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Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas 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 ...
. 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 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 the ...
(dandruff). It may be used in combination with ultraviolet light therapy. Industrially it is a railroad tie 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 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 derm ...
, and skin discoloration. It is unclear if use during
pregnancy Pregnancy is the time during which one or more offspring develops (gestation, gestates) inside a woman, woman's uterus (womb). A multiple birth, multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occur ...
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 br ...
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 compounds. It demonstrates antifungal,
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 o ...
, 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 age ...
properties.


Uses


Medicine

Coal tar is used in medicated shampoo,
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 use ...
and ointment. It demonstrates antifungal,
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 o ...
, 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 age ...
properties. It may be applied topically as a treatment for dandruff 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 thi ...
. It may be used in combination with ultraviolet light therapy. 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, 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 and ...
 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 Tarmacadam, tarmac in 1902, he founded Tarmac Group, Tar Macadam Syndicate Ltd the following year and registered tarmac as a trademark. Following a merger ...
, tarmac was tar covered with granite chips. Later the filler used was industrial slag. 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 pavements, primarily in asphalt road paving, car parks and walkways. Coal tar is incorporated into some parking-lot sealcoat 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 territo ...
, 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. Like most heavy oils, it must be heated before it will flow easily. A large part of the binder used in the graphite 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 era, there were many companies in Britain whose business was to distill 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 (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 derm ...
, and skin discoloration. It is unclear if use during
pregnancy Pregnancy is the time during which one or more offspring develops (gestation, gestates) inside a woman, woman's uterus (womb). A multiple birth, multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occur ...
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 br ...
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, 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 (BCC) ...
s. Evidence is inconclusive whether medical coal tar, which does not remain on the skin for the long periods seen in occupational exposure, 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. ...
, and it is believed that their metabolites bind to DNA, damaging it. The PAHs found in coal tar and air pollution induce immunosenescence 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. 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 wa ...
. 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 lists coal tars as
Group 1 Group 1 may refer to: * Alkali metal, a chemical element classification for Alkali metal * Group 1 (racing), a historic (until 1981) classification for Touring car racing, applied to standard touring cars. Comparable to modern FIA Group N * Group On ...
carcinogens, 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 heat ...
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, l ...
by the European Chemicals Agency.


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 compounds. It is a keratolytic 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 ''py ...
) 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 ...
. Its composition varies with the process and type of coal used – lignite,
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 ...
or anthracite. 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,
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, triphenylene, 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 Pitch (resin), pitchy residue obtained in the distillation of peat tar and of petroleum. This is distilled to dryness and the distillate repeatedly Recrystallization (chemistry), recrystallized from cymene. It ...
, benzo yrene, benzo yrene, benzofluoranthenes, perylene, 6-rings: dibenzopyrenes, dibenzofluoranthenes,
benzoperylene Benzo 'ghi''erylene is a polycyclic aromatic hydrocarbon with the chemical formula C22H12. Occurrence and safety Benzo 'ghi''erylene occurs naturally in crude oil and coal tar. It is a product of incomplete combustion and is found in tobacco ...
s, 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 compounds. 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, xylenes,
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. Near ...
s, coumarone,
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 i ...
,
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 is ...
, naphthalene 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,
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 ...
, cresols, pyridine,
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 unspecified ...
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 sli ...
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 coal tar derivatives have analgesic (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, and paracetamol aka acetaminophen. 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 ...
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. Coal tar is generally available as a generic medication 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 (OSHA) has set the permissible exposure limit) 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 safet ...
(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. 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 List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
(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 seve ...
*
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 black bi ...


References


External links

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