Dihydroxybenzene
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Dihydroxybenzene
In organic chemistry, dihydroxybenzenes (benzenediols) are organic compounds in which two hydroxyl groups () are substituted onto a benzene ring (). These aromatic compounds are classed as phenols. There are three structural isomers: 1,2-dihydroxybenzene (the ''ortho'' isomer) is commonly known as catechol, 1,3-dihydroxybenzene (the ''meta'' isomer) is commonly known as resorcinol, and 1,4-dihydroxybenzene (the ''para'' isomer) is commonly known as hydroquinone. : All three of these compounds are colorless to white granular solids at room temperature and pressure, but upon exposure to oxygen they may darken. All three isomers have the chemical formula . Similar to other phenols, the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic. Each benzenediol can lose an from one of the hydroxyls to form a type of phenolate ion. The Dakin oxidation is an organic redox reaction in which an ''ortho''- or ''para''-hydroxylated phenyl aldehyde () or ketone () reac ...
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Hydrochinon
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. Production Hydroquinone is produced industrially in two main ways.Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. . * The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with propene to give 1,4-diisopropylbenzene. This compound reacts with air to afford the bis(hydroperoxide), which is structurally similar to cumene hydroperoxide and rearranges in acid to give acetone and hydroquinone. * A sec ...
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Hydroquinone
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. Production Hydroquinone is produced industrially in two main ways.Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. . * The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with propene to give 1,4-diisopropylbenzene. This compound reacts with air to afford the bis(hydroperoxide), which is structurally similar to cumene hydroperoxide and rearranges in acid to give acetone and hydroquinone. * A se ...
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Hydroquinone
Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843. Production Hydroquinone is produced industrially in two main ways.Phillip M. Hudnall "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 2005 Wiley-VCH, Weinheim. . * The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with propene to give 1,4-diisopropylbenzene. This compound reacts with air to afford the bis(hydroperoxide), which is structurally similar to cumene hydroperoxide and rearranges in acid to give acetone and hydroquinone. * A se ...
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Phenols
In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule. Phenols are both synthesized industrially and produced by plants and microorganisms. Properties Acidity Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pKa is usually between 10 and 12). Deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion, and the corresponding salts are called phenolates or phenoxides (aryloxides according to the IUPAC Gold Book). Condensation with aldehydes and ketones Phenols are susceptible to Electrophilic aromatic substitutions. Condensation with formald ...
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Catechol
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Catechol occurs as feathery white crystals that are very rapidly soluble in water. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' (''Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) ...
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Catechol
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Catechol occurs as feathery white crystals that are very rapidly soluble in water. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' (''Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) ...
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Acidic
In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequence of database operations that satisfies the ACID properties (which can be perceived as a single logical operation on the data) is called a ''transaction''. For example, a transfer of funds from one bank account to another, even involving multiple changes such as debiting one account and crediting another, is a single transaction. In 1983, Andreas Reuter and Theo Härder coined the acronym ''ACID'', building on earlier work by Jim Gray who named atomicity, consistency, and durability, but not isolation, when characterizing the transaction concept. These four properties are the major guarantees of the transaction paradigm, which has influenced many aspects of development in database systems. According to Gray and Reuter, the IBM Informa ...
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Hydron (chemistry)
In chemistry, the hydron, informally called proton, is the cationic form of atomic hydrogen, represented with the symbol . The general term "hydron", endorsed by the IUPAC, encompasses cations of hydrogen regardless of their isotopic composition: thus it refers collectively to protons (1H+) for the protium isotope, deuterons (2H+ or D+) for the deuterium isotope, and tritons (3H+ or T+) for the tritium isotope. Unlike most other ions, the hydron consists only of a bare atomic nucleus. The negatively charged counterpart of the hydron is the hydride anion, . Properties Solute properties Other things being equal, compounds that readily donate hydrons (Brønsted acids, see below) are generally polar, hydrophilic solutes and are often soluble in solvents with high relative static permittivity (dielectric constants). Examples include organic acids like acetic acid (CH3COOH) or methanesulfonic acid (CH3SO3H). However, large nonpolar portions of the molecule may attenuate these pro ...
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Phenolate
Phenolates (also called phenoxides) are anions, salts, and esters of phenols. They may be formed by reaction of phenols with strong base. Properties Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions. At pH = 10, phenol and phenolate are in approximately 1:1 proportions. Phenolate anions are enolates. As such, they react as nucleophiles at both oxygen and carbon positions. In general, reaction at oxygen occurs under kinetic control, whereas reaction at carbon occurs under thermodynamic control. Uses Alkyl aryl ethers can be synthesized through the Williamson ether synthesis by treating sodium phenolate with an alkyl halide: :C6H5ONa + CH3I → C6H5OCH3 + NaI :C6H5ONa + (CH3O)2SO2 → C6H5OCH3 + (CH3O)SO3Na Production of salicylic acid Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and sodium phenolate. : See also * Sodium phenolate Sodium phenoxide (sodium phenolate) is an organ ...
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Dakin Oxidation
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an '' ortho''- or '' para''-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced. The Dakin oxidation, which is closely related to the Baeyer–Villiger oxidation, is not to be confused with the Dakin–West reaction, though both are named after Henry Drysdale Dakin. Reaction mechanism The Dakin oxidation starts with nucleophilic addition of a hydroperoxide anion to the carbonyl carbon, forming a tetrahedral intermediate (2). The intermediate collapses, causing ,2aryl migration, hydroxide elimination, and formation of a phenyl ester (3). The phenyl ester is subsequently hydrolyzed: nucleophilic addition of hydroxide from solution to the ester carbonyl carbon forms a second tetrahedral intermediate (4), wh ...
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Redox Reaction
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state. There are two classes of redox reactions: * ''Electron-transfer'' – Only one (usually) electron flows from the reducing agent to the oxidant. This type of redox reaction is often discussed in terms of redox couples and electrode potentials. * ''Atom transfer'' – An atom transfers from one substrate to another. For example, in the rusting of iron, the oxidation state of iron atoms increases as the iron converts to an oxide, and simultaneously the oxidation state of oxygen decreases as it accepts electrons released by the iron. Although oxidation reactions are commonly associated with the formation of oxides, other chemical species can serve the same function. In hydrogenation, C=C (and other) bonds ar ...
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Pressure
Pressure (symbol: ''p'' or ''P'') is the force applied perpendicular to the surface of an object per unit area over which that force is distributed. Gauge pressure (also spelled ''gage'' pressure)The preferred spelling varies by country and even by industry. Further, both spellings are often used ''within'' a particular industry or country. Industries in British English-speaking countries typically use the "gauge" spelling. is the pressure relative to the ambient pressure. Various units are used to express pressure. Some of these derive from a unit of force divided by a unit of area; the SI unit of pressure, the pascal (Pa), for example, is one newton per square metre (N/m2); similarly, the pound-force per square inch (psi) is the traditional unit of pressure in the imperial and U.S. customary systems. Pressure may also be expressed in terms of standard atmospheric pressure; the atmosphere (atm) is equal to this pressure, and the torr is defined as of this. Manometric u ...
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