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Coal tar is a thick dark liquid which is a by-product of the production of coke and
coal gas Coal gas is a flammable gaseous fuel made from coal and supplied to the user via a piped distribution system. It is produced when coal is heated strongly in the absence of air. Town gas is a more general term referring to manufactured gaseous ...
from
coal Coal is a combustible black or brownish-black sedimentary rock, formed as rock strata called coal seams. Coal is mostly carbon with variable amounts of other elements, chiefly hydrogen, sulfur, oxygen, and nitrogen. Coal is formed when dead ...
. It is a type of
creosote Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood or fossil fuel. They are typically used as preservatives or antiseptics. Some creosote types were ...
. It has both medical and industrial uses. Medicinally it is a
topical medication A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...
applied to
skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different de ...
to treat
psoriasis Psoriasis is a long-lasting, noncontagious autoimmune disease characterized by raised areas of abnormal skin. These areas are red, pink, or purple, dry, itchy, and scaly. Psoriasis varies in severity from small, localized patches to complete ...
and
seborrheic dermatitis Seborrhoeic dermatitis, sometimes inaccurately referred to as seborrhoea, is a long-term skin disorder. Symptoms include red, scaly, greasy, itchy, and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including th ...
(dandruff). It may be used in combination with
ultraviolet light therapy Ultraviolet light therapy or ultraviolet phototherapy is a form of treatment for certain skin disorders including atopic skin disorder and vitiligo when used with psoralen to form the PUVA treatment. It consists of irradiation of the patient wi ...
. Industrially it is a
railroad tie A railroad tie, crosstie (American English), railway tie (Canadian English) or railway sleeper (Australian and British English) is a rectangular support for the rails in railroad tracks. Generally laid perpendicular to the rails, ties transfer ...
preservative and used in the surfacing of roads. Coal tar was listed as a known human carcinogen in the first Report on Carcinogens from the U.S. Federal Government. Coal tar was discovered circa 1665 and used for medical purposes as early as the 1800s. Circa 1850, the discovery that it could be used as the main ingredient in
synthetic dyes A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and ...
engendered an entire industry. It is on the
World Health Organization's List of Essential Medicines The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...
. Coal tar is available as a
generic medication A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active c ...
and
over the counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
. Side effects include skin irritation, sun sensitivity,
allergic reactions Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic dermati ...
, and skin discoloration. It is unclear if use during
pregnancy Pregnancy is the time during which one or more offspring develops ( gestates) inside a woman's uterus (womb). A multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occurs by sexual intercourse, but can ...
is safe for the baby and use during
breastfeeding Breastfeeding, or nursing, is the process by which human breast milk is fed to a child. Breast milk may be from the breast, or may be expressed by hand or pumped and fed to the infant. The World Health Organization (WHO) recommends that brea ...
is not typically recommended. The exact mechanism of action is unknown. It is a complex mixture of
phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are ...
,
polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
s (PAHs), and
heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
s. It demonstrates
antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryp ...
,
anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as op ...
, anti-itch, and
antiparasitic Antiparasitics are a class of medications which are indicated for the treatment of parasitic diseases, such as those caused by helminths, amoeba, ectoparasites, parasitic fungi, and protozoa, among others. Antiparasitics target the parasitic agent ...
properties.


