Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthine, terebenthene, terebinthine and, colloquially, turps) is a fluid obtainable by the distillation of

resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...

harvested from living trees, mainly

pine A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. ''World Flora Online'' accepts 134 species-rank taxa (119 species and 15 nothospecies) of pines as cu ...

s. Principally used as a specialized

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

, it is also a source of material for organic syntheses. Turpentine is composed of

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...

s, primarily the monoterpenes alpha- and beta-pinene, with lesser amounts of carene, camphene,

limonene Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, ...

, and terpinolene.Kent, James A. ''Riegel's Handbook of Industrial Chemistry'' (Eighth Edition) Van Nostrand Reinhold Company (1983) p.569 Nowadays, turpentine is rarely the product of distillation of pine resin, but is a byproduct of pulping. Pulping is achieved by two processes, the

Kraft process The kraft process (also known as kraft pulping or sulfate process) is a process for conversion of wood into wood pulp, which consists of almost pure cellulose fibres, the main component of paper. The kraft process involves treatment of wood chip ...

and the sulfite process. The turpentines obtained from these two processes differ in their chemical compositions. The sulfite process gives a product that is rich in cymene, whereas the Kraft process gives a pinene-rich product. Substitutes include

white spirit White spirit (AU, UK and Ireland)Primarily in the United Kingdom and Australia. In New Zealand "white spirit" can also refer to Coleman fuel (white gas). or mineral spirits (US, Canada), also known as mineral turpentine (AU/NZ/ZA), turpentine sub ...

or other

petroleum Petroleum, also known as crude oil or simply oil, is a naturally occurring, yellowish-black liquid chemical mixture found in geological formations, consisting mainly of hydrocarbons. The term ''petroleum'' refers both to naturally occurring un ...

distillates, 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 languages, Italic branch of the Indo-European languages. Latin was originally spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...

) from the Greek word ''τερεβινθίνη'', ''terebinthine'' in English, 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

conifer Conifers () are a group of conifer cone, cone-bearing Spermatophyte, seed plants, a subset of gymnosperms. Scientifically, they make up the phylum, division Pinophyta (), also known as Coniferophyta () or Coniferae. The division contains a sin ...

ous trees, namely crude turpentine (e.g. Venice turpentine is the oleoresin of larch), or the volatile oil part thereof, namely oil (spirit) of turpentine; the latter usage is much more common today.

Source trees

Important pines for turpentine production include maritime pine ('' Pinus pinaster''), Aleppo pine ('' Pinus halepensis''), Masson's pine ('' Pinus massoniana''), Sumatran pine ('' Pinus merkusii''), longleaf pine (''Pinus palustris''), loblolly pine ('' Pinus taeda''), slash pine ('' Pinus elliottii''), and ponderosa pine ('' Pinus ponderosa'').

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; it has symbol Cu (from Latin ) 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 pinkish-orang ...

still. Molten

rosin Rosin (), also known as colophony or Greek pitch (), is a resinous material obtained from pine trees and other plants, mostly conifers. The primary components of rosin are diterpenoids, i.e., C20 carboxylic acids. Rosin consists mainly of r ...

remains in the still bottoms after turpentine has been distilled out.Kent p.571 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 Destructive distillation is a chemical process in which decomposition of unprocessed material is achieved by heating it to a high temperature; the term generally applies to processing of organic material in the absence of air or in the presence o ...

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 that 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 Pulp is a fibrous Lignocellulosic biomass, lignocellulosic material prepared by chemically, semi-chemically, or mechanically isolating the cellulose fiber, cellulosic fibers of wood, fiber crops, Paper recycling, waste paper, or cotton paper, rag ...

from

s or other coniferous trees, sulfate turpentine may be condensed from the gas generated in

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 Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...

compounds.

Industrial and other end uses

Solvent

As a solvent, turpentine is used for thinning oil-based

paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...

s, for producing

varnish Varnish is a clear Transparency (optics), transparent hard protective coating or film. It is not to be confused with wood stain. It usually has a yellowish shade due to the manufacturing process and materials used, but it may also be pigmente ...

es, 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

such as

. A solution of turpentine and

beeswax Bee hive wax complex Beeswax (also known as cera alba) is a natural wax produced by honey bees of the genus ''Apis''. The wax is formed into scales by eight wax-producing glands in the abdominal segments of worker bees, which discard it in o ...

or carnauba wax has long been used as a furniture wax.

Lighting

Spirits of turpentine, called camphine, were burned in lamps with glass chimneys in the 1830s through the 1860s. Turpentine blended with grain alcohol was known as burning fluid. Both were used as domestic lamp fuels, gradually replacing

whale oil Whale oil is oil obtained from the blubber of whales. Oil from the bowhead whale was sometimes known as train-oil, which comes from the Dutch word ''traan'' ("tear drop"). Sperm oil, a special kind of oil used in the cavities of sperm whales, ...

