methyl acetate: The Tennessee Eastman acetic anhydride process involves the conversion of methyl acetate to methyl iodide and an acetate salt. Carbonylation of the methyl iodide in turn affords acetyl iodide, which reacts with acetate salts or acetic acid to give the product. Rhodium chloride in the presence of lithium iodide is employed as catalysts. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions. To a decreasing extent, acetic anhydride is also prepared by the reaction of ketene (ethenone) with acetic acid at 45–55 °C and low

title: Acetic anhydride

text: Acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CHCO)O. Commonly abbreviated AcO, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air. Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers

title: Acetic formic anhydride

text: Acetic formic anhydride Acetic formic anhydride is an organic compound with the chemical formula and a structural formula of -(C=O)-O-(C=O)H. It can be viewed as the mixed anhydride of acetic acid and formic acid. Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C. It can be prepared by aceticanhydride and formic acid at 0 oC Acetic formic anhydride is a formylation agent for amines, amino acids, and alcohols. It is also a starting material for other compounds such as formyl fluoride. An example of Acetic formic anhydride being used

title: Acetic formic anhydride

text: was in the synthesis of Quazodine (). Acetic formic anhydride Acetic formic anhydride is an organic compound with the chemical formula and a structural formula of -(C=O)-O-(C=O)H. It can be viewed as the mixed anhydride of acetic acid and formic acid. Acetic formic anhydride can be produced by reacting sodium formate with acetyl chloride in anhydrous diethyl ether between 23–27 °C. It can be prepared by aceticanhydride and formic acid at 0 oC Acetic formic anhydride is a formylation agent for amines, amino acids, and alcohols. It is also a starting material for other compounds such as formyl fluoride. An

title: Acetic oxalic anhydride

text: pressure. It can also be obtained by reacting anhydrous oxalic acid with ketene (=C=O). Acetic oxalic anhydride is an unstable colorless crystalline solid, soluble in diethyl ether, that decomposes at about −3 °C into acetic anhydride (-(C=O)-)O, carbon dioxide () and carbon monoxide (CO). It is hydrolyzed by water into acetic and oxalic acids. Acetic oxalic anhydride was conjectured to be an intermediate in the decomposition of anhydrous oxalic acid by acetic anhydride. Acetic oxalic anhydride Acetic oxalic anhydride is an organic compound with a chemical formula of and a structural formula of (HC-(C=O)-O-(C=O)-). It can be viewed as a

title: Acetic anhydride

text: pressure (0.05–0.2 bar). The route from acetic acid to acetic anhydride via ketene was developed by Wacker Chemie in 1922, when the demand for acetic anhydride increased due to the production of cellulose acetate. Due to its low cost, acetic anhydride is usually purchased, not prepared, for use in research laboratories. Acetic anhydride is a versatile reagent for acetylations, the introduction of acetyl groups to organic substrates. In these conversions, acetic anhydride is viewed as a source of CHCO. Alcohols and amines are readily acetylated. For example, the reaction of acetic anhydride with ethanol yields ethyl acetate: Often a base

title: Acetic anhydride

text: Similarly it is used in the production of aspirin (acetylsalicylic acid), which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer-lasting timber. In starch industry, acetic anhydride is a common acetylation compound, used for the production of modified starches (E1414, E1420, E1422) Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride is listed as a U.S. DEA List II precursor, and restricted in many other countries. Acetic anhydride is an irritant and combustible liquid. Because of its reactivity toward

title: Acetic anhydride

text: such as pyridine is added to function as catalyst. In specialized applications, Lewis acidic scandium salts have also proven effective catalysts. Aromatic rings are acetylated by acetic anhydride. Usually acid catalysts are used to accelerate the reaction. Illustrative are the conversions of benzene to acetophenone and ferrocene to acetylferrocene: Dicarboxylic acids are converted to the anhydrides upon treatment with acetic anhydride. It is also used for the preparation of mixed anhydrides such as that with nitric acid, acetyl nitrate. Aldehydes react with acetic anhydride in the presence of an acidic catalyst to give geminal diacetates. A former industrial route to

