Any of a family of industrial compounds produced by chlorination of biphenyl, noted primarily as an environmental pollutant that accumulates in animal tissue with resultant pathogenic and teratogenic effects.
[P(OLY)C(HLORINATED) B(IPHENYL).]
Dictionary:
PCB (pē'sē-bē') ![]() |
Any of a family of industrial compounds produced by chlorination of biphenyl, noted primarily as an environmental pollutant that accumulates in animal tissue with resultant pathogenic and teratogenic effects.
[P(OLY)C(HLORINATED) B(IPHENYL).]
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| Sci-Tech Encyclopedia: Polychlorinated biphenyls |
A generic term for a family of 209 chlorinated isomers of biphenyl. The biphenyl molecule is composed of two six-sided carbon rings connected at one carbon site on each ring. Ten sites remain for chlorine atoms to join the biphenyl molecule. The term polychlorinated biphenyl (PCB) has been used to refer to the biphenyl molecule with one to ten chlorine substitutions, as shown in the following structure.

The major use of PCBs has been as dielectric fluid in electrical equipment, particularly transformers capacitors, electromagnets, circuit breakers, voltage regulators, and switches. PCBs have also been used in heat transfer systems and hydraulic systems, and as plasticizers and additives in lubricating and cutting oils.
PCBs have been reported in animals, plants, soil, and water all over the world, even in animals living under 11,000 ft (3400 m) of water. These phenomena are the result of bioaccumulation and biomagnification in the food chain. In a few instances, poultry products, cattle, and hogs have been found to contain high concentrations of PCBs after the animals have eaten feed contaminated with PCBs. It is not known what quantities of PCBs have been released to the environment, but major sources are industrial and municipal waste disposal, spills and leaks from PCB-containing equipment, and manufacture and handling of PCB mixtures.
PCBs can enter the body through the lungs, gastrointestinal tract, and skin, circulate throughout the body, and be stored in adipose tissue. PCBs have been detected in human adipose tissues and in the milk of cows and humans. Some PCBs have the ability to alter reproductive processes in mammals. There is concern that PCBs may be carcinogenic in humans.
| Real Estate Dictionary: Polychlorinated Biphenyls (PCBS) |
Carcinogenic chemicals used in electrical transformers.
Example: When disposing of electric equipment, any PCBs must be disposed of carefully to prevent them from contaminating the environment. If PCBs are found on property, an environmental disposal company should be contacted because they are Hazardous Waste.
| Dental Dictionary: polychlorinated biphenyls |
More than 30 isomers and compounds used in plastics, insulation, and flame retardants and varying in physical form from oily liquid to crystals and resins. All are potentially toxic and carcinogenic. Mild exposure may cause chloracne; severe exposure may result in hepatic damage.
| Encyclopedia of Public Health: PCBs |
Polychlorinated biphenyls (PCBs) are a group of synthetic chlorinated organic compounds that are of public health concern because of their persistence in the environment and their potential cancer-causing and endocrine-disruptive effects. There are 209 individual PCB congeners of varying toxicity, but a smaller number accounts for most of the commercially distributed mixtures. PCBs usually have been sold as clear oily mixtures whose lubricating, insulating, and coolant properties have led to their being widely distributed for many industrial and commercial uses. They are relatively inert, making them particularly valuable for such uses as fireproofing, but their lack of reactivity is also responsible for environmental persistence and for bioaccumulation in the food chain.
Heavy exposure to PCBs due to contamination of cooking oil occurred in two episodes in Japan and Taiwan in which skin manifestations, including chloracne, were prominent effects. Also observed were abnormal hepatic function, neurophysiological alterations, and developmental effects in offspring.
Exposure to high levels of PCBs at the workplace can cause skin and upper respiratory tract irritation. Environmental exposure to PCBs primarily occur through ingestion of contaminated seafood, but exposure can also occur through children ingesting contaminated soil and through the skin in landfill sites. PCBs are stored in fat and are present in breast milk. Inhalation of PCBs can also occur, particularly when there are indoor sources. PCBs can be carried long distances in air, which accounts for their distribution and accumulation in food chains in otherwise pristine arctic areas.
