Terephthaloyl Chloride
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Terephthaloyl Chloride
Terephthaloyl chloride (TCL, 1,4-benzenedicarbonyl chloride) is the acyl chloride of terephthalic acid. It is a white solid. It is one of two precursors used to make Kevlar(R), the other being ''p''-phenylenediamine. TCL is used as a key component in performance polymers and aramid fibers, where it imparts flame resistance, chemical resistance, temperature stability, light weight, and very high strength. TCL is also an effective water scavenger, used to stabilize isocyanates and urethane prepolymers. Preparation Terephthalic acid dichloride is produced commercially by the reaction of 1,4-bis(trichloromethyl)benzene with terephthalic acid: : C6H4(CCl3)2 + C6H4(CO2H)2 → 2 C6H4(COCl)2 + 2 HCl It can also be obtained by chlorination of dimethyl terephthalate. Use TCL is used for making various copolymers and aramid polymers such as Heracron, Twaron and Kevlar(R): References {{Reflist External links * * Aramid Aramid fibers, short for aromatic polyamide, are a class ...
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Royal Society Of Chemistry
The Royal Society of Chemistry (RSC) is a learned society (professional association) in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the Royal Institute of Chemistry, the Faraday Society, and the Society for Analytical Chemistry with a new Royal Charter and the dual role of learned society and professional body. At its inception, the Society had a combined membership of 34,000 in the UK and a further 8,000 abroad. The headquarters of the Society are at Burlington House, Piccadilly, London. It also has offices in Thomas Graham House in Cambridge (named after Thomas Graham (chemist), Thomas Graham, the first president of the Chemical Society) where ''RSC Publishing'' is based. The Society has offices in the United States, on the campuses of The University of Pennsylvania and Drexel University, at the University City Science Center in Philadelphia, Pennsylvania, in both Beijing a ...
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Dimethyl Terephthalate
Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.Richard J. Sheehan "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Production Dimethyl terephthalate (DMT) has been produced in a number of ways. Conventionally, and still of commercial value, is the direct esterification of terephthalic acid. Alternatively, it can be prepared by alternating oxidation and methyl-esterification steps from p-xylene via methyl ''p''-toluate (PT). Dimethyl terephthalate by the Witten process The method for the production of DMT from ''p''-xylene (PX) and methanol consists of a multistep process involving both oxidation and esterification. A mixture of p-xylene (PX) and methyl ''p''-toluate is oxidized with air in the presence of cobalt a ...
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Acyl Chlorides
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example of an acyl chloride is acetyl chloride, . Acyl chlorides are the most important subset of acyl halides. Nomenclature Where the acyl chloride moiety takes priority, acyl chlorides are named by taking the name of the parent carboxylic acid, and substituting ''-yl chloride'' for ''-ic acid''. Thus: : : When other functional groups take priority, acyl chlorides are considered prefixes — ''chlorocarbonyl-'': : Properties Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1. The simplest s ...
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Aramid
Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, marine hull reinforcement, and as an asbestos substitute. The chain molecules in the fibers are highly oriented along the fiber axis. As a result, a higher proportion of the chemical bond contributes more to fiber strength than in many other synthetic fibers. Aramids have a very high melting point (>500 °C). Common aramid brand names include Kevlar, Nomex, and Twaron. Terminology and chemical structure ''Aramid'' is a shortened form of aromatic polyamide. The term was introduced in 1972, accepted in 1974 by the Federal Trade Commission of the USA as the name of a generic category of fiber distinct from nylon, and adopted by the International Standards Organisation in 1977. Aromatic in the name refers to the presence of aromatic rings ...
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Kevlar Chemical Synthesis
Kevlar (para-aramid) is a strong, heat-resistant synthetic fiber, related to other aramids such as Nomex and Technora. Developed by Stephanie Kwolek at DuPont in 1965, the high-strength material was first used commercially in the early 1970s as a replacement for steel in racing tires. It is typically spun into ropes or fabric sheets that can be used as such, or as an ingredient in composite material components. Kevlar has many applications, ranging from bicycle tires and racing sails to bulletproof vests, all due to its high tensile strength-to-weight ratio; by this measure it is five times stronger than steel. It is also used to make modern marching drumheads that withstand high impact; and for mooring lines and other underwater applications. A similar fiber called Twaron with the same chemical structure was developed by Akzo in the 1970s; commercial production started in 1986, and Twaron is now manufactured by Teijin. History Poly-paraphenylene terephthalamide (K2 ...
