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Caprolactam
Caprolactam (CPL) is an organic compound with the chemical formula, 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 Cyclohexanone oxime, oxime (2). Treatment of this ox ...
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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 rea ...
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Lactam
A lactam is a Cyclic compound, cyclic amide, formally derived from an amino alkanoic acid through cyclization reactions. The term is a portmanteau of the words ''lactone'' + ''amide''. Nomenclature Greek_alphabet#Letters, Greek prefixes in alphabetical order indicate ring size. This ring-size nomenclature stems from the fact that hydrolysis of an α-lactam gives an α-amino acid and that of a β-Lactam gives a β-amino acid, and so on. Synthesis General synthetic methods are used for the organic synthesis of lactams. Beckmann rearrangement Lactams form by the Acid catalysis, acid-catalyzed Rearrangement reaction, rearrangement of oximes in the Beckmann rearrangement. Schmidt reaction Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction. Cyclohexanone with hydrazoic acid, forms Caprolactam, ε - Caprolactum, which upon treatment with excess acid forms Pentylenetetrazol, Cardiazole, a heart stimulant. Cyclization of amino acids Lactams can be formed fr ...
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Nylon 6
Nylon 6 or polycaprolactam is a polymer, in particular semicrystalline polyamide. Unlike most other nylons, nylon 6 is not a condensation polymer, but instead is formed by ring-opening polymerization; this makes it a special case in the comparison between condensation and addition polymers. Its competition with nylon 66 and the example it set have also shaped the economics of the synthetic fibre industry. It is sold under numerous trade names including Perlon (Germany), Dederon (former East Germany), Nylatron, Capron, Ultramid, Akulon, Kapron (former Soviet Union and satellite states), Rugopa (Turkey) and Durethan. History Polycaprolactam was developed by Paul Schlack at IG Farben in late 1930s (first synthesized in 1938) to reproduce the properties of Nylon 66 without violating the patent on its production. (Around the same time, Kohei Hoshino at Toray also succeeded in synthesizing nylon 6.) It was marketed as Perlon, and industrial production with a capacity of 3,500 tons ...
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Nitrosylsulfuric Acid
Nitrosylsulfuric acid is the chemical compound with the formula . It is a colourless solid that is used industrially in the production of caprolactam, and was formerly part of the lead chamber process for producing sulfuric acid. The compound is the mixed anhydride of sulfuric acid and nitrous acid. In organic chemistry, it is used as a reagent for nitrosating, as a diazotizing agent, and as an oxidizing agent. Synthesis and reactions A typical procedure entails dissolving sodium nitrite in cold sulfuric acid: : It can also be prepared by the reaction of nitric acid and sulfur dioxide. This procedure generates the nitrosylsulfuric acid as an intermediate en route to NOCl. is used in organic chemistry to prepare diazonium salts from amines, for example in the Sandmeyer reaction. Related NO-delivery reagents include nitrosonium tetrafluoroborate and nitrosyl chloride. In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and cyclohexanecarboxylic ...
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Beckmann Rearrangement
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement reaction, rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams. The Beckmann rearrangement is often catalyzed by acid; however, other reagents have been known to promote the rearrangement. These include tosyl chloride, thionyl chloride, phosphorus pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. The Beckmann fragmentation is another reaction that often competes with the rearrangement, though careful selection of promoting reagent and solvent conditions can favor the formation of one over the other, sometimes giving almost exclusively one product. The rearrangement occurs Stereospecificity, stereospecifically for ketoximes and N-chloro/N-fluoro imines, with the migrating group be ...
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Cyclohexanone
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon. History and synthesis The compound was discovered by in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol. He named it hydrophenoketone and correctly suggested that phenol was first hydrogenated by electrolytic hydrogen to cyclohexanol, which he wasn't able to isolate, and then oxidized by electrolytic oxygen. Laboratory synthesis Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide ( Jones oxidation). An alternative method utilizes the safer and more readily avai ...
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Cyclohexanone Oxime
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon. History and synthesis The compound was discovered by in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol. He named it hydrophenoketone and correctly suggested that phenol was first hydrogenated by electrolytic hydrogen to cyclohexanol, which he wasn't able to isolate, and then oxidized by electrolytic oxygen. Laboratory synthesis Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide (Jones oxidation). An alternative method utilizes the safer and more readily availab ...
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Nitrosyl Chloride
Nitrosyl chloride is the chemical compound with the formula NOCl. It is a yellow gas that is commonly encountered as a component of aqua regia, a mixture of 3 parts concentrated hydrochloric acid and 1 part of concentrated nitric acid. It is a strong electrophile and oxidizing agent. It is sometimes called Tilden's reagent, after William A. Tilden, who was the first to produce it as a pure compound. Structure and synthesis The molecule is bent. A double bond exists between N and O (distance = 1.16 Å) and a single bond between N and Cl (distance = 1.96 Å). The O=N–Cl angle is 113°. Production Nitrosyl chloride can be produced in many ways. * Combining nitrosylsulfuric acid and HCl affords the compound. This method is used industrially. :HCl + NOHSO4 → H2SO4 + NOCl * A more convenient laboratory method involves the (reversible) dehydration of nitrous acid by HCl : HNO2 + HCl → H2O + NOCl * By the direct combination of chlorine and nitric ...
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Meptazinol
Meptazinol, sold under the brand 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, sold under the brand name Subutex among others, 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 a .... Review: References External links * Synthetic opioids A ...
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Hydrazoic Acid
Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide, This also contains a detailed description of the contemporaneous production process. is a compound with the chemical formula . It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. It was first isolated in 1890 by Theodor Curtius. The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes. Hydrazoic acid, like its fellow mineral acids, is soluble in water. Undiluted hydrazoic acid is dangerously explosive with a standard enthalpy of formation ΔfHo (l, 298K) = +264 kJ/mol. When dilute, the gas and aqueous solutions (<10%) can be safely prepared but should be used immediately; because of its low boiling point, hydrazoic acid is enriched upon evaporation and condensation such that dilute solutions incapable of explosion can form droplets in the headspace of th ...
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Pentylenetetrazol
Pentylenetetrazol (PTZ), also known as pentylenetetrazole, pentetrazol (INN), and pentamethylenetetrazol, is a drug formerly used as a circulatory and respiratory stimulant. High doses cause convulsions, as discovered by Hungarian-American neurologist and psychiatrist Ladislas J. Meduna in 1934. It has been used in convulsive therapy, and was found to be effective in treating depression, but side effects such as uncontrolled seizures were difficult to avoid. In 1939, pentylenetetrazol was replaced by electroconvulsive therapy, which is easier to administer, as the preferred method for inducing seizures in England's mental hospitals. In the US, Pentylenetetrazol's approval by the Food and Drug Administration (FDA) was revoked in 1982. It is used in Italy as a cardio-respiratory stimulant in combination with dihydrocodeine in a cough suppressant drug. Side effects Pentylenetetrazol is anxiogenic and has been known to induce severe anxiety in humans. Mechanism of action The mechan ...
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