Ethylbenzene
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Ethylbenzene
Ethylbenzene is an organic compound with the formula . It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene. Occurrence and applications Ethylbenzene occurs naturally in coal tar and petroleum. The dominant application of ethylbenzene is its role as an intermediate in the production of polystyrene. Catalytic dehydrogenation of ethylbenzene gives hydrogen and styrene: : → C6H5CH=CH2 + As of May 2012, more than 99% of all the ethylbenzene produced is used for this purpose. Ethylbenzene hydroperoxide, a reagent and radical initiator, is produced by autoxidation of ethylbenzene: :C6H5CH2CH3 + O2 → C6H5CH(O2H)CH3 Niche uses Ethylbenzene is added to gasoline as ...
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Styrene
Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers. Approximately 25 million tonnes of styrene were produced in 2010, increasing to around 35 million tonnes by 2018. Natural occurrence Styrene is named after storax balsam (often commercially sold as ''styrax''), the resin of Liquidambar trees of the Altingiaceae plant family. Styrene occurs naturally in small quantities in some plants and foods (cinnamon, coffee beans, balsam tree (other), balsam trees and peanuts) and is also found in coal tar. History In 1839, the German apothecary Eduard Simon isolated a volatile liquid from the resin (called ''storax'' or ''styrax'' (Latin)) of the Liquidambar styraciflua, American sweetgu ...
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Xylenes
In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value. The mixture is referred to as both xylene and, more precisely, xylenes. Mixed xylenes refers to a mixture of the xylenes plus ethylbenzene. The four compounds have identical empirical formulas . Typically the four compounds are produced together by various catalytic reforming and pyrolysis methods. Occurrence and production Xylenes are an important petrochemical produced by catalytic reforming and also by coal carbonisation in the manufacture of coke fuel. They also occur in crude oil in concentrations of about 0.5–1%, depending on the source. Small quantities occur in gasoline and aircraft f ...
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Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. History Discovery The word "''benzene''" derives from "''gum benzoin''" (benzoin res ...
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Ethylbenzene Hydroperoxide
Ethylbenzene hydroperoxide is the organic compound with the formula C6H5CH(O2H)CH3. A colorless liquid, EBHP is a common hydroperoxide. It has been used as an O-atom donor in organic synthesis. It is chiral. Together with tert-butyl hydroperoxide and cumene hydroperoxide, ethylbenzene hydroperoxide is important commercially. The compound is produced by direct reaction of ethylbenzene with oxygen, an autoxidation.{{cite journal , doi=10.1021/jo070040m, title=Autoxidation of Ethylbenzene: The Mechanism Elucidated, year=2007, last1=Hermans, first1=Ive, last2=Peeters, first2=Jozef, last3=Jacobs, first3=Pierre A., journal=The Journal of Organic Chemistry, volume=72, issue=8, pages=3057–3064, pmid=17362045 References Hydroperoxides Oxidizing agents Benzene derivatives ...
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Gasoline
Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. On average, U.S. refineries produce, from a barrel of crude oil, about 19 to 20 gallons of gasoline; 11 to 13 gallons of distillate fuel (most of which is sold as diesel fuel); and 3 to 4 gallons of jet fuel. The product ratio depends on the processing in an oil refinery and the crude oil assay. A barrel of oil is defined as holding 42 US gallons, which is about 159 liters or 35 imperial gallons. The characteristic of a particular gasoline blend to resist igniting too early (which causes knocking and reduces efficiency in reciprocating engines) is measured by its octane rating, which is produced in several grades. Tetraethyl lead and o ...
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Ethene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths. Ethylene is also an important natural plant hormone and is used in agriculture to force the ripening of fruits. The hydrate of ethylene is ethanol. Structure and properties This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are connected by a double bond. All six atoms that comprise ethylene are coplanar. The H-C-H angle is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively weak: rotati ...
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Toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent. As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causing severe neurological harm. History The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it ''rétinnaphte''. In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree ''Myroxylon balsamum''), which Deville recognized as similar to Wa ...
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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 only be ...
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Dehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At its simplest, it is useful way of converting alkanes, which are relatively inert and thus low-valued, to olefins, which are reactive and thus more valuable. Alkenes are precursors to aldehydes (), alcohols (), polymers, and aromatics. As a problematic reaction, the fouling and inactivation of many catalysts arises via coking, which is the dehydrogenative polymerization of organic substrates. Enzymes that catalyze dehydrogenation are called dehydrogenases. Heterogeneous catalytic routes Styrene Dehydrogenation processes are used extensively to produce aromatics in the petrochemical industry. Such processes are highly endothermic and require temperatures of 500 °C and above. Dehydrogenation also converts saturated fats to unsatura ...
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Aromatic Hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties are understood. The current definition of aromatic compounds does not have any relation with their smell. Heteroarenes are closely related, since at least one carbon atom of CH group is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Benzene ring model Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one named as such ...
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Polystyrene
Polystyrene (PS) is a synthetic polymer made from monomers of the aromatic hydrocarbon styrene. Polystyrene can be solid or foamed. General-purpose polystyrene is clear, hard, and brittle. It is an inexpensive resin per unit weight. It is a poor barrier to oxygen and water vapour and has a relatively low melting point. Polystyrene is one of the most widely used plastics, the scale of its production being several million tonnes per year. Polystyrene can be naturally transparent, but can be colored with colorants. Uses include protective packaging (such as packing peanuts and in the jewel cases used for storage of optical discs such as CDs and occasionally DVDs), containers, lids, bottles, trays, tumblers, disposable cutlery, in the making of models, and as an alternative material for phonograph records. As a thermoplastic polymer, polystyrene is in a solid (glassy) state at room temperature but flows if heated above about 100 °C, its glass transition temperature. I ...
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Anti-knock Agent
An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuel's octane rating by raising the temperature and pressure at which auto-ignition occurs. The mixture known as gasoline or petrol, when used in high compression internal combustion engines, has a tendency to knock (also called "pinging" or "pinking") and/or to ignite early before the correctly timed spark occurs (''pre-ignition'', refer to engine knocking). Notable early antiknock agents, especially Tetraethyllead, added to gasoline included large amounts of toxic lead. The chemical was responsible for global negative impacts on health, and the phase out of leaded gasoline from the 1970s onward was reported by the UN to be responsible for $2.4 trillion in annual benefits, 1.2 million fewer premature deaths, higher overall intelligence and 58 million fewer crimes," the United Nations Environmental Programme said. Some other chemicals used as gasoline additives are thought to be less toxic. ...
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