Ε-caprolactone
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Ε-caprolactone
ε-Caprolactone or simply caprolactone is a lactone (a cyclic ester) possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to caprolactam. Production and uses Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid. Caprolactone is a monomer used in the production of highly specialised polymers. Ring-opening polymerization, for example, gives polycaprolactone. Another polymer is polyglecaprone, used as suture material in surgery. Reactions Although no longer economical, caprolactone was once produced as a precursor to caprolactam. Caprolactone is treated with ammonia at elevated temperatures to give the lactam: :(CH2)5CO2 + NH3 → (CH2)5C(O)NH + H2O Carbonylation of caprolactone gives, after hydrolysis, pimelic acid. The lactone ring is easily opened with nucleophiles including alcohols a ...
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Lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Lactones are formed by intramolecular esterification of the corresponding hydroxycarboxylic acids, which takes place spontaneously when the ring that is formed is five- or six-membered. Lactones with three- or four-membered rings (α-lactones and β-lactones) are very reactive, making their isolation difficult. Special methods are normally required for the laboratory synthesis of small-ring lactones as well as those that contain rings larger than six-membered. Nomenclature Lactones are usually named according to the precursor acid molecule (''aceto'' = 2 carbon atoms, ''propio'' = 3, ''butyro'' = 4, ''valero'' = 5, ''capro'' = 6, etc.), with a ''-lactone'' suffix and a Greek letter prefix that specifies the number of carbon atoms in the heterocycle — that is, the distance between the relevant -OH ...
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Carbonylation
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains. Organic chemistry Several industrially useful organic chemicals are prepared by carbonylations, which can be highly selective reactions. Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids and esters. Carbonylations are the basis of many types of reactions, including hydroformylation and Reppe reactions. These reactions require metal catalysts, which bind and activate the CO. These processes involve transition metal acyl complexes as intermediates. Much of this theme was developed by Walter Reppe. Hydroformylation Hydroformylation entails the addition of both carbon monoxide and hydrogen to unsaturated ...
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Aluminum
Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. It has a great affinity towards oxygen, and forms a protective layer of oxide on the surface when exposed to air. Aluminium visually resembles silver, both in its color and in its great ability to reflect light. It is soft, non-magnetic and ductile. It has one stable isotope, 27Al; this isotope is very common, making aluminium the twelfth most common element in the Universe. The radioactivity of 26Al is used in radiodating. Chemically, aluminium is a post-transition metal in the boron group; as is common for the group, aluminium forms compounds primarily in the +3 oxidation state. The aluminium cation Al3+ is small and highly charged; as such, it is polarizing, and bonds aluminium forms tend towards covalency. The strong affinity towards ox ...
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Ammonium Nitrate
Ammonium nitrate is a chemical compound with the chemical formula . It is a white crystalline salt consisting of ions of ammonium and nitrate. It is highly soluble in water and hygroscopic as a solid, although it does not form hydrates. It is predominantly used in agriculture as a high-nitrogen fertilizer.Karl-Heinz Zapp "Ammonium Compounds" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2012, Wiley-VCH, Weinheim. Global production was estimated at 21.6 million tonnes in 2017. Its other major use is as a component of explosive mixtures used in mining, quarrying, and civil construction. It is the major constituent of ANFO, a popular industrial explosive which accounts for 80% of explosives used in North America; similar formulations have been used in improvised explosive devices. Many countries are phasing out its use in consumer applications due to concerns over its potential for misuse.
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Ammonium Perchlorate
Ammonium perchlorate ("AP") is an inorganic compound with the formula NH4 ClO4. It is a colorless or white solid that is soluble in water. It is a powerful oxidizer. Combined with a fuel, it can be used as a rocket propellant called ammonium perchlorate composite propellant. Its instability has involved it in a number of accidents, such as the PEPCON disaster. Production Ammonium perchlorate (AP) is produced by reaction between ammonia and perchloric acid. This process is the main outlet for the industrial production of perchloric acid. The salt also can be produced by salt metathesis reaction of ammonium salts with sodium perchlorate. This process exploits the relatively low solubility of NH4ClO4, which is about 10% of that for sodium perchlorate.Helmut Vogt, Jan Balej, John E. Bennett, Peter Wintzer, Saeed Akbar Sheikh, Patrizio Gallone "Chlorine Oxides and Chlorine Oxygen Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH. AP crystallises as colorle ...
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Pheromone
A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are ''alarm signal, alarm pheromones'', ''food trail pheromones'', ''sex pheromones'', and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology. Background The portmanteau word "pheromone" was coined by Peter Karlson and Martin Lüscher in 1959, based on the Greek φερω ''pheroo'' ('I carry') and ὁρμων ''hormon'' ('stimulating'). P ...
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Khapra Beetle
The khapra beetle (''Trogoderma granarium''), also called cabinet beetle, which originated in South Asia, is one of the world's most destructive pests of grain products and seeds.Stibick, J. (2007) ''New Pest Response Guidelines: Khapra Beetle''
APHIS–PPQ–Emergency and Domestic Programs, United States Department of Agriculture, Riverdale, Maryland, p. 1-1
It is considered one of the 100 worst in the world.
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Floral Scent
Floral scent, or flower scent, is composed of all the volatile organic compounds (VOCs), or aroma compounds, emitted by floral tissue (e.g. flower petals). Other names for floral scent include, aroma, fragrance, floral odour or perfume. Flower scent of most flowering plant species encompasses a diversity of VOCs, sometimes up to several hundred different compounds. The primary functions of floral scent are to deter herbivores and especially folivorous insects (see Plant defense against herbivory), and to attract pollinators. Floral scent is one of the most important communication channels mediating plant-pollinator interactions, along with visual cues (flower color, shape, etc.). Biotic interactions Perception by flower visitors Flower visitors such as insects and bats detect floral scents thanks to chemoreceptors of variable specificity to a specific VOC. The fixation of a VOC on a chemoreceptor triggers the activation of an antennal glomerulus, further projecting on an olfac ...
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Pimelic Acid
Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H. Pimelic acid is one unit longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides. However compared to adipic acid, pimelic acid is relatively small in importance industrially. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid lysine and the vitamin biotin. Synthesis Biosynthesis The biosynthesis of pimelic acid is unknown but is speculated to start with malonyl CoA. Chemical and industrial routes Like other simple dicarboxylic acids, many methods have been developed for producing pimelic acid. Pimelic acid is produced commercially by oxidation of cycloheptanone with dinitrogen tetroxide. Other routes include the relatively unselective oxidation of palmitic acid and the carbonylation of caprolactone. Niche methods Many other methods exist. Pimelic acid has been synthesized from cyclohexanone and from salicylic acid. In the forme ...
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Polyglecaprone
Monocryl is a synthetic, absorbable suture manufactured in Cornelia, Georgia, USA, and trademarked by Ethicon. It is composed of poliglecaprone 25, which is a copolymer of glycolide and epsilon-caprolactone. It comes both dyed (violet) and undyed (clear) and is an absorbable monofilament suture. It is generally used for soft-tissue approximation and ligation. It is used frequently for subcuticular dermis closures of the face. It has less of a tendency to exit through the skin after it breaks down, such as Vicryl Vicryl (polyglactin 910) is an absorbable, synthetic, usually braided suture, manufactured by Ethicon Inc., a subsidiary of Johnson and Johnson. A monofilament version is also made for use in ophthalmic practice. It is indicated for soft tissue .... It is contraindicated for use in cardiovascular and neurologic tissues and for usage in ophthalmic and microsurgery. The use of poliglecaprone suture may be inappropriate in patients who are older, malnourished, or debilita ...
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Ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology Th ...
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