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Isobutene
Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Production Polymer and chemical grade isobutylene is typically obtained by dehydrating tertiary butyl alcohol (TBA) or catalysis, catalytic dehydrogenation of isobutane.. Gasoline additives methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE), respectively, are produced by reacting methanol or ethanol with isobutylene contained in butene streams from olefin steam crackers or refineries, or with isobutylene from dehydrated TBA. Isobutylene is not isolated from the olefin or refinery butene stream before the reaction, as separating the ethers from the remaining butenes is simpler. Isobutylene can also be produced in high purities by "back-cracking" MTBE or ETBE at high temperatures and then separating the isobutylene by distillation from m ...
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Diisobutene
Diisobutene (also known as Diisobutylene and Isooctene) refers to a pair of organic compounds with the overall formula C8H16. The isomers have the same carbon skeleton but differ in the location of the C=C bond. Both are colorless liquids with very similar physical properties. These compounds arise via the acid catalysis, acid catalyzed dimerization of isobutene, a reaction that proceeds via the carbocation . The process also leads to some triisobutenes and tetraisobutenes. Applications Hydrogenation is performed at a significant scale to give isooctane, which is an important fuel additive. Diisobutene is used as precursors to isononylol and octylphenols by hydroformylation/hydrogenation and phenol alkylation, respectively. Both are precursors to plasticizers. The isononylol (3,5,5-trimethyl-hexan-1-ol) is a precursor to 3,5,5-trimethylhexyl acetate, a commercial fragrance. Diisobutenes were once of interest as components for automotive fuels. See also * 1-Octene - the corres ...
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Butylated Hydroxytoluene
Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids (e.g. fuels, oils) and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. Natural occurrence Phytoplankton, including the green algae '' Botryococcus braunii'', as well as three different cyanobacteria ('' Cylindrospermopsis raciborskii'', '' Microcystis aeruginosa'' and '' Oscillatoria'' sp.) are capable of producing BHT as a natural product. The fruit lychee also produces BHT in its pericarp. Several fungi (for example '' As ...
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Isooctane
2,2,4-Trimethylpentane, also known as isooctane or iso-octane, is an organic compound with the formula (CH3)3CCH2CH(CH3)2. It is one of several isomers of octane (C8H18). This particular isomer is the standard 100 point on the octane rating scale (the zero point is ''n''-heptane). It is an important component of gasoline, frequently used in relatively large proportions (around 10%) to increase the knock resistance of fuel. Strictly speaking, if the standard meaning of ‘iso’ is followed, the name ''isooctane'' should be reserved for the isomer 2-methylheptane. However, 2,2,4-trimethylpentane is by far the most important isomer of octane and historically it has been assigned this name. Production Isooctane is produced on a massive scale in the petroleum industry by alkylation of isobutene with isobutane. This process is conducted in alkylation units in the presence of acid catalysts. : It can also be produced from isobutylene by dimerization using an Amberlyst cata ...
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Ethenolysis
In organic chemistry, ethenolysis is a chemical process in which internal olefins are degraded using ethylene () as the reagent. The reaction is an example of olefin metathesis, cross metathesis. The utility of the reaction is driven by the low cost of ethylene as a reagent and its selectivity. It produces compounds with terminal alkene functional groups (α-olefins), which are more amenable to other reactions such as polymerization and hydroformylation. The general reaction equation is: :\ce + \longrightarrow \ce + \ce Ethenolysis is a form of methylenation, i.e., the installation of Methylene group, methylene () groups. Applications Terminal alkenes Using ethenolysis, higher molecular weight internal alkenes can be converted to more valuable terminal alkenes. The Shell higher olefin process (SHOP process) uses ethenolysis on an industrial scale. SHOP α-olefin mixtures are first separated by distillation. Higher molecular weight fractions are Isomerization, isomerized ...
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Ethyl Tert-butyl Ether
Ethyl ''tertiary''-butyl ether (ETBE), also known as ethyl ''tert''-butyl ether, is commonly used as an oxygenate gasoline additive in the production of gasoline from crude oil. ETBE offers equal or greater air quality benefits than ethanol, while being technically and logistically less challenging. Unlike ethanol, ETBE does not induce evaporation of gasoline, which is one of the causes of smog, and does not absorb moisture from the atmosphere. Production Ethyl tert-butyl ether is manufactured industrially by the acidic etherification of isobutylene with ethanol at a temperature of 30–110 °C and a pressure of 0,8–1,3 MPa. The reaction is carried out with an acidic ion-exchange resin as a catalyst. Suitable reactors are fixed-bed reactors such as tube bundle or circulation reactors in which the reflux can be cooled optionally. Ethanol, produced by fermentation and distillation, is more expensive than methanol, which is derived from natural gas. There ...
