|
Adiponitrile
Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adipic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Production Early methods Because of the industrial value of adiponitrile, many methods have been developed for its synthesis. Early industrial methods started from furfural and later by the chlorination of butadiene to give 1,4-dichloro-2-butene, which with sodium cyanide, converts to 3-hexenedinitrile, which in turn can be hydrogenated to adiponitrile: :ClCH2CH=CHCH2Cl + 2 NaCN → NCCH2CH=CHCH2CN + 2 NaCl :NCCH2CH=CHCH2CN + H2 → NC(CH2)4CN Adiponitrile has also been produced from adipic acid, by dehydration of the diamide, but this is rarely employed. Modern methods After patent application in 2004, the majority of adiponitrile is prepar ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
2-Methylglutaronitrile
2-Methylglutaronitrile is the organic compound with the formula NCCH2CH2CH(CH3)CN. This dinitrile is obtained in the large-scale synthesis of adiponitrile. It is a colorless liquid with an unpleasant odor. It is the starting compound for the vitamin nicotinamide and for the diester dimethyl-2-methylglutarate and the ester amide methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, which are promoted as green solvents. 2-Methylglutaronitrile is chiral but is mainly encountered as the racemate. Occurrence and production 2-Methylglutaronitrile is a by-product of the production of adiponitrile, the precursor of hexamethylenediamine and adipic acid as building blocks for nylon 66. Starting from 1,3-butadiene or a butadiene-rich C4-section (> 40% by volume) from a naphtha steamcracker in the first stage a mixture of pentenenitriles is obtained through hydrocyanation (using as Catalysis, catalyst Ni0-phosphine [PR3] or phosphite or phosphonite [P(OR)2R]). The mixture contains mainly trans- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrocyanation
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of precursors to nylon. Hydrocyanation of unactivated alkenes Industrially, hydrocyanation is commonly performed on alkenes catalyzed by nickel complexes of phosphite () ligands. A general reaction is shown:Piet W.N.M. van Leeuwen "Homogeneous Catalysis: Understanding the Art", 2004, Wiley-VCH, Weinheim. :RCH=CH2 + HCN -> RCH2-CH2-CN Stoichiometry and mechanism The reaction involves the addition of and cyanide () to the substrate. Usually the substrate is an alkene and the product is a nitrile. The reaction proceeds via the oxidative addition of HCN to a low-valent metal complex to give a hydrido cyanide complex. Subsequent binding of the alkene gives the intermediate , which then undergoes migratory insertion to give an alkylmetal cya ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,6-diaminohexane
Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Synthesis Hexamethylenediamine was first reported by Theodor Curtius. It is produced by the hydrogenation of adiponitrile: :NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2 The hydrogenation is conducted on molten adiponitrile diluted with ammonia, typical catalysts being based on cobalt and iron. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriam ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Butadiene
1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene. Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance. History In 1863, the French chemist E. Caventou isolated butadiene from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene and obtained a material wit ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrodimerization
Hydrodimerization is an organic reaction that couples two alkenes to give a symmetrical hydrocarbon. The reaction is often implemented electrochemically; in that case the reaction is called electrodimerization. The reaction can also be induced with samarium diiodide, a one-electron reductant. Hydrodimerization is the basis of the Monsanto adiponitrile synthesis: :2CH2=CHCN + 2e− + 2H+ → NCCH2CH2CH2CH2CN : The reaction applies to a number electrophilic alkenes (Michael acceptor In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon ...s). References Electrochemistry Industrial processes Organic chemistry Chemical synthesis Chemical processes Dimers_(chemistry) {{electrochem-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acrylonitrile
Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular structure, it consists of a vinyl group () linked to a nitrile (). It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses. Acrylonitrile was first synthesized by the French chemist Charles Moureu (1863–1929) in 1893. Occurrence Acrylonitrile is not naturally formed on Earth. It has been detected at the sub-ppm level at industrial sites. It persists in the air for up to a week. It decomposes by reacting with oxygen and hydroxyl radical to form formyl cyanide and formaldehyde. Acrylonitrile is harmful to aquatic life. Acrylonitrile has been detected in the atmosphere of Titan, a moon of Saturn. Computer simulations suggest that on Titan conditions exist ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nitrile
In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons. Inorganic compounds containing the group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic. Structure and basic properties The N−C−C geometry is linear in nitriles, reflecting the sp hybridization of the triply bonded carbon. The C−N distance is short at 1.16 Å, consistent with a triple bond. Nitriles a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
William C
William is a male given name of Germanic origin.Hanks, Hardcastle and Hodges, ''Oxford Dictionary of First Names'', Oxford University Press, 2nd edition, , p. 276. It became very popular in the English language after the Norman conquest of England in 1066,All Things William"Meaning & Origin of the Name"/ref> and remained so throughout the Middle Ages and into the modern era. It is sometimes abbreviated "Wm." Shortened familiar versions in English include Will, Wills, Willy, Willie, Bill, and Billy. A common Irish form is Liam. Scottish diminutives include Wull, Willie or Wullie (as in Oor Wullie or the play ''Douglas''). Female forms are Willa, Willemina, Wilma and Wilhelmina. Etymology William is related to the given name ''Wilhelm'' (cf. Proto-Germanic ᚹᛁᛚᛃᚨᚺᛖᛚᛗᚨᛉ, ''*Wiljahelmaz'' > German ''Wilhelm'' and Old Norse ᚢᛁᛚᛋᛅᚼᛅᛚᛘᛅᛋ, ''Vilhjálmr''). By regular sound changes, the native, inherited English form of th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pentanenitrile
Pentanenitrile, valeronitrile or butyl cyanide is a nitrile with the formula C4H9CN. This can be written BuCN, with Bu representing an ''n''-butyl (linear butyl group). Production Pentanenitrile can be produced by heating 1-chlorobutane with sodium cyanide in dimethyl sulfoxide. This reaction takes about 20 minutes, keeping the temperature below 160 °C. The yield is about 93%. Another way to get the substance is by heating valeraldehyde with hydroxylamine. Pentanenitrile is contained in bone oil. Properties The pentanenitrile molecule is flexible and can adopt a number of different conformers, so that it will naturally be a mixture. These conformers are called anti-anti (30%), anti-gauche (46%), gauche-anti, gauche-gauche-cis, and gauche-gauche-trans. Biology Pentanenitrile is toxic to animals, and produces its action by the liberation of cyanide by cytochrome P450. The cyanide is detoxified and excreted in urine as thiocyanate. Pentanenitrile is found in ''Brassica'' sp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glutaronitrile
Glutaronitrile, also pentanedinitrile, is a nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix ''cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including met ..., with formula C3H6(CN)2. References External links WebBook page for glutaronitrile {{Organic-compound-stub Alkanedinitriles ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkene Metathesis
Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry. Catalysts The reaction requires metal catalysts. Most commercially important processes employ heterogeneous catalysts. The heterogeneous catalysts are often prepared by in-situ activation of a metal halides (MClx) using organoaluminium or organotin compounds, e.g. combining MClx–EtAlCl2. A typical catalyst support is alumina. Commercial catalysts are often based on molybdenum and ruthenium. Well-defined organometallic compo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