The different PCB congeners have different rates of persistence, bioaccumulation, and toxicity. In general, as the extent of chlorination increases, the rate of metabolism and detoxification decreases. The position of the chlorine atoms on the phenyl rings also affects metabolic rate and toxicity. Contamination of commercial PCB mixtures, particularly with chlorinated dibenzofurans, may also contribute to toxicity.
Acute toxicity due to PCBs is not of concern. However, PCBs are definitely carcinogenic to laboratory animals and are considered to be carcinogenic to humans. Concern about the potential for endocrine-disruptive effects, including developmental abnormalities, is similar to the concern for other persistent chlorinated compounds. Polybrominated biphenyls (PBBs) are in many ways similar to PCBs although far lesser amounts have been produced. An episode of PBB-contaminated cattle feed in Michigan led to human consumption of contaminated meat and dairy products, resulting in evidence of immunological dysfunction.
PCBs have been among the persistent organic pollutants (POPs) that have been considered to be of particular concern in many national and international deliberations. The United States banned the manufacture of PCBs in 1977, but PCB mixtures still remain in old electrical equipment and other items manufactured before 1977. There is also substantial PCB contamination of landfills and rivers. The Hudson River has been heavily contaminated by dumping from an electrical-device manufacturing facility. There has been much controversy concerning whether dredging the Hudson River to remove PCBs may do more harm than good by causing pockets of PCBs to be stirred up and to enter the ecosystem food chain.
The United States Food and Drug Administration has established allowable tolerances for PCBs in a variety of foods, particularly dairy products and seafoods. With the possible exception of the arctic, in recent years there has been a decline in PCB levels in human fat and in the general environment.
(SEE ALSO: Toxicology)
Bibliography
Chen, Y. C.; Guo, Y. L.; Hsu, C. C.; and Rogen, W. J. (1997). "Cognitive Development of Yu-Cheng ("Oil Disease") Children Prenatally Exposed to Heat Degraded PCBs." Journal of the American Medical Association 268(22):3213–3218.
Guo, Y. L.; Hsu, P. C.; Hsu, C. C.; and Lambert, G. H. (2000). "Semen Quality after Prenatal Exposure to Polychlorinated Biphenyls and Dibenzofurans." Lancet 356(9237):1240–1241.
Jacobsen, J. L., and Jacobsen, S. W. (1996). "Intellectual Impairment in Children Exposed to Polychlorinated Biphenyls in Utero." New England Journal of Medicine 335(11):783–789.
Kimbrough, R. D. (1997). "Human Health Effects of Polychlorinated Biphenyls (PCBs) and Polybrominated Biphenyls (PBBs)." Annual Review of Pharmacological Toxicology 27:87.
— BERNARD D. GOLDSTEIN
| Britannica Concise Encyclopedia: PCB |
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| Columbia Encyclopedia: polychlorinated biphenyl |
| Science Q&A: What are PCBs? |
Polychlorinated biphenyls (PCBs) are a group of chemicals that were widely used before 1970 in the electrical industry as coolants for transformers and in capacitors and other electrical devices. They caused environmental problems because they do not break down and can spread through the water, soil, and air. They have been linked by some scientists to cancer and reproductive disorders and have been shown to cause liver function abnormalities. Government action has resulted in the control of the use, disposal, and production of PCBs in nearly all areas of the world, including the United States.
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| Wikipedia: Polychlorinated biphenyl |
Polychlorinated biphenyls (PCBs) are a class of organic compounds with 1 to 10 chlorine atoms attached to biphenyl, which is a molecule composed of two benzene rings. The chemical formula for PCBs is C12H10-xClx, where x > 1. PCB's were widely used for many applications, especially as dielectric fluids in transformers and capacitors and coolants. Due to PCB's toxicity and classification as persistent organic pollutants, PCB production was banned by the United States Congress in 1976 and by the Stockholm Convention on Persistent Organic Pollutants in 2001.
