Chlorophenols
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Chlorophenols
A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. There are five basic types of chlorophenols (mono- to pentachlorophenol) and 19 different chlorophenols in total when positional isomerism is taken into account. Chlorophenols are produced by electrophilic halogenation of phenol with chlorine. Most chlorophenols are solid at room temperature. They have a strong, medicinal taste and smell. Chlorophenols are commonly used as pesticides, herbicides, and disinfectants. List of chlorophenols There is a total of 19 chlorophenols, corresponding to the different ways in which chlorine atoms can be attached to the five carbons in the benzene ring of the phenol molecule, excluding the carbon atom to which the hydroxy group is attached. Monochlorophenols have three isomers because there is only one chlorine atom that can occupy one of three ring positions on the phenol molecule; 2-chlorophenol, for example, is the isomer that ha ...
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2,6-Dichlorophenol
2,6-Dichlorophenol is a compound with formula C6H3Cl2OH. It is one of the six isomers of dichlorophenol. It is a colorless solid. Its pKa is 6.78, which is about 100x more acidic than 2-chlorophenol (8.52) and 1000x more acidic than phenol itself (9.95). Preparation It can be produced in a multistep process from phenol, which is converted to its 4-sulfonic acid derivative. The resulting phenol sulfonic acid chlorinates at the positions flanking the phenol. Hydrolysis releases the sulfonic acid group. An alternative synthesis starts with the ethyl ester of 4-hydroxybenzoic acid, which chlorinates at the positions flanking the phenolic center. Ester hydrolysis followed by decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ... affords 2,6-dichlorophenol. References ...
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Pentachlorophenol
Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which dissolves easily in water. It can be biodegraded by some bacteria, including ''Sphingobium chlorophenolicum''. Uses PCP has been used as a herbicide, insecticide, fungicide, algaecide, and disinfectant and as an ingredient in antifouling paint. Some applications were in agricultural seeds (for nonfood uses), leather, masonry, wood preservation, cooling-tower water, rope, and paper. It has previously been used in the manufacture of food packaging materials. Its use has declined due to its high toxicity and slow biodegradation. Two general methods are used for preserving wood. The pressure process method involves placing wood in a pressure-treating vessel, where it is immersed in PCP and then subjected to applied pressure. In the nonpressure p ...
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Dichlorophenol
Dichlorophenols (DCPs) are any of several chemical compounds which are derivatives of phenol containing two chlorine atoms. There are six isomers: * 2,3-Dichlorophenol * 2,4-Dichlorophenol * 2,5-Dichlorophenol * 2,6-Dichlorophenol * 3,4-Dichlorophenol * 3,5-Dichlorophenol Dichlorophenols are used as intermediates in the manufacture of more complex chemical compounds, including the common herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). See also * Chlorophenol * Trichlorophenol * Pentachlorophenol Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which diss ... References Chloroarenes Phenols {{chemistry index ...
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4-Chlorophenol
4-Chlorophenol is an organic compound with the formula ClC6H4OH. It is one of three monochlorophenol isomers. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Its pKa is 9.14. Preparation and reaction It is prepared by chlorination of phenol, preferably in polar solvents, which tends to yield the 4-chloro derivative. Direct chlorination of molten phenol favors the formation of 2-chlorophenol. It once was produced on a large scale as a precursor to hydroquinone. It is a classic precursor, upon reaction with phthalic anhydride, to quinizarin. The commercial dye quinizarin is produced by the reaction of phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commerc ... and 4-chlorophenol followed by hydrolysis of the chloride. l ...
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3-Chlorophenol
3-Chlorophenol is an organic compound with the molecular formula ClC6H4OH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was i ..., which starts with the alkylation of chlorobenzene with propylene. References {{DEFAULTSORT:Chlorophenol, 3- Phenols Chlorobenzenes ...
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2,4,6-Trichlorophenol
2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic, defoliant, and glue preservative. It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine. Preparation 2,4,6-Trichlorophenol is produced industrially by the electrophilic chlorination of phenol: : Health effects In animal models, consumption of 2,4,6-trichlorophenol leads to an increased incidence of lymphomas, leukemia, and liver cancer. It is classified as ''Group B2'' (probable human carcinogen) by the United States Environmental Protection Agency. The technical grade of this substance may contain polychlorinated dibenzodioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and other contaminants. Environmental effects 2,4,6-Trichlorophenol is an environmental pollutant tha ...
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Phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Properties Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water at phenol ...
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Trichlorophenol
A trichlorophenol is any organochloride of phenol that contains three covalently bonded chlorine atoms. Trichlorophenols are produced by electrophilic halogenation of phenol with chlorine. Different isomers of trichlorophenol exist according to which ring positions on the phenol contain chlorine atoms. 2,4,6-Trichlorophenol, for example, has two chlorine atoms in the '' ortho'' positions and one chlorine atom in the ''para'' position. There are six different isomers: * 2,3,4-Trichlorophenol * 2,3,5-Trichlorophenol * 2,3,6-Trichlorophenol * 2,4,5-Trichlorophenol * 2,4,6-Trichlorophenol * 3,4,5-Trichlorophenol See also * Chlorophenol * Dichlorophenol * Pentachlorophenol Pentachlorophenol (PCP) is an organochlorine compound used as a pesticide and a disinfectant. First produced in the 1930s, it is marketed under many trade names. It can be found as pure PCP, or as the sodium salt of PCP, the latter of which diss ... References {{chemistry index Chlorobenzenes Phenols
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2,4,5-Trichlorophenol
2,4,5-Trichlorophenol is an organochloride with the molecular formula C6 H3 Cl3 O1. 2,4,5-Trichlorophenol has been used as a fungicide and herbicide. References See also * Agent Orange Agent Orange is a chemical herbicide and defoliant, one of the "tactical use" Rainbow Herbicides. It was used by the U.S. military as part of its herbicidal warfare program, Operation Ranch Hand, during the Vietnam War from 1961 to 1971. It ... * 2,4,5-Trichlorophenoxyacetic acid * 2,4-Dichlorophenoxyacetic acid {{DEFAULTSORT:Trichlorophenol, 2, 4, 5- Organochlorides Fungicides Herbicides Phenols ...
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