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Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthene, terebinthine and (colloquially) turps) is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Mainly used as a specialized solvent, it is also a source of material for organic syntheses. Turpentine is composed of terpenes, primarily the monoterpenes alpha- and beta-pinene, with lesser amounts of
carene 3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine, with a content as high as 42% depending on the source. Carene has a sweet and pungent odor, best described as a ...
,
camphene Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As for other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell. It is a minor constituent of many essential oils such as ...
, dipentene, and
terpinolene The terpinenes are a group of isomeric hydrocarbons that are classified as monoterpenes. They each have the same molecular formula and carbon framework, but they differ in the position of carbon-carbon double bonds. α-Terpinene has been isolate ...
.Kent, James A. ''Riegel's Handbook of Industrial Chemistry'' (Eighth Edition) Van Nostrand Reinhold Company (1983) p.569 Mineral turpentine or other petroleum distillates are used to replace turpentine – although the constituent chemicals are very different.


Etymology

The word ''turpentine'' derives (via French and
Latin Latin (, or , ) is a classical language belonging to the Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through the power of the ...
), from the
Greek Greek may refer to: Greece Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group. *Greek language, a branch of the Indo-European language family. **Proto-Greek language, the assumed last common ancestor ...
word τερεβινθίνη ''terebinthine'', in turn the feminine form (to conform to the feminine gender of the Greek word, which means "resin") of an adjective (τερεβίνθινος) derived from the Greek noun (τερέβινθος), for the terebinth tree. Although the word originally referred to the resinous exudate of terebinth trees (e.g. Chios turpentine, Cyprus turpentine, and Persian turpentine), it now refers to that of coniferous trees, namely crude turpentine (e.g. Venice turpentine is the oleoresin of
larch Larches are deciduous conifers in the genus ''Larix'', of the family Pinaceae (subfamily Laricoideae). Growing from tall, they are native to much of the cooler temperate northern hemisphere, on lowlands in the north and high on mountains fur ...
.), or the
volatile oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
part thereof, namely oil (spirit) of turpentine; the later usage is much more common today.


Source trees

Important pines for turpentine production include: maritime pine (''
Pinus pinaster ''Pinus pinaster'', the maritime pine or cluster pine, is a pine native to the south Atlantic Europe region and parts of the western Mediterranean. It is a hard, fast growing pine bearing small seeds with large wings. Description ''Pinus pina ...
''), Aleppo pine (''
Pinus halepensis ''Pinus halepensis'', commonly known as the Aleppo pine, also known as the Jerusalem pine, is a pine native to the Mediterranean region. Description ''Pinus halepensis'' is a small to medium-sized tree, tall, with a trunk diameter up to , exce ...
''), Masson's pine ('' Pinus massoniana''), Sumatran pine ('' Pinus merkusii''),
longleaf pine The longleaf pine (''Pinus palustris'') is a pine species native to the Southeastern United States, found along the coastal plain from East Texas to southern Virginia, extending into northern and central Florida. In this area it is also known as ...
(''Pinus palustris''), loblolly pine (''
Pinus taeda ''Pinus taeda'', commonly known as loblolly pine, is one of several pines native to the Southeastern United States, from East Texas to Florida, and north to southern New Jersey. The wood industry classifies the species as a southern yellow pine. ...
''), slash pine ('' Pinus elliottii''), and ponderosa pine ('' Pinus ponderosa''). To tap into the sap producing layers of the tree, turpentiners used a combination of hacks to remove the pine bark. Once debarked, pine trees secrete crude turpentine (
oleoresin Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvents used for their production. The oleoresin of conifers is known as crude turpentine or gum turpentine, which consists of oil of ...
) onto the surface of the wound as a protective measure to seal the opening, resist exposure to micro-organisms and insects, and prevent vital sap loss. Turpentiners wounded trees in V-shaped streaks down the length of the trunks to channel the crude turpentine into containers. It was then collected and processed into spirits of turpentine. Crude turpentine yield may be increased by as much as 40% by applying paraquat herbicides to the exposed wood.Kent p.571 The V-shaped cuts are called "catfaces" for their resemblance to a cat's whiskers. These marks on a pine tree signify it was used to collect resin for turpentine production.