Contents |
PCB congeners are odorless, tasteless, clear to pale-yellow, viscous liquids. They are formed by electrophilic chlorination of biphenyl with chlorine gas. Theoretically 209 different PCB congeners are possible, although only about 130 are found in commercial PCB mixtures.[1] Commercial PCBs preparations are usually mixtures of 50 or more PCB congeners.[1] Commercial PCB mixtures are clear to pale-yellow, viscous liquids (the more highly chlorinated mixtures are more viscous and deeper yellow - for example , Aroclor 1260 is a sticky yellowish resin). PCBs have low water solubilities — 0.0027-0.42 ng/L for Aroclors,[2] and low vapor pressures at room temperature, but they have high solubilities in most organic solvents, oils, and fats. They have high dielectric constants, very high thermal conductivity,[2] high flash points (from 170 to 380 °C)[2] and are chemically fairly inert, being extremely resistant to oxidation, reduction, addition, elimination, and electrophilic substitution.[3] The density varies from 1.182 to 1.566 kg/L.[2] Other physical and chemical properties vary widely across the class. As the degree of chlorination increases, melting point and lipophilicity increase, but vapour pressure and water solubility decrease.[2]
PCBs readily penetrate skin, PVC (polyvinyl chloride), and latex (natural rubber).[4] PCB-resistant materials include Viton, polyethylene, polyvinyl acetate (PVA), polytetrafluoroethylene (PTFE), butyl rubber, nitrile rubber, and Neoprene.[4]
PCBs are very stable compounds and do not degrade readily. Their destruction by chemical, thermal, and biochemical processes is extremely difficult, and presents the risk of generating extremely toxic dibenzodioxins and dibenzofurans through partial oxidation. Degradation processes are difficult to sustain. Intentional degradation as a treatment of unwanted PCBs generally requires high heat or catalysis.
Commercial PCB mixtures were marketed under the following names.[2][5]:
Brazil
Former Czechoslovakia
France
Germany
Italy
Japan
United Kingdom
United States
Former USSR
PCBs were used as coolants and insulating fluids (dielectric fluids) for transformers and capacitors, plasticizers in paints and cements, stabilizing additives in flexible PVC coatings of electrical wiring and electronic components, pesticide extenders, cutting oils, reactive flame retardants, lubricating oils, hydraulic fluids, sealants (for caulking in schools and commercial buildings[6]), adhesives, wood floor finishes (such as Fabulon and other products of Halowax in the U.S.),[6] paints, de-dusting agents, water-proofing compounds, casting agents, vacuum pump fluids, fixatives in microscopy, surgical implants, and in carbonless copy ("NCR") paper.[2]
PCBs, originally termed "chlorinated diphenyls," were commercially produced as complex mixtures containing multiple isomers at different degrees of chlorination. In the United States, commercial production of PCBs was taken over in 1929 by Monsanto from Swann Chemical Company. Manufacturing levels increased in response to the electrical industry's need for a "safer" (than flammable mineral oil) cooling and insulating fluid for industrial transformers and capacitors. PCBs were also commonly used as stabilizing additives in the manufacture of flexible PVC coatings for electrical wiring and electronic components to enhance the heat and fire resistance of the PVC.[7]
The toxicity associated with PCBs and other chlorinated hydrocarbons, including polychlorinated naphthalenes was recognized very early due to a variety of industrial incidents [8]. A conference about the hazards was organized at Harvard School of Public Health in 1937, and a number of publications referring to the toxicity of various chlorinated hydrocarbons were published before 1940 [9]. Robert Brown reminded chemists in 1947 that Arochlors were "objectionably toxic. Thus the maximum permissible concentration for an 8-hr. day is 1 mg/m3 of air[citation needed]. They also produce a "serious and disfiguring dermatitis".[10] However, PCB manufacture and use continued with few restraints until the 1970s.
