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Dimethyl Adipate
Dimethyl adipate is the organic compound with the formula (CH2CH2CO2CH3)2. It is a colorless oily liquid. Although the main commercial interest in adipates is related to the production of nylons, this diester is used as a plasticizer, a solvent for paint stripping and resins, and a pigment dispersant. Preparation Dimethyl adipate is prepared by esterification of adipic acid with methanol. Less conventional routes include the hydroesterification of butadiene and the carbonylation of 1,4-dimethoxy-2-butene. It reacts with concentrated ammonia to give the diamide (CH2CH2C(O)NH2)2. Toxicity Esters of adipic acid exhibit low acute toxicities in animal models. The LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ... of this dimethyl ester is estimated at 1800 mg/kg (rat, i.p.). R ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Nylon
Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic. Nylon is a silk-like thermoplastic, generally made from petroleum, that can be melt-processed into fibers, films, or shapes. Nylon polymers can be mixed with a wide variety of additives to achieve many property variations. Nylon polymers have found significant commercial applications in fabric and fibers (apparel, flooring and rubber reinforcement), in shapes (molded parts for cars, electrical equipment, etc.), and in films (mostly for food packaging). History DuPont and the invention of nylon Researchers at DuPont began developing cellulose based fibers, culminating in the synthetic fiber rayon. DuPont's experience with rayon was an important precursor to its development and marketing of nylon. DuPont's invention of nylon spanned an eleven-year period, ranging from the initial research pr ...
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Plasticizer
A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizers are commonly added to polymers such as plastics and rubber, either to facilitate the handling of the raw material during fabrication, or to meet the demands of the end product's application. For example, plasticizers are commonly added to polyvinyl chloride (PVC), which otherwise is hard and brittle, to make it soft and pliable; which makes it suitable for products such as shower curtains, vinyl flooring, clothing, bags, flexible plastic tubing, and electric wire insulation/coating. Plasticizers are also often added to concrete formulations to make them more workable and fluid for pouring, thus allowing the water contents to be reduced. Similarly, they are often added to clays, stucco, solid rocket fuel, and other pastes prior t ...
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Adipic Acid
Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon. Adipic acid otherwise rarely occurs in nature, but it is known as manufactured E number food additive E355. Preparation and reactivity Adipic acid is produced from a mixture of cyclohexanone and cyclohexanol called KA oil, the abbreviation of ketone-alcohol oil. The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction, the cyclohexanol is converted to the ketone, releasing nitrous acid: :HOC6H11 + HNO3 → OC(CH2)5 + HNO2 + H2O Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C-C bond: :HNO2 + HNO3 → NO+NO3− + H2O :OC6H10 + NO+ → OC6H9-2-NO + H+ Side products of ...
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Hydroesterification
In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols A commercial application is the carbomethoxylation of ethylene to give methyl propionate: :C2H4 + CO + MeOH → MeO2CC2H5 The process is catalyzed by Pd 6H4(CH2PBu-t)2sub>2. Under similar conditions, other Pd-diphosphines catalyze formation of polyethyleneketone. Methyl propionate ester is a precursor to methyl methacrylate, which is used in plastics and adhesives. Carboalkoxylation has been incorporated into various telomerization Telomerization is a reaction that produces a particular kind of oligomer with two distinct end groups. The oligomer is called a telomer. Some telomerizations proceed by radical pathways, many do not. A generic equation is: : A-B + n M -> A-M_ ... schemes. For example carboalkoxylation has been coupled with the dim ...
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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 ...
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Carbonylation
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains. Organic chemistry Several industrially useful organic chemicals are prepared by carbonylations, which can be highly selective reactions. Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids and esters. Carbonylations are the basis of many types of reactions, including hydroformylation and Reppe reactions. These reactions require metal catalysts, which bind and activate the CO. These processes involve transition metal acyl complexes as intermediates. Much of this theme was developed by Walter Reppe. Hydroformylation Hydroformylation entails the addition of both carbon monoxide and hydrogen to unsaturated ...
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LD50
In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the dose required to kill half the members of a tested population after a specified test duration. LD50 figures are frequently used as a general indicator of a substance's acute toxicity. A lower LD50 is indicative of increased toxicity. The test was created by J.W. Trevan in 1927. The term semilethal dose is occasionally used in the same sense, in particular with translations of foreign language text, but can also refer to a sublethal dose. LD50 is usually determined by tests on animals such as laboratory mice. In 2011, the U.S. Food and Drug Administration approved alternative methods to LD50 for testing the cosmetic drug Botox without animal tests. Conventions The LD50 is usually expressed as the mass of substance administered per unit ...
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Adipate Esters
Adipates are the salts and esters of adipic acid. The anionic (HO2C(CH2)4CO2−) and dianionic (−O2C(CH2)4CO2−) forms of adipic acid are also referred to as adipate. Some adipate salts are used as acidity regulators, including: * Sodium adipate (E number E356) * Potassium adipate (E357) Some adipate esters are used as plasticizers, including: * Bis(2-ethylhexyl) adipate * Dioctyl adipate * Dimethyl adipate Dimethyl adipate is the organic compound with the formula (CH2CH2CO2CH3)2. It is a colorless oily liquid. Although the main commercial interest in adipates is related to the production of nylons, this diester is used as a plasticizer, a solvent ... {{HealthIssuesOfPlastics ...
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Methyl Esters
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many organic compounds. It is a very stable group in most molecules. While the methyl group is usually part of a larger molecule, bounded to the rest of the molecule by a single covalent bond (), it can be found on its own in any of three forms: methanide anion (), methylium cation () or methyl radical (). The anion has eight valence electrons, the radical seven and the cation six. All three forms are highly reactive and rarely observed. Methyl cation, anion, and radical Methyl cation The methylium cation () exists in the gas phase, but is otherwise not encountered. Some compounds are considered to be sources of the cation, and this simplification is used pervasively in organic chemistry. For example, protonation of methanol gives an electr ...
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Plasticizers
A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizers are commonly added to polymers such as plastics and rubber, either to facilitate the handling of the raw material during fabrication, or to meet the demands of the end product's application. For example, plasticizers are commonly added to polyvinyl chloride (PVC), which otherwise is hard and brittle, to make it soft and pliable; which makes it suitable for products such as shower curtains, vinyl flooring, clothing, bags, flexible plastic tubing, and electric wire insulation/coating. Plasticizers are also often added to concrete formulations to make them more workable and fluid for pouring, thus allowing the water contents to be reduced. Similarly, they are often added to clays, stucco, solid rocket fuel, and other pastes prior to ...
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