title: Acetic oxalic anhydride

text: Acetic oxalic anhydride Acetic oxalic anhydride is an organic compound with a chemical formula of and a structural formula of (HC-(C=O)-O-(C=O)-). It can be viewed as a mixed anhydride, formally derived from acetic acid (HC-(C=O)OH) and oxalic acid ((-(C=O)OH)), in 2:1 molecular ratio, by the loss of two water molecules. Unlike some other anhydrides, Acetic oxalic anhydride cannot be obtained directly from the acids. It was synthesized in 1953 by W. Edwards and W. M. Henley, by reacting silver oxalate () suspended in diethyl ether with acetyl chloride at temperatures below −5 °C and distilling off the solvent under low

title: Peracetic acid

text: Peracetic acid Peracetic acid (also known as peroxyacetic acid, or PAA), is an organic compound with the formula CHCOH. This organic peroxide is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Peracetic acid is a weaker acid than the parent acetic acid, with a p"K" of 8.2. Peracetic acid is produced industrially by the autoxidation of acetaldehyde: It forms upon treatment of acetic acid with hydrogen peroxide with a strong acid catalyst: As an alternative, acetyl chloride and acetic anhydride can be used to generate a solution of the acid with

title: Acid dissociation constant

text: much weaker base than water. Compare this reaction with what happens when acetic acid is dissolved in the more acidic solvent pure sulfuric acid The unlikely geminal diol species is stable in these environments. For aqueous solutions the pH scale is the most convenient acidity function. Other acidity functions have been proposed for non-aqueous media, the most notable being the Hammett acidity function, "H", for superacid media and its modified version "H" for superbasic media. In aprotic solvents, oligomers, such as the well-known acetic acid dimer, may be formed by hydrogen bonding. An acid may also form hydrogen bonds to

title: Acid–base reaction

text: the Brønsted-Lowry model, the solvent does not necessarily have to be water that is required by the Arrhenius Acid-Base model. For example, consider what happens when acetic acid, CHCOOH, dissolves in liquid ammonia. An H ion is removed from acetic acid, forming its conjugate base, the acetate ion, CHCOO. The addition of an H ion to an ammonia molecule of the solvent creates its conjugate acid, the ammonium ion, . The Brønsted–Lowry model calls hydrogen-containing substances (like HCl) acids. Thus, some substances, which many chemists considered to be acids, such as SO or BCl, are excluded from this classification due

title: Acetic anhydride

text: to bond rotation between each of the optimal aplanar conformations are quite low. Like most acid anhydrides, the carbonyl carbon of acetic anhydride has electrophilic character, as the leaving group is carboxylate. The internal asymmetry may contribute to acetic anhydride's potent electrophilicity as the asymmetric geometry makes one side of a carbonyl carbon more reactive than the other, and in doing so tends to consolidate the electropositivity of a carbonyl carbon to one side (see electron density diagram). Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt (1816-1856) by heating potassium acetate with benzoyl chloride.

title: Thioacetic acid

text: Thioacetic acid Thioacetic acid is an organosulfur compound with the molecular formula CHCOSH. It is a yellow coloured liquid with a strong thiol-like odor. It is used in organic synthesis for the introduction of thiol groups in molecules Thioacetic acid is prepared by the reaction of acetic anhydride with hydrogen sulfide: It has also been produced by the action of phosphorus pentasulfide on glacial acetic acid, followed by distillation. Thioacetic acid is typically contaminated by acetic acid. The compound exists exclusively as the thiol tautomer, consistent with the strength of the C=O double bond. Reflecting the influence of hydrogen-bonding, the

title: Etidronic acid

text: rinsed from the skin after use. Etidronic acid is also included among swimming pool chemicals. It is used as a stain inhibitor to prevent metal ions coming out of solution and staining the sides of swimming pools. Etidronic acid can be prepared by reaction of Phosphorus trichloride with acetic acid in a tertiary amine, or by reaction of an acetic acid/acetic anhydride mixture with phosphorous acid. Etidronic acid (tradename "Didronel") is a bisphosphonate used to strengthen bone, treat osteoporosis, and treat Paget's disease of bone. Bisphosphonates primarily reduce osteoclastic activity, which prevents bone resorption, and thus moves the bone resorption/formation