PCBs are persistent organic pollutants and have entered the environment through both use and disposal. The environmental transport of PCBs is complex and nearly global in scale. The public, legal, and scientific concerns about PCBs arose from research indicating they were likely carcinogens having the potential to adversely impact the environment and therefore undesirable as commercial products. Despite active research spanning five decades, extensive regulatory actions, and an effective ban on their production since the 1970s, PCBs still persist in the environment and remain a focus of attention.[2]
The only North American producer, Monsanto, marketed PCBs under the trade name Aroclor from 1930 to 1977. These were sold under trade names followed by a 4 digit number. The first two digits generally refer to the number of carbon atoms in the biphenyl skeleton (for PCBs this is 12), the second two numbers indicate the percentage of chlorine by mass in the mixture. Thus, Aroclor 1260 has 12 carbon atoms and contains 60% chlorine by mass. An exception is Aroclor 1016, which also has 12 carbon atoms, but has 42% chlorine by mass. Different Aroclors were used at different times and for different applications. In electrical equipment manufacturing in the USA, Aroclor 1260 and Aroclor 1254 were the main mixtures used before 1950, Aroclor 1242 was the main mixture used in the 1950s and 1960s until it was phased out in 1971 and replaced by Aroclor 1016.[2]
Manufacture peaked in the 1960s, by which time the electrical industry had lobbied the U.S. Congress to make them mandatory safety equipment. In 1966, they were determined by Swedish chemist Dr. Soren Jensen to be an environmental contaminant[11], and it was Dr. Jensen, according to a 1994 article in Sierra, who named them PCBs. Previously, they had simply been called "phenols" or referred to by various trade names, such as Aroclor, Kennechlor, Pyrenol, Chlorinol and others.
Their commercial utility was based largely on their chemical stability, including low flammability, and desirable physical properties, including electrical insulating properties. Their chemical and physical stability has also been responsible for their continuing persistence in the environment, and the lingering interest decades after regulations were imposed to control environmental contamination.
In 1972, PCB production plants existed in Austria, the then Federal Republic of Germany, France, Great Britain, Italy, Japan, Spain, USSR, and USA.[2]
In 1973 the use of PCBs was banned in "open" or "dissipative" sources, such as:
However, they continued to be allowed in "totally enclosed uses" such as transformers and capacitors, which, in certain failure modes or out-of-specification conditions, can leak, catch fire, or explode. It was Ward B. Stone of the New York State Department of Environmental Conservation who first published his findings in the early 1970s that PCBs were leaking from transformers and had contaminated the soil at the bottom of utility poles[citation needed]. Concern over the toxicity and persistence (chemical stability) of PCBs in the environment led the United States Congress to ban their domestic production in 1979[12], although some use continues in closed systems such as capacitors and transformers.
"Enclosed uses" of PCBs include:
In the UK, closed uses of PCBs in new equipment were banned in 1981, when nearly all UK PCB synthesis ceased, but closed uses in existing equipment containing in excess of 5 litres of PCBs were not stopped until December 2000.[13]
In Japan, PCBs were first produced by Kanegafuchi Chemical Co. Ltd. (Kaneka) in 1954 and production continued until 1972 when the Japanese government banned the production, use, and import of PCBs.[2]
Estimates have put the total global production of PCBs on the order of 1.5 million tons. The United States was the single largest producer with over 600,000 tons produced between 1930 and 1977. The European region follows with nearly 450,000 tons through 1984. It is unlikely that a full inventory of global PCB production will ever be accurately tallied, as there were factories in Poland, East Germany, and Austria that produced unknown amounts of PCBs.[14]
Between approximately 1947 and 1977 General Electric Company (GE) released up to 1,300,000 pounds (590,000 kg) of PCBs into the Hudson River[15]. The PCBs came from the company's two capacitor manufacturing plants at Hudson Falls and Fort Edward in New York State.[15]
In 1976, because of concern over continuing high levels of PCBs in local fish and other aquatic organisms, and the unacceptable risk to the health of consumers of such fish, the New York State Department of Environmental Conservation banned all fishing in the Upper Hudson River, as well as commercial fishing of striped bass and several other species in the Lower Hudson River,[16][15] and also issued advisories restricting the consumption of fish caught within a 20-mile (30 km) long segment of the Hudson River from Hudson Falls to Troy.[15][17]
There have been many programs of remediation work to reduce the PCB pollution. In 1984, approximately 200 miles (320 km) of the Hudson River was designated a Superfund site, and attempts to cleanup the Upper Hudson River began, including the removal in 1977-8 of 180,000 cubic yards (140,000 m3) of contaminated river sediments near Fort Edward.[16] In 1991, further PCB pollution was found at Bakers Falls near the former GE Hudson Falls factory, and a program of remediation was started.[16] In August 1995, a 40-mile (64 km) reach of the Upper Hudson was re-opened to fishing but only on a catch-and-release basis.[16] Removal of contaminated soil from Rogers Island was completed in December 1999.[16] In 2002, the United States Environmental Protection Agency announced a further 2,650,000 cubic yards (2,030,000 m3) of contaminated sediments in the Upper Hudson River would be removed.
