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Anthrone
Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates. Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including ''Rhamnus frangula'', ''Aloe ferox'', ''Rheum officinale'', and ''Cassia senna''. Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible. Synthesis and reactions Anthrone can be prepared from anthraquinone by reduction with tin or copper. An alternative synthesis involves cyclization of ''o''-benzylbenzoic acid induced with hydrogen fluoride. Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment. Tautomer center, 314px, Tautomeric equilibrium for anthrone. Anthrone i ...
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Anthrone Synthesis
Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates. Derivatives of anthrone are used in pharmacy as laxative. They stimulate the motion of the colon and reduce water reabsorption. Some anthrone derivatives can be extracted from a variety of plants, including ''Rhamnus frangula'', ''Aloe ferox'', '' Rheum officinale'', and ''Cassia senna''. Glycosides of anthrone are also found in high amounts in rhubarb leaves, and alongside concentrated amounts of oxalic acid are the reason for the leaves being inedible. Synthesis and reactions Anthrone can be prepared from anthraquinone by reduction with tin or copper. An alternative synthesis involves cyclization of ''o''-benzylbenzoic acid induced with hydrogen fluoride. Anthrone condenses with glyoxal to give, following dehydrogenation, acedianthrone, a useful octacyclic pigment. Tautomer center, 314px, Tautomeric equilibrium for anthrone. Ant ...
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Acedianthrone
Acedianthrone is an octacyclic relative of anthraquinone that is used as a pigment. It is produced from anthrone by condensation with glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ... followed by dehydrogenation.{{ Ullmann , last1= Bien, first1=H.-S., last2=Stawitz , first2=J., last3= Wunderlich, first3=K. , title = Anthraquinone Dyes and Intermediates , doi = 10.1002/14356007.a02_355, year=2005 References Anthraquinone dyes ...
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Anthraquinone
Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoanthracene) wherein the keto groups are located on the central ring. It is a building block of many dyes and is used in bleaching pulp for papermaking. It is a yellow, highly crystalline solid, poorly soluble in water but soluble in hot organic solvents. It is almost completely insoluble in ethanol near room temperature but 2.25 g will dissolve in 100 g of boiling ethanol. It is found in nature as the rare mineral hoelite. Synthesis There are several current industrial methods to produce 9,10-anthraquinone: # The oxidation of anthracene. Chromium(VI) is the typical oxidant. # The Friedel-Crafts reaction of benzene and phthalic anhydride in presence of AlCl3. o-Benzoylbenzoic acid is an intermediate. This reaction is useful for produc ...
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Rhubarb
Rhubarb is the fleshy, edible stalks ( petioles) of species and hybrids (culinary rhubarb) of '' Rheum'' in the family Polygonaceae, which are cooked and used for food. The whole plant – a herbaceous perennial growing from short, thick rhizomes – is also called rhubarb. Historically, different plants have been called "rhubarb" in English. The large, triangular leaves contain high levels of oxalic acid and anthrone glycosides, making them inedible. The small flowers are grouped in large compound leafy greenish-white to rose-red inflorescences. The precise origin of culinary rhubarb is unknown. The species '' Rheum rhabarbarum'' (syn. ''R. undulatum'') and '' R. rhaponticum'' were grown in Europe before the 18th century and used for medicinal purposes. By the early 18th century, these two species and a possible hybrid of unknown origin, ''R.'' × ''hybridum'', were grown as vegetable crops in England and Scandinavia. They readily hybridize, and culina ...
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Anthrol
Anthrols (sometimes called anthranols) are the hydroxylated derivatives of anthracene. For the monohydroxo derivatives, three isomers are possible: 1-anthrol, 2-anthrol, and 9-anthrol. The latter exists as a minor tautomer of 9-anthrone. Despite their simplicity, these compounds have little commercial value. 1- and 2-substituted anthracenes typically are prepared via the hydroxy anthroquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoa ...s, which means that the preparation of these derivatives is arduous. References {{Reflist Anthracenes Hydroxyarenes ...
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Oxalic Acid
Oxalic acid is an organic acid with the systematic name ethanedioic acid and formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus '' Oxalis'', commonly known as wood-sorrels. It occurs naturally in many foods. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous. Oxalic acid has much greater acid strength than acetic acid. It 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 . History The preparation of salts of oxalic acid (crab acid) from plants had been known, at least since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from wood sorrel. By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid fr ...
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Glyoxal
Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid is yellow, and the vapor is green.O'Neil, M.J. (2001): ''The Merck Index'', 13th Edition, page 803. Pure glyoxal is not commonly encountered because glyoxal is usually handled as a 40% aqueous solution (density near 1.24 g/mL). It forms a series of hydrates, including oligomers. For many purposes, these hydrated oligomers behave equivalently to glyoxal. Glyoxal is produced industrially as a precursor to many products. Production Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid. Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-p ...
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Hydrogen Fluoride
Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is widely used in the petrochemical industry as a component of superacids. Hydrogen fluoride boils at near room temperature, much higher than other hydrogen halides. Hydrogen fluoride is an extremely dangerous gas, forming corrosive and penetrating hydrofluoric acid upon contact with moisture. The gas can also cause blindness by rapid destruction of the corneas. History In 1771 Carl Wilhelm Scheele prepared the aqueous solution, hydrofluoric acid in large quantities, although hydrofluoric acid had been known in the glass industry before then. French chemist Edmond Frémy (1814–1894) is credited with discov ...
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Cyclization
A cyclic compound (or ring compound) is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon (i.e., are carbocycles), none of the atoms are carbon (inorganic cyclic compounds), or where both carbon and non-carbon atoms are present (heterocyclic compounds). Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size (e.g., < 17 total atoms) numbers in the ma ...
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Aromaticity
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many ...
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Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered re ...
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