Chemistry:Turpentine

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Short description: Liquid distilled from pine resin
Turpentine
Turpentine distilled old way.jpg
Turpentine distilled at the Georgia Museum of Agriculture & Historic Village as it was done circa 1900
Identifiers
EC Number
  • 232-688-5
UNII
Properties[1]
C10H16
Molar mass 136.238 g·mol−1
Appearance Viscous liquid
Odor Resinous
Melting point −55 °C (−67 °F; 218 K)
Boiling point 154 °C (309 °F; 427 K)
20 mg/L
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 codeNFPA 704 four-colored diamond
3
1
0
Flash point 35 °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
Tracking categories (test):

Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthine, terebenthene, terebinthine and, colloquially, turps)[2] is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Principally 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, camphene, dipentene, and terpinolene.[3]

Substitutes include white spirit or other petroleum distillates – although the constituent chemicals are very different.[4]

Etymology

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 (τερέβινθος) for the terebinth tree.[5]

Although the word originally referred to the resinous exudate of terebinth trees (e.g. Chios turpentine, Cyprus turpentine, and Persian turpentine),[6][7] it now refers to that of coniferous trees, namely crude turpentine (e.g. Venice turpentine is the oleoresin of larch),[8] or the volatile oil part thereof, namely oil (spirit) of turpentine; the later usage is much more common today.[9]

Source trees

"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).

To tap into the sap producing layers of the tree, harvesters used a series of hacks to remove the pine bark. Once debarked, pine trees secrete crude turpentine (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. Harvesters 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.[10]

The V-shaped cuts are called "catfaces" for their resemblance to a cat's whiskers. These marks on a pine tree indicate it was used to collect resin for turpentine production.[11]

Turpentine (and rosin) are produced as naval stores.[12] Pine trees especially in North Carolina were tapped for sap which was doubly distilled to make turpentine and rosin (aka resin)–hence the name tar heel. The trees were scored with a ledge called a “box” to collect the sap. Large numbers of slaves were used to score the trees, collect and process the sap. Zallen describes this as industrial slavery–different from the more common vision of slaves in agriculture. By the 1840s camphine became the dominant lamp fuel in the US.

The pine trees of North Carolina were well suited to camphine production. The business also provided additional need for slaves as production expanded. Backwoods became more productive. Slaves were often leased in winter when agriculture was slower. The value of many was protected by life insurance. Wilmington, NC became a center of the camphine industry. In cities, gaslighting was also available, but used by the upper classes. Camphine was the fuel of the average family.

Zallen reports that after Ft. Sumter, turpentine producers were cut off from major markets. Emancipation left them without manpower to collect and process turpentine. The camps were flammable. Many were burned in William Tecumseh Sherman’s march from Savannah to Goldsboro, NC.

Converting crude turpentine to oil of turpentine

Crude turpentine collected from the trees may be evaporated by steam distillation in a copper still. Molten rosin remains in the still bottoms after turpentine has been distilled out.[10] Such turpentine is called gum turpentine.[13] 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,[3] such as 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. 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.[14]

Sulfate turpentine

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.[15] Unless burned at the mill for energy production, sulfate turpentine may require additional treatment measures to remove traces of sulfur compounds.[16]

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 has long been used as a furniture wax.

Lighting

Turpentine blended with grain alcohol was known as camphine or "burning fluid." It was used as a lamp fuel replacing whale oil from roughly 1840 to 1865, until the arrival of kerosene during the Civil War.

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.

Folk medicine

Turpentine and petroleum distillates such as coal oil and kerosene, were used in folk medicine 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.[17][18] Vicks chest rubs still contain turpentine in their formulations, although not as an active ingredient.[19]

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's fleet during the first circumnavigation of the globe.[20] Taken internally it was used as a treatment for intestinal parasites. This is dangerous, due to the chemical's toxicity.[21][22]

Turpentine enemas, a very harsh purgative, had formerly been used for stubborn constipation or impaction.[23] They were also given punitively to political dissenters in post-independence Argentina.[24]

Niche uses

  • 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 odour.[25] A blend of ethanol and turpentine called camphine served as the dominant lamp fuel replacing whale oil until the advent of kerosene.[26]
  • Honda 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.[27]
  • 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).[28]
  • Turpentine was added extensively into gin during the Gin Craze.[29]

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 codeNFPA 704 four-colored diamond
3
1
0

As an organic solvent, turpentine’s 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.[30] Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea, tachycardia, unconsciousness, respiratory failure,[31] 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 (NIOSH) as the recommended exposure limit (REL). At levels of 800 ppm (4480 mg/m3), turpentine is immediately dangerous to life and health.[32]

See also

  • Chemistry:Galipot – Resin of turpentine obtained from pine trees
  • McCranie's Turpentine Still – a historic site in Willacoochee, Georgia
  • Engineering:Naval stores industry
  • Patent medicine – over-the-counter “proprietary” medications
  • Russia leather – a water-resistant leather curried after tanning with a birch oil distillate similar to turpentine