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Butene
Butene, also known as butylene, is an alkene with the formula . The word ''butene'' may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation. Butene can be used as the monomer for polybutene, but this polymer is more expensive than alternatives with shorter carbon chains such as polypropylene. Polybutene is therefore used in more specialized applications. Butenes are more commonly used to make copolymer (mixed with another monomer such as ethylene). Butenes are major constituents of raffinates, the C4 fractions in oil processing. The raffinates containing butadiene are considered carcinogenic and mutagenic. They can be used as feedstocks ...
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Butyl Rubber
Butyl rubber, sometimes just called butyl, is a synthetic rubber, a copolymer of isobutylene with isoprene. The abbreviation IIR stands for isobutylene isoprene rubber. Polyisobutylene, also known as "PIB" or polyisobutene, (C4H8)n, is the homopolymer of isobutylene, or 2-methyl-1-propene, on which butyl rubber is based. Butyl rubber is produced by polymerization of about 98% of isobutylene with about 2% of isoprene. Structurally, polyisobutylene resembles polypropylene, but has two methyl groups substituted on every other carbon atom, rather than one. Polyisobutylene is a colorless to light yellow viscoelastic material. It is generally odorless and tasteless, though it may exhibit a slight characteristic odor. Properties Butyl rubber has excellent impermeability to gas diffusion, and the long polyisobutylene segments of its polymer chains give it good flex properties. The formula for PIB is: –(–CH2–C(CH3)2–)n– The formula for IIR is: It can be made from the monomer ...
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Isomers Of Butylene
Butene, also known as butylene, is an alkene with the formula . The word ''butene'' may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation. Butene can be used as the monomer for polybutene, but this polymer is more expensive than alternatives with shorter carbon chains such as polypropylene. Polybutene is therefore used in more specialized applications. Butenes are more commonly used to make copolymer (mixed with another monomer such as ethylene). Butenes are major constituents of raffinates, the C4 fractions in oil processing. The raffinates containing butadiene are considered carcinogenic and mutagenic. They can be used as feedstocks ...
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Tert-Butylamine
''tert''-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. ''tert''-Butylamine is one of the four isomeric amines of butane, the others being ''n''-butylamine, ''sec''-butylamine and isobutylamine. Preparation ''tert''-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts: :NH3 + CH2=C(CH3)2 → H2NC(CH3)3 The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste. :(CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO :(CH3)3CNHCHO + H2O → (CH3)3CNH2 + HCO2H In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via ''tert''-butylphthalimide. Uses ''tert''-Butylamine is used as an intermediate in the preparation of the sulfenamides such as ''N''-''tert''-butyl-2-benzothiazylsulfenamide and ''N''-''tert''-butyl-2-benzothiazylsulfeni ...
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Neohexene
Neohexene is the hydrocarbon compound with the chemical formula . It is a colorless liquid, with properties similar to other hexenes. It is a precursor to commercial synthetic musk perfumes. Preparation and reactions Neohexene is prepared by ethenolysis of diisobutene, an example of a metathesis reaction: :(CH3)3C-CH=C(CH3)2 + → (CH3)3C-CH= + (CH3)2C= It is a building block to synthetic musks by its reaction with ''p''-cymene. It is also used in the industrial preparation of terbinafine Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat pityriasis versicolor, onychomycosis, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either oral adminis .... In the study of C-H activation, neohexene is often used as a hydrogen acceptor.{{cite journal, last1 = Liu, first1 = Fuchen, last2 = Pak, first2 = Esther B., last3 = Singh, first3 = Bharat, last4 = Jensen, first4 = Craig M., last5 = Go ...
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Methyl Tert-butyl Ether
Methyl ''tert''-butyl ether (MTBE), also known as ''tert''-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions. Production and properties MTBE is manufactured via the chemical reaction of methanol and isobutylene. Methanol is primarily derived from natural gas, where steam reforming converts the various light hydrocarbons in natural gas (primarily methane) into carbon monoxide and hydrogen. The resulting gases then further react in the presence of a catalyst to form methanol. Isobutylene can be produced through a variety of methods. ''n''-butane can be isomerized into isobutane which can be dehydrogenated to isobutylene. In the Halcon process, ''t''-Butyl hydroperoxide derived from isobutane oxygenation is tr ...
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Liquefied Petroleum Gas
Liquefied petroleum gas, also referred to as liquid petroleum gas (LPG or LP gas), is a fuel gas which contains a flammable mixture of hydrocarbon gases, specifically propane, Butane, ''n''-butane and isobutane. It can also contain some propylene, butylene, and isobutylene/Isobutylene, isobutene. LPG is used as a fuel gas in HVAC, heating appliances, cooking equipment, and vehicles, and is used as an aerosol propellant and a refrigerant, replacing chlorofluorocarbons in an effort to reduce the damage it causes to the ozone layer. When specifically used as a vehicle fuel, it is often referred to as autogas or just as Autogas#Terminology variations and confusion, gas. Varieties of LPG that are bought and sold include mixes that are mostly propane (), mostly butane (), and, most commonly, mixes including both propane and butane. In the northern hemisphere winter, the mixes contain more propane, while in summer, they contain more butane. In the United States, mainly two grad ...
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