Uses


Medicine

Coal tar is used in medicated
shampoo Shampoo () is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the s ...
,
soap Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are used ...
and
ointment A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes ...
. It demonstrates
antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryp ...
,
anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as op ...
, anti-itch, and
antiparasitic Antiparasitics are a class of medications which are indicated for the treatment of parasitic diseases, such as those caused by helminths, amoeba, ectoparasites, parasitic fungi, and protozoa, among others. Antiparasitics target the parasitic agent ...
properties. It may be applied topically as a treatment for
dandruff Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, ...
and
psoriasis Psoriasis is a long-lasting, noncontagious autoimmune disease characterized by raised areas of abnormal skin. These areas are red, pink, or purple, dry, itchy, and scaly. Psoriasis varies in severity from small, localized patches to complete ...
, and to kill and repel
head lice The head louse (''Pediculus humanus capitis'') is an obligate ectoparasite of humans. Head lice are wingless insects that spend their entire lives on the human scalp and feeding exclusively on human blood. Humans are the only known hosts of th ...
. It may be used in combination with
ultraviolet light therapy Ultraviolet light therapy or ultraviolet phototherapy is a form of treatment for certain skin disorders including atopic skin disorder and vitiligo when used with psoralen to form the PUVA treatment. It consists of irradiation of the patient wi ...
. Coal tar may be used in two forms: crude coal tar ( la, pix carbonis) or a coal tar solution ( la, liquor picis carbonis, LPC) also known as liquor carbonis detergens (LCD). Named brands include Denorex, Balnetar, Psoriasin, Tegrin, T/Gel, and Neutar. When used in the extemporaneous preparation of topical medications, it is supplied in the form of coal tar topical solution USP, which consists of a 20% w/v solution of coal tar in
alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...
, with an additional 5% w/v of
polysorbate 80 Polysorbate 80 is a nonionic surfactant and emulsifier often used in pharmaceuticals, foods, and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid. Chemistry Polysorbate 80 is derived from polyethoxylated sorbitan an ...
 USP; this must then be diluted in an ointment base such as
petrolatum Petroleum jelly, petrolatum, white petrolatum, soft paraffin, or multi-hydrocarbon, CAS number 8009-03-8, is a semi-solid mixture of hydrocarbons (with carbon numbers mainly higher than 25), originally promoted as a topical ointment for its he ...
.


Construction

Coal tar was a component of the first sealed roads. In its original development by
Edgar Purnell Hooley Edgar Purnell Hooley (5 June 1860 – 26 January 1942) was a Welsh inventor. After inventing tarmac in 1902, he founded Tar Macadam Syndicate Ltd the following year and registered tarmac as a trademark. Following a merger in 2013 the business be ...
, tarmac was tar covered with granite chips. Later the filler used was industrial
slag Slag is a by-product of smelting ( pyrometallurgical) ores and used metals. Broadly, it can be classified as ferrous (by-products of processing iron and steel), ferroalloy (by-product of ferroalloy production) or non-ferrous/base metals (by-pr ...
. Today, petroleum derived binders and sealers are more commonly used. These sealers are used to extend the life and reduce maintenance cost associated with
asphalt Asphalt, also known as bitumen (, ), is a sticky, black, highly viscous liquid or semi-solid form of petroleum. It may be found in natural deposits or may be a refined product, and is classed as a pitch. Before the 20th century, the term a ...
pavements, primarily in asphalt road paving, car parks and walkways. Coal tar is incorporated into some parking-lot
sealcoat Sealcoating, or pavement sealing, is the process of applying a protective coating to asphalt-based pavements to provide a layer of protection from the elements: water, oils, and U.V. damage. The effects of asphalt sealers have been debated. Aspha ...
products used to protect the structural integrity of the underlying pavement. Sealcoat products that are coal-tar based typically contain 20 to 35 percent coal-tar pitch. Research shows it is used throughout the
United States of America The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...
, however several areas have banned its use in sealcoat products, including the District of Columbia; the city of Austin, Texas; Dane County, Wisconsin; the state of Washington; and several municipalities in Minnesota and others.