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Twaron
Twaron (a brand name of Teijin Aramid) is a para-aramid. It is a heat-resistant and strong synthetic fibre developed in the early 1970s by the Dutch company Akzo Nobel's division Enka BV, later Akzo Industrial Fibers. The research name of the para-aramid fibre was originally Fiber X, but it was soon called Arenka. Although the Dutch para-aramid fiber was developed only a little later than DuPont's Kevlar, the introduction of Twaron as a commercial product came much later than Kevlar due to financial problems at the AKZO company in the 1970s. History This is a chronology of the development of Twaron: * In 1960s a research program starts for "Fiber X." * In 1972 the ENKA Research laboratory develops a para-aramid called Arenka. * In 1973 Akzo decides to use sulfuric acid (H2SO4) as a solvent for spinning. * In 1974 New process route was found at Akzo Research laboratory, using N-methylpyrrolidone (NMP) with a co-solvent (auxiliary solvent) with an ionic component (Calcium Chloride ( ...
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Heracron
Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, marine hull reinforcement, and as an asbestos substitute. The chain molecules in the fibers are highly oriented along the fiber axis. As a result, a higher proportion of the chemical bond contributes more to fiber strength than in many other synthetic fibers. Aramids have a very high melting point (>500 °C). Common aramid brand names include Kevlar, Nomex, and Twaron. Terminology and chemical structure ''Aramid'' is a shortened form of aromatic polyamide. The term was introduced in 1972, accepted in 1974 by the Federal Trade Commission of the USA as the name of a generic category of fiber distinct from nylon, and adopted by the International Standards Organisation in 1977. Aromatic in the name refers to the presence of aromatic ring ...
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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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Bayer AG
Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of business include pharmaceuticals; consumer healthcare products, agricultural chemicals, seeds and biotechnology products. The company is a component of the Euro Stoxx 50 stock market index. Bayer was founded in 1863 in Barmen as a partnership between dye salesman Friedrich Bayer and dyer Friedrich Weskott. As was common in this era, the company was established as a dyestuffs producer. The versatility of aniline chemistry led Bayer to expand their business into other areas, and in 1899 Bayer launched the compound acetylsalicylic acid under the trademarked name Aspirin. In 1904 Bayer received a trademark for the "Bayer Cross" logo, which was subsequently stamped onto each aspirin tablet, creating an iconic product that is still sold by Bayer. Other commonly known produ ...
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1,4-Bis(trichloromethyl)benzene
1,4-Bis(trichloromethyl)benzene is an organic compound with the formula C6H4(CCl3)2. A white solid, it is prepared industrially by chlorination of para-xylene. It reacts with terephthalic acid to give terephthaloyl chloride, a precursor to Kevlar. It also reacts with sulfur dioxide to give the same acid chloride and thionyl chloride. It reacts with hydrogen fluoride in 1,2-dichloroethane to form 1,4-bis(chlorodifluoromethyl)benzene in a yield of 79%. See also *Benzotrichloride Benzotrichloride (BTC), also known as α,α,α-trichlorotoluene, phenyl chloroform or (trichloromethyl)benzene, is an organic compound with the formula C6H5CCl3. Benzotrichloride is an unstable, colorless (to yellowish), viscous, chlorinated hydro ... References {{DEFAULTSORT:Bis(trichloromethyl)benzene, 1,4- Trichloromethyl compounds Benzene derivatives ...
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Acyl Chloride
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example of an acyl chloride is acetyl chloride, . Acyl chlorides are the most important subset of acyl halides. Nomenclature Where the acyl chloride moiety takes priority, acyl chlorides are named by taking the name of the parent carboxylic acid, and substituting ''-yl chloride'' for ''-ic acid''. Thus: : : When other functional groups take priority, acyl chlorides are considered prefixes — ''chlorocarbonyl-'': : Properties Lacking the ability to form hydrogen bonds, acyl chlorides have lower boiling and melting points than similar carboxylic acids. For example, acetic acid boils at 118 °C, whereas acetyl chloride boils at 51 °C. Like most carbonyl compounds, infrared spectroscopy reveals a band near 1750 cm−1. The simplest s ...
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Ethyl Carbamate
Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks. Synthesis It is produced industrially by heating urea and ethyl alcohol. It arise also by the action of ammonia on ethyl chloroformate. Uses Biomedical applications Ethyl carbamate has been used as an antineoplastic agent and for other medicinal purposes, but this application ended after it was discovered to be carcinogenic in 1943. However, Japanese usage in medical injections continued and from 1950 to 1975 an estimated 100 million 2 ml ampules of 7-to-15% solutions of ethyl carbamate were injected into patients as a co-solvent in water for dissolving water-insoluble analgesics used for post-operation pain. These doses were estimated to b ...
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