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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 prepa ... [...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 1,4 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 c ...s). References Electrochemistry Industrial processes Organic chemistry Chemical synthesis Chemical processes Dimers (chemistry) {{chem-process-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,6-diaminohexane
Hexamethylenediamine or hexane-1,6-diamine, 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. 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(hexamethylenetriamine). An alternative process uses Raney nickel as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent ... [...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 name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ..., 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 if the substrate alkene is unactivated. This conversion is conducted on an industrial scale for the production of precursors to nylon. Direct hydrocyanation is rare in the laboratory because hydrogen cyanide is extremely toxic, but transfer variants can allow other nitrilic compounds to serve as hydrogen cyanide synthons. 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. : Mechanism The reaction proceeds via oxidative addition of HCN to a low-valent metal complex to give a hydrido cyanide complex. Subsequently the alkene binds to the complex. The intermediate then undergoes m ... [...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 clear brown 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 * 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, "Adipi ... References External links MSDS Safety data {{Navbox acyl chlorides Acyl chlorides Monomers ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Metric Ton
The tonne ( or ; symbol: t) is a unit of mass equal to 1,000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton in the United States to distinguish it from the non-metric units of the short ton (United States customary units) and the long ton ( British imperial units). It is equivalent to approximately 2,204.6 pounds, 1.102 short tons, and 0.984 long tons. The official SI unit is the megagram (Mg), a less common way to express the same amount. Symbol and abbreviations The BIPM symbol for the tonne is t, adopted at the same time as the unit in 1879.Table 6 . BIPM. Retrieved on 2011-07-10. Its use is also official for the metric ton in the United States, having been adopted by the United States |
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 redox, reduce or Saturated and unsaturated compounds, 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 bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, 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 cataly ... [...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-ten U.S. 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 mode ... [...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. It has a pungent odor of garlic or onions. Its molecular structure 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 is one of the components of ABS plastic (acrylonitrile butadiene styrene). Structure and basic properties 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. Its molecular structure 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. Production Acrylonitrile was first synthesized by the French chemist Charle ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkene Metathesis
In organic chemistry, Olefin Metathesis or Alkene 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 halide (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 r ... [...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. It is also used to make 2-Methylpentamethylenediamine, Dytek A. 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 phosphi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
