Names | |
---|---|
Preferred IUPAC name Dibenzo[b,d]furan | |
Identifiers | |
3D model (JSmol) | |
3DMet | |
121100 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.612 |
EC Number |
|
67825 | |
KEGG | |
PubChem CID | |
UNII | |
UN number | 3077 |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C12H8O | |
Molar mass | 168.19 g/mol |
Appearance | white crystalline powder |
Melting point | 81 to 85 °C (178 to 185 °F; 354 to 358 K) |
Boiling point | 285 °C (545 °F; 558 K) |
Insoluble | |
Hazards | |
GHS labelling: | |
Warning | |
H302, H312, H332, H411 | |
P273, P391, P501 | |
Related compounds | |
Related compounds | Furan Benzofuran Dibenzodioxin Dibenzothiophene Carbazole Polyozellin (compound with a kernel with two dibenzofurans that share the same benzene ring) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Dibenzofuran is a heterocyclic organic compound with the chemical structure shown at right. It is an aromatic compound that has two benzene rings fused to a central furan ring. All the numbered carbon atoms have a hydrogen atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from coal tar, where it exists as a 1% component. [1]
Dibenzofuran is thermally robust with a convenient liquid range. These properties, together with its low toxicity, are exploited by the use of DBF as a heat transfer agent. [1]
It undergoes electrophilic reactions, such as halogenation and Friedel-Crafts reactions. Reaction of DBF with butyl lithium results in dilithiation. [2]
Dibenzofuran is the precursor to the drug furobufen by Friedel-Crafts reaction with succinic anhydride.
Dibenzofuran is a relatively non-toxic compound as evidenced by rats being unaffected after a 200-day diet consisting of 0.025 – 0.4% of DBF. [1] The polychlorinated dibenzofurans are however among the potentially toxic dioxins and dioxin-like compounds.
Dibenzofuran is cited in the United States Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act (SARA) Section 110 placed dibenzofuran on the revised Agency for Toxic Substances and Disease Registry (ATSDR) priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance’s frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA) National Priorities List sites, its toxicity, and/or its potential for human exposure. [3]
A pollutant or novel entity is a substance or energy introduced into the environment that has undesired effects, or adversely affects the usefulness of a resource. These can be both naturally forming or anthropogenic in origin. Pollutants result in environmental pollution or become public health concerns when they reach a concentration high enough to have significant negative impacts.
Polychlorinated biphenyls (PCBs) are highly carcinogenic chemical compounds, formerly used in industrial and consumer products, whose production was banned in the United States by the Toxic Substances Control Act in 1979 and internationally by the Stockholm Convention on Persistent Organic Pollutants in 2001. They are organic chlorine compounds with the formula C12H10−xClx; they were once widely used in the manufacture of carbonless copy paper, as heat transfer fluids, and as dielectric and coolant fluids for electrical equipment.
Polychlorinated dibenzodioxins (PCDDs), or simply dioxins, are a group of long-lived polyhalogenated organic compounds that are primarily anthropogenic, and contribute toxic, persistent organic pollution in the environment.
Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.
Phytoremediation technologies use living plants to clean up soil, air, and water contaminated with hazardous contaminants. It is defined as "the use of green plants and the associated microorganisms, along with proper soil amendments and agronomic techniques to either contain, remove or render toxic environmental contaminants harmless". The term is an amalgam of the Greek phyto (plant) and Latin remedium. Although attractive for its cost, phytoremediation has not been demonstrated to redress any significant environmental challenge to the extent that contaminated space has been reclaimed.
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class provides 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.
Dibenzo-1,4-dioxin, also dibenzodioxin or dibenzo-p-dioxin (dibenzo-para-dioxin), is a polycyclic heterocyclic organic compound in which two benzene rings are connected by a 1,4-dioxin ring. Its molecular formula is C12H8O2. The two oxygen atoms occupy opposite (para-) positions in the six-membered dioxin ring.
Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.
Persistent organic pollutants (POPs), sometimes known as "forever chemicals", are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. They are toxic chemicals that 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.
The National Emission Standards for Hazardous Air Pollutants (NESHAP) are air pollution standards issued by the United States Environmental Protection Agency (EPA). The standards, authorized by the Clean Air Act, are for pollutants not covered by the National Ambient Air Quality Standards (NAAQS) that may cause an increase in fatalities or in serious, irreversible, or incapacitating illness.
