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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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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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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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Para-xylene
''p''-Xylene ( ''para''-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The ''p-'' stands for ''para-'', indicating that the two methyl groups in ''p''-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, ''o''-xylene and ''m''-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of ''p''-xylene is 0.62 parts per million (ppm). Production The production of ''p''-xylene is industrially significant, with annual demand estimated at 37 million tons in 2014, and still on the increase. ''p''-Xylene is produced by catalytic reforming of petroleum naphtha as part of the BTX aromatics (benzene, toluene and the xylene isomers) extracted from the catalytic reformate. The ''p''-xylene is then separated out ...
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Kevlar
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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Sulfur Dioxide
Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic activity and is produced as a by-product of copper extraction and the burning of sulfur- bearing fossil fuels. Structure and bonding SO2 is a bent molecule with ''C''2v symmetry point group. A valence bond theory approach considering just ''s'' and ''p'' orbitals would describe the bonding in terms of resonance between two resonance structures. The sulfur–oxygen bond has a bond order of 1.5. There is support for this simple approach that does not invoke ''d'' orbital participation. In terms of electron-counting formalism, the sulfur atom has an oxidation state of +4 and a formal charge of +1. Occurrence Sulfur dioxide is found on Earth and exists in very small concentrations and in the atmosphere at about 1 ppm. On other planets, ...
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Thionyl Chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons. Thionyl chloride is sometimes confused with sulfuryl chloride, , but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. Production The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride: This synthesis can be adapted to the laboratory by heating oleum to slowly distill the sulfur trioxide into a cooled flask of sulfur dichloride. :SO3 + SCl2 -> SOCl2 + SO2 Other methods includ ...
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Hydrogen Fluoride
Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is widely used in the petrochemical industry as a component of superacids. Hydrogen fluoride boils at near room temperature, much higher than other hydrogen halides. Hydrogen fluoride is an extremely dangerous gas, forming corrosive and penetrating hydrofluoric acid upon contact with moisture. The gas can also cause blindness by rapid destruction of the corneas. History In 1771 Carl Wilhelm Scheele prepared the aqueous solution, hydrofluoric acid in large quantities, although hydrofluoric acid had been known in the glass industry before then. French chemist Edmond Frémy (1814–1894) is credited with discoveri ...
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1,2-dichloroethane
The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water (at a boiling point of ) and other chlorocarbons. History In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists ( nl, Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. Although the ' ...
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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 hydrocarbon with a penetrating odor. Benzotrichloride is used extensively as a chemical intermediate for products of various classes, i.e. dyes and antimicrobial agents. History Benzotrichloride is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and hence its use is subject to a list of reporting requirements by companies or institutions which synthesize, store or use it in large quantities. In 2018, EU member states have approved a European Commission proposal to restrict the use of carcinogenic, mutagenic and reprotoxic (CMR) substances in clothing, textiles and footwear. In 2015, the Commission published a preli ...
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Trichloromethyl Compounds
The trichloromethyl group is a functional group that has the formula –CCl3. The naming of is group is derived from the methyl group (which has the formula –CH3), by replacing each hydrogen atom by a chlorine atom. Compounds with this group are a subclass of the organochlorines. Some notable examples of compounds with this group are trichloromethane H–, 1,1,1-trichloroethane –, and chloral –. The trichloromethyl group has a significant electronegativity. For this reason, trichloromethyl-substituted acids, such as trichloromethanesulfonic acid, are often stronger than the original. For example, the acidity constant (pKa) of trichloroacetic acid – is 0.77, whereas that of acetic acid is 4.76. By the same principle, the trichloromethyl group generally lowers the basicity of organic compounds, e.g. trichloroethanol 2,2,2-Trichloroethanol is the chemical compound with formula . Its molecule can be described as that of ethanol, with the three hydrogen atoms at position ...
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