Converting crude turpentine to oil of turpentine

Crude turpentine collected from the trees may be evaporated by steam distillation in a
copper Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkis ...
still. Molten
rosin Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene comp ...
remains in the still bottoms after turpentine has been distilled out. Such turpentine is called gum turpentine. The term gum turpentine may also refer to crude turpentine, which may cause some confusion. Turpentine may alternatively be extracted from destructive distillation of pine wood, such as shredded pine stumps, roots, and slash, using the light end of the heavy naphtha fraction (boiling between ) from a crude oil refinery. Such turpentine is called wood turpentine. Multi-stage counter-current extraction is commonly used so fresh naphtha first contacts wood leached in previous stages and naphtha laden with turpentine from previous stages contacts fresh wood before vacuum distillation to recover naphtha from the turpentine. Leached wood is steamed for additional naphtha recovery prior to burning for energy recovery.


Sulfate turpentine

When producing chemical wood pulp from pines or other
coniferous trees Conifers are a group of cone-bearing seed plants, a subset of gymnosperms. Scientifically, they make up the division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a single extant class, Pinopsida. All extan ...
, sulfate turpentine may be condensed from the gas generated in Kraft process pulp digesters. The average yield of crude sulfate turpentine is 5–10 kg/t pulp. Unless burned at the mill for energy production, sulfate turpentine may require additional treatment measures to remove traces of sulfur compounds.


Industrial and other end uses


Solvent

As a solvent, turpentine is used for thinning oil-based paints, for producing varnishes, and as a raw material for the chemical industry. Its use as a solvent in industrialized nations has largely been replaced by the much cheaper turpentine substitutes obtained from petroleum such as white spirit. A solution of turpentine and beeswax or
carnauba wax Carnauba (; pt, carnaúba ), also called Brazil wax and palm wax, is a wax of the leaves of the carnauba palm ''Copernicia prunifera'' (synonym: ''Copernicia cerifera''), a plant native to and grown only in the northeastern Brazilian states of ...
has long been used as a furniture wax.


Source of organic compounds

Turpentine is also used as a source of raw materials in the synthesis of fragrant chemical compounds. Commercially used camphor, linalool, alpha-terpineol, and geraniol are all usually produced from
alpha-pinene α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also ...
and beta-pinene, which are two of the chief chemical components of turpentine. These pinenes are separated and purified by distillation. The mixture of
diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...
s and
triterpene Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squa ...
s that is left as residue after turpentine distillation is sold as
rosin Rosin (), also called colophony or Greek pitch ( la, links=no, pix graeca), is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene comp ...
.


Medicinal elixir

Turpentine and petroleum distillates such as
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 ...
and kerosene have been used medicinally since ancient times, as topical and sometimes internal home remedies. Topically, it has been used for abrasions and wounds, as a treatment for lice, and when mixed with animal fat it has been used as a chest rub, or inhaler for nasal and throat ailments. Vicks chest rubs still contain turpentine in their formulations, although not as an active ingredient. Turpentine, now understood to be dangerous for consumption, was a common medicine among seamen during the Age of Discovery. It was one of several products carried aboard
Ferdinand Magellan Ferdinand Magellan ( or ; pt, Fernão de Magalhães, ; es, link=no, Fernando de Magallanes, ; 4 February 1480 – 27 April 1521) was a Portuguese explorer. He is best known for having planned and led the 1519 Spanish expedition to the Eas ...
's fleet during the first circumnavigation of the globe. Taken internally it was used as a treatment for
intestinal parasite An intestinal parasite infection is a condition in which a parasite infects the gastro-intestinal tract of humans and other animals. Such parasites can live anywhere in the body, but most prefer the intestinal wall. Routes of exposure and inf ...
s. This is dangerous, due to the chemical's toxicity. Turpentine
enema An enema, also known as a clyster, is an injection of fluid into the lower bowel by way of the rectum.Cullingworth, ''A Manual of Nursing, Medical and Surgical'':155 The word enema can also refer to the liquid injected, as well as to a device ...
s, a very harsh purgative, had formerly been used for stubborn constipation or impaction. Turpentine enemas were also given punitively to political dissenters in post-independence Argentina.