, until

kerosene Kerosene, or paraffin, is a combustibility, combustible hydrocarbon liquid which is derived from petroleum. It is widely used as a fuel in Aviation fuel, aviation as well as households. Its name derives from the Greek (''kērós'') meaning " ...

gas lighting Gas lighting is the production of artificial light from combustion of a fuel gas such as methane, propane, butane, acetylene, ethylene, hydrogen, carbon monoxide, coal gas (town gas) or natural gas. The light is produced either directly by ...

, and electric lights began to predominate.

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 and beta-pinene, which are two of the chief chemical components of turpentine. These pinenes are separated and purified by distillation. The mixture of diterpenes and triterpenes that is left as residue after turpentine distillation is sold as

Niche uses

* Turpentine is also added to many cleaning and sanitary products due to its

antiseptic An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...

properties and its "clean scent". * In early 19th-century America, spirits of turpentine ( camphine) were burned in lamps as a cheap alternative to

. It produced a bright light but had a strong odour. Camphine and burning fluid (a mix of alcohol and turpentine) served as the dominant lamp fuels replacing whale oil until the advent of

, electric lights, and

. *

Honda commonly known as just Honda, is a Japanese multinational corporation, multinational Conglomerate (company), conglomerate automotive manufacturer headquartered in Minato, Tokyo, Japan. Founded in October 1946 by Soichiro Honda, Honda has bee ...

motorcycles, first manufactured in 1946, ran on a blend of gasoline and turpentine, due to the scarcity of gasoline in Japan following

World War II World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...

. The French Emeraude rocket uses a similar fuel mixture. Turpentine has also been researched as a potential biofuel for mixing into gasoline. * In his book '' If Only They Could Talk'', veterinarian and author James Herriot 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).

Safety and health considerations

Turpentine is highly flammable, so much so that it has been considered as an automotive fuel. Turpentine was added extensively into gin during the Gin Craze. Turpentine's vapour can irritate the skin and eyes, damage the

lungs The lungs are the primary organs of the respiratory system in many animals, including humans. In mammals and most other tetrapods, two lungs are located near the backbone on either side of the heart. Their function in the respiratory syste ...

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, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...

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 Tachycardia, also called tachyarrhythmia, is a heart rate that exceeds the normal resting rate. In general, a resting heart rate over 100 beats per minute is accepted as tachycardia in adults. Heart rates above the resting rate may be normal ...

, unconsciousness, respiratory failure, and chemical pneumonia. The US

Occupational Safety and Health Administration The Occupational Safety and Health Administration (OSHA; ) is a regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. The United States Congress established ...

(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 (NIOSH) as the recommended exposure limit (REL). At levels of 800 ppm (4480 mg/m³), turpentine is immediately dangerous to life and health.

Folk medicine

Turpentine and petroleum distillates such as coal oil and kerosene, were used in

folk medicine Traditional medicine (also known as indigenous medicine or folk medicine) refers to the knowledge, skills, and practices rooted in the cultural beliefs of various societies, especially Indigenous groups, used for maintaining health and treatin ...

for abrasions and wounds, as a treatment for lice, and when mixed with animal fat, 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 The Age of Discovery (), also known as the Age of Exploration, was part of the early modern period and overlapped with the Age of Sail. It was a period from approximately the 15th to the 17th century, during which Seamanship, seafarers fro ...

. It was one of several products carried aboard Ferdinand Magellan's fleet during the first circumnavigation of the globe. Taken internally, it was used as a treatment for intestinal parasites. This is dangerous, due to the chemical's toxicity. Turpentine

enema An enema, also known as a clyster, is the rectal administration of a fluid by injection into the Large intestine, lower bowel via the anus.Cullingworth, ''A Manual of Nursing, Medical and Surgical'':155 The word ''enema'' can also refer to the ...

s, a very harsh purgative, had formerly been used for stubborn constipation or impaction. They were also given punitively to political dissenters in post-independence Argentina."Ribbons and Rituals". In "Problems in Modern Latin American History". Ed. Chasteen and Wood. Oxford, UK: Scholarly Resources, 2005. p. 97, ISBN 9781442218598 and 9781442218604

References

External links

Inchem.org
IPCS INCHEM Turpentine classification, hazard, and property table.
CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine
{{Authority control Household chemicals Hydrocarbon solvents Painting materials Patent medicines Resins Terpenes and terpenoids Papermaking Non-timber forest products Wood extracts