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Hexanedinitrile
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 prepa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexanedioyl Dichloride
Adipoyl chloride (or adipoyl dichloride) is the organic compound with the formula (CH2CH2C(O)Cl)2. It is a colorless liquid. It reacts with water to give adipic acid. It is prepared by treatment of adipic acid with thionyl chloride. Adipoyl chloride reacts with hexamethylenediamine to form nylon 6,6. See also * Adipamide Adipamide is the organic compound with the formula (CH2CH2C(O)NH2)2. It is a white solid. The dominant commercial interest in adipamides is related to their presence in nylons. Adipamide is formed by treating dimethyl adipate Dimethyl adipate ... * Adiponitrile References External links MSDS Safety data {{Navbox acyl chlorides Acyl chlorides Monomers ... [...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 me ..., with formula C3H6(CN)2. References External links WebBook page for glutaronitrile {{Organic-compound-stub Alkanedinitriles ... [...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 cyani ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Invista
Invista (stylized as INVISTA), headquartered in Wichita, Kansas, United States, is a fiber, resin and intermediates company. It has about 10,000 employees in over 20 countries worldwide. The predecessor DuPont Textiles and Interiors was formed from DuPont's textile fibers division in February 2003. The company was given the trademarked name INVISTA and was then sold to privately owned Koch Industries on April 30, 2004 for billion. Koch Industries combined the newly acquired organization with their KoSa subsidiary to complete the INVISTA company. Operations INVISTA's products include many brands. In 2008, Invista sued Rhodia, a chemical company, for theft and misappropriation of a chemical process technology used to produce nylon 6,6. In February 2009, INVISTA announced a refinancing and capitalization plan that had reduced its debt by $1.6 billion since the previous June. In the same year, Invista was the launch sponsor for WWDChina Week in Review, a weekly fashion publicati ... [...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(hexamethylenetriami ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons. Process Hydrogenation has three components, the unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same catalysts and conditions that are used for hydrogenation reactions can also lead to isomerization of the alkenes f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Monsanto Company
The Monsanto Company () was an American agrochemical and agricultural biotechnology corporation founded in 1901 and headquartered in Creve Coeur, Missouri. Monsanto's best known product is Roundup, a glyphosate-based herbicide, developed in the 1970s. Later the company became a major producer of genetically engineered crops. In 2018, the company ranked 199th on the Fortune 500 of the largest United States corporations by revenue. Monsanto was one of four groups to introduce genes into plants in 1983, and was among the first to conduct field trials of genetically modified crops in 1987. It was one of the top 10 US chemical companies until it divested most of its chemical businesses between 1997 and 2002, through a process of mergers and spin-offs that focused the company on biotechnology. Monsanto was one of the first companies to apply the biotechnology industry business model to agriculture, using techniques developed by biotech drug companies. In this business model, companie ... [...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 exi ... [...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 carb ...s). References Electrochemistry Industrial processes Organic chemistry Chemical synthesis Chemical processes Dimers_(chemistry) {{electrochem-stub ... [...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 catalyst Ni0-phosphine R3ref name="Huser" > or phosphite or phosphonite (OR)2Rref name="BASF" >). The mixture c ... [...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] |