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From the late 1950s through 1977, Westinghouse Electric used PCBs in the manufacture of capacitors in its Bloomington, Indiana plant. Reject capacitors were hauled and dumped in area salvage yards and landfills. Workers also dumped PCB oil down factory drains which contaminated the city sewage treatment plant.[citation needed] The City of Bloomington gave away the sludge to area farmers and gardeners, creating anywhere from 200 to 2000 sites which remain unaddressed. Over 2 million pounds of PCBs were estimated to have been dumped in Monroe and Owen Counties, which would make it the biggest concentration of PCBs in the world.[citation needed] Although federal and state authorities have been working on the site remediations, many areas remain contaminated. Concerns have been raised regarding the removal of PCBs from the karst limestone topography, and regarding the possible disposal options. To date, the Westinghouse Bloomington PCB Superfund site case does not have a RI/FS (Remedial Investigation/Feasibility Study) and ROD (Record of Decision), although Westinghouse signed a US Department of Justice Consent Decree in 1985.[citation needed] On February 15, 2008, Monroe County approved a plan to clean up the 3 remaining contaminated sites in the City of Bloomington, at a cost of $9.6m to CBS Corp., the successor of Westinghouse. [18]
Much of the Great Lakes area is still heavily polluted with PCBs, despite extensive remediation work.[19] Locally caught fresh water fish and shellfish are contaminated with PCBs and their consumption is restricted.
From 1959 to 1971, Waukegan Harbor in Illinois on Lake Michigan was contaminated with PCB's discharged by the Outboard Marine Corp.
In 1999, the Dioxine affair caused serious trouble for the Belgian government when PCBs were found in chicken and eggs.
In December of 2008 a number of Irish news sources reported that testing had revealed "extremely high"[20] levels of PCBs in pork products, ranging from 80 to 200 times the EU's upper safe limit of 1.5 pg/μg i.e. 0.12 to 0.3 parts per billion.[21][22] The PCB levels involved are small in comparison to other contamination incidents, indeed in 1986 the breast milk of healthy nursing mothers in the US contained between 1020 to 1770 ppb of PCBs and the PCB contaminated rice-bran oil that caused mass poisoning (Yu-Cheng) in Taiwan in 1979 contained between 53,000 to 99,000 ppb of PCBs.[23][24][25]
Brendan Smith, the Minister for Agriculture, Fisheries & Food, stated that pork contamination was caused by PCB contaminated feed that was used on 9 out of the 400 of Ireland's pig farms and only one feed supplier was involved.[21][26] Smith added that 38 beef farms also used the same contaminated feed, but those farms were quickly isolated and no contaminated beef entered the food chain.[27] While the contamination was limited to just 9 pig farms, the Irish government requested the immediate withdrawal and disposal of all pork-containing products produced in Ireland and purchased since September 1st 2008.
This request for withdrawal of pork products was confirmed in a press release by the Food Safety Authority of Ireland on December 6th.[28]
PCBs have been detected globally in the atmosphere, from the most urbanized areas that are the centers for PCB pollution, to regions north of the Arctic Circle. The atmosphere serves as the primary route for global transport of PCBs, particularly for those congeners with 1 to 4 chlorine atoms.
