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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: : The process is catalyzed by . 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 schemes. For example carboalkoxylation has been coupled with the dimerization of 1,3-butadiene. This step produces a doubly unsaturated C9-ester: : Hydroesterification Related to carboalkoxylation is hydroesterification, the insertion of alkenes and alkynes into the H-O bond of carboxylic acids. Vinyl acetate is produced industrially by the addition of acetic acid to acetylen ...
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Carbonylation
In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) 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 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 ...
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Ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid ...
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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: : where M is the monomer, and A and B are the end groups, and n is the degree of polymerization. One example is the coupled dimerization and hydroesterification of buta-1,3-diene. This step produces a doubly unsaturated C9-ester: :2CH2=CH-CH=CH2 + CO + CH3OH → CH2=CH(CH2)3CH=CHCH2CO2CH3 The monomer in this reaction is butadiene, the degree of polymerization is 2, and the end groups are vinyl and the carboxy methyl (CO2CH3). This and several related reactions proceed with palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ... catalysts. Many telomeriz ...
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Vinyl Acetate
Vinyl acetate is an organic compound with the Chemical formula, formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers. Production The worldwide production capacity of vinyl acetate was estimated at 6,969,000 tonnes/year in 2007, with most capacity concentrated in the United States (1,585,000 all in Texas), China (1,261,000), Japan (725,000) and Taiwan (650,000). The average list price for 2008 was US$1600/tonne. Celanese is the largest producer (ca 25% of the worldwide capacity), while other significant producers include China Petrochemical Corporation (7%), Chang Chun Group (6%), and LyondellBasell (5%). Vinyl acetate is mainly (80%) polymerized, and the resulting polymer is hydrolyzed to give polyvinvyl alcohol. Preparation Vinyl acetate is the acetate ester of vinyl alcohol. Since vinyl alcohol is highly unstable (with respect to acetaldehyde), the prepara ...
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Industrial Chemistry
The chemical industry comprises the company, companies and other organizations that develop and produce industrial, specialty and other chemicals. Central to the modern world economy, the chemical industry converts raw materials (Petroleum, oil, natural gas, air, water, metals, and minerals) into commodity chemicals for industrial and consumer Product (business), products. It includes industries for petrochemical industry, petrochemicals such as polymers for Plastics industry, plastics and synthetic fibers; Inorganic compound, inorganic chemicals such as acids and alkalis; Agrochemical, agricultural chemicals such as fertilizers, pesticides and herbicides; and other categories such as industrial gases, speciality chemicals and Pharmaceutical industry, pharmaceuticals. Various professionals are involved in the chemical industry including chemical engineers, chemists and lab technicians. History Although chemicals were made and used throughout history, the birth of the heavy chemic ...
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Alkene
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) Preferred IUPAC name, recommends using the name "alkene" only for Open-chain compound, acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for Cyclic compound, cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with ''n'' being a >1 natural number (which is two hydrogens less than the corresponding alkane). When ''n'' is four or more, isomers are possible, ...
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Alcohol (chemistry)
In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of Hydrocarbon, hydrocarbons, conferring Hydrophile, hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur. History The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus (–287 BCE), and Pliny the Elder (23/24–79 CE). However, this did not immediately lead to the isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt. An important recognition, first found in one of the writings attributed to Jabir ibn Hayyan, J� ...
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Ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward creating polyethylene, which is a widely used plastic containing polymer chains of ethylene units in various chain lengths. Production greenhouse gas emissions, emits greenhouse gases, including methane from feedstock production and carbon dioxide from any non-sustainable energy used. Ethylene is also an important natural plant hormone and is used in agriculture to induce ripening of fruits. The hydrate of ethylene is ethanol. Structure and properties This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are con ...
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Methyl Propionate
Methyl propionate, also known as methyl propanoate, is an organic compound with the molecular formula . It is a colorless liquid with a fruity, rum-like odor. Preparation Methyl propionate can be prepared by esterification of propionic acid with methanol. Industrially, it is prepared by carboalkoxylation, i.e., the reaction of ethylene with carbon monoxide and methanol in the presence of a catalyst: : The reaction is catalyzed by nickel carbonyl and palladium(0) complexes.(mayth and yafs)Scott D. Barnicki "Synthetic Organic Chemicals" in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed. . Uses Condensation of Methyl propionate with formaldehyde followed by dehydration yields methyl methacrylate: : : Methyl propionate is used as a solvent for cellulose nitrate and lacquers, and as a raw material for the production of paints, varnishes and other chemicals such as methyl methacrylate Methyl methacrylate (MMA) is an ...
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Polyketone
Polyketones are a family of high-performance thermoplastic polymers. The polar ketone groups in the polymer backbone of these materials gives rise to a strong attraction between polymer chains, which increases the material's melting point (255 °C for copolymer (carbon monoxide ethylene), 220 °C for terpolymer (carbon monoxide, ethylene, propylene). Trade names include Poketone, Carilon, Karilon, Akrotek, and Schulaketon. Such materials also tend to resist solvents and have good mechanical properties. Unlike many other engineering plastics, aliphatic polyketones such as Shell Chemicals' Carilon are relatively easy to synthesize and can be derived from inexpensive monomers. Carilon is made with a palladium(II) catalyst from ethylene and carbon monoxide. A small fraction of the ethylene is generally replaced with propylene to reduce the melting point somewhat. Shell Chemical commercially launched Carilon thermoplastic polymer in the U.S. in 1996, but discontinued it in 200 ...
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Methyl Methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula . This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA). History MMA was discovered by Bernhard Tollens and his student W. A. Caspary in 1873, who noticed and described its tendency to change into a clear, hard, transparent substance especially in sunlight. Studies on acrylic esters slowly developed until the Staudinger's theory of macromolecules and his research into the nature of polyacrylates allowed control over polymerization. Company Rohm and Haas founded by German chemist Otto Röhm, who investigated the topic for three decades, was finally able to start its industrial production in 1931. Production and properties Given the scale of production, many methods have been developed starting from diverse two- to four-carbon precursors. Two principal routes appear to be commonly practiced. Cyanohydrin ...
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