Niche uses

* Turpentine is also added to many cleaning and sanitary products due to its
antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...
properties and its "clean scent". * In early 19th-century America, turpentine was sometimes burned in lamps as a cheap alternative to whale oil. It was most commonly used for outdoor lighting, due to its strong odour. A blend of
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
and turpentine called
camphine Camphine, the burning fluid lamp fuel, not to be confused with camphene, the chemical. Composition Camphine was the trade name of a purified spirit of turpentine formerly used for lamps, generally prepared by distilling turpentine with quicklime. ...
served as the dominant lamp fuel replacing whale oil until the advent of kerosene. * In 1946,
Soichiro Honda was a Japanese engineer and industrialist. In 1948, he established Honda Motor Co., Ltd. and oversaw its expansion from a wooden shack manufacturing bicycle motors to a multinational automobile and motorcycle manufacturer. Early years Honda ...
fueled the first Honda motorcycles with a blend of gasoline and turpentine to cover the smell of gasoline, due to the scarcity of gasoline in Japan following
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposing ...
. * In his book '' If Only They Could Talk'', veterinarian and author
James Herriot James Alfred Wight (3 October 1916 – 23 February 1995), better known by his pen name James Herriot, was a British veterinary surgeon and author. Born in Sunderland, Wight graduated from Glasgow Veterinary College in 1939, returning to Eng ...
describes the use of the reaction of turpentine with resublimed iodine to "drive the iodine into the tissue" - or perhaps just impress the watching customer with a spectacular treatment (a dense cloud of purple smoke). * Turpentine was added extensively into gin during the
Gin Craze The Gin Craze was a period in the first half of the 18th century when the consumption of gin increased rapidly in Great Britain, especially in London. Daniel Defoe commented: "the Distillers have found out a way to hit the palate of the Poor, by ...
.


Hazards

As an organic solvent, its vapour can irritate the skin and eyes, damage the
lungs The lungs are the primary organs of the respiratory system in humans and most other animals, including some snails and a small number of fish. In mammals and most other vertebrates, two lungs are located near the backbone on either side ...
and respiratory system, as well as the
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all p ...
when inhaled, and cause damage to the renal system when ingested, among other things. Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea, tachycardia, unconsciousness, respiratory failure, and chemical pneumonia. The Occupational Safety and Health Administration (OSHA) has set the legal limit ( permissible exposure limit) for turpentine exposure in the workplace as 100 ppm (560 mg/m3) over an 8-hour workday. The same threshold was adopted by 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) as the
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). At levels of 800 ppm (4480 mg/m3), turpentine is immediately dangerous to life and health.


See also

* * * McCranie's Turpentine Still * * * * , a water-resistant leather, using a birch oil distillate similar to turpentine in its manufacture. * / / Mineral spirit


References


External links


Inchem.org
IPCS INCHEM Turpentine classification, hazard, and property table.
CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine


Gum naval stores: Turpentine and rosin from pine resin
FloridaMemory.com
Florida State Archive photographs of turpentine camps and laborers

Timber and Turpentine Industries
Distil my beating heart



Turpentine Industry
a
A History of Central Florida Podcast
{{Authority control Household chemicals Hydrocarbon solvents Painting materials Patent medicines Resins Terpenes and terpenoids Papermaking Non-timber forest products