Industry

Being flammable, coal tar is sometimes used for heating or to fire
boilers A boiler is a closed vessel in which fluid (generally water) is heated. The fluid does not necessarily boil. The heated or vaporized fluid exits the boiler for use in various processes or heating applications, including water heating, central h ...
. Like most heavy oils, it must be heated before it will flow easily. A large part of the binder used in the
graphite Graphite () is a crystalline form of the element carbon. It consists of stacked layers of graphene. Graphite occurs naturally and is the most stable form of carbon under standard conditions. Synthetic and natural graphite are consumed on lar ...
industry for making "green blocks" is coke oven volatiles (COV), a considerable portion of which is coal tar. During the baking process of the green blocks as a part of commercial graphite production, most of the coal tar binders are vaporised and are generally burned in an incinerator to prevent release into the atmosphere, as COV and coal tar can be injurious to health. Coal tar is also used to manufacture paints, synthetic dyes (notably
tartrazine Tartrazine is a synthetic lemon yellow azo dye primarily used as a food coloring. It is also known as E number E102, C.I. 19140, FD&C Yellow 5, Yellow 5 Lake, Acid Yellow 23, Food Yellow 4, and trisodium 1-(4-sulfonatophenyl)-4-(4-sulfonatop ...
/Yellow #5), and photographic materials. In the
coal gas Coal gas is a flammable gaseous fuel made from coal and supplied to the user via a piped distribution system. It is produced when coal is heated strongly in the absence of air. Town gas is a more general term referring to manufactured gaseous ...
era, there were many companies in Britain whose business was to
distill Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heating ...
coal tar to separate the higher-value fractions, such as
naphtha Naphtha ( or ) is a flammable liquid hydrocarbon mixture. Mixtures labelled ''naphtha'' have been produced from natural gas condensates, petroleum distillates, and the distillation of coal tar and peat. In different industries and regions '' ...
,
creosote Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood or fossil fuel. They are typically used as preservatives or antiseptics. Some creosote types were ...
and pitch. Many industrial chemicals were first isolated from coal tar during this time. These companies included: * Bonnington Chemical Works * British Tar Products * Lancashire Tar Distillers * Midland Tar Distillers *
Newton, Chambers & Company Newton, Chambers & Co. was one of England's largest industrial companies. It was founded in 1789 by George Newton and Thomas Chambers. History George Newton and Thomas Chambers were partners in the Phoenix foundry at Snow Hill, Sheffield an ...
(owners of Izal brand disinfectant) * Sadlers Chemicals In modern times, coal tar is mostly traded as fuel and an application for tar, such as roofing. The total value of the trade in coal tar is around US$20 billion each year.


Safety

Side effects of coal tar products include skin irritation, sun sensitivity,
allergic reactions Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic dermati ...
, and skin discoloration. It is unclear if use during
pregnancy Pregnancy is the time during which one or more offspring develops ( gestates) inside a woman's uterus (womb). A multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occurs by sexual intercourse, but can ...
is safe for the baby and use during
breastfeeding Breastfeeding, or nursing, is the process by which human breast milk is fed to a child. Breast milk may be from the breast, or may be expressed by hand or pumped and fed to the infant. The World Health Organization (WHO) recommends that brea ...
is not typically recommended. According to the National Psoriasis Foundation, coal tar is a valuable, safe and inexpensive treatment option for millions of people with
psoriasis Psoriasis is a long-lasting, noncontagious autoimmune disease characterized by raised areas of abnormal skin. These areas are red, pink, or purple, dry, itchy, and scaly. Psoriasis varies in severity from small, localized patches to complete ...
and other scalp or skin conditions. According to the
FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food s ...
, coal tar concentrations between 0.5% and 5% are considered safe and effective for psoriasis.


