Chloroprene
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Chloroprene
Chloroprene is the common name for 2-chlorobuta-1,3-diene (IUPAC name) with the chemical formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, better known as neoprene, a type of synthetic rubber. History Although it may have been discovered earlier, chloroprene was largely developed by DuPont during the early 1930s, specifically with the formation of neoprene in mind. The chemists Elmer K. Bolton, Wallace Carothers, Arnold Collins and Ira Williams are generally accredited with its development and commercialisation although the work was based upon that of Julius Arthur Nieuwland, with whom they collaborated. Production Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination of 3,4-dichlorobut-1-ene. Chlorine adds to 1,3-butadiene to afford a mixture of 3,4-dichlorobut-1-ene ...
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Neoprene
Neoprene (also polychloroprene) is a family of synthetic rubbers that are produced by polymerization of chloroprene.Werner Obrecht, Jean-Pierre Lambert, Michael Happ, Christiane Oppenheimer-Stix, John Dunn and Ralf Krüger "Rubber, 4. Emulsion Rubbers" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. Neoprene exhibits good chemical stability and maintains flexibility over a wide temperature range. Neoprene is sold either as solid rubber or in latex form and is used in a wide variety of commercial applications, such as laptop sleeves, orthopaedic braces (wrist, knee, etc.), electrical insulation, liquid and sheet-applied elastomeric membranes or flashings, and automotive fan belts. Production Neoprene is produced by free-radical polymerization of chloroprene. In commercial production, this polymer is prepared by free radical emulsion polymerization. Polymerization is initiated using potassium persulfate. Bifunctional nucleophiles, metal oxides (e.g ...
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Neoprene
Neoprene (also polychloroprene) is a family of synthetic rubbers that are produced by polymerization of chloroprene.Werner Obrecht, Jean-Pierre Lambert, Michael Happ, Christiane Oppenheimer-Stix, John Dunn and Ralf Krüger "Rubber, 4. Emulsion Rubbers" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. Neoprene exhibits good chemical stability and maintains flexibility over a wide temperature range. Neoprene is sold either as solid rubber or in latex form and is used in a wide variety of commercial applications, such as laptop sleeves, orthopaedic braces (wrist, knee, etc.), electrical insulation, liquid and sheet-applied elastomeric membranes or flashings, and automotive fan belts. Production Neoprene is produced by free-radical polymerization of chloroprene. In commercial production, this polymer is prepared by free radical emulsion polymerization. Polymerization is initiated using potassium persulfate. Bifunctional nucleophiles, metal oxides (e.g ...
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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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Synthetic Rubber
A synthetic rubber is an artificial elastomer. They are polymers synthesized from petroleum byproducts. About 32-million metric tons of rubbers are produced annually in the United States, and of that amount two thirds are synthetic. Synthetic rubber, just like natural rubber, has many uses in the automotive industry for tires, door and window profiles, Seal (mechanical), seals such as O-rings and gaskets, hoses, Belt (mechanical), belts, Rubber mat, matting, and flooring. They offer a different range of physical and chemical properties, so can improve the reliability of a given product or application. Synthetic rubbers are superior to natural rubbers in two major respects, thermal stability and resistance to oils and related compounds. They are more resistant to oxidizing agents, such as oxygen and ozone which can reduce the life of products like tires. History of synthetic rubber The expanded use of bicycles, and particularly their pneumatic tires, starting in the 1890s, create ...
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Wallace Carothers
Wallace Hume Carothers (; April 27, 1896 – April 29, 1937) was an American chemist, inventor and the leader of organic chemistry at DuPont, who was credited with the invention of nylon. Carothers was a group leader at the DuPont Experimental Station laboratory, near Wilmington, Delaware, where most polymer research was done. Carothers was an organic chemist who, in addition to first developing nylon, also helped lay the groundwork for neoprene. After receiving his Ph.D., he taught at several universities before he was hired by DuPont to work on fundamental research. He married Helen Sweetman on February 21, 1936. Carothers had been troubled by periods of depression since his youth. Despite his success with nylon, he felt that he had not accomplished much and had run out of ideas. His unhappiness was exacerbated by the death of his sister, and on April 28, 1937, he committed suicide by drinking potassium cyanide. His daughter, Jane, was born on November 27, 1937. Educatio ...
