ε-caprolactam
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ε-caprolactam
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics. Synthesis and production Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam. World demand for caprolactam was estimated to reach five million tons per year for 2015. 90% of caprolactam produced is used to make filament and fiber, 10% for plastics, and a small amount is used as a chemical intermediate. Due to its commercial significance, many methods have been developed for the production of caprolactam. It was estimated that 90% of all caprolactam is synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime with acid induces the Beckmann rear ...
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Cyclohexanone Oxime
Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer. Preparation Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine:J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. :C5H10CO + H2NOH → C5H10C=NOH + H2O Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone. Reactions The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam: This reaction is catalyzed by sulfuric acid, but industrial scale reactions use solid acids. Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine.W. H. Lyc ...
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Lactam
A lactam is a cyclic amide, formally derived from an amino alkanoic acid. The term is a portmanteau of the words ''lactone'' + ''amide''. Nomenclature Greek prefixes in alphabetical order indicate ring size: * α-Lactam (3-atom rings) * β-Lactam (4-atom rings) * γ-Lactam (5-atom rings) * δ-Lactam (6-atom rings) * ε-Lactam (7-atom rings) This ring-size nomenclature stems from the fact that a hydrolyzed α-Lactam leads to an α-amino acid and a β-Lactam to a β-amino acid, ''etc''. Synthesis General synthetic methods exist for the organic synthesis of lactams. Beckmann rearrangement Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement. Schmidt reaction Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction. Cyclization of amino acids Lactams can be formed from cyclisation of amino acids via the coupling between an amine and a carboxylic acid within the same molecule. Lactamization is most efficient in this ...
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Caprolactam Polymerization
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics. Synthesis and production Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam. World demand for caprolactam was estimated to reach five million tons per year for 2015. 90% of caprolactam produced is used to make filament and fiber, 10% for plastics, and a small amount is used as a chemical intermediate. Due to its commercial significance, many methods have been developed for the production of caprolactam. It was estimated that 90% of all caprolactam is synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime with acid induces the Beckmann rear ...
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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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Schmidt Ring Expansion
Schmidt may refer to: * Schmidt (surname), including list of people with the surname * Schmidt (singer) (born 1990), German pop and jazz singer * Schmidt (lunar crater), a small lunar impact crater * Schmidt (Martian crater), a crater on Mars * Schmidt (volcano), in Kamchatka * Schmidt Block, listed on the National Register of Historic Places in Scott County, Iowa, USA * Schmidt Brewery, a St. Paul brewery * Schmidt camera, an astronomical telescope designed for photography * Schmidt–Cassegrain telescope, a version of the Schmidt camera * Schmidt Site, an archeological site in Michigan, USA, listed on the National Register of Historic Places in 1973 * Schmidt Spiele, a German games manufacturer * Schmidt Baking Company, makers of Schmidt's Blue Ribbon Bread * von Schmidt auf Altenstadt, a German baronial family in Kirchgattendorf, part of the municipality of Gattendorf * Schmidt Island, an island in the Novaya Zemlya archipelago in the Arctic Ocean * Schmidt Peninsula (Sakha ...
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Permissible Exposure Limit
The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational Safety and Health Administration (OSHA). Most of OSHA's PELs were issued shortly after adoption of the Occupational Safety and Health (OSH) Act in 1970. For chemicals, the chemical regulation is usually expressed in parts per million (ppm), or sometimes in milligrams per cubic meter (mg/m3). Units of measure for physical agents such as noise are specific to the agent. A PEL is usually given as a time-weighted average (TWA), although some are short-term exposure limits (STEL) or ceiling limits. A TWA is the average exposure over a specified period, usually a nominal eight hours. This means that, for limited periods, a worker may be exposed to concentration excursions higher than the PEL, so long as the TWA is not exceeded and any applicab ...
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International Agency For Research On Cancer
The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also collects and publishes surveillance data regarding the occurrence of cancer worldwide. Its IARC monographs programme identifies carcinogenic hazards and evaluates environmental causes of cancer in humans. IARC has its own governing council, and in 1965 the first members were the Federal Republic of Germany, France, Italy, the United Kingdom, and the United States of America. Today, IARC's membership has grown to 27 countries. History In late February 1963, after he experienced his spouse suffering and dying of cancer, journalist and peace activist Yves Poggioli sent a letter to Emmanuel d'Astier de la Vignerie relating his story, and urging support for the creation of an intern ...
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Clean Air Act (1990)
The Clean Air Act (CAA) is the United States' primary federal air quality law, intended to reduce and control air pollution nationwide. Initially enacted in 1963 and amended many times since, it is one of the United States' first and most influential modern environmental laws. As with many other major U.S. federal environmental statutes, the Clean Air Act is administered by the U.S. Environmental Protection Agency (EPA), in coordination with state, local, and tribal governments. EPA develops extensive administrative regulations to carry out the law's mandates. The associated regulatory programs are often technical and complex. Among the most important, the National Ambient Air Quality Standards program sets standards for concentrations of certain pollutants in outdoor air; the National Emissions Standards for Hazardous Air Pollutants program sets standards for emissions of particular hazardous pollutants from specific sources. Other programs create requirements for vehicle ...
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Toxic
Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a substructure of the organism, such as a cell ( cytotoxicity) or an organ such as the liver (hepatotoxicity). By extension, the word may be metaphorically used to describe toxic effects on larger and more complex groups, such as the family unit or society at large. Sometimes the word is more or less synonymous with poisoning in everyday usage. A central concept of toxicology is that the effects of a toxicant are dose-dependent; even water can lead to water intoxication when taken in too high a dose, whereas for even a very toxic substance such as snake venom there is a dose below which there is no detectable toxic effect. Toxicity is species-specific, making cross-species analysis problematic. Newer paradigms and metrics are evolving to bypass ...
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Irritation
Irritation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant. Irritants are typically thought of as chemical agents (for example phenol and capsaicin) but mechanical, thermal (heat), and radiative stimuli (for example ultraviolet light or ionising radiations) can also be irritants. Irritation also has non-clinical usages referring to bothersome physical or psychological pain or discomfort. Irritation can also be induced by some allergic response due to exposure of some allergens for example contact dermatitis, irritation of mucosal membranes and pruritus. Mucosal membrane is the most common site of irritation because it contains secretory glands that release mucous which attracts the allergens due to its sticky nature. Chronic irritation is a medical term signifying that afflictive health conditions have been present for a while. There are many dis ...
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Meptazinol
Meptazinol (trade name Meptid) is an opioid analgesic developed by Wyeth in the 1970s. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth). Meptazinol is a 3-phenylazepane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes. A partial μ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full μ agonists like morphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine Buprenorphine is an opioid used to treat opioid use disorder, acute pain, and chronic pain. It can be used under the tongue (sublingual), in the cheek (buccal), by injection (intravenous and subcutaneous), as a skin patch (transdermal), .... References External links * Synthetic opioids Azepanes Phenols { ...
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