Cancer

Long-term, consistent exposure to coal tar likely increases the risk of non-melanoma
skin cancer Skin cancers are cancers that arise from the skin. They are due to the development of abnormal cells that have the ability to invade or spread to other parts of the body. There are three main types of skin cancers: basal-cell skin cancer (BC ...
s. Evidence is inconclusive whether medical coal tar, which does not remain on the skin for the long periods seen in occupational
exposure Exposure or Exposures may refer to: People * The Exposures, a pseudonym for German electronic musician Jan Jeline Arts, entertainment, and media Films * ''Exposure'' (film), a 1932 American film * ''Exposure'', another name for the 1991 movie ...
, causes cancer, because there is insufficient data to make a judgment. While coal tar consistently causes cancer in cohorts of workers with chronic occupational exposure, animal models, and mechanistic studies, the data on short-term use as medicine in humans has so far failed to show any consistently significant increase in rates of cancer. Coal tar contains many
polycyclic aromatic hydrocarbons A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. P ...
, and it is believed that their metabolites bind to DNA, damaging it. The PAHs found in coal tar and air pollution induce
immunosenescence Immunosenescence is the gradual deterioration of the immune system, brought on by natural age advancement. A 2020 review concluded that the adaptive immune system is affected more than the innate immune system. Immunosenescence involves both the h ...
and cytotoxicity in epidermal cells. It's possible that the skin can repair itself from this damage after short-term exposure to PAHs but not after long-term exposure. Long-term skin exposure to these compounds can produce " tar warts", which can progress to
squamous cell carcinoma Squamous-cell carcinomas (SCCs), also known as epidermoid carcinomas, comprise a number of different types of cancer that begin in squamous cells. These cells form on the surface of the skin, on the lining of hollow organs in the body, and on th ...
. Coal tar was one of the first chemical substances proven to cause cancer from occupational exposure, during research in 1775 on the cause of
chimney sweeps' carcinoma Chimney sweep's cancer, also called soot wart, is a squamous cell carcinoma of the skin of the scrotum. It has the distinction of being the first reported form of occupational cancer, and was initially identified by Percivall Pott in 1775. It ...
. Modern studies have shown that working with coal tar pitch, such as during the paving of roads or when working on roofs, increases the risk of cancer. The
International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...
lists coal tars as
Group 1 Group 1 may refer to: * Alkali metal, a chemical element classification for Alkali metal * Group 1 (racing) The Group 1 racing class referred to FIA regulations for cars in touring car racing and rallying. Throughout its existence the group reta ...
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substa ...
s, meaning they directly cause cancer. The U.S. Department of Health and Human Services lists coal tars as known human carcinogens. In response to public health concerns regarding the carcinogenicity of PAHs some municipalities, such as the city of Milwaukee, have banned the use of common coal tar-based road and driveway sealants citing concerns of elevated PAH content in groundwater.


Other

Coal tar causes increased sensitivity to sunlight, so skin treated with topical coal tar preparations should be protected from sunlight. The residue from the
distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heating ...
of high-temperature coal tar, primarily a complex mixture of three or more membered condensed ring
aromatic hydrocarbon Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
s, was listed on 13 January 2010 as a
substance of very high concern A substance of very high concern (SVHC) is a chemical substance (or part of a group of chemical substances) concerning which it has been proposed that use within the European Union be subject to authorisation under the REACH Regulation. Indeed, li ...
by the
European Chemicals Agency The European Chemicals Agency (ECHA; ) is an agency of the European Union which manages the technical and administrative aspects of the implementation of the European Union regulation called Registration, Evaluation, Authorisation and Restrict ...
.


Mechanism of action

The exact mechanism of action is unknown. Coal tar is a complex mixture of
phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are ...
,
polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
s (PAHs), and
heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
s. It is a
keratolytic Keratolytic () therapy is a type of medical treatment to remove warts, calluses and other lesions in which the epidermis produces excess skin. In this therapy, acidic topical medicines, such as Whitfield's ointment or Jessner's solution, are ap ...
agent, which reduces the growth rate of skin cells and softens the skin's
keratin Keratin () is one of a family of structural fibrous proteins also known as ''scleroproteins''. Alpha-keratin (α-keratin) is a type of keratin found in vertebrates. It is the key structural material making up scales, hair, nails, feathers, ho ...
.


