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Glycol
A diol is a chemical compound containing two hydroxyl groups ( groups). An Aliphatic compound, aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is ethylene glycol. Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol and 1,3-Propanediol, propylene-1,3-diol, or beta propylene glycol, . Synthesis of classes of diols Geminal diols A geminal diol has two hydroxyl groups bonded to the same atom. These species arise by hydration of the carbonyl compounds. The hydration is usually unfavorable, but a notable exception is formaldehyde which, in water, exists in equilibrium with methanediol H2C(OH)2. Another example is (F3C)2C(OH)2, the hydrated form of hexafluoroacetone. Many gem-diols undergo further condensation to give dimeric and oligomeric derivatives. This reaction applies to glyoxal and related aldehydes. ...
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Propane-1,2-diol
Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. Containing two alcohol groups, it is classed as a diol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility. It is produced on a large scale primarily for the production of polymers. In the European Union, it has E-number E1520 for food applications. For cosmetics and pharmacology, the number is E490. Propylene glycol is also present in propylene glycol alginate, which is known as E405. Propylene glycol is a compound which is GRAS (generally recognized as safe) by the US Food and Drug Administration under 21 CFR x184.1666, and is also approved by the FDA for certain uses as an indirect food additive. Propylene glycol is approved and used as a vehicle for topical, oral, and some intravenous pharm ...
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Ethylene Glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. Ethylene glycol has a sweet taste, but it is toxic in high concentrations. Production Industrial routes Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation: This reaction can be catalyzed by either acids or bases, or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of th ...
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Ethylene Glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. Ethylene glycol has a sweet taste, but it is toxic in high concentrations. Production Industrial routes Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation: This reaction can be catalyzed by either acids or bases, or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of thes ...
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Ethylene Glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. Ethylene glycol has a sweet taste, but it is toxic in high concentrations. Production Industrial routes Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation: This reaction can be catalyzed by either acids or bases, or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of th ...
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Antifreeze
An antifreeze is an additive which lowers the freezing point of a water-based liquid. An antifreeze mixture is used to achieve freezing-point depression for cold environments. Common antifreezes also increase the boiling point of the liquid, allowing higher coolant temperature. However, all common antifreeze additives also have lower heat capacities than water, and do reduce water's ability to act as a coolant when added to it. Because water has good properties as a coolant, water plus antifreeze is used in internal combustion engines and other heat transfer applications, such as HVAC chillers and solar water heaters. The purpose of antifreeze is to prevent a rigid enclosure from bursting due to expansion when water freezes. Commercially, both the ''additive'' (pure concentrate) and the ''mixture'' (diluted solution) are called antifreeze, depending on the context. Careful selection of an antifreeze can enable a wide temperature range in which the mixture remains in the liquid p ...
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Potassium Permanganate
Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution. Potassium permanganate is widely used in the chemical industry and laboratories as a strong oxidizing agent, and also as a medication for dermatitis, for cleaning wounds, and general disinfection. It is on the World Health Organization's List of Essential Medicines. In 2000, worldwide production was estimated at 30,000 tonnes. Properties Potassium permanganate is the potassium salt of the tetrahedral transition metal oxo complex permanganate, in which four O2- ligands are bound to a manganese(VII) center. Structure KMnO4 forms orthorhombic crystals with constants: ''a'' = 910.5  pm, ''b'' = 572.0 pm, ''c'' = 742.5 pm. The overall motif is similar to that for barium sulfate, with which it forms solid solutions. In the solid (as in solution), each MnO4− centre is t ...
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Acyloin
Acyloins or α-hydroxy ketones are a class of organic compounds which all possess a hydroxy group adjacent to a ketone group. The name acyloin is derived from the fact that they are formally derived from reductive coupling of carboxylic acyl groups. Synthesis Classic organic reactions exist for the synthesis of acyloins. * The acyloin condensation is a reductive coupling of esters * The benzoin condensation is condensation reaction between aldehydes catalyzed by a nucleophile * Oxidation of carbonyls is possible with molecular oxygen but not selective * Better alternative is oxidation of corresponding silyl enol ethers with ''m''CPBA in the Rubottom oxidation * MoOPH oxidation of carbonyls is a system with molybdenum peroxide, pyridine and hexamethylphosphoramide. Enolate oxidation by sulfonyloxaziridines Enolates can be oxidized by sulfonyloxaziridines. The enolate reacts by nucleophilic displacement at the electron deficient oxygen of the oxaziridine ring. : This rea ...
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Geminal Diol
In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached to the same carbon atom, as in methanediol. Also the shortened prefix ''gem'' may be applied to a chemical name to denote this relationship, as in a ''gem''-dibromide for "geminal dibromide". The concept is important in many branches of chemistry, including synthesis and spectroscopy, because functional groups attached to the same atom often behave differently from when they are separated. Geminal diols, for example, are easily converted to ketones or aldehydes with loss of water.Peter Taylor (2002)''Mechanism and synthesis'' Book 10 of ''Molecular world''. Open University, Royal Society of Chemistry; . 368 pages The related term vicinal refers to the relationship between two functional groups that are attached to adjacent atoms. T ...
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Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with '' ...
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Prévost Reaction
The Prévost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereochemistry. The reaction was discovered by the French chemist Charles Prévost (1899–1983). Reaction mechanism The reaction between silver benzoate (1) and iodine is very fast and produces a very reactive iodinium benzoate intermediate (2). The reaction of the iodinium salt (2) with an alkene gives another short-lived iodinium salt (3). Nucleophilic substitution ( SN2) by the benzoate salt gives the ester (4). Another silver ion causes the neighboring group substitution of the benzoate ester to give the oxonium salt (5). A second SN2 substitution by the benzoate anion gives the desired diester (6). In the final step hydrolysis of the ester groups gives the anti-diol. This outcome is the opposite of that of the related Woodward cis-hydroxylation which gives syn addition In organic chemistry, syn- and anti-additio ...
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Woodward Cis-hydroxylation
The Woodward cis-hydroxylation (also known as the Woodward reaction) is the chemical reaction of alkenes with iodine and silver acetate in wet acetic acid to form cis-diols. Woodward, R. B., (conversion of olefin into cis-diol) The reaction is named after its discoverer, Robert Burns Woodward. This reaction has found application in steroid synthesis. Reaction mechanism The reaction of the iodine with the alkene is promoted by the silver acetate, thus forming an iodinium ion (3). The iodinium ion is opened via SN2 reaction by acetic acid (or silver acetate) to give the first intermediate, the iodo-acetate (4). Through anchimeric assistance, the iodine is displaced via another SN2 reaction to give an oxonium ion (5), which is subsequently hydrolyzed to give the mono-ester (6). References See also * Prévost reaction The Prévost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereoche ...
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