Turpentine

Last updated
Turpentine
Alpha-pinen.svg
Chemical structure of α-pinene, a major component of turpentine
Identifiers
ECHA InfoCard 100.029.407
EC Number
  • 232-688-5
UNII
Properties
C10H16
Molar mass 136.238 g·mol−1
AppearanceViscous liquid [1]
Odor Resinous [1]
Melting point −55 [1]  °C (−67 °F; 218 K)
Boiling point 154 [1]  °C (309 °F; 427 K)
20 mg/L [1]
Hazards
GHS pictograms GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg [2]
GHS Signal word Danger
Flash point 35 [1]  °C (95 °F; 308 K)
220 [1]  °C (428 °F; 493 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Turpentine (which is also called spirit of turpentine, oil of turpentine, wood turpentine, terebenthene, terebinthine and (colloquially), turps) [3] is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. It is mainly used as a solvent, and as a source of material for organic syntheses.

Contents

Turpentine is composed of terpenes, primarily the monoterpenes alpha- and beta-pinene, with lesser amounts of carene, camphene, dipentene, and terpinolene. [4]

The word turpentine derives (via French and Latin), from the Greek 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 (τερέβινθο), for the tree species terebinth [5] Mineral turpentine or other petroleum distillates are used to replace[ why? ] turpentine -- although their chemistries are very different.[ how? ] [6]

Source trees

"Herty system" in use on turpentine trees in Northern Florida, circa 1936 CupGutterSystem.jpg
"Herty system" in use on turpentine trees in Northern Florida, circa 1936
Chipping a turpentine tree in Georgia (US), circa 1906-20 Chipping a turpentine tree.jpg
Chipping a turpentine tree in Georgia (US), circa 1906-20
Turpentine distillery at Manlyn, North Carolina PSM V48 D518 Turpentine still at Manlyn North Carolina.jpg
Turpentine distillery at Manlyn, North Carolina

One of the earliest sources of turpentine was the terebinth or turpentine tree (Pistacia terebinthus), a Mediterranean tree related to the pistachio. 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) and ponderosa pine (Pinus ponderosa).

Canada balsam, also called Canada turpentine or balsam of fir, is a turpentine which is made from the oleoresin of the balsam fir. Venice turpentine is produced from the western larch Larix occidentalis.

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 oleoresin 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 oleoresin into containers. It was then collected and processed into spirits of turpentine. Oleoresin yield may be increased by as much as 40% by applying paraquat herbicides to the exposed wood. [7]

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. [8]

Converting oleoresin to turpentine

Crude oleoresin collected from wounded trees may be evaporated by steam distillation in a copper still. Molten rosin remains in the still bottoms after turpentine has been evaporated and recovered from a condenser. [7] Turpentine may alternatively be condensed from destructive distillation of pine wood. [4]

Oleoresin may also be extracted from shredded pine stumps, roots, and slash using the light end of the heavy naphtha fraction (boiling between 90 and 115 °C or 195 and 240 °F) from a crude oil refinery. 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. [9]

When producing chemical wood pulp from pines or other coniferous trees, 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. [10] Unless burned at the mill for energy production, sulfate turpentine may require additional treatment measures to remove traces of sulfur compounds. [11]

Industrial and other end uses

Solvent

The two primary uses of turpentine in industry are as a solvent and as a source of materials for organic synthesis. As a solvent, turpentine is used for thinning oil-based paints, for producing varnishes, 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. Turpentine has long been used as a solvent, mixed with beeswax or with carnauba wax, to make fine furniture wax for use as a protective coating over oiled wood finishes (e.g., tung oil).

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 rosin.

Medicinal elixir

Turpentine and petroleum distillates such as coal oil 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. [12] Many modern chest rubs, such as the Vicks variety, still contain turpentine in their formulations.

Turpentine, now understood to be dangerous for consumption, was a common medicine among seamen during the Age of Discovery. It is one of several products carried aboard Ferdinand Magellan's fleet in his first circumnavigation of the globe. [13] Taken internally it was used as a treatment for intestinal parasites. This is dangerous, due to the chemical's toxicity. [14] [15]

Turpentine enemas, a very harsh purgative, had formerly been used for stubborn constipation or impaction. [16] Turpentine enemas were also given punitively to political dissenters in post-independence Argentina. [17]

Niche uses

Hazards

NFPA 704
fire diamond
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeTurpentine
3
1
0

As an organic solvent, its vapour can irritate the skin and eyes, damage the lungs and respiratory system, as well as the central nervous system when inhaled, and cause damage to the renal system when ingested, among other things. [23] Being combustible, it also poses a fire hazard. While it is a fire hazard, in large quantities turpentine can be used to smother and extinguish flames due to its liquid state. Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea, and unconsciousness. [24] Because turpentine can cause spasms of the airways particularly in people with asthma and whooping cough, it can contribute to a worsening of breathing issues in persons with these diseases if inhaled.