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Ira Williams
Ira Williams (1894–1977) was an American chemist at DuPont's Jackson Laboratory in New Jersey, who in 1930 made commercial Neoprene possible by producing a soft, plastic form of chloroprene that could be processed by the rubber industry. He won the 1946 Charles Goodyear Medal The Charles Goodyear Medal is the highest honor conferred by the American Chemical Society, Rubber Division. Established in 1941, the award is named after Charles Goodyear, the discoverer of vulcanization, and consists of a gold medal, a framed c .... References 20th-century American chemists Polymer scientists and engineers 1894 births 1977 deaths {{US-chemist-stub ...
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Elmer Keiser Bolton
Elmer Keiser Bolton (June 23, 1886 – July 30, 1968) was an American chemist and research director for DuPont, notable for his role in developing neoprene and directing the research that led to the discovery of nylon. Personal life Bolton was born in Frankford, Philadelphia, Pennsylvania, the oldest of two brothers. His father ran the furniture store on Main Street, and both he and his brother attended public school in Frankford and went on to college. Bolton went to Bucknell University in Lewisburg, Pennsylvania, and took the ''Classical Course'', receiving a B.A. degree in 1908. From there he went to Harvard University, receiving his A.M. degree in 1910 and his Ph.D. in organic chemistry in 1913. His thesis advisor was Charles Loring Jackson, and his dissertation concerned the chemistry of periodoquinones. Several other prominent contemporaries of Bolton's at Harvard Graduate School were Roger Adams, Farrington Daniels, Frank C. Whitmore, James B. Sumner and James B ...
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Vinylacetylene
Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups and is the simplest enyne. Vinylacetylene is extremely dangerous because in high enough concentrations (typically > 30 mole percent, but pressure dependent) it can auto-detonate (explode without air being present) especially at elevated pressures, such as those seen in chemical plants processing C4 hydrocarbons. An example of such an explosion occurred at a Union Carbide plant in Texas City in 1969. Synthesis Vinylacetylene was first synthesized by Hofmann elimination of the related quaternary ammonium salt: : CH3)3NCH2CH=CHCH2N(CH3)32 → 2 CH3)3NH + HC≡C-CH=CH2 It is usually synthesized by dehydrohalogenation of 1,3-dichloro-2-butene. It also arises via the dimerization of acetylene or dehydrogenation of 1,3-butadiene. Application At one time, chloroprene (2-chloro-1,3-butadiene), an industrially im ...
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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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Common Noun
A proper noun is a noun that identifies a single entity and is used to refer to that entity (''Africa'', ''Jupiter'', ''Sarah'', ''Microsoft)'' as distinguished from a common noun, which is a noun that refers to a class of entities (''continent, planet, person, corporation'') and may be used when referring to instances of a specific class (a ''continent'', another ''planet'', these ''persons'', our ''corporation''). Some proper nouns occur in plural form (optionally or exclusively), and then they refer to ''groups'' of entities considered as unique (the ''Hendersons'', the ''Everglades'', ''the Azores'', the ''Pleiades''). Proper nouns can also occur in secondary applications, for example modifying nouns (the ''Mozart'' experience; his ''Azores'' adventure), or in the role of common nouns (he's no ''Pavarotti''; a few would-be ''Napoleons''). The detailed definition of the term is problematic and, to an extent, governed by convention. A distinction is normally made in current ling ...
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Dehydrochlorination
In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halides Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol via a benzyne intermediate. Base-promoted reactions to alkenes When treated with a strong base many alkyl chlorides convert to corresponding alkene. It is also called a β-elimination reaction and is a type of elimination reaction. Some prototypes are shown below: :\begin \ce\ &\ce \\ \ce\ &\ce \\ \ce\ &\ce \end Here ethyl chloride reacts with potassium hydroxide, typically in a solvent such as ethanol, giving ethylene. ...
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Julius Arthur Nieuwland
Julius Aloysius Arthur Nieuwland, CSC, (14 February 1878 – 11 June 1936) was a Belgian-born Holy Cross priest and professor of chemistry and botany at the University of Notre Dame, Indiana. He is known for his contributions to acetylene research and its use as the basis for one type of synthetic rubber, which eventually led to the invention of neoprene by DuPont. Life and work Nieuwland's parents emigrated from Hansbeke, Belgium in 1880 to South Bend, Indiana. As a young man, Nieuwland enrolled at the University of Notre Dame, where he studied Latin and Greek and received his undergraduate degree in 1899. He soon after began studies for the priesthood. Ordained in 1903, Nieuwland attended graduate school at The Catholic University of America, where he studied botany and chemistry. During his doctoral studies into the chemistry of acetylene, he discovered the chemical compound lewisite, which would later gain fame as a chemical warfare agent. Nieuwland had to be ...
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