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Hydroperoxide
Hydroperoxides or peroxols are compounds containing the hydroperoxide functional group (ROOH). If the R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds. Properties The O−O bond length in peroxides is about 1.45 Å, and the R−O−O angles (R = H, C) are about 110° (water-like). Characteristically, the C−O−O−H dihedral angles are about 120°. The O−O bond is relatively weak, with a bond dissociation energy of , less than half the strengths of C−C, C−H, and C−O bonds. Hydroperoxides are typically more volatile than the corresponding alcohols: * ''tert''-BuOOH (b.p. 36°C) vs ''tert''-BuOH (b.p. 82-83°C) * CH3OOH (b.p. 46°C) vs CH3OH (b.p. 65°C * cumene hydroperoxide (b.p. 153°C) vs cumyl alcohol (b.p. 202°C) Mis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tert-Butyl Hydroperoxide
''tert''-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, ''tert''-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable. Application Industrially, ''tert''-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction: :(CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3 The byproduct t-butanol, which can be dehydrated to isobutene and converted to MTBE. On a much smaller scale, ''tert''-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation. Synthesis and pro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tert-butyl Hydroperoxide
''tert''-Butyl hydroperoxide (tBuOOH) is the organic compound with the formula (CH3)3COOH. It is one of the most widely used hydroperoxides in a variety of oxidation processes, for example the Halcon process. It is normally supplied as a 69–70% aqueous solution. Compared to hydrogen peroxide and organic peracids, ''tert''-butyl hydroperoxide is less reactive and more soluble in organic solvents. Overall, it is renowned for the convenient handling properties of its solutions. Its solutions in organic solvents are highly stable. Application Industrially, ''tert''-butyl hydroperoxide is used to prepare propylene oxide. In the Halcon process, molybdenum-based catalysts are used for this reaction: :(CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3 The byproduct t-butanol, which can be dehydrated to isobutene and converted to MTBE. On a much smaller scale, ''tert''-butyl hydroperoxide is used to produce some fine chemicals by the Sharpless epoxidation. Synthesis and pro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Peroxide
In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group (). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily breaks, producing free radicals of the form (the dot represents an unpaired electron). Thus, organic peroxides are useful as initiators for some types of polymerisation, such as the epoxy resins used in glass-reinforced plastics. MEKP and benzoyl peroxide are commonly used for this purpose. However, the same property also means that organic peroxides can explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful bleaching agents. Types of organic peroxides Tert-Butyl hydroperoxide Structural Formula V2.svg, ''tert''-Butyl hydroperoxide, a hydroperoxide (formula: ROOH) that is used to epoxide alkenes. Dicumyl peroxide.svg, Dicumyl peroxide, a dialkyl peroxide (formula: ROOR) that is used to initia ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cumene Hydroperoxide
Cumene hydroperoxide is the organic compound with the formula C6H5CMe2OOH (Me = CH3). An oily liquid, it is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol. Its formula is C6H5C(CH3)2OOH. It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene: : + O2 → Dicumyl peroxide is a side product. Applications Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propene. :: Cumene hydroperoxide is a free radical initiator for production of acrylates. Cumene hydroperoxide is involved as an organic peroxide in the manufacturing of propylene oxide by the oxidation of propylene. This technology was commercialized by Sumitomo Chemical. The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct cumyl alcohol. The reaction ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methyl Hydroperoxide
Methyl hydroperoxide is the organic compound with the formula CH3OOH. It is a volaltile colorless liquid. In addition to being of theoretical interest as the simplest organic hydroperoxide, methyl hydroperoxide is an intermediate in the oxidation of methane Methane ( , ) is a chemical compound with the chemical formula (one carbon atom bonded to four hydrogen atoms). It is a group-14 hydride, the simplest alkane, and the main constituent of natural gas. The relative abundance of methane on Ea ... in the atmosphere. When condensed or in concentrated form methyl hydroperoxide is rather explosive, unlike tertiary hydroperoxides such as tert-butylhydroperoxide. Its laboratory preparation was first reported in 1929. References {{Reflist Hydroperoxides Oxidizing agents Organic compounds with 1 carbon atom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cumene Process
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR)., and independently by Heinrich Hock in 1944 This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method. In 2003, nearly 7 million tonnes of phenol was produced by the cumene process.Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH. . In order for this process to be economical, there must also be demand for the acetone by-product as well as the phenol. Steps of the p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Epoxide
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile. Nomenclature A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound ''1,2-epoxyheptane'', which can also be called ''1,2-heptene oxide''. A polymer formed from epoxide precursors is called an ''epoxy'', but such materials do not contain epoxide groups (or contain only a few residual epoxy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Propylene Oxide
Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture. This compound is sometimes called 1,2-propylene oxide to distinguish it from its isomer 1,3-propylene oxide, better known as oxetane. Production Industrial production of propylene oxide starts from propylene. Two general approaches are employed, one involving hydrochlorination and the other involving oxidation. In 2005, about half of the world production was through chlorohydrin technology and one half via oxidation routes. The latter approach is growing in importance. Hydrochlorination route The traditional route proceeds via the conversion of propene to propylene chlorohy ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Drying Oil
A drying oil is an oil that hardens to a tough, solid film after a period of exposure to air, at room temperature. The oil hardens through a chemical reaction in which the components crosslink (and hence, polymerize) by the action of oxygen (not through the evaporation of water or other solvents). Drying oils are a key component of oil paint and some varnishes. Some commonly used drying oils include linseed oil, tung oil, poppy seed oil, perilla oil, and walnut oil. Their use has declined over the past several decades, as they have been replaced by alkyd resins and other binders. Since oxidation is the key to curing in these oils, those that are susceptible to chemical drying are often unsuitable for cooking, and are also highly susceptible to becoming rancid through autoxidation, the process by which fatty foods develop off-flavors. Rags, cloth, and paper saturated with drying oils may spontaneously combust (ignite) after a few hours as heat is released during the oxi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. F ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Properties Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 an odor reminiscent of acetone. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon. Production Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: :C6H12 + O2 → (CH2)5CO + H2O This process forms cyclohexanol as a by-product, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. The oxidation involves radicals and the hydroperoxide C6H11O2H as an intermediate. In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. Alternatively, cyclohexanone can be produced by the partia ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