Atmospheric concentrations of PCBs tend to be lowest in rural areas, where they are typically in the picogram per cubic meter range, higher in suburban and urban areas, and highest in city centres, where they can reach 1 ng/m³ or more. In Milwaukee, an atmospheric concentration of 1.9 ng/m³ has been measured, and this source alone was estimated to account for 120 kg/year of PCBs entering Lake Michigan.[29] Concentrations as high as 35 ng/m³, 10 times higher than the EPA guideline limit of 3.4 ng/m³, have been found inside some houses in the U.S.[6]
Volatilization of PCBs in soil was thought to be the primary source of PCBs in the atmosphere, but recent research suggests that ventilation of PCB-contaminated indoor air from buildings is the primary source of PCB contamination in the atmosphere.[30]
The toxicity of PCBs to animals was first noticed in the 1970s when emaciated seabird corpses with very high PCB body burdens washed up on beaches. Since seabirds may die far out at sea and still wash ashore, the true sources of the PCBs were unknown. Where they were found is no reliable indicator of where they had died.
The toxicity of PCBs varies considerably among congeners. The coplanar PCBs, known as non-ortho PCBs because they are not substituted at the ring positions ortho to (next to) the other ring, (i.e. PCBs 77, 126, 169, etc), tend to have dioxin-like properties, and generally are among the most toxic congeners. Because PCBs are almost invariably found in complex mixtures, the concept of toxic equivalency factors (TEFs) has been developed to facilitate risk assessment and regulatory control, where more toxic PCB congeners are assigned higher TEF values. One of the most toxic compounds known, 2,3,7,8-tetrachlorodibenzo[p]dioxin, is assigned a TEF of 1.[31]
A few studies of workers indicate that PCBs were associated with specific kinds of cancer in humans, such as cancer of the liver and biliary tract. Rats that ate food containing high levels of PCBs for two years developed liver cancer. The Department of Health and Human Services (DHHS) has concluded that PCBs may reasonably be anticipated to be carcinogens. The US Environmental Protection Agency (EPA) and the International Agency for Research on Cancer (IARC) have determined that PCBs are probably carcinogenic to humans. PCBs are also classified as probable human carcinogens by the National Cancer Institute, World Health Organization, and the Agency for Toxic Substances and Disease Registry. Recent research by the National Toxicology Program has confirmed that PCB126 (Technical Report 520) and a binary mixture of PCB126 and PCB153 (Technical Report 531) are carcinogens.
As discussed, PCBs exhibit a wide range of toxic effects. These effects may vary depending on the specific PCB. Similar to dioxin, toxicity of coplanar PCBs and mono-ortho-PCBs are thought to be primarily mediated via binding to aryl hydrocarbon receptor (AhR).[37][38] Because AhR is a transcription factor, abnormal activation may disrupt cell function by altering the transcription of genes. The concept of toxic equivalency factors (TEF) is based on the ability of a PCB to activate AhR.
However, not all effects may be mediated by the AhR receptor. For example, di-ortho-substituted non-coplanar PCBs interfere with intracellular signal transduction dependent on calcium; this may lead to neurotoxicity.[39] Ortho-PCBs may disrupt thyroid hormone transport by binding to transthyretin.[40]
Landfill – Large quantities of PCBs have been placed in landfill sites, mainly in the form of transformers and capacitors. Many municipal sites are not designed to contain these pollutants and PCBs are able to escape into the atmosphere or ground water. No emissions above background are seen if the landfill is designed correctly.
These can be separated into three distinct categories: physical, microbial, and chemical destruction.
Incineration – Although PCBs do not ignite themselves, they can be combusted under extreme and carefully controlled conditions. The current regulations require that PCBs are burnt at a temperature of 1200 °C for at least two seconds, in the presence of fuel oil and excess oxygen. A lack of oxygen can result in the formation of PCDDs, PCDFs and dioxins, or the incomplete destruction of the PCBs. Such specific conditions mean that it is extremely expensive to destroy PCBs on a tonnage scale, and it can only be used on PCB containing equipment and contaminated liquid. This method is not suitable for the decontamination of affected soils.
