Dihydroanthracene
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Dihydroanthracene
9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H2 as a hydrogen-donor. Preparation Because the aromaticity is not compromised for the flanking rings, anthracene is susceptible to hydrogenation at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/ethanol, an application of the Bouveault–Blanc reduction developed by Louis Bouveault and Gustave Louis Blanc in 1903. The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling of benzyl chloride using aluminium chloride as a catalyst. The bond dissociation energy The bond-dissociation energy (BDE, ''D''0, or ''DH°'') is one measure of the strength of a chemical bond . It can be defined as the standard enthalpy change when i ...
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Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the Economic production, production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation. Occurrence and production Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are phenanthrene and carbazole. The mineral form of anthracene is called freitalite and is related to a coal deposit. A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from ''o''-tolyl phenyl ketone. Reactions Reduction Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Hydrogenation gives 9 ...
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Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated and unsaturated compounds, saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces Double bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same ca ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Louis Bouveault
Louis Bouveault (11 February 1864 – 5 September 1909) was a French scientist who became professor of organic chemistry at the Faculty of Sciences of the University of Paris. He is known for the Bouveault aldehyde synthesis and the Bouveault–Blanc reduction. Life Louis Bouveault was born on 11 February 1864 in Nevers. He obtained doctorates in Paris in medicine and physical sciences. Bouveault defended his thesis on β-keto nitriles and their derivatives in Paris in 1890. He taught for a short period at the Medical Faculty in Lyon, then became a lecturer in general chemistry in Lyon. He influenced Victor Grignard to take up chemistry in 1894. In Lyon he investigated syntheses with camphor and terpenes. He worked with Philippe Barbier on terpene derivatives used in the manufacture of perfumes like citral, rhodinal and geraniol. Bouveault moved on from Lyon to Lille, Nancy and finally to Paris. He was appointed professor of organic chemistry at the Faculty of Sciences of the U ...
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Catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst. Catalysis may be classified as either homogeneous, whose components are dispersed in the same phase (usually gaseous or liquid) as the reactant, or heterogeneous, whose components are not in the same phase. Enzymes and other biocatalysts are often considered as a third category. Catalysis is ubiquitous in chemical industry of all kinds. Estimates are that 90% of all commercially produced chemical products involve catalysts at some s ...
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Aluminium Chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contaminated with iron(III) chloride, giving a yellow color. The anhydrous material is important commercially. It has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large amounts are also used in other areas of the chemical industry. The compound is often cited as a Lewis acid. It is an example of an inorganic compound that reversibly changes from a polymer to a monomer at mild temperature. Structure Anhydrous adopts three structures, depending on the temperature and the state (solid, liquid, gas). Solid has a sheet-like layered structure with cubic close-packed chloride ions. In this framework, the Al centres exhibit octahedral coordination geometry. In contrast, has a more mol ...
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Benzyl Chloride
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block. Preparation Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: :C6H5CH3 + Cl2 → C6H5CH2Cl + HCl In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. Side products of the reaction include benzal chloride and benzotrichloride. Other methods of production exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid. Uses and reactions Industrially, benzyl chloride is the precursor to benzyl esters, which are used as plasticizers, flavorants, and perfumes. Phenylacetic acid, a precursor to pharmaceuticals, is produced from benzyl cyan ...
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Bull
A bull is an intact (i.e., not castrated) adult male of the species ''Bos taurus'' (cattle). More muscular and aggressive than the females of the same species (i.e., cows), bulls have long been an important symbol in many religions, including for sacrifices. These animals play a significant role in beef ranching, dairy farming, and a variety of sporting and cultural activities, including bullfighting and bull riding. Due to their temperament, handling requires precautions. Nomenclature The female counterpart to a bull is a cow, while a male of the species that has been castrated is a ''steer'', '' ox'', or ''bullock'', although in North America, this last term refers to a young bull. Use of these terms varies considerably with area and dialect. Colloquially, people unfamiliar with cattle may refer to both castrated and intact animals as "bulls". A wild, young, unmarked bull is known as a ''micky'' in Australia.Sheena Coupe (ed.), ''Frontier Country, Vol. 1'' (Weldon R ...
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Ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a hydroxyl group). Ethanol is a Volatility (chemistry), volatile, Combustibility and flammability, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, the active ingredient in alcoholic drinks. Ethanol is naturally produced by the fermentation process of Carbohydrate, sugars by yeasts or via Petrochemistry, petrochemical processes such as ethylene hydration. It has medical applications as an antiseptic and disinfectant. It is used as a chemical solvent and in the Chemical synthesis, synthesis of organic compounds, and as a Alcohol fuel, fuel source. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2006, world produ ...
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Bouveault–Blanc Reduction
The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and ''n''-butyl oleate to oleyl alcohol. modified versions of which were subsequently refined and published in ''Organic Syntheses''. : This reaction is used commercially although for laboratory scale reactions it was made obsolete by the introduction of lithium aluminium hydride. Reaction mechanism Sodium metal is a one-electron reducing agent. Four equivalents of sodium are required to fully reduce each ester. Ethanol serves as a proton source. The reaction produces sodium alkoxides, according to the following stoichiometry: :   +   6 Na   +   4    →     +     +   4  In practice, considerable sodium is consumed by the formation of ...
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Polycyclic Aromatic Hydrocarbon
A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in coal and in oil deposits, and are also produced by the combustion of organic matter—for example, in engines and incinerators or when biomass burns in forest fires. Polycyclic aromatic hydrocarbons are discussed as possible starting materials for abiotic syntheses of materials required by the earliest forms of life. Nomenclature and structure The terms polyaromatic hydrocarbon or polynuclear aromatic hydrocarbon are also used for this concept. By definition, polycyclic aromatic hydrocarbons have multiple rings, precluding benzene from being considered a PAH. Some sources, such as the US EPA and CDC, consider naphthalene to be the simplest PAH. ...
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