Composition

Coal tar is produced through thermal destruction (
pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''pyr ...
) of
coal Coal is a combustible black or brownish-black sedimentary rock, formed as rock strata called coal seams. Coal is mostly carbon with variable amounts of other elements, chiefly hydrogen, sulfur, oxygen, and nitrogen. Coal is formed when dead ...
. Its composition varies with the process and type of coal used –
lignite Lignite, often referred to as brown coal, is a soft, brown, combustible, sedimentary rock formed from naturally compressed peat. It has a carbon content around 25–35%, and is considered the lowest rank of coal due to its relatively low hea ...
,
bituminous Asphalt, also known as bitumen (, ), is a sticky, black, highly viscous liquid or semi-solid form of petroleum. It may be found in natural deposits or may be a refined product, and is classed as a pitch. Before the 20th century, the term a ...
or
anthracite Anthracite, also known as hard coal, and black coal, is a hard, compact variety of coal that has a submetallic luster. It has the highest carbon content, the fewest impurities, and the highest energy density of all types of coal and is the high ...
. Coal tar is a mixture of approximately 10,000 chemicals, of which only about 50% have been identified. Most of the chemical compounds are
polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
: *
polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...
s (4-rings:
chrysene Chrysene is a polycyclic aromatic hydrocarbon (PAH) with the molecular formula that consists of four fused benzene rings. It is a natural constituent of coal tar, from which it was first isolated and characterized. It is also found in creosote ...
,
fluoranthene 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 ...
,
pyrene Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is . This yellow solid is the smallest peri-fused PAH (one where the rings are fused through mor ...
,
triphenylene Triphenylene is an organic compound with the formula (C6H4)3. A flat polycyclic aromatic hydrocarbon (PAH), it consists of four fused benzene rings. Triphenylene has delocalized 18-''π''-electron systems based on a planar structure, correspondin ...
, naphthacene,
benzanthracene Benz 'a''nthracene or benzo 'a''nthracene is a polycyclic aromatic hydrocarbon with the chemical formula C18H12. It is produced during incomplete combustion of organic matter. Benz 'a''nthracene is one of carcinogenic constituents of tobacco sm ...
, 5-rings:
picene Picene is a hydrocarbon found in the pitchy residue obtained in the distillation of peat tar and of petroleum. This is distilled to dryness and the distillate repeatedly recrystallized from cymene. It may be synthetically prepared by the acti ...
, benzo yrene, benzo yrene, benzofluoranthenes,
perylene Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry ...
, 6-rings:
dibenzopyrenes Dibenzopyrenes are a group of high molecular weight polycyclic aromatic hydrocarbons with the molecular formula C24H14. There are five isomers of dibenzopyrene which differ by the arrangement of aromatic rings: dibenzo 'a'',''e''yrene, dibenzo 'a ...
, dibenzofluoranthenes, benzoperylenes, 7-rings:
coronene Coronene (also known as superbenzene and cyclobenzene) is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is . It is a yellow material that dissolves in common solvents including benzene, tol ...
) * methylated and polymethylated derivatives, mono- and polyhydroxylated derivatives, and
heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
s. Others:
benzene 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 ...
,
toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...
,
xylene In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are su ...
s,
cumene Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearl ...
s,
coumarone 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 ...
,
indene Indene is a flammable polycyclic hydrocarbon with chemical formula . It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of in ...
,
benzofuran 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 i ...
,
naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08  ppm by mass. As an aromati ...
and methyl-naphthalenes,
acenaphthene Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound. Production and reactions Acenaph ...
,
fluorene Fluorene , or 9''H''-fluorene is an organic compound with the formula (C6H4)2CH2. It forms white crystals that exhibit a characteristic, aromatic odor similar to that of naphthalene. It has a violet fluorescence, hence its name. For commercial p ...
,
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 requir ...
,
cresol Cresols (also hydroxytoluene or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also categorized as methylphenols. ...
s,
pyridine Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with ...
,
picoline Picoline refers to any of three isomers of methylpyridine (CH3C5H4N). They are all colorless liquids with a characteristic smell similar to that of pyridine. They are miscible with water and most organic solvents. The CAS number of an unspecifie ...
s, phenanthracene,
carbazole Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole str ...
,
quinoline Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only sl ...
s,
fluoranthene 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 ...
. Many of these constituents are known carcinogens.


Derivatives

Various
phenolic Phenolic is an adjective and a substantive (noun) that may apply to : * Phenol (or carbolic acid), a colorless crystalline solid and aromatic compound * Phenols, a class of chemical compounds that include phenol * Phenolic content in wine * Phenol ...
coal tar derivatives have
analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It i ...
(pain-killer) properties. These included
acetanilide Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It is also known as ''N''-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin. Preparation and properties Acetanilide can be ...
,
phenacetin Phenacetin (acetophenetidin, ''N''-(4-ethoxyphenyl)acetamide) is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn ...
, and
paracetamol Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
aka
acetaminophen Paracetamol, also known as acetaminophen, is a medication used to treat fever and mild to moderate pain. Common brand names include Tylenol and Panadol. At a standard dose, paracetamol only slightly decreases body temperature; it is inferior ...
. Paracetamol may be the only coal-tar derived analgesic still in use today. Industrial
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 requir ...
is now usually synthesized from crude oil rather than coal tar. Coal tar derivatives are contra-indicated for people with the inherited red cell blood disorder
glucose-6-phosphate dehydrogenase deficiency Glucose-6-phosphate dehydrogenase deficiency (G6PDD), which is the most common enzyme deficiency worldwide, is an inborn error of metabolism that predisposes to red blood cell breakdown. Most of the time, those who are affected have no symptoms. ...
(G6PD deficiency), as they can cause oxidative stress leading to red blood cell breakdown.


Society and culture

Coal tar is on the
World Health Organization's List of Essential Medicines The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...
, the most effective and safe medicines needed in a
health system Health, according to the World Health Organization, is "a state of complete physical, Mental health, mental and social well-being and not merely the absence of disease and infirmity".World Health Organization. (2006)''Constitution of the World H ...
. Coal tar is generally available as a
generic medication A generic drug is a pharmaceutical drug that contains the same chemical substance as a drug that was originally protected by chemical patents. Generic drugs are allowed for sale after the patents on the original drugs expire. Because the active c ...
and
over the counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
.


Regulation

Exposure to coal tar pitch volatiles can occur in the workplace by breathing, skin contact, or eye contact. The
Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agenc ...
(OSHA) has set the
permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational S ...
) to 0.2 mg/m3
benzene 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 ...
-soluble fraction over an 8-hour workday. The
National Institute for Occupational Safety and Health The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...
(NIOSH) has set a
recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...
(REL) of 0.1 mg/m3 cyclohexane-extractable fraction over an 8-hour workday. At levels of 80 mg/m3, coal tar pitch volatiles are
immediately dangerous to life and health The term immediately dangerous to life or health (IDLH) is defined by the US National Institute for Occupational Safety and Health (NIOSH) as exposure to airborne contaminants that is "likely to cause death or immediate or delayed permanent advers ...
. When used as a medication in the United States, coal tar preparations are considered
over-the-counter drug Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid prescr ...
pharmaceuticals and are subject to regulation by the
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food s ...
(FDA).


See also

*
Coal oil Coal oil is a shale oil obtained from the destructive distillation of cannel coal, mineral wax, or bituminous shale, once used widely for illumination. Chemically similar to the more refined, petroleum-derived kerosene, it consists mainly of se ...
*
Wood tar Tar is a dark brown or black viscous liquid of hydrocarbons and free carbon, obtained from a wide variety of organic materials through destructive distillation. Tar can be produced from coal, wood, petroleum, or peat. "a dark brown or bl ...


References


External links

* * * * {{Authority control Antipsoriatics Coal IARC Group 1 carcinogens Materials World Health Organization essential medicines Wikipedia medicine articles ready to translate