Ultrasound – In a similar process to combustion, high power ultrasonic waves are applied to water, generating cavitation bubbles. These then implode or fragment, creating microregions of extreme pressures and temperatures where the PCBs are destroyed. Water is thought to undergo thermolysis, oxidising the PCBs to CO, CO2 and hydrocarbons such as biphenyl, and releasing chlorine. The scope of this method is limited to those congeners which are the most water soluble; those isomers with the least chlorine substitution.
Irradiation – If a deoxygenated mixture of PCBs in isopropanol or mineral oil is subject to irradiation with gamma rays then the PCBs will be dechlorinated to form inorganic chloride and biphenyl. The reaction works best in isopropanol if potassium hydroxide (caustic potash) is added. Solvated electrons are thought to be responsible for the reaction. If oxygen, nitrous oxide, sulfur hexafluoride or nitrobenzene is present in the mixture then the reaction rate is reduced. This work has been done recently in the US often with used nuclear fuel as the radiation source[2][3].
Pyrolysis – Destruction of PCBs with pyrolysis using plasma arc processes, like incineration uses heat, however unlike incineration, there is no combustion. The long chain molecules are broken with extreme temperature provided by an electric arc in an inert environment. Adequate post pyrolisis post treatment of the resultant products is required in order to prevent the risk of back reactions.
Much recent work has centered on the study of micro-organisms that are able to decompose PCBs. Generally, these organisms work in one of two ways: either they use the PCB as a carbon source, or destruction takes place through reductive dechlorination, with the replacement of chlorine with hydrogen on the biphenyl skeleton. However, there are significant problems with this approach. Firstly, these microbes tend to be highly selective in their dechlorination, with lower chlorinated biphenyls being readily transformed, and with preference to dechlorination in the para and meta positions. Secondly, microbial dechlorination tends to be rather slow acting on PCB as a soil contaminant in comparison to other methods. Finally, while microbes work well in laboratory conditions, there is often a problem in transferring a successful laboratory strain to a natural system. This is because the microbes can access other sources of carbon, which they decompose in preference to PCBs.
Further recent developments have focused on testing enzymes and vitamins extracted from microbes which show PCB activity. Especially promising seems to be the use of vitamin B12, in which a cobalt ion is in oxidation state (III) under normal redox conditions. Using titanium (III) citrate as a strong reductant converts the cobalt from Co(III) to Co(I), giving a new vitamin known as B12s, which is a powerful nucleophile and reducing catalyst. This can then be used on PCBs, which it dechlorinates in a rapid and selective manner.[41]
Many chemical methods are available to destroy or reduce the toxicity of PCBs.
Nucleophilic aromatic substitution is a method of destroying low concentration PCB mixtures in oils, such as transformer oil. Substitution of chlorine by polyethylene glycols) occurs in under two hours under a blanket of nitrogen, to prevent oxidation of the oil, to produce aryl polyglycols, which are insoluble in the oil and precipitate out.
Between 700 and 925 °C, H2 cleaves the carbon-chlorine bond, and cleaves the biphenyl nucleus into benzene yielding HCl without a catalyst. This can be performed at lower temperatures with a copper catalyst, and to yield biphenyl. However, since both of these routes require an atmosphere of hydrogen gas and relatively high temperatures, they are prohibitively expensive.
Reaction with highly electropositive metals, or strong reducing agents such as sodium naphthalide, in aprotic solvents results in a transfer of electrons to the PCB, the expulsion of a chloride ion, and a coupling of the PCBs. This is analogous to the Wurtz reaction for coupling halogenoalkanes. The effect is to polymerise many molecules, therefore reducing the volatility, solubility and toxicity of the mixture. This methodology is most successful on low strength PCB mixtures and can also be performed electrochemically in a partly aqueous bicontinuous microemulsion.
