Turpentine

Turpentine

Overview
Turpentine is a fluid obtained by the distillation
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....

 of resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

 obtained from trees, mainly pine
Pine
Pines are trees in the genus Pinus ,in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species.-Etymology:...

 trees. It is composed of terpene
Terpene
Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...

s, mainly the monoterpenes alpha-pinene
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 found in the essential oil of rosemary...

 and beta-pinene
Beta-Pinene
beta-Pinene is a colorless liquid, soluble in alcohol, but not water. It has a woody-green pine-like smell. It occurs naturally in rosemary, parsley, dill, basil, yarrow, and rose. It is also a major constituent of hop aroma and flavor....

. It is sometimes known as turps.

The word turpentine derives (via French
French language
French is a Romance language spoken as a first language in France, the Romandy region in Switzerland, Wallonia and Brussels in Belgium, Monaco, the regions of Quebec and Acadia in Canada, and by various communities elsewhere. Second-language speakers of French are distributed throughout many parts...

 and Latin
Latin
Latin is an Italic language originally spoken in Latium and Ancient Rome. It, along with most European languages, is a descendant of the ancient Proto-Indo-European language. Although it is considered a dead language, a number of scholars and members of the Christian clergy speak it fluently, and...

) from the Greek word τερεβινθίνη terebinthine, the name of a species of tree, the terebinth tree, from whose sap the spirit was originally distilled.

Mineral turpentine
Mineral turpentine
Mineral turpentine, also known as turpentine substitute, turps substitute, or just turps is an inexpensive petroleum-based replacement for the vegetable-based turpentine...

 or other petroleum distillates are used to replace turpentine.

One of the earliest sources was the terebinth or turpentine tree (Pistacia terebinthus), a Mediterranean tree related to the pistachio
Pistachio
The pistachio, Pistacia vera in the Anacardiaceae family, is a small tree originally from Persia , which now can also be found in regions of Syria, Lebanon, Turkey, Greece, Kyrgyzstan, Turkmenistan, India, Pakistan, Egypt, Sicily and possibly Afghanistan , as well as in the United States,...

.

Important pines for turpentine production include: Maritime Pine
Maritime Pine
Pinus pinaster, the Maritime Pine, is a pine native to the western and southwestern Mediterranean region. The pejorative name 'pinaster' is derived from pinus + aster, translating as 'a poor imitation of a pine' Pinus pinaster, the Maritime Pine, is a pine native to the western and southwestern...

 (Pinus pinaster), Aleppo Pine
Aleppo Pine
Pinus halepensis, commonly known as the Aleppo Pine, is a pine native to the Mediterranean region. Their range extends from Morocco and Spain north to southern France, Italy and Croatia, and east to Greece and northern Tunisia, and Libya, with an outlying population in Syria, Lebanon, southern...

 (Pinus halepensis), Masson's Pine (Pinus massoniana), Sumatran Pine
Sumatran Pine
Pinus merkusii, the Sumatran Pine, is a pine native to the Malesia region of southeast Asia, mainly in Indonesia in the mountains of northern Sumatra, and with two outlying populations in central Sumatra on Mount Kerinci and Mount Talang, and in the Philippines on Mindoro and in the Zambales...

 (Pinus merkusii), Longleaf Pine
Longleaf Pine
Pinus palustris, commonly known as the Longleaf Pine, is a pine native to the southeastern United States, found along the coastal plain from eastern Texas to southeast Virginia extending into northern and central Florida....

 (Pinus palustris), Loblolly Pine
Loblolly Pine
Pinus taeda is one of several pines native to the Southeastern United States, from central Texas east to Florida, and north to Delaware. It is particularly dominant in the eastern half of North Carolina, where there are huge expanses consisting solely of Loblolly Pine trees...

 (Pinus taeda) and Ponderosa Pine
Ponderosa Pine
Pinus ponderosa, commonly known as the Ponderosa Pine, Bull Pine, Blackjack Pine, or Western Yellow Pine, is a widespread and variable pine native to western North America. It was first described by David Douglas in 1826, from eastern Washington near present-day Spokane...

 (Pinus ponderosa).

Turpentine distilled from the California pines such as Ponderosa Pine
Ponderosa Pine
Pinus ponderosa, commonly known as the Ponderosa Pine, Bull Pine, Blackjack Pine, or Western Yellow Pine, is a widespread and variable pine native to western North America. It was first described by David Douglas in 1826, from eastern Washington near present-day Spokane...

 (Pinus ponderosa) and Gray Pine
Gray Pine
Pinus sabiniana , with the common names gray pine, California foothill pine, and the more historically and internationally used digger pine, is a pine endemic to California in the United States...

 (Pinus sabiniana) yield a form of turpentine that is almost pure heptane
Heptane
n-Heptane is the straight-chain alkane with the chemical formula H3C5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale...