Fluoranthene is a polycyclic aromatic hydrocarbon (PAH). The molecule can be viewed as the fusion of naphthalene and benzene unit connected by a five-membered ring. Although samples are often pale yellow, the compound is colorless. It is soluble in nonpolar organic solvents. It is a member of the class of PAHs known as non-alternant PAHs because it has rings other than those with six carbon atoms. It is a structural isomer of the alternant PAH pyrene. It is not as thermodynamically stable as pyrene. Its name is derived from its fluorescence under UV light.
1,4-Dioxin (also referred as dioxin or p-dioxin) is a heterocyclic, organic, non-aromatic compound with the chemical formula C4H4O2. There is an isomeric form of 1,4-dioxin, 1,2-dioxin (or o-dioxin). 1,2-Dioxin is very unstable due to its peroxide-like characteristics.
More thorough treatise of all groups with similar actions and binding to aryl hydrocarbon receptor is given in Dioxins and dioxin-like compounds.
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.
Dioxins and dioxin-like compounds (DLCs) are a group of chemical compounds that are persistent organic pollutants (POPs) in the environment. They are mostly by-products of burning or various industrial processes - or, in case of dioxin-like PCBs and PBBs, unwanted minor components of intentionally produced mixtures.
Chlorinated polycyclic aromatic hydrocarbons (Cl-PAHs) are a group of compounds comprising polycyclic aromatic hydrocarbons with two or more aromatic rings and one or more chlorine atoms attached to the ring system. Cl-PAHs can be divided into two groups: chloro-substituted PAHs, which have one or more hydrogen atoms substituted by a chlorine atom, and chloro-added Cl-PAHs, which have two or more chlorine atoms added to the molecule. They are products of incomplete combustion of organic materials. They have many congeners, and the occurrences and toxicities of the congeners differ. Cl-PAHs are hydrophobic compounds and their persistence within ecosystems is due to their low water solubility. They are structurally similar to other halogenated hydrocarbons such as polychlorinated dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and polychlorinated biphenyls (PCBs). Cl-PAHs in the environment are strongly susceptible to the effects of gas/particle partitioning, seasonal sources, and climatic conditions.
The environmental effects of paper are significant, which has led to changes in industry and behaviour at both business and personal levels. With the use of modern technology such as the printing press and the highly mechanized harvesting of wood, disposable paper became a relatively cheap commodity, which led to a high level of consumption and waste. The rise in global environmental issues such as air and water pollution, climate change, overflowing landfills and clearcutting have all lead to increased government regulations. There is now a trend towards sustainability in the pulp and paper industry as it moves to reduce clear cutting, water use, greenhouse gas emissions, fossil fuel consumption and clean up its influence on local water supplies and air pollution.
Pentachlorobenzene (PeCB) is a chemical compound 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. Pentachlorobenzene is a known persistent organic pollutant (POP) and banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.
In an oil and gas production, flash-gas is a spontaneous vapor that is produced from the heating or depressurization of the extracted oil mixture during different phases of production. Flash evaporation, or flashing, is the process of volatile components suddenly vaporizing from their liquid state. This often happens during the transportation of petroleum products through pipelines and into vessels, such as when the stream from a common separation unit flows into an on-site atmospheric storage tank. Vessels that are used to intentionally “flash” a mixture of gas and saturated liquids are aptly named "flash drums." A type of vapor-liquid separator. A venting apparatus is used in these vessels to prevent damage due to increasing pressure, extreme cases of this are referred to as boiling liquid expanding vapor explosion (BLEVE).
Brook Industrial Park (BIP) is an industrial area occupying 4.5 acres of the Borough of Bound Brook, New Jersey, in the United States of America. It is located on the northern bank of the Raritan River. Industrial, chemical and pesticide operations began in 1971 and eventually lead to the contamination of groundwater and exposure of workers to harmful dioxins. Throughout 1980 to 1988 the United States Environmental Protection Agency (EPA) and the New Jersey Department of Environmental Protection (NJDEP) conducted studies to determine if there were any threats being posed on the workers, community or environment by the BIP companies in their disposal of processed and stored chemicals.
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