The solution photochemistry of PCBs is based on the transfer of an electron to a photochemically excited PCB from a species such as an amine, to give a radical anion. This either expels a chloride ion and the resulting aryl radical extracts a hydrogen atom from the solvent, or immediately becomes protonated, leading to the loss of a chlorine atom. It is useful only for water soluble PCBs.
The major pathway for atmospheric destruction of PCBs is via attack by OH radicals. Direct photolysis can occur in the upper atmosphere, but the ultraviolet wavelengths necessary to excite PCBs are shielded from the troposphere by the ozone layer. It has, however, been shown that higher wavelengths of light (> 300 nm) can degrade PCBs in the presence of a photosensitizer, such as acetone.
The Schwartz reaction is the subject of much study, and has significant benefits over other routes. It is advantageous since it proceeds via a reductive process, and thus yields no dioxins through oxidation. The proposed reaction scheme involves the electron transfer from a titanium (III) organometallic species to form a radical anion on the PCB molecule which expels chlorine to eventually form the relatively non-toxic biphenyl.
For a complete list of PCB congeners, see PCB Congener List. Note that biphenyl, while not technically a PCB congener due to its lack of chlorine substituents, is still typically included in the literature.
| PCB Homolog | CASRN | Cl Substituents | Number of Congeners |
|---|---|---|---|
| Biphenyl | 92-52-4 | 0 | 1 |
| Monochlorobiphenyl | 27323-18-8 | 1 | 3 |
| Dichlorobiphenyl | 55512-42-9 | 2 | 12 |
| Trichlorobiphenyl | 25323-68-6 | 3 | 24 |
| Tetrachlorobiphenyl | 26914-33-0 | 4 | 42 |
| Pentachlorobiphenyl | 25429-29-2 | 5 | 46 |
| Hexachlorobiphenyl | 26601-64-9 | 6 | 42 |
| Heptachlorobiphenyl | 28655-71-2 | 7 | 24 |
| Octachlorobiphenyl | 55722-26-4 | 8 | 12 |
| Nonachlorobiphenyl | 53742-07-7 | 9 | 3 |
| Decachlorobiphenyl | 2051-24-3 | 10 | 1 |
|
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| Translations: Pcb |
Dansk (Danish)
abbr. - printed circuit board; printplade, polychlorinated biphenol (polychloreret biphenyl)
n. - printed circuit board; printplade
Nederlands (Dutch)
PCB (polychloorbifenyl), printplaat
Français (French)
abbr. - polychlorobiphénile
n. - polychlorobiphénile
Deutsch (German)
abbr. - Polychlorinbiphenyl
n. - (Elektr.) Druckschaltung, (Chem.) Polychlorinbiphenyl
Ελληνική (Greek)
abbr. - (Η/Υ) κάρτα τυπωμένου κυκλώματος
Italiano (Italian)
policlorurato
Português (Portuguese)
abbr. - bifenil (m) policlorado (Quím.)
Русский (Russian)
полихлоробифенил
Español (Spanish)
abbr. - tarjeta de circuito impreso
n. - tarjeta de circuito impreso
Svenska (Swedish)
abbr. - polychlorinated biphenyl
中文(简体)(Chinese (Simplified))
零用现金簿, 进程控制块, 多氯化联苯, 印刷电路板
中文(繁體)(Chinese (Traditional))
abbr. - 零用現金簿, 進程控制塊, 多氯化聯苯
n. - 印刷電路板
한국어 (Korean)
abbr. - polychlorinated biphenyl(폴리 염화 비페닐)
n. - 폴리 염화 비페닐
日本語 (Japanese)
abbr. - ポリ塩化ビフェニール
العربيه (Arabic)
(اختصار) مادة كيماويه سامه
עברית (Hebrew)
abbr. - (כימיה) חומר שקוף ורעיל ליצור רכיבים אלקטרוניים
n. - לוח מעגלים מודפסים (מחשבים)
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| polychlorinated biphenyl (organic chemistry) | |
| circuit trace (technology) | |
| Luís Carlos Prestes (Brazilian politician) |
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![]() | Columbia Encyclopedia. The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2003, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/ Read more | |
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