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Turpentine

From Wikipedia, the free encyclopedia
Liquid distilled from pine resin
This article is about oil of turpentine. For crude turpentine, seeoleoresin. For other uses, seeturpentine (disambiguation).
Turpentine
Turpentine distilled at theGeorgia Museum of Agriculture & Historic Village as it was done circa 1900
Identifiers
ECHA InfoCard100.029.407Edit this at Wikidata
EC Number
  • 232-688-5
UNII
Properties[1]
C10H16
Molar mass136.238 g·mol−1
AppearanceViscous liquid
OdorResinous
Melting point−55 °C (−67 °F; 218 K)
Boiling point154 °C (309 °F; 427 K)
20 mg/L
Hazards
NFPA 704 (fire diamond)
Flash point35 °C (95 °F; 308 K)
220[1] °C (428 °F; 493 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Turpentine (which is also calledspirit of turpentine,oil of turpentine,terebenthine,terebenthene,terebinthine and, colloquially,turps)[2] is a fluid obtained by thedistillation ofresin harvested from living trees, mainlypines. Principally used as a specializedsolvent, it is also a source of material fororganic syntheses.

Turpentine is composed ofterpenes, primarily the monoterpenesalpha- andbeta-pinene, with lesser amounts ofcarene,camphene,limonene, andterpinolene.[3] Nowadays, turpentine is rarely the product of distillation of pine rosin, but is a byproduct of pulping. Pulping is achieved by two processes,Kraft process and theSulfite process. The turpentine obtained from these two processes differ in their chemical composition. Sulfite process gives a product that is rich incymene, whereas the Kraft process gives a pinene-rich product.[4]

Substitutes includewhite spirit or otherpetroleum distillates – although the constituent chemicals are very different.[5]

Etymology

[edit]

The wordturpentine derives (viaFrench andLatin) from theGreek word,τερεβινθίνη,terebinthine in English, in turn the feminine form (to conform to thefeminine gender of the Greek word, which means 'resin') of an adjective (τερεβίνθινος) derived from the Greek noun (τερέβινθος) for theterebinth tree.[6]

Although the word originally referred to the resinous exudate of terebinth trees (e.g.Chios turpentine,Cyprus turpentine, andPersian turpentine),[7][8] it now refers to that ofconiferous trees, namelycrude turpentine (e.g. Venice turpentine is theoleoresin oflarch),[9] or thevolatile oil part thereof, namely oil (spirit) of turpentine; the latter usage is much more common today.[10]

Source trees

[edit]
"Herty system" in use on turpentine trees in Northern Florida, circa 1936
Chipping a turpentine tree in Georgia (US), circa 1906–20
"Cat face" on a pine tree
Turpentine distillery at Manlyn, North Carolina

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

[edit]
See also:Rosin § Purification

Crude turpentine collected from the trees may be evaporated bysteam distillation in acopper still. Moltenrosin remains in the still bottoms after turpentine has been distilled out.[11] Such turpentine is calledgum turpentine.[12] The termgum turpentine may also refer to crude turpentine, which may cause some confusion.

Turpentine may alternatively be extracted fromdestructive distillation of pine wood,[3] such as shredded pine stumps, roots, and slash, using the light end of the heavynaphtha fraction (boiling between 90 and 115 °C or 195 and 240 °F) from a crudeoil refinery. Such turpentine is calledwood turpentine. Multi-stage counter-currentextraction is commonly used so fresh naphtha first contacts wood leached in previous stages and naphtha laden with turpentine from previous stages contacts fresh wood beforevacuum distillation to recover naphtha from the turpentine. Leached wood is steamed for additional naphtha recovery prior to burning forenergy recovery.[13]

Sulfate turpentine

[edit]

When producing chemicalwood pulp frompines or otherconiferous trees, sulfate turpentine may be condensed from the gas generated inKraft process pulpdigesters. The average yield of crude sulfate turpentine is 5–10 kg/t pulp.[14] Unless burned at the mill for energy production, sulfate turpentine may require additional treatment measures to remove traces ofsulfur compounds.[15]

Industrial and other end uses

[edit]

Solvent

[edit]

As a solvent, turpentine is used for thinning oil-basedpaints, for producingvarnishes, and as a raw material for the chemical industry. Its use as a solvent in industrialized nations has largely been replaced by the much cheaperturpentine substitutes obtained frompetroleum such aswhite spirit. A solution of turpentine andbeeswax orcarnauba wax has long been used as a furniture wax.

Lighting

[edit]

Spirits of turpentine, calledcamphine, was burned in lamps with glass chimneys in the 1830s through the 1860s. Turpentine blended withgrain alcohol was known as burning fluid. Both were used as domestic lamp fuels, gradually replacingwhale oil, untilkerosene,gas lighting andelectric lights began to predominate.

