Names | |
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Preferred IUPAC name Pentachlorobenzene | |
Other names PeCB | |
Identifiers | |
3D model (JSmol) | |
1911550 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.009.248 |
EC Number |
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51144 | |
KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6HCl5 | |
Molar mass | 250.32 g·mol−1 |
Appearance | White or colorless crystals |
Density | 1.8 g/cm3 [1] |
Melting point | 86 °C (187 °F; 359 K) [1] |
Boiling point | 275 to 277 °C (527 to 531 °F; 548 to 550 K) [1] |
0.68 mg/L [2] | |
Hazards | |
GHS labelling: | |
Danger | |
H228, H302, H410 | |
P210, P240, P241, P264, P270, P273, P280, P301+P312, P330, P370+P378, P391, P501 | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | rat: 1080 mg/kg [3] mouse: 1175 mg/kg [3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Pentachlorobenzene (PeCB) is an aryl chloride and a five-substituted chlorobenzene with the molecular formula C6HCl5 which is a chlorinated aromatic hydrocarbon. It consists of a benzene ring substituted with five chlorine atoms. PeCB was once used industrially for a variety of uses, but because of environmental concerns there are currently no large scale uses of PeCB. [4] Pentachlorobenzene is a known persistent organic pollutant (POP) and banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009. [5]
PeCB can be produced as a byproduct of the manufacture of carbon tetrachloride and benzene. It is extracted by distillation and crystallization. The direct production of pure PeCB is not practical because of the simultaneous production of other chlorinated compounds. Since PeCB is generally produced in small quantities in the chlorination of benzene, it is also contained in other chlorobenzenes (dichlorobenzenes, trichlorobenzenes etc.)
Today, a majority of the PeCB released into the environment is a result of backyard trash burning and municipal waste incineration. [4]
PeCB was used as an intermediate in the manufacture of pesticides, particularly the fungicide pentachloronitrobenzene. [3] Pentachloronitrobenzene is now made by the chlorination of nitrobenzene in order to avoid the use of PeCB. [4]
PeCB was a component of a mixture of chlorobenzenes added to products containing polychlorinated biphenyls in order to reduce viscosity. [4] PeCB has also been used as a fire retardant. [3]
PeCB is a persistent organic pollutant, allowing an accumulation in the food chain. [1] [4] Consequently, pentachlorobenzene was added in 2009 to the list of chemical compounds covered by the Stockholm Convention, an international treaty which restricts the production and use of persistent organic pollutants. [6] [7] PeCB has been banned in the European Union since 2002.
PeCB is very toxic to aquatic organisms, and decomposes on heating or on burning with the formation of toxic, corrosive fumes including hydrogen chloride. [1] Combustion of PeCB may also result in the formation of polychlorinated dibenzodioxins ("dioxins") and polychlorinated dibenzofurans.
1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.
Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.
In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. Haloarenes are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.
Halocarbon compounds are chemical compounds in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms resulting in the formation of organofluorine compounds, organochlorine compounds, organobromine compounds, and organoiodine compounds. Chlorine halocarbons are the most common and are called organochlorides.
Stockholm Convention on Persistent Organic Pollutants is an international environmental treaty, signed on 22 May 2001 in Stockholm and effective from 17 May 2004, that aims to eliminate or restrict the production and use of persistent organic pollutants (POPs).
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.
Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.
Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.
Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
Toxaphene was an insecticide used primarily for cotton in the southern United States during the late 1960s and the 1970s. Toxaphene is a mixture of over 670 different chemicals and is produced by reacting chlorine gas with camphene. It can be most commonly found as a yellow to amber waxy solid.
Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.
Polychlorinated naphthalene (PCN) are the products obtained upon treatment of naphthalene with chlorine. The generic chemical formula is C10H8−(m+n)Cl(m+n). Commercial PCNs are mixtures of up to 75 components and byproducts. The material is an oil or a waxy solid, depending on the degree of chlorination. PCNs were once used in insulating coatings for electrical wires, as well as other applications, but their use has been largely phased out.
β-Hexachlorocyclohexane (β-HCH) is an organochloride which is one of the isomers of hexachlorocyclohexane (HCH). It is a byproduct of the production of the insecticide lindane (γ-HCH). It is typically constitutes 5–14% of technical-grade lindane, though it has not been produced or used in the United States since 1985. As of 2009, the Stockholm Convention on Persistent Organic Pollutants classified α-hexachlorocyclohexane and β-HCH as persistent organic pollutants (POPs), due to the chemical's ability to persist in the environment, bioaccumulative, biomagnifying, and long-range transport capacity.
Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.
1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.
Hexachlorocyclohexane (HCH), C
6H
6Cl
6, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. This structure has nine stereoisomers, which differ by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees.
Polychlorinated dibenzofurans (PCDFs) are a family of organic compounds with one or several of the hydrogens in the dibenzofuran structure replaced by chlorines. For example, 2,3,7,8-tetrachlorodibenzofuran (TCDF) has chlorine atoms substituted for each of the hydrogens on the number 2, 3, 7, and 8 carbons. Polychlorinated dibenzofurans with chlorines at least in positions 2,3,7 and 8 are much more toxic than the parent compound dibenzofurane, with properties and chemical structures similar to polychlorinated dibenzodioxins. These groups together are often inaccurately called dioxins. They are known developmental toxicants, and suspected human carcinogens. PCDFs tend to co-occur with polychlorinated dibenzodioxins (PCDDs). PCDFs can be formed by pyrolysis or incineration at temperatures below 1200 °C of chlorine containing products, such as PVC, PCBs, and other organochlorides, or of non-chlorine containing products in the presence of chlorine donors. Dibenzofurans are known persistent organic pollutants (POP), classified among the dirty dozen in the Stockholm Convention on Persistent Organic Pollutants.
Global distillation or the grasshopper effect is the geochemical process by which certain chemicals, most notably persistent organic pollutants (POPs), are transported from warmer to colder regions of the Earth, particularly the poles and mountain tops. Global distillation explains why relatively high concentrations of POPs have been found in the Arctic environment and in the bodies of animals and people who live there, even though most of the chemicals have not been used in the region in appreciable amounts.
Perfluorooctanesulfonyl fluoride (POSF) is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid (PFOS) and PFOS-based compounds. These compounds have a variety of industrial and consumer uses, but POSF-derived substances ultimately degrade to form PFOS.
Persistent, bioaccumulative and toxic substances (PBTs) are a class of compounds that have high resistance to degradation from abiotic and biotic factors, high mobility in the environment and high toxicity. Because of these factors PBTs have been observed to have a high order of bioaccumulation and biomagnification, very long retention times in various media, and widespread distribution across the globe. Most PBTs in the environment are either created through industry or are unintentional byproducts.
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