People can be exposed to turpentine in the workplace by breathing it in, skin absorption, swallowing it, and eye contact. 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 (NIOSH) as the recommended exposure limit (REL). At levels of 8000 ppm (4,448 mg/m3), turpentine is immediately dangerous to life and health. [25]

See also

Sources

Related Research Articles

Toluene, also known as toluol, is an 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 CH3 group attached to a phenyl group. As such, its IUPAC systematic name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

Resin solid or highly viscous substance, of plant or synthetic origin, which can be polymerized into a solid

In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on naturally occurring resins.

Naphtha is a flammable liquid hydrocarbon mixture.

Oil refinery industrial process plant where crude oil is processed and refined into more useful products

An oil refinery or petroleum refinery is an industrial process plant where crude oil is transformed and refined into more useful products such as petroleum naphtha, gasoline, diesel fuel, asphalt base, heating oil, kerosene, liquefied petroleum gas, jet fuel and fuel oils. Petrochemicals feed stock like ethylene and propylene can also be produced directly by cracking crude oil without the need of using refined products of crude oil such as naphtha.

Varnish transparent, hard, protective finish or film used in painting

Varnish is a clear transparent hard protective finish or film. Varnish has little or no color and has no added pigment as opposed to paint or wood stain which contains pigment. However, some varnish products are marketed as a combined stain and varnish. Varnish is primarily used in wood finishing applications where the natural tones and grains in the wood are intended to be visible. It is applied over wood stains as a final step to achieve a film for gloss and protection. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss sheens by the addition of "flatting" agents.

Rosin organic substance

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. At room temperature rosin is brittle, but it melts at stove-top temperature. It chiefly consists of various resin acids, especially abietic acid. The term "colophony" comes from colophonia resina, Latin for "resin from Colophon", an ancient Ionic city.

Abietic acid chemical compound

Abietic acid is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. Its ester or salt is called an abietate.

White spirit Petroleum-derived clear, transparent liquid

White spirit (UK) or mineral spirits, also known as mineral turpentine (AU/NZ), turpentine substitute, and petroleum spirits, is a petroleum-derived clear liquid used as a common organic solvent in painting. There are also terms for specific kinds of mineral spirits, including Stoddard solvent and solvent naphtha (petroleum). Mineral spirits are often used as a paint thinner, or as a component thereof, though paint thinner is a broader category of solvent.

<i>Pinus roxburghii</i> species of plant, Chir Pine

Pinus roxburghii, commonly known as chir pine or longleaf Indian pine, is a species of pine, native to the Himalayas. It was named after William Roxburgh.

Tar Dark viscous organic liquid

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.

Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvent(s) used for their production. Naturally occurring oleoresins are also known as balsams.

Pine oil essential oil

Pine oil is an essential oil obtained by the steam distillation of stumps, needles, twigs and cones from a variety of species of pine, particularly Pinus sylvestris. As of 1995, synthetic pine oil was the "biggest single turpentine derivative." Synthetic pine oils accounted for 90% of sales as of 2000.

Pinene chemical compound

Pinene (C10H16) is a bicyclic monoterpene chemical compound. There are two structural isomers of pinene found in nature: α-pinene and β-pinene. As the name suggests, both forms are important constituents of pine resin; they are also found in the resins of many other conifers, as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). Both isomers are used by many insects in their chemical communication system. The two isomers of pinene constitute the major component of turpentine.

Tall oil, also called "liquid rosin" or tallol, is a viscous yellow-black odorous liquid obtained as a by-product of the Kraft process of wood pulp manufacture when pulping mainly coniferous trees. The name originated as an anglicization of the Swedish "tallolja". Tall oil is the third largest chemical by-product in a Kraft mill after lignin and hemicellulose; the yield of crude tall oil from the process is in the range of 30–50 kg / ton pulp. It may contribute to 1.0–1.5% of the mill's revenue if not used internally.

Naval stores are all products derived from pine resin, which are used to manufacture soap, paint, varnish, shoe polish, lubricants, linoleum, and roofing materials.

Naval stores industry part of shipbuilding

The naval stores industry collects, processes, and markets forest products refined from the oleoresin of the slash pine and longleaf pine trees. The industry was associated with the maintenance of the wooden ships and sailing tackle of pre-20th century navies, which were caulked and waterproofed using the pitch of the pine tree.