Source of organic compounds

[edit]

Turpentine is also used as a source of raw materials in the synthesis of fragrant chemical compounds. Commercially usedcamphor,linalool,alpha-terpineol, andgeraniol are all usually produced fromalpha-pinene andbeta-pinene, which are two of the chief chemical components of turpentine. These pinenes are separated and purified by distillation. The mixture ofditerpenes andtriterpenes that is left as residue after turpentine distillation is sold asrosin.

Niche uses

[edit]
  • Turpentine is also added to many cleaning and sanitary products due to itsantiseptic properties and its "clean scent".
  • In early 19th-century America, spirits of turpentine (camphine) was burned in lamps as a cheap alternative towhale oil. It produced a bright light but had a strong odour.[16] Camphine andburning fluid (a mix of alcohol and turpentine) served as the dominant lamp fuels replacing whale oil until the advent ofkerosene,electric lights andgas lighting.[17]
  • Honda motorcycles, first manufactured in 1946, ran on a blend of gasoline and turpentine, due to the scarcity of gasoline in Japan followingWorld War II.[18] The FrenchEmeraude rocket uses a similar fuel mixture.[19] Turpentine has also been researched as a potential biofuel for mixing into gasoline.[20][21]
  • In his bookIf Only They Could Talk, veterinarian and authorJames Herriot describes the use of the reaction of turpentine withresublimed 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).[22]

Safety and health considerations

[edit]
NFPA 704
safety square

Turpentine is highly flammable, so much so that it has been considered as an automotive fuel.

Turpentine was added extensively into gin during theGin Craze.[23]

Turpentine's vapour can irritate the skin and eyes, damage thelungs and respiratory system, as well as thecentral nervous system when inhaled, and cause damage to therenal system when ingested, among other things.[24] Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea,tachycardia, unconsciousness, respiratory failure,[25] andchemical pneumonia.

The USOccupational 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 theNational Institute for Occupational Safety and Health (NIOSH) as therecommended exposure limit (REL). At levels of 800 ppm (4480 mg/m3), turpentine isimmediately dangerous to life and health.[26]

Folk medicine

[edit]

Turpentine and petroleum distillates such ascoal oil and kerosene, were used infolk medicine for abrasions and wounds, as a treatment forlice, and when mixed withanimal fat, as a chest rub or inhaler for nasal and throat ailments.[27][28]Vickschest rubs still contain turpentine in their formulations, although not as an active ingredient.[29]

Turpentine, now understood to be dangerous for consumption, was a common medicine among seamen during theAge of Discovery. It was one of several products carried aboardFerdinand Magellan's fleet during thefirst circumnavigation of the globe.[30] Taken internally it was used as a treatment forintestinal parasites. This is dangerous, due to the chemical's toxicity.[31][32]

Turpentineenemas, a very harsh purgative, had formerly been used for stubborn constipation or impaction.[33] They were also given punitively to political dissenters in post-independence Argentina.[34]

See also

[edit]
  • Galipot – Resin of turpentine obtained from pine trees
  • McCranie's Turpentine Still – a historic site in Willacoochee, Georgia
  • Naval stores industry – Term for resins used in shipbuildingPages displaying short descriptions of redirect targets
  • Patent medicine – over-the-counter "proprietary" medications
  • Retsina – Greek wine flavored with Aleppo pine resin
  • Russia leather – a water-resistant leather curried after tanning with a birch oil distillate similar to turpentine

