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Cyclohexylbenzene
Cyclohexylbenzene (or phenylhexamethylene, as it was initially called) is the organic compound with the structural formula . It is a derivative of benzene with a cyclohexyl substituent (C6H11). It is a colorless liquid. History and synthesis Cyclohexylbenzene was first obtained in 1899 by Markovnikov's student Nikolay Kirsanov (1874–1921). He used a Friedel–Crafts alkylation of benzene with cyclohexyl chloride using a catalyst such as aluminum trichloride: : Cyclohexylbenzene is now industrially produced by the acid-catalyzed alkylation of benzene with cyclohexene. The process can proceed using benzene as the exclusive organic precursor. Its partial hydrogenation gives cyclohexene, which alkylates the unhydrogenated benzene. It is also generated by the hydrodesulfurization of dibenzothiophene, and ExxonMobil took a patent in 2009 for a process based on direct hydroalkylation of two benzene molecules. Applications A route to phenol analogous to the cumene process begin ...
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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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Cyclohexene
Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Production and uses Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company. The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene. In the laboratory, it can be prepared by dehydration reaction, dehydration of cyclohexanol. : Reactions and uses Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenation, dehydrogenated to give cyclohexanone, a precursor to caprolactam. The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxid ...
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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 2022, nearly 10.8 million tonnes of phenol was produced by the cumene process. 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 process Cumene is formed in the gas-phase Friedel–Crafts alkylation of benzene by propene. Benzene and propene are compr ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). 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, and even ...
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ExxonMobil
Exxon Mobil Corporation ( ) is an American multinational List of oil exploration and production companies, oil and gas corporation headquartered in Spring, Texas, a suburb of Houston. Founded as the Successors of Standard Oil, largest direct successor of John D. Rockefeller's Standard Oil, the modern company was formed in 1999 following the merger of Exxon and Mobil. It is Vertical integration, vertically integrated across the entire oil and gas industry, as well as within its chemicals division, which produces plastic, synthetic rubber, and other chemical products. As the largest U.S.-based oil and gas company, ExxonMobil is the List of largest companies in the United States by revenue, seventh-largest company by revenue in the U.S. and List of largest companies by revenue, 13th-largest in the world. It is the largest investor-owned oil company in the world. Approximately 55.56% of the company's shares are held by institutions, the largest of which as of 2019 were The Vanguard ...
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Nylon
Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieties exhibiting a silk-like appearance. As Thermoplastic, thermoplastics, nylons can be melt-processed into fibres, Thin film, films, and diverse shapes. The properties of nylons are often modified by blending with a variety of additives. Numerous types of nylon are available. One family, designated nylon-XY, is derived from diamines and dicarboxylic acids of carbon chain lengths X and Y, respectively. An important example is nylon-6,6 (). Another family, designated nylon-Z, is derived from amino acid, aminocarboxylic acids with carbon chain length Z. An example is nylon-[6]. Nylon polymers have extensive commercial applications, including uses in textiles and fibres (such as apparel, flooring and rubber reinforcement), molded components fo ...
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Cumene Hydroperoxide
Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol. 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 Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ... and propene. : Cumene hydroperoxide is a radical initiator for production of acrylates. Cumene hydroperoxide is involved as an organic peroxide in the production of propyl ...
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Hydroperoxide
Hydroperoxides or peroxols are Chemical compound, compounds of the form ROOH, where R stands for any group, typically Organic compound, organic, which contain the hydroperoxy functional group (). Hydroperoxide also refers to the hydroperoxide anion () and its Salt (chemistry), salts, and the neutral hydroperoxyl, hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When 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 saturated bond, saturated chemical bonds. Properties The bond length in peroxides is about 1.45 Ångström, Å, and the angles (R = Hydrogen, H, Carbon, C) are about 110° (water-like). Characteristically, the dihedral angles are about 120°. The bond is relatively weak, with a bond dissociation energy of , less than half the strength ...
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Autoxidation
Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the ' drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation. The common mechanism is a free radical chain reaction, where the addition of oxygen gives rise to hydroperoxides and their associated peroxy radicals (ROO•). Typically, an induction period is seen at the start where there is little activity; this is followed by a gradually accelerating take-up of oxygen, giving an autocatalytic reaction which can on ...
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Dibenzothiophene
Dibenzothiophene (DBT, diphenylene sulfide) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It has the chemical formula C12H8S. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its disubstituted derivative 4,6-dimethyldibenzothiophene are problematic impurities in petroleum. Synthesis and reactions Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride. Reduction with lithium Lithium (from , , ) is a chemical element; it has chemical symbol, symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard temperature and pressure, standard conditions, it is the least dense metal and the ... results in scission of one C-S bond. With butyllithium, this heterocycle undergoes stepwise lithiation at the 4-position. S-oxidation with peroxides gives the sulfoxide. ...
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Cyclohexyl
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon. Cyclohexyl () is the alkyl substituent of cyclohexane and is abbreviated Cy. Production Cyclohexane is one of components of naphtha, from which it can be extracted by advanced distillation methods. Distillation is usually combined with isomerization of methylcyclopentane, a similar component extracted from naphtha by similar methods. Together, these processes cover only a minority (15-20%) of the modern industrial demand, and are complemented by synthesis. Modern industrial synthesis On an industrial scale, cyclohexane is produced by hydrogenation of benzene in the presence of a Raney nickel catalyst. Producers of c ...
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Hydrodesulfurization
Hydrodesulfurization (HDS), also called hydrotreatment or hydrotreating, is a catalytic chemical process widely used to desulfurization, remove sulfur (S) from natural gas and from oil refinery, refined petroleum products, such as gasoline, gasoline or petrol, jet fuel, kerosene, diesel fuel, and fuel oils. The purpose of removing the sulfur, and creating products such as ultra-low-sulfur diesel, is to reduce the sulfur dioxide () emissions that result from using those fuels in automotive vehicles, aircraft, railroad locomotives, ships, gas or oil burning Fossil-fuel power station, power plants, residential and industrial furnaces, and other forms of fuel combustion. Another important reason for removing sulfur from the Petroleum naphtha, naphtha streams within a petroleum refinery is that sulfur, even in extremely low concentrations, catalyst poisoning, poisons the noble metal catalysts (platinum and rhenium) in the catalytic reforming units that are subsequently used to upgr ...
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