title: Conjugate acid

text: buffers. A second common application with an organic compound would be the production of a buffer with acetic acid. If acetic acid, a weak acid with the formula , was made into a buffer solution, it would need to be combined with its conjugate base in the form of a salt. The resulting mixture is called an acetate buffer, consisting of aqueous and aqueous . Acetic acid, along with many other weak acids, serve as useful components of buffers in different lab settings, each useful within their own pH range. An example with an inorganic compound would be the medicinal

title: Silicotungstic acid

text: Silicotungstic acid Silicotungstic acid (also known as tungstosilicic acid) is the most commonly encountered heteropoly acid. It is a pale yellow solid with the chemical formula H[WSiO]. It is used as a catalyst in the chemical industry. Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene: It has also been commercialized for the oxidation of ethylene to acetic acid: This route is claimed as a "greener" than methanol carbonylation. The heteropoly acid is dispersed on silica gel at 20-30 wt% to maximize catalytic ability. It has also recently been proposed as a mediator

title: Trichloroacetic acid

text: and Berzelius. Featured in the 1958 independent film The Blob but did not affect the gelatinous mass from outer space. Trichloroacetic acid Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are called trichloroacetates. It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst. Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde. It is widely used in biochemistry for the precipitation

title: Trichloroacetic acid

text: Trichloroacetic acid Trichloroacetic acid (TCA; TCAA; also known as trichloroethanoic acid) is an analogue of acetic acid in which the three hydrogen atoms of the methyl group have all been replaced by chlorine atoms. Salts and esters of trichloroacetic acid are called trichloroacetates. It is prepared by the reaction of chlorine with acetic acid in the presence of a suitable catalyst. Another route to trichloroacetic acid is the oxidation of trichloroacetaldehyde. It is widely used in biochemistry for the precipitation of macromolecules, such as proteins, DNA, and RNA. TCA and DCA are both used in cosmetic treatments (such as chemical

title: Organic acid anhydride

text: Organic acid anhydride An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))O. Symmetrical acid anhydrides of this type are named by replacing the word "acid" in the name of the parent carboxylic acid by the word "anhydride". Thus, (CHCO)O is called "acetic anhydride." Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride

title: Terephthalic acid

text: bromide, hydrogen bromide or tetrabromoethane. Bromine functions as a regenerative source of free radicals. Acetic acid is the solvent and oxygen from compressed air is the oxidant. The combination of bromine and acetic acid is found to be highly corrosive, requiring specialized reactors, such as those lined with titanium. A mixture of "p"-xylene, acetic acid, the catalyst system, and compressed air is fed to a reactor. The oxidation of "p"-xylene proceed by a free radical process. Bromine radicals decompose cobalt and manganese hydroperoxides. The resulting O-based radicals abstract hydrogen from a methyl group, which have weaker C-H bonds than does

title: Trifluoroacetic acid

text: Trifluoroacetic acid Trifluoroacetic acid (TFA) is an organofluorine compound with the chemical formula CFCOH. It is a structural analogue of acetic acid with all three of the acetyl group’s hydrogen atoms replaced by fluorine atoms and is a colorless liquid with a vinegar like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant that is approximately 34,000 times higher, as the highly electronegative fluorine atoms and consequent electron-withdrawing nature of the trifluoromethyl group weakens the oxygen-hydrogen bond (allowing for greater acidity) and stabilises the anionic conjugate base. TFA is widely used in organic chemistry for

title: Formic acid

text: from the water by liquid-liquid extraction with an organic base. A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals. At one time, acetic acid was produced on a large scale by oxidation of alkanes, by a process that cogenerates significant formic acid. This oxidative route to acetic acid is declining in importance, so that the aforementioned dedicated routes to formic acid have become more important. The catalytic hydrogenation of CO to formic acid has long been studied. This reaction can be conducted homogeneously. Formic acid can also be obtained by aqueous catalytic

title: Pyroligneous acid

text: Pyroligneous acid Pyroligneous acid, also called wood vinegar or wood acid, is a dark liquid produced by the destructive distillation of wood and other plant materials. The principal components of pyroligneous acid are acetic acid, acetone and methanol. It was once used as a commercial source for acetic acid. In addition, the vinegar often contains 80-90% water along with some 200 organic compounds. Pyroligneous acid (acetum lignorum) was investigated by German chemist Johann Rudolph Glauber. The acid was eaten as a substitute for vinegar. It was also used topically for treating wounds, ulcers and other ailments. A salt can be