1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.

Hash oil Resinous matrix of cannabinoids derived from cannabis

Hash oil, also known as honey oil or cannabis oil, is an oleoresin obtained by the extraction of cannabis or hashish. It is a cannabis concentrate containing many of its resins and terpenes – in particular, tetrahydrocannabinol (THC), cannabidiol (CBD), and other cannabinoids. There are various extraction methods, most involving a solvent, such as butane or ethanol. Hash oil is usually consumed by smoking, vaporizing or eating. Hash oil may be sold in cartridges used with pen vaporizers. Preparations of hash oil may be solid or colloidal depending on both production method and temperature and are usually identified by their appearance or characteristics. Color most commonly ranges from transparent golden or light brown, to tan or black. Cannabis retailers in California have reported about 40% of their sales are from cannabis oils. Hash oil is an extracted cannabis product that may use any part of the plant, with minimal or no residual solvent. It is generally thought to be indistinct from traditional hashish, according to the 1961 UN Single Convention on Narcotic Drugs, as it is "the separated resin, whether crude or purified, obtained from the cannabis plant".

Petroleum naphtha is an intermediate hydrocarbon liquid stream derived from the refining of crude oil with CAS-no 64742-48-9. It is most usually desulfurized and then catalytically reformed, which rearranges or restructures the hydrocarbon molecules in the naphtha as well as breaking some of the molecules into smaller molecules to produce a high-octane component of gasoline.

Levopimaric acid chemical compound

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. About 18 to 25% of levopimaric acid is found in pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.

References

  1. 1 2 3 4 5 6 7 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. "Turpentine". European Chemicals Agency.
  3. Mayer, Ralph (1991). The Artist's Handbook of Materials and Techniques (Fifth ed.). New York: Viking. p.  404. ISBN   0-670-83701-6.
  4. 1 2 Kent p.569
  5. Barnhart, R. K. (1995). The Barnhart Concise Dictionary of Etymology. New York: Harper Collins. ISBN   0-06-270084-7.
  6. Dieter Stoye "Solvents" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Wienheim. doi : 10.1002/14356007.a24_437
  7. 1 2 Kent p.571
  8. Prizer, Tom (June 11, 2010). "Catfaces: Totems of Georgia's Turpentiners | Daily Yonder | Keep It Rural". dailyyonder.com. Retrieved June 5, 2012.
  9. Kent pp.571&572
  10. Stenius, Per, ed. (2000). "2". Forest Products Chemistry. Papermaking Science and Technology. 3. Finland. pp. 73–76. ISBN   952-5216-03-9.
  11. Kent p.572
  12. "Surviving 'The Spanish Lady' (Spanish flu), 06:09, Residents of a small Alberta town recall their deadly brush with 1918's Spanish flu". CBC Digital Archives. 2003-04-10. Event occurs at 03:20. Lay summary. A turpentine and hot water, and [wring hot towels out of there], and put it on their chest and back. --Elsie Miller (nee Smith)
  13. Laurence Bergreen (2003). "Over the edge of the world : Magellan's terrifying circumnavigation of the globe" . ISBN   0066211735 . Retrieved 2009-09-14.
  14. "Home Remedies - American Memory Timeline- Classroom Presentation". American Memory Timeline. The Library of Congress. Retrieved 2017-02-06.
  15. "ICSC 1063 - TURPENTINE". www.inchem.org.
  16. "Turpentine enema". Biology-Online Dictionary. Biology-Online. Retrieved 2019-12-26.
  17. "Ribbons and Rituals". In Problems in Modern Latin American History. Ed. Chasteen and Wood. Oxford, UK: Scholarly Resources, 2005. p. 97
  18. Charles H. Haswell. "Reminiscences of New York By an Octogenarian (1816 - 1860)".
  19. "The "Whale Oil Myth"". PBS NewsHour. 20 August 2008.
  20. "Honda History". Smokeriders.com.
  21. "If Only They Could Talk" . Retrieved 28 June 2018 via www.amazon.co.uk., summarised at "James Herriot Books" . Retrieved 28 June 2018.
  22. Rohrer, Finlo (28 July 2014). "When gin was full of sulphuric acid and turpentine" . Retrieved 2 January 2018 via www.bbc.com.
  23. "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine - Symptoms". www.cdc.gov. Retrieved 2015-11-27.
  24. "Turpentine". International Programme on Chemical Safety, World Health Organization.
  25. "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine". www.cdc.gov. Retrieved 2015-11-27.