References

[edit]
  1. ^abRecord ofTurpentine in theGESTIS Substance Database of theInstitute for Occupational Safety and Health
  2. ^Mayer, Ralph (1991).The Artist's Handbook of Materials and Techniques (Fifth ed.). New York: Viking. p. 404.ISBN 0-670-83701-6.
  3. ^abKent, James A.Riegel's Handbook of Industrial Chemistry (Eighth Edition) Van Nostrand Reinhold Company (1983)ISBN 0-442-20164-8 p.569
  4. ^Golets, Mikhail; Ajaikumar, Samikannu; Mikkola, Jyri-Pekka (2015). "Catalytic Upgrading of Extractives to Chemicals: Monoterpenes to "EXICALS"".Chemical Reviews.115 (9):3141–3169.doi:10.1021/cr500407m.PMID 25906177.
  5. ^"Solvents".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002.doi:10.1002/14356007.a24_437.ISBN 978-3-527-30673-2.
  6. ^Barnhart, R. K. (1995).The Barnhart Concise Dictionary of Etymology. New York: Harper Collins.ISBN 0-06-270084-7.
  7. ^Skeat, Walter W. (1882).A Concise Etymological Dictionary of the English Language. Oxford, UK: Oxford University Press. p. 579.
  8. ^Mills, John S.; White, Raymond (1977)."Natural Resins of Art and Archaeology Their Sources, Chemistry, and Identification".Studies in Conservation.22 (1):12–31.doi:10.2307/1505670.ISSN 0039-3630.JSTOR 1505670.
  9. ^Mahood, S. A. (1921-03-01)."Larch (Venice) Turpentine from Western Larch (Larix occidentalis)".Journal of Forestry.19 (3):274–282.doi:10.1093/jof/19.3.274 (inactive 1 November 2024).ISSN 0022-1201.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
  10. ^"Turpentine".Britannica. Retrieved2022-03-02.
  11. ^Kent p.571
  12. ^"Turpentine".Encyclopedia Britannica. Retrieved2022-05-16.
  13. ^Kent pp.571&572
  14. ^Stenius, Per, ed. (2000). "2".Forest Products Chemistry. Papermaking Science and Technology. Vol. 3. Finland: Fapet Oy : Published in cooperation with the Finnish Paper Engineers' Association andTAPPI. pp. 73–76.ISBN 952-5216-03-9.
  15. ^Kent p.572
  16. ^Charles H. Haswell."Reminiscences of New York By an Octogenarian (1816 - 1860)".Archived from the original on 2008-07-24. Retrieved2008-10-07.
  17. ^"The "Whale Oil Myth"".PBS NewsHour. 20 August 2008.Archived from the original on 10 May 2019. Retrieved25 March 2018.
  18. ^"Honda History". Smokeriders.com.Archived from the original on 2009-04-28. Retrieved2009-09-17.
  19. ^Huon, William (2007).Ariane: Une Épopée Européenne. Boulogne-Billancourt, France: ETAI. p. 45.ISBN 9782726887097.LCCN 2008398197.OCLC 422135584. AEE.
  20. ^Arpa, O.; Yumrutas, R.; Alma, M.H. (September 2010). "Effects of turpentine and gasoline-like fuel obtained from waste lubrication oil on engine performance and exhaust emission".Energy.35 (9):3603–3613.Bibcode:2010Ene....35.3603A.doi:10.1016/j.energy.2010.04.050.
  21. ^Knuuttila, Pekka (February 2013). "Wood sulphate turpentine as a gasoline bio-component".Fuel.104:101–108.Bibcode:2013Fuel..104..101K.doi:10.1016/j.fuel.2012.06.036.
  22. ^If Only They Could Talk. 28 June 2012.Archived from the original on 13 February 2021. Retrieved28 June 2018 – via www.amazon.co.uk., summarised at"James Herriot Books". Retrieved28 June 2018.[permanent dead link]
  23. ^Rohrer, Finlo (28 July 2014)."When gin was full of sulphuric acid and turpentine".BBC News.Archived from the original on 19 July 2018. Retrieved2 January 2018.
  24. ^"CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine - Symptoms".www.cdc.gov.Archived from the original on 2015-12-08. Retrieved2015-11-27.
  25. ^"Turpentine". International Programme on Chemical Safety, World Health Organization.Archived from the original on 2006-04-27. Retrieved2006-04-02.
  26. ^"CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine".www.cdc.gov.Archived from the original on 2015-12-08. Retrieved2015-11-27.
  27. ^"Surviving 'The Spanish Lady' (Spanish flu)".CBC News. 2003-04-10. Event occurs at 03:20.Archived from the original on 2020-08-07. Retrieved2018-12-29.A turpentine and hot water, and [wring hot towels out of there], and put it on their chest and back. --Elsie Miller (nee Smith)
  28. ^Sarah Rieger (December 29, 2018)."100 years ago, a train carrying Spanish flu pulled into Calgary. Within weeks, Alberta was in crisis".CBC News.Archived from the original on December 29, 2018. RetrievedDecember 29, 2018.
  29. ^"DailyMed - VICKS VAPORUB (camphor- synthetic, eucalyptus oil, and menthol ointment".dailymed.nlm.nih.gov.Archived from the original on 2021-05-05. Retrieved2021-05-05.
  30. ^Laurence Bergreen (2003).Over the edge of the world : Magellan's terrifying circumnavigation of the globe. HarperCollins.ISBN 0066211735. Retrieved2009-09-14.
  31. ^"Home Remedies - American Memory Timeline- Classroom Presentation".American Memory Timeline. The Library of Congress.Archived from the original on 2017-02-07. Retrieved2017-02-06.
  32. ^"ICSC 1063 - TURPENTINE".www.inchem.org.Archived from the original on 2006-04-27. Retrieved2006-04-02.
  33. ^"Turpentine enema".Biology-Online Dictionary. Biology-Online. 7 October 2019.Archived from the original on 2019-04-21. Retrieved2019-12-26.
  34. ^"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

External links

[edit]
Wikimedia Commons has media related toTurpentine.
Wikisource has the text of the 1879American Cyclopædia articleTurpentine.
Wikisource has the text of theEncyclopædia Britannica (9th ed.) articleTurpentine.
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