title: Thioacetic acid

text: boiling point (93 °C) and melting points are 20 and 75K lower than those for acetic acid. With a pK near 3.4, thioacetic acid is about 15x more acidic than acetic acid. The conjugate base is thioacetate: In neutral water, thioacetic acid is fully ionized. Most of the reactivity of thioacetic acid arises from the conjugate base, thioacetate. Salts of this anion, e.g. potassium thioacetate, are used to generate thioacetate esters. Thioacetate esters undergo hydrolysis to give thiols. A typical method for preparing a thiol from an alkyl halide using thioacetic acid proceeds in four discrete steps, some of which

title: Chloroacetic acid

text: Chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCHCOH. This carboxylic acid is a useful building-block in organic synthesis. Chloroacetic acid was first prepared (in impure form) by the French chemist Félix LeBlanc (1813–1886) in 1843 by chlorinating acetic acid in the presence of sunlight, and in 1857 (in pure form) by the German chemist Reinhold Hoffmann (1831–1919) by refluxing glacial acetic acid in the presence of chlorine and sunlight, and then by the French chemist Charles-Adolphe Wurtz by reacting chloroacetyl chloride (ClCHCOCl) with water, also in 1857. The production of

title: Acid strength

text: > HCl. Acetic acid is said to be a differentiating solvent for the three acids, while water is not. An important example of a solvent which is more basic than water is dimethyl sulfoxide, DMSO, (CH)SO. A compound which is a weak acid in water may become a strong acid in DMSO. Acetic acid is an example of such a substance. An extensive bibliography of p"K" values in solution in DMSO and other solvents can be found at Acidity–Basicity Data in Nonaqueous Solvents. Superacids are strong acids even in solvents of low dielectric constant. Examples of superacids are fluoroantimonic acid

title: Orthoacetic acid

text: Orthoacetic acid Orthoacetic acid or ethane-1,1,1-triol is an hypothetical organic compound with formula or HC-C(OH). It would be a triple alcohol with the ethane backbone. Since the hydroxyl groups could lose protons, it can also be viewed as an ortho acid. Orthoacetic acid is believed to be impossible to isolate, since it would readily decompose into acetic acid and water. It may have a fleeting existence in aqueous solutions of acetic acid. In theory, removal of one to three protons from the hydroxyls would produce the anions (dihydrogenorthoacetate), (hydrogenorthoacetate), and (orthoacetate). One author claims that sodium orthoacetate is formed by

title: Chloroacetic acid

text: chloroacetic acid was 706,000 tonnes/year in 2010, of which over half is produced in China. Other countries with significant production capacity are Germany (105,000), the Netherlands (100,000), India (>65,000), and the United States (55,000). Chloroacetic acid is prepared industrially via two routes. The predominant method involves chlorination of acetic acid, with acetic anhydride as a catalyst. The other main industrial route to chloroacetic acid is hydrolysis of trichloroethylene using sulfuric acid as a catalyst. The hydrolysis method produces a highly pure product, which can be important since mono-, di-, and trichloroacetic acids are difficult to separate by distillation. Approximately, 420,000,000

title: Acid dissociation constant

text: is less polar and so dissolves non-polar, hydrophobic substances more easily. It has a measurable p"K" range of about 1 to 30. Acetonitrile is less basic than DMSO, and, so, in general, acids are weaker and bases are stronger in this solvent. Some p"K" values at 25 °C for acetonitrile (ACN) and dimethyl sulfoxide (DMSO) are shown in the following tables. Values for water are included for comparison. Ionization of acids is less in an acidic solvent than in water. For example, hydrogen chloride is a weak acid when dissolved in acetic acid. This is because acetic acid is a

title: Organic acid anhydride

text: secondary amines), aromatic ring (see Friedel-Crafts acylation). Acid anhydrides tend to be less electrophilic than acyl chlorides, and only one acyl group is transferred per molecule of acid anhydride, which leads to a lower atom efficiency. The low cost, however, of acetic anhydride makes it a common choice for acetylation reactions. Acetic anhydride is a major industrial chemical widely used for preparing acetate esters, e.g. cellulose acetate. Maleic anhydride is the precursor to various resins by copolymerization with styrene. Maleic anhydride is a dienophile in the Diels-Alder reaction. Dianhydrides, molecules containing two acid anhydride functions, are used to synthesize polyimides