.

When producing chemical wood pulp
Wood pulp
Pulp is a lignocellulosic fibrous material prepared by chemically or mechanically separating cellulose fibres from wood, fibre crops or waste paper. Wood pulp is the most common raw material in papermaking.-History:...

 from pines
Pines
Pines may refer to:*Pine, coniferous trees of the genus Pinus, in the family Pinaceae*PINES or Public Information Network for Electronic Services- People with the surname :...

 or other coniferous trees with the Kraft process
Kraft process
The kraft process describes a technology for conversion of wood into wood pulp consisting of almost pure cellulose fibers...

, turpentine is collected as a byproduct.
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Encyclopedia
Turpentine is a fluid obtained by the distillation
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....

 of resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

 obtained from trees, mainly pine
Pine
Pines are trees in the genus Pinus ,in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species.-Etymology:...

 trees. It is composed of terpene
Terpene
Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...

s, mainly the monoterpenes alpha-pinene
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 found in the essential oil of rosemary...

 and beta-pinene
Beta-Pinene
beta-Pinene is a colorless liquid, soluble in alcohol, but not water. It has a woody-green pine-like smell. It occurs naturally in rosemary, parsley, dill, basil, yarrow, and rose. It is also a major constituent of hop aroma and flavor....

. It is sometimes known as turps.

The word turpentine derives (via French
French language
French is a Romance language spoken as a first language in France, the Romandy region in Switzerland, Wallonia and Brussels in Belgium, Monaco, the regions of Quebec and Acadia in Canada, and by various communities elsewhere. Second-language speakers of French are distributed throughout many parts...

 and Latin
Latin
Latin is an Italic language originally spoken in Latium and Ancient Rome. It, along with most European languages, is a descendant of the ancient Proto-Indo-European language. Although it is considered a dead language, a number of scholars and members of the Christian clergy speak it fluently, and...

) from the Greek word τερεβινθίνη terebinthine, the name of a species of tree, the terebinth tree, from whose sap the spirit was originally distilled.

Mineral turpentine
Mineral turpentine
Mineral turpentine, also known as turpentine substitute, turps substitute, or just turps is an inexpensive petroleum-based replacement for the vegetable-based turpentine...

 or other petroleum distillates are used to replace turpentine.

Production


One of the earliest sources was the terebinth or turpentine tree (Pistacia terebinthus), a Mediterranean tree related to the pistachio
Pistachio
The pistachio, Pistacia vera in the Anacardiaceae family, is a small tree originally from Persia , which now can also be found in regions of Syria, Lebanon, Turkey, Greece, Kyrgyzstan, Turkmenistan, India, Pakistan, Egypt, Sicily and possibly Afghanistan , as well as in the United States,...

.

Important pines for turpentine production include: Maritime Pine
Maritime Pine
Pinus pinaster, the Maritime Pine, is a pine native to the western and southwestern Mediterranean region. The pejorative name 'pinaster' is derived from pinus + aster, translating as 'a poor imitation of a pine' Pinus pinaster, the Maritime Pine, is a pine native to the western and southwestern...

 (Pinus pinaster), Aleppo Pine
Aleppo Pine
Pinus halepensis, commonly known as the Aleppo Pine, is a pine native to the Mediterranean region. Their range extends from Morocco and Spain north to southern France, Italy and Croatia, and east to Greece and northern Tunisia, and Libya, with an outlying population in Syria, Lebanon, southern...

 (Pinus halepensis), Masson's Pine (Pinus massoniana), Sumatran Pine
Sumatran Pine
Pinus merkusii, the Sumatran Pine, is a pine native to the Malesia region of southeast Asia, mainly in Indonesia in the mountains of northern Sumatra, and with two outlying populations in central Sumatra on Mount Kerinci and Mount Talang, and in the Philippines on Mindoro and in the Zambales...

 (Pinus merkusii), Longleaf Pine
Longleaf Pine
Pinus palustris, commonly known as the Longleaf Pine, is a pine native to the southeastern United States, found along the coastal plain from eastern Texas to southeast Virginia extending into northern and central Florida....

 (Pinus palustris), Loblolly Pine
Loblolly Pine
Pinus taeda is one of several pines native to the Southeastern United States, from central Texas east to Florida, and north to Delaware. It is particularly dominant in the eastern half of North Carolina, where there are huge expanses consisting solely of Loblolly Pine trees...

 (Pinus taeda) and Ponderosa Pine
Ponderosa Pine
Pinus ponderosa, commonly known as the Ponderosa Pine, Bull Pine, Blackjack Pine, or Western Yellow Pine, is a widespread and variable pine native to western North America. It was first described by David Douglas in 1826, from eastern Washington near present-day Spokane...

 (Pinus ponderosa).