References

  1. ↑ 1.0 1.1 Record of Turpentine in the GESTIS Substance Database of the Institute 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. https://archive.org/details/artistshandbooko00maye_0/page/404. 
  3. ↑ 3.0 3.1 Kent, James A. Riegel's Handbook of Industrial Chemistry (Eighth Edition) Van Nostrand Reinhold Company (1983) ISBN:0-442-20164-8 p.569
  4. ↑ "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a24_437. 
  5. ↑ Barnhart, R. K. (1995). The Barnhart Concise Dictionary of Etymology. New York: Harper Collins. ISBN 0-06-270084-7. 
  6. ↑ Skeat, Walter W. (1882). A Concise Etymological Dictionary of the English Language. Oxford, UK: Oxford University Press. pp. 579. https://archive.org/details/conciseetymologi002983mbp/page/579/mode/2up. 
  7. ↑ 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. https://www.jstor.org/stable/1505670. 
  8. ↑ 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. ISSN 0022-1201. https://academic.oup.com/jof/article-abstract/19/3/274/4752261. 
  9. ↑ "Turpentine". https://www.britannica.com/topic/turpentine. 
  10. ↑ 10.0 10.1 Kent p.571
  11. ↑ Prizer, Tom (June 11, 2010). "Catfaces: Totems of Georgia's Turpentiners | Daily Yonder | Keep It Rural". dailyyonder.com. https://www.dailyyonder.com/totems-georgias-lost-turpentine-industry/2010/06/10/2788. 
  12. ↑ Zallen, Jeremy (2019). American Lucifers: The Dark History of Artificial Light, 1750-1865. Chapel Hill, NC: University of North Carolina Press. 
  13. ↑ "Turpentine". https://www.britannica.com/topic/turpentine. 
  14. ↑ Kent pp.571&572
  15. ↑ Stenius, Per, ed (2000). "2". Forest Products Chemistry. Papermaking Science and Technology. 3. Finland: Fapet Oy : Published in cooperation with the Finnish Paper Engineers' Association and TAPPI. pp. 73–76. ISBN 952-5216-03-9. 
  16. ↑ Kent p.572
  17. ↑ "Surviving 'The Spanish Lady' (Spanish flu)". CBC News. 2003-04-10. https://www.cbc.ca/player/play/1606945926/. "A turpentine and hot water, and [wring hot towels out of there], and put it on their chest and back. --Elsie Miller (nee Smith)" 
  18. ↑ Sarah Rieger (December 29, 2018). "100 years ago, a train carrying Spanish flu pulled into Calgary. Within weeks, Alberta was in crisis". CBC News. https://www.cbc.ca/news/canada/calgary/spanish-flu-alberta-history-1.4948081. 
  19. ↑ "DailyMed - VICKS VAPORUB (camphor- synthetic, eucalyptus oil, and menthol ointment". https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e69a7c9b-fd04-4109-a7c8-6edfd83855fc. 
  20. ↑ Laurence Bergreen (2003). Over the edge of the world : Magellan's terrifying circumnavigation of the globe. HarperCollins. ISBN 0066211735. https://archive.org/details/overedgeofworl00berg. Retrieved 2009-09-14. 
  21. ↑ "Home Remedies - American Memory Timeline- Classroom Presentation". American Memory Timeline. The Library of Congress. https://www.loc.gov/teachers/classroommaterials/presentationsandactivities/presentations/timeline/riseind/rural/remedies.html. 
  22. ↑ "ICSC 1063 - TURPENTINE". https://www.inchem.org/documents/icsc/icsc/eics1063.htm. 
  23. ↑ "Turpentine enema". Biology-Online. 7 October 2019. https://www.biology-online.org/dictionary/Turpentine_enema. 
  24. ↑ "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
  25. ↑ Charles H. Haswell. "Reminiscences of New York By an Octogenarian (1816 - 1860)". https://www.jmisc.net/octo/octo-17.htm. 
  26. ↑ "The "Whale Oil Myth"". 20 August 2008. https://www.pbs.org/newshour/economy/this-post-is-hopelessly-long-w. 
  27. ↑ "Honda History". Smokeriders.com. https://smokeriders.com/History/Honda_History/body_honda_history.html. 
  28. ↑ If Only They Could Talk. 28 June 2012. https://www.amazon.co.uk/Only-They-Could-Talk-Collectors-ebook/dp/B008I33ZWQ/ref=sr_1_1?ie=UTF8&qid=1530212880&sr=8-1&keywords=if+only+they+could+talk. Retrieved 28 June 2018. , summarised at "James Herriot Books". https://jamesherriotbooks.blogspot.com/2008/08/if-only-they-could-talk-ch-3.html/. [yes|permanent dead link|dead link}}]
  29. ↑ Rohrer, Finlo (28 July 2014). "When gin was full of sulphuric acid and turpentine". BBC News. https://www.bbc.com/news/magazine-28486017. 
  30. ↑ "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine - Symptoms". https://www.cdc.gov/niosh/npg/npgd0648.html. 
  31. ↑ "Turpentine". International Programme on Chemical Safety, World Health Organization. https://www.inchem.org/documents/icsc/icsc/eics1063.htm. 
  32. ↑ "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine". https://www.cdc.gov/niosh/npg/npgd0648.html. 

External links



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