title: Pyruvic acid

text: as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid fermentation). In 1834, Théophile-Jules Pelouze distilled both tartaric acid (-tartaric acid) and racemic acid (a mix of and -tartaric acid) and isolated pyrotartaric acid (methyl succinic acid) and another acid that Jöns Jacob Berzelius characterized the following year and named pyruvic acid. Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid and is miscible with water. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and

title: Lactic acid

text: ten times more easily than acetic acid does. This higher acidity is the consequence of the intramolecular hydrogen bonding between the α-hydroxyl and the carboxylate group. Lactic acid is chiral, consisting of two optical isomers. One is known as -(+)-lactic acid or ("S")-lactic acid and the other, its mirror image, is -(−)-lactic acid or ("R")-lactic acid. A mixture of the two in equal amounts is called -lactic acid, or racemic lactic acid. Lactic acid is hygroscopic. -lactic acid is miscible with water and with ethanol above its melting point which is around 17 or 18 °C. -lactic acid and -lactic

title: Deoxycholic acid

text: Deoxycholic acid Deoxycholic acid (conjugate base deoxycholate), also known as cholanoic acid, Kybella, Celluform Plus, Belkyra, and 3α,12α-dihydroxy-5β-cholan-24-oic acid, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it comes in a white to

title: Acid strength

text: Acid strength Acid strength refers to the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a proton, H, and an anion, A. The dissociation of a strong acid in solution is effectively complete except, in its most concentrated solutions. Examples of strong acids are hydrochloric acid (HCl), perchloric acid (HClO), nitric acid (HNO) and sulfuric acid (HSO). A weak acid is only partially dissociated, with both the undissociated acid and its dissociation products being present, in solution, in equilibrium with each other. Acetic acid (CHCOOH) is an example of a weak acid. The strength of

title: Acid strength

text: a weak acid is quantified by its acid dissociation constant, pK value. The strength of a weak organic acid may depend on substituent effects. The strength of an inorganic acid is dependent on the oxidation state for the atom to which the proton may be attached. Acid strength is solvent-dependent. For example, hydrogen chloride is a strong acid in aqueous solution, but is a weak acid when dissolved in glacial acetic acid. The usual measure of the strength of an acid is its acid dissociation constant ("K"), which can be determined experimentally by titration methods. Stronger acids have a larger

title: Glyoxylic acid

text: rats of 2500 mg/kg. Glyoxylic acid Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially. Glyoxylic acid is usually described with the chemical formula OCHCOH, i.e. containing an aldehyde functional group (see image in upper right). The aldehyde in fact is not observed in solution or as a solid. As seen for many other aldehydes, it exists most commonly as the hydrate. Thus, the formula for glyoxylic acid is really

title: Glyoxylic acid

text: Glyoxylic acid Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially. Glyoxylic acid is usually described with the chemical formula OCHCOH, i.e. containing an aldehyde functional group (see image in upper right). The aldehyde in fact is not observed in solution or as a solid. As seen for many other aldehydes, it exists most commonly as the hydrate. Thus, the formula for glyoxylic acid is really (HO)CHCOH, described as the

title: Propiolic acid

text: Propiolic acid Propiolic acid is the organic compound with the formula HCCOH. It is the simplest acetylenic carboxylic acid. It is a colourless liquid that crystallises to give silky crystals. Near its boiling point, it decomposes. It is soluble in water and possesses an odor like that of acetic acid. It is prepared commercially by oxidizing propargyl alcohol at a lead electrode. It can also be prepared by decarboxylation of acetylenedicarboxylic acid. Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses

title: Hydroiodic acid

text: process is a major end use of hydroiodic acid, which serves as a co-catalyst for the production of acetic acid by the carbonylation of methanol. Hydroiodic acid is listed as a U.S. Federal DEA List I Chemical, owing to its use as a reducing agent related to the production methamphetamine from pseudoephedrine (recovered from nasal decongestant pills). This reaction is stereospecific, producing only (d)-methamphetamine. Hydroiodic acid Hydroiodic acid (or hydriodic acid) is a highly acidic aqueous solution of hydrogen iodide (HI) (concentrated solution usually 48 - 57% HI). It is the second strongest hydrohalic acid, after hydroastatic acid. Hydroiodic acid

