Turpentine
Turpentine distilled old way.jpg

Turpentine distilled at the Georgia Museum of Agriculture & Historic Village as it was circa 1900
Identifiers
ECHA InfoCard 100.029.407 Edit this at Wikidata
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)
1
3
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).

Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthene, terebinthine and (colloquially) turps)[2] is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Mainly 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] Mineral turpentine or other petroleum distillates are used to replace turpentine – 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
"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 in Georgia (US), circa 1906-20
Turpentine distillery at Manlyn, North Carolina
Turpentine distillery at Manlyn, North Carolina
Chemical structure of α-pinene, a major component of turpentine
Chemical structure of α-pinene, a major component of turpentine

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, turpentiners used a combination 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. Turpentiners 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 signify it was used to collect resin for turpentine production.[11]

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.[12] The term gum turpentine may also refer to crude turpentine, which causes considerable 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.[13]

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

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. A solution of turpentine and beeswax or carnauba wax has long been used as a furniture wax.

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.[16] Vicks chest rubs still contain turpentine in their formulations, although not as an active ingredient.[17]

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 during the first circumnavigation of the globe.[18] Taken internally it was used as a treatment for intestinal parasites. This is dangerous, due to the chemical's toxicity.[19][20]

Turpentine enemas, a very harsh purgative, had formerly been used for stubborn constipation or impaction.[21] Turpentine enemas were also given punitively to political dissenters in post-independence Argentina.[22]

Niche uses

Hazards

NFPA 704
fire diamond
1
3
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.[28] Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea, tachycardia, unconsciousness, respiratory failure, and death.[29]

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.[30]

See also

References

  1. ^ a b 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.
  3. ^ a b Kent, James A. Riegel's Handbook of Industrial Chemistry (Eighth Edition) Van Nostrand Reinhold Company (1983) ISBN 0-442-20164-8 p.569
  4. ^ "Solvents". 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. p. 579.
  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. JSTOR 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.
  9. ^ "Turpentine". Britannica. Retrieved 2022-03-02.
  10. ^ a b Kent p.571
  11. ^ Prizer, Tom (June 11, 2010). "Catfaces: Totems of Georgia's Turpentiners | Daily Yonder | Keep It Rural". dailyyonder.com. Archived from the original on July 26, 2015. Retrieved June 5, 2012.
  12. ^ "Turpentine". Encyclopedia Britannica. Retrieved 2022-05-16.
  13. ^ Kent pp.571&572
  14. ^ Stenius, Per, ed. (2000). "2". Forest Products Chemistry. Papermaking Science and Technology. Vol. 3. Finland. pp. 73–76. ISBN 952-5216-03-9.
  15. ^ Kent p.572
  16. ^ "Surviving 'The Spanish Lady' (Spanish flu)". CBC News. 2003-04-10. Event occurs at 03:20. Archived from the original on 2020-08-07. Retrieved 2018-12-29. A turpentine and hot water, and [wring hot towels out of there], and put it on their chest and back. --Elsie Miller (nee Smith)
  17. ^ "DailyMed - VICKS VAPORUB (camphor- synthetic, eucalyptus oil, and menthol ointment". dailymed.nlm.nih.gov. Archived from the original on 2021-05-05. Retrieved 2021-05-05.
  18. ^ Laurence Bergreen (2003). Over the edge of the world : Magellan's terrifying circumnavigation of the globe. ISBN 0066211735. Retrieved 2009-09-14.
  19. ^ "Home Remedies - American Memory Timeline- Classroom Presentation". American Memory Timeline. The Library of Congress. Archived from the original on 2017-02-07. Retrieved 2017-02-06.
  20. ^ "ICSC 1063 - TURPENTINE". www.inchem.org. Archived from the original on 2006-04-27. Retrieved 2006-04-02.
  21. ^ "Turpentine enema". Biology-Online Dictionary. Biology-Online. 7 October 2019. Archived from the original on 2019-04-21. Retrieved 2019-12-26.
  22. ^ "Ribbons and Rituals". In Problems in Modern Latin American History. Ed. Chasteen and Wood. Oxford, UK: Scholarly Resources, 2005. p. 97
  23. ^ Charles H. Haswell. "Reminiscences of New York By an Octogenarian (1816 - 1860)". Archived from the original on 2008-07-24. Retrieved 2008-10-07.
  24. ^ "The "Whale Oil Myth"". PBS NewsHour. 20 August 2008. Archived from the original on 10 May 2019. Retrieved 25 March 2018.
  25. ^ "Honda History". Smokeriders.com. Archived from the original on 2009-04-28. Retrieved 2009-09-17.
  26. ^ If Only They Could Talk. 28 June 2012. Archived from the original on 13 February 2021. Retrieved 28 June 2018 – via www.amazon.co.uk., summarised at "James Herriot Books". Retrieved 28 June 2018.[permanent dead link]
  27. ^ Rohrer, Finlo (28 July 2014). "When gin was full of sulphuric acid and turpentine". BBC News. Archived from the original on 19 July 2018. Retrieved 2 January 2018.
  28. ^ "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine - Symptoms". www.cdc.gov. Archived from the original on 2015-12-08. Retