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Dicyclopentadiene Formation
Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12. At room temperature, it is a white brittle wax, although lower purity samples can be straw coloured liquids. The pure material smells somewhat of soy wax or camphor, with less pure samples possessing a stronger acrid odor. Its energy density is 10,975 Watt-hour, Wh/l. Dicyclopentadiene is a co-produced in large quantities in the steam cracking of naphtha and gas oils to ethylene. The major use is in resins, particularly, unsaturated polyester resins. It is also used in inks, adhesives, and paints. The top seven suppliers worldwide together had an annual capacity in 2001 of 179 kilotonnes (395 million pounds). Synthesis and structure The spontaneous dimerization of cyclopentadiene at room temperature to form dicyclopentadiene proceeds to around 50% conversion over 24 hours and yields the ''endo'' isomer in better than 99:1 ratio as the kinetically favored product (about 150:1 ''endo'':''exo'' at 80 ...
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Camphor
Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel ('' Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapur tree ( ''Dryobalanops'' sp.), a tall timber tree from South East Asia. It also occurs in some other related trees in the laurel family, notably '' Ocotea usambarensis''. Rosemary leaves (''Rosmarinus officinalis'') contain 0.05 to 0.5% camphor, while camphorweed (''Heterotheca'') contains some 5%. A major source of camphor in Asia is camphor basil (the parent of African blue basil). Camphor can also be synthetically produced from oil of turpentine. The compound is chiral, existing in two possible enantiomers as shown in the structural diagrams. The structure on the left is the naturally occurring (+)-camphor ((1''R'',4''R'')-bornan-2-one), while its mirror image shown on the right is the (−)-camphor ((1''S'',4''S'')-bornan-2-one). ...
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Diels–Alder Reaction
In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally-allowed +2cycloaddition with Woodward–Hoffmann symbol π4s_+_π2s.html" ;"title="sub>π4s + π2s">sub>π4s + π2s It was first described by Otto Diels and Kurt Alder in 1928. For the discovery of this reaction, they were awarded the Nobel Prize in Chemistry in 1950. Through the simultaneous construction of two new carbon–carbon bonds, the Diels–Alder reaction provides a reliable way to form six-membered rings with good control over the regio- and stereochemical outcomes. Consequently, it has served as a powerful and widely applied tool for the introduction of chemical complexity in the synthesis of natural products and new materials. The ...
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Dicarboxylic Acid
In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids. Dicarboxylic acids are used in the preparation of copolymers such as polyamides and polyesters. The most widely used dicarboxylic acid in the industry is adipic acid, which is a precursor in the production of nylon. Other examples of dicarboxylic acids include aspartic acid and glutamic acid, two amino acids in the human body. The name can be abbreviated to diacid. Linear saturated dicarboxylic acids The general formula is .Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2014, Wiley-VCH, Weinheim. The PubChem links gives access to more information on the compounds, including other names, ids, toxicity and safety ...
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Polydicyclopentadiene
Polydicyclopentadiene (PDCPD) is a polymer material which is formed through ring-opening metathesis polymerization(ROMP) of dicyclopentadiene (DCPD). PDCPD exhibits high crosslinking, which grants its properties, such as high impact resistance, good chemical corrosion resistance, and high heat deflection temperature. PDCPD is frequently used in the automotive industry to make body panels, bumpers, and other components for trucks, buses, tractors, and construction equipment. PDCPD is being investigated for the creation of porous materials for tissue engineering or gas storage applications, as well as for self-healing polymers. Polymerization can be achieved through the use of different transition metal catalysts as ruthenium, molybdenum, tungsten, and titanium, as well as under metal-free conditions through photoredox catalysis. The exact structure of the PDCPD polymer depends upon the reaction conditions used for the polymerization. While the crosslinked polymer may arise from t ...
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Ring-opening Metathesis Polymerization
Ring-opening metathesis polymerization (ROMP) is a type of olefin metathesis chain-growth polymerization. The driving force of the reaction is relief of ring strain in cyclic olefins (e.g. norbornene or cyclopentene). A variety of heterogeneous and homogeneous catalysts have been developed. Most large-scale commercial processes rely on the former while some fine chemical syntheses rely on the homogeneous catalysts. Catalysts are based on transition metals such as W, Mo, Re, Ru, and Ti. Heterogeneous catalysis and applications : Ring-opening metathesis polymerization of cycloalkenes has been commercialized since the 1970s. Examples of polymers produced on an industrial level through ROMP catalysis are Vestenamer or trans-polyoctenamer, which is the metathetical polymer of cyclooctene. Norsorex or polynorbornene is another important ROMP product on the market. Telene and Metton are polydicyclopentadiene products produced in a side reaction of the polymerization of norbornene. ...
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Macromolecules (journal)
''Macromolecules'' is a peer-reviewed scientific journal that has been published since 1968 by the American Chemical Society. Initially published bimonthly, it became monthly in 1983 and then, in 1990, biweekly. ''Macromolecules'' is abstracted and indexed in Scopus, EBSCOhost, PubMed, Web of Science, and SwetsWise. The editor-in-chief An editor-in-chief (EIC), also known as lead editor or chief editor, is a publication's editorial leader who has final responsibility for its operations and policies. The highest-ranking editor of a publication may also be titled editor, managing ... is Marc A. Hillmyer. Its first editor was Dr. Field H. Winslow. References External links * {{DEFAULTSORT:Macromolecules (Journal) American Chemical Society academic journals Bimonthly journals English-language journals Publications established in 1968 Polymer chemistry ...
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Norbornene
Norbornene or norbornylene or norcamphene is a highly strained bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carries a double bond which induces significant ring strain and significant reactivity. Production Norbornene is made by a Diels–Alder reaction of cyclopentadiene and ethylene. Many substituted norbornenes can be prepared similarly. Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane which is prepared by hydrogenation of norbornene. Reactions Norbornene undergoes an acid-catalyzed hydration reaction to form norborneol. This reaction was of great interest in the elucidation of the non-classical carbonion controversy. Norbornene is used in the Catellani reaction and in norbornene-mediated ''meta''-C−H activation. Certain substituted norbornenes undergo unusual sub ...
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Styrene
Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concentrations have a less pleasant odor. Styrene is the precursor to polystyrene and several copolymers. Approximately 25 million tonnes of styrene were produced in 2010, increasing to around 35 million tonnes by 2018. Natural occurrence Styrene is named after storax balsam (often commercially sold as ''styrax''), the resin of Liquidambar trees of the Altingiaceae plant family. Styrene occurs naturally in small quantities in some plants and foods (cinnamon, coffee beans, balsam tree (other), balsam trees and peanuts) and is also found in coal tar. History In 1839, the German apothecary Eduard Simon isolated a volatile liquid from the resin (called ''storax'' or ''styrax'' (Latin)) of the Liquidambar styraciflua, American sweetgu ...
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Copolymer
In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are sometimes called ''bipolymers''. Those obtained from three and four monomers are called ''terpolymers'' and ''quaterpolymers'', respectively. Copolymers can be characterized by a variety of techniques such as NMR spectroscopy and size-exclusion chromatography to determine the molecular size, weight, properties, and composition of the material. Commercial copolymers include acrylonitrile butadiene styrene (ABS), styrene/butadiene co-polymer (SBR), nitrile rubber, styrene-acrylonitrile, styrene-isoprene-styrene (SIS) and ethylene-vinyl acetate, all of which are formed by chain-growth polymerization. Another production mechanism is step-growth polymerization, which is used to produce the nylon-12/6/66 copolymer of nylon 12, nylon 6 and nylon ...
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Polymerization
In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many forms of polymerization and different systems exist to categorize them. In chemical compounds, polymerization can occur via a variety of reaction mechanisms that vary in complexity due to the functional groups present in the reactants and their inherent steric effects. In more straightforward polymerizations, alkenes form polymers through relatively simple free-radical reaction, radical reactions; in contrast, reactions involving substitution at a carbonyl group require more complex synthesis due to the way in which reactants polymerize. Alkanes can also be polymerized, but only with the help of strong acids. As alkenes can polymerize in somewhat straightforward radical reactions, they form useful compounds such as polyethylene and p ...
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Organometallic Chemistry
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term " metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are repres ...
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