Turpentine distilled from the California pines such as Ponderosa Pine
Ponderosa Pine
Pinus ponderosa, commonly known as the Ponderosa Pine, Bull Pine, Blackjack Pine, or Western Yellow Pine, is a widespread and variable pine native to western North America. It was first described by David Douglas in 1826, from eastern Washington near present-day Spokane...

 (Pinus ponderosa) and Gray Pine
Gray Pine
Pinus sabiniana , with the common names gray pine, California foothill pine, and the more historically and internationally used digger pine, is a pine endemic to California in the United States...

 (Pinus sabiniana) yield a form of turpentine that is almost pure heptane
Heptane
n-Heptane is the straight-chain alkane with the chemical formula H3C5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale...

.

When producing chemical wood pulp
Wood pulp
Pulp is a lignocellulosic fibrous material prepared by chemically or mechanically separating cellulose fibres from wood, fibre crops or waste paper. Wood pulp is the most common raw material in papermaking.-History:...

 from pines
Pines
Pines may refer to:*Pine, coniferous trees of the genus Pinus, in the family Pinaceae*PINES or Public Information Network for Electronic Services- People with the surname :...

 or other coniferous trees with the Kraft process
Kraft process
The kraft process describes a technology for conversion of wood into wood pulp consisting of almost pure cellulose fibers...

, turpentine is collected as a byproduct. Often it is burned at the mill for energy production. The average yield of crude turpentine is 5–10 kg/t pulp.

Industrial and other end uses



The two primary uses of turpentine in industry are as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

 and as a source of materials for organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

.

As a solvent, turpentine is used for thinning oil-based paint
Paint
Paint is any liquid, liquefiable, or mastic composition which after application to a substrate in a thin layer is converted to an opaque solid film. One may also consider the digital mimicry thereof...

s, for producing varnish
Varnish
Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss...

es, and as a raw material for the chemical industry. Its industrial use as a solvent in industrialized nations has largely been replaced by the much cheaper turpentine substitutes distilled from crude oil.

Canada balsam
Canada balsam
Canada balsam, also called Canada turpentine or balsam of fir, is a turpentine which is made from the resin of the balsam fir tree of boreal North America...

, also called Canada turpentine or balsam of fir
Fir
Firs are a genus of 48–55 species of evergreen conifers in the family Pinaceae. They are found through much of North and Central America, Europe, Asia, and North Africa, occurring in mountains over most of the range...

, is a turpentine which is made from the resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

 of the balsam fir.

Venice turpentine is produced from the Western Larch
Western Larch
Western Larch is a species of larch native to the mountains of western North America, in Canada in southeastern British Columbia and southwestern Alberta, and in the United States in eastern Washington, eastern Oregon, northern Idaho and western Montana.It is a large deciduous coniferous tree...

 Larix occidentalis.

Turpentine is also used as a source of raw materials in the synthesis of fragrant chemical compounds. Commercially used camphor
Camphor
Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula C10H16O. It is found in wood of the camphor laurel , a large evergreen tree found in Asia and also of Dryobalanops aromatica, a giant of the Bornean forests...

, linalool, alpha-terpineol
Terpineol
Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond...

, and geraniol
Geraniol
Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil . It also occurs in small quantities in geranium, lemon, and many other essential oils. It appears as a clear to pale-yellow oil that is insoluble in water, but soluble in most common...

 are all usually produced from alpha-pinene
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 found in the essential oil of rosemary...

 and beta-pinene
Beta-Pinene
beta-Pinene is a colorless liquid, soluble in alcohol, but not water. It has a woody-green pine-like smell. It occurs naturally in rosemary, parsley, dill, basil, yarrow, and rose. It is also a major constituent of hop aroma and flavor....

, which are two of the chief chemical components of turpentine. These pinenes are separated and purified by distillation. The mixture of diterpene
Diterpene
Diterpenes are a type of terpenes composed of four isoprene units. They derive from geranylgeranyl pyrophosphate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol...

s and triterpene
Triterpene
Triterpenes are terpenes consisting of six isoprene units and have the molecular formula C30H48.The pentacyclic triterpenes can be classified into lupane, oleanane or ursane groups.Animal- and plant-derived triterpenes exist, such as:*squalene...

s that is left as residue after turpentine distillation is sold as rosin
Rosin
.Rosin, also called colophony or Greek pitch , 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 components. It is semi-transparent and varies in color from yellow to black...

.

Turpentine is also added to many cleaning and sanitary products due to its antiseptic 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 odor. A blend of ethanol and turpentine added as an illuminant called burning fluid was also important for several decades.