title: Acid

text: in the solution. Chemicals or substances having the property of an acid are said to be acidic. Common aqueous acids include hydrochloric acid (a solution of hydrogen chloride which is found in gastric acid in the stomach and activates digestive enzymes), acetic acid (vinegar is a dilute aqueous solution of this liquid), sulfuric acid (used in car batteries), and citric acid (found in citrus fruits). As these examples show, acids (in the colloquial sense) can be solutions or pure substances, and can be derived from acids (in the strict sense) that are solids, liquids, or gases. Strong acids and some

title: Diglycolic acid

text: Diglycolic acid Diglycolic acid is an aliphatic dicarboxylic acid, its acidity is between the one of acetic acid and oxalic acid. It is formed in the oxidation of diethylene glycol in the body and can lead to severe complications with fatal outcome. Oxidation of diethylene glycol with concentrated nitric acid was described by A. Wurtz in 1861 In parallel, W. Heintz reported the synthesis of diglycolic acid from chloroacetic acid by heating with sodium hydroxide solution. In a version with barium hydroxide solution as an alkaline medium, diglycolic acid is obtained in 68% yield after acidification. The yields of the

title: Diphenolic acid

text: Diphenolic acid Diphenolic acid is a carboxylic acid with molecular formula CHO. Its IUPAC name is 4,4-bis(4-hydroxyphenyl)pentanoic acid, and it can be prepared by the condensation reaction of phenol with levulinic acid in the presence of hydrochloric acid. The equation for this synthesis is: Diphenolic acid is a solid at room temperature, melting at 168–171 °C and boiling at 507 °C. According to its MSDS, diphenolic acid is soluble in ethanol, isopropanol, acetone, acetic acid, and methyl ethyl ketone, but insoluble in benzene, carbon tetrachloride, and xylene. Diphenolic acid may be a suitable replacement for bisphenol A as a plasticizer.

title: Formic acid

text: Formic acid Formic acid, systematically named methanoic acid, is the simplest carboxylic acid. The chemical formula is HCOOH or HCOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. The word "formic" comes from the Latin word for ant, "formica", referring to its early isolation by the distillation of ant bodies. Esters, salts, and the anion derived from formic acid are called formates. Industrially formic acid is produced from methanol. Formic acid is a colorless liquid having a pungent, penetrating odor at room temperature, not unlike the related acetic acid. It is miscible

title: Oxalic acid

text: Oxalic acid Oxalic acid is an organic compound with the formula CHO. It is a colorless crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid. Its acid strength is much greater than that of acetic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate (), is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate with the formula CHO·2HO. It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

title: Acid

text: solutions thus have a pH of less than 7. While the Arrhenius concept is useful for describing many reactions, it is also quite limited in its scope. In 1923 chemists Johannes Nicolaus Brønsted and Thomas Martin Lowry independently recognized that acid-base reactions involve the transfer of a proton. A Brønsted-Lowry acid (or simply Brønsted acid) is a species that donates a proton to a Brønsted-Lowry base. Brønsted-Lowry acid-base theory has several advantages over Arrhenius theory. Consider the following reactions of acetic acid (CHCOOH), the organic acid that gives vinegar its characteristic taste: Both theories easily describe the first reaction: CHCOOH

title: Acid strength

text: a weak acid is often a weak base and "vice versa". The strength of an acid varies from solvent to solvent. An acid which is strong in water may be weak in a less basic solvent, and an acid which is weak in water may be strong in a more basic solvent. According to Brønsted–Lowry acid–base theory, the solvent S can accept a proton. For example hydrochloric acid is a weak acid in solution in pure acetic acid, HOCCH, which is more acidic than water. The extent of ionization of the hydrohalic acids decreases in the order HI > HBr

title: Oxalic acid

text: acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite which can also cause acute kidney failure. Unless otherwise cited, all measurements are based on raw vegetable weights with original moisture content. Oxalic acid Oxalic acid is an organic compound with the formula CHO. It is a colorless crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid. Its acid strength is much greater than that of acetic acid. Oxalic acid