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Acetic Anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of cellulose acetate as well 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. Structure and properties Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure. The C=O and C-O distances are 1.19 and 1.39 Å. The Pi bond, pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole, dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low. Production Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt ...
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Hour
An hour (symbol: h; also abbreviated hr) is a unit of time historically reckoned as of a day and defined contemporarily as exactly 3,600 seconds ( SI). There are 60 minutes in an hour, and 24 hours in a day. The hour was initially established in the ancient Near East as a variable measure of of the night or daytime. Such seasonal hours, also known as temporal hours or unequal hours, varied by season and latitude. Equal hours or equinoctial hours were taken as of the day as measured from noon to noon; the minor seasonal variations of this unit were eventually smoothed by making it of the mean solar day. Since this unit was not constant due to long term variations in the Earth's rotation, the hour was finally separated from the Earth's rotation and defined in terms of the atomic or physical second. It is a non-SI unit that is accepted for use with SI. In the modern metric system, one hour is defined as 3,600 atomic seconds. However, on rare occasions an hour may inc ...
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Carbonyl
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes, ketones and carboxylic acid), as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e.g. nickel carbonyl). The remainder of this article concerns itself with the organic chemistry definition of carbonyl, such that carbon and oxygen share a double bond. Carbonyl compounds In organic chemistry, a carbonyl group characterizes the following types of compounds: Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides, chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, Hydro ...
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Acetylation
: In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply ''acetates''. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound. Acetylation/deacetylation in biology Histone deacetylases "play crucial roles in gene transcription and most likely in all eukaryotic biological processes that involve chromatin". Acetylation is one type of post-translational modification of proteins. The acetylation of the ε-amino group of lysine, which is common, converts a charged side chain to a neutral one. Acetylation/deacetylation of histones also plays a role in gene expression and cancer. These modifications are effected by enzymes called histone acetyltransferases (HATs) and histone deacetylases (HDACs). Two general mechanisms are known for deacetylation. One mechanism involves zinc binding to the acetyl o ...
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Wacker Chemie
Wacker Chemie AG is a German multinational chemical company which was founded in 1914 by Alexander Wacker. The company is controlled by the Wacker family holding more than 50 percent of the shares. The corporation operates more than 25 production sites in Europe, Asia, and the Americas. The product range includes silicone rubbers, polymer products like ethylene vinyl acetate redispersible polymer powder, chemical materials, polysilicon and wafers for the semiconductor industry. The company sells its products in more than 100 countries. As of 31 December 2015, 16,972 employees have been with Wacker. Corporate annual sales in 2015, were about 5,3 billion Euros, up 10% compared to 2014. History On 13 October 1914, Alexander Wacker established "Dr. Alexander Wacker, Gesellschaft für elektrochemische Industrie KG". The production plant in Burghausen, Upper Bavaria was constructed in 1916 and in December that year the first acetylaldehyde and acetic acid products were manufactu ...
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Ethenone
Ethenone is the formal name for ketene, an organic compound with formula or . It is the simplest member of the ketene class. It is an important reagent for acetylations. Properties Ethenone is a highly reactive gas (at Standard temperature and pressure, standard conditions) and has a sharp irritating odour. It is only reasonably stable at low temperatures (−80 °C). It must therefore always be prepared for each use and processed immediately, otherwise a dimerization to diketene occurs or it reacts to polymers that are difficult to handle. The polymer content formed during the preparation is reduced, for example, by adding sulfur dioxide to the ketene gas. Because of its cumulative double bonds, ethenone is highly reactive and reacts in an addition reaction H-acidic compounds to the corresponding acetic acid derivatives. It does for example react with water to acetic acid or with Primary amine, primary or secondary amines to the corresponding acetamides. Preparation Et ...
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Lithium Iodide
Lithium iodide, or LiI, is a compound of lithium and iodine. When exposed to air, it becomes yellow in color, due to the oxidation of iodide to iodine. It crystallizes in the NaCl motif. It can participate in various hydrates.Wietelmann, Ulrich and Bauer, Richard J. (2005) "Lithium and Lithium Compounds" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH: Weinheim. . Applications Lithium iodide is used as a solid-state electrolyte for high-temperature batteries. It is also the standard electrolyte in artificial pacemakers due to the long cycle life it enables. The solid is used as a phosphor for neutron detection. It is also used, in a complex with Iodine, in the electrolyte of dye-sensitized solar cells. In organic synthesis, LiI is useful for cleaving C-O bonds. For example, it can be used to convert methyl esters to carboxylic acids: : Similar reactions apply to epoxides and aziridines. Lithium iodide was used as a radiocontrast agent for CT scans. Its use was ...
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Rhodium Chloride
Rhodium is a chemical element; it has symbol Rh and atomic number 45. It is a very rare, silvery-white, hard, corrosion-resistant transition metal. It is a noble metal and a member of the platinum group. It has only one naturally occurring isotope, which is 103Rh. Naturally occurring rhodium is usually found as a free metal or as an alloy with similar metals and rarely as a chemical compound in minerals such as bowieite and rhodplumsite. It is one of the rarest and most valuable precious metals. Rhodium is a group 9 element (cobalt group). Rhodium is found in platinum or nickel ores with the other members of the platinum group metals. It was discovered in 1803 by William Hyde Wollaston in one such ore, and named for the rose color of one of its chlorine compounds. The element's major use (consuming about 80% of world rhodium production) is as one of the catalysts in the three-way catalytic converters in automobiles. Because rhodium metal is inert against corrosion and most ag ...
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Acetyl Iodide
Acetyl iodide is an organoiodine compound with the formula CH3COI. It is a colourless liquid. It is formally derived from acetic acid. Although far rarer in the laboratory than the related acetyl bromide and acetyl chloride, acetyl iodide is produced, transiently at least, on a far larger scale than any other acid halide. Specifically, it is generated by the carbonylation of methyl iodide in the Cativa and Monsanto processes, which are the main industrial processes that generate acetic acid. It is also an intermediate in the production of acetic anhydride from methyl acetate. Upon treatment with carboxylic acids, acetyl iodide does not exhibit reactions typical of acyl halides, such as acetyl chloride. Instead, acetyl iodide undergoes iodide/hydroxide exchange with most carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an Substituent, R-group. The general formula of a carboxylic acid is often writ ...
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Iodomethane
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted in small amounts by rice plantations. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups. Preparation and handling Iodomethane is formed via the exothermic reaction that occurs when iodine is added to a mixture of methanol with red phosphorus. The iodinating reagent is phosphorus triiodide that is formed ''in situ:'' :3 CH3OH + PI3 → 3 CH3I + H2PO3H Alternatively, it is prepared from the reaction of dimethyl sulfate with potassium iodide in the presence of c ...
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Monsanto Process
The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol. The Monsanto process has largely been supplanted by the Cativa process, a similar iridium-based process developed by BP Chemicals Ltd, which is more economical and environmentally friendly. This process operates at a pressure of 30–60 atm and a temperature of 150–200 °C and gives a selectivity greater than 99%. It was developed in 1960 by the German chemical company BASF and improved by the Monsanto Company in 1966, which introduced a new catalyst system. Catalytic cycle The catalytically active species is the anion ''cis''- h(CO)2I2sup>− (top of scheme). The first organometallic step is the oxidative addition of methyl iodide to ''cis''- h(CO)2I2sup>− to form the hexacoordinate species CH3)Rh(CO)2I3sup>−. This anion rapidly transforms, via the migration of a methyl group to an adjacent carbonyl ligand, affording the pentacoordinat ...
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Methyl Acetate
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not regulated as a volatile organic compound in the USA. Preparation and reactions Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid. Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong a ...
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