Turpentine has long been used as a solvent, mixed with beeswax
Beeswax
Beeswax is a natural wax produced in the bee hive of honey bees of the genus Apis. It is mainly esters of fatty acids and various long chain alcohols...

 or with carnauba wax
Carnauba wax
Carnauba , also called Brazil wax and palm wax, is a wax of the leaves of the palm Copernicia prunifera, a plant native to and grown only in the northeastern Brazilian states of Piauí, Ceará, and Rio Grande do Norte. It is known as "queen of waxes" and usually comes in the form of hard yellow-brown...

, to make fine furniture wax for use as a protective coating over oiled wood finishes (e.g., lemon oil).

In 1946, Soichiro Honda
Soichiro Honda
was a Japanese engineer and industrialist, and founder of Honda Motor Co., Ltd..Honda was born in Hamamatsu, Shizuoka, Japan on November 17, 1906. He spent his early childhood helping his father, Gihei, a blacksmith, with his bicycle repair business. At the time his mother, Mika, was a weaver. At...

 used turpentine as a fuel for the first Honda motorcycle
Motorcycle
A motorcycle is a single-track, two-wheeled motor vehicle. Motorcycles vary considerably depending on the task for which they are designed, such as long distance travel, navigating congested urban traffic, cruising, sport and racing, or off-road conditions.Motorcycles are one of the most...

s as gasoline was almost totally unavailable following World War II
World War II
World War II, or the Second World War , was a global conflict lasting from 1939 to 1945, involving most of the world's nations—including all of the great powers—eventually forming two opposing military alliances: the Allies and the Axis...

.

Hazards


Turpentine is an organic
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 solvent. Its vapor can irritate the skin and eyes, damage the lungs and respiratory system, as well as the central nervous system
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...

 when inhaled, and cause renal failure
Renal failure
Renal failure or kidney failure describes a medical condition in which the kidneys fail to adequately filter toxins and waste products from the blood...

 when ingested, among other things. Being combustible, it also poses a fire hazard.

Medicinal elixir


Turpentine and petroleum distillates such as coal oil
Coal oil
Coal oil is a term once used for a specific shale oil used for illuminating purposes. Coal oil is obtained from the destructive distillation of cannel coal, mineral wax, and bituminous shale, while kerosene is obtained by the distillation of petroleum...

 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
Animal fat
Animal fats are rendered tissue fats that can be obtained from a variety of animals.- Pet nutrition :In pet nutrition, the source of animal fat concerns food manufacturers. AAFCO states that animal fat is "obtained from the tissues of mammals and/or poultry in the commercial processes of rendering...

 it has been used as a chest rub, or inhaler for nasal and throat ailments. Many modern chest rubs, such as the Vicks
Vicks
Vicks is a line of over-the-counter medications owned by the American company Procter & Gamble. Vicks manufactures NyQuil and its sister medication, DayQuil. The Vicks brand also produces Formula 44 cough medicines, cough drops, VapoRub, and a number of inhaled breathing treatments...

 variety, still contain turpentine in their formulations.

Taken internally it was used as treatment for intestinal parasite
Intestinal parasite
Intestinal parasites are parasites that populate the gastro-intestinal tract in humans and other animals. They can live throughout the body, but most prefer the intestinal wall. Means of exposure include: ingestion of undercooked meat, drinking infected water, and skin absorption...

s because of its alleged antiseptic
Antiseptic
Antiseptics are antimicrobial substances that are applied to living tissue/skin to reduce the possibility of infection, sepsis, or putrefaction...

 and diuretic
Diuretic
A diuretic provides a means of forced diuresis which elevates the rate of urination. There are several categories of diuretics. All diuretics increase the excretion of water from bodies, although each class does so in a distinct way.- Medical uses :...

 properties, and a general cure-all as in Hamlin's Wizard Oil
Hamlin's Wizard Oil
Hamlin's Wizard Oil was an American patent medicine sold as a cure-all under the slogan "There is no Sore it will Not Heal, No Pain it will not Subdue." First produced in 1861 in Chicago by former magician John Austen Hamlin and his brother Lysander B...

. Sugar, molasses or honey were sometimes used to mask the taste. Internal administration of these toxic products is no longer common today.

Turpentine was a common medicine among seamen during the Age of Discovery
Age of Discovery
The Age of Discovery, also known as the Age of Exploration and the Great Navigations , was a period in history starting in the early 15th century and continuing into the early 17th century during which Europeans engaged in intensive exploration of the world, establishing direct contacts with...

, and one of several products carried aboard Ferdinand Magellan
Ferdinand Magellan
Ferdinand Magellan was a Portuguese explorer. He was born in Sabrosa, in northern Portugal, and served King Charles I of Spain in search of a westward route to the "Spice Islands" ....

's fleet in his first circumnavigation of the globe.

Turpentine was a common additive in cheap gin until the 20th century and gave it its characteristic juniper berry flavor without the need for pricier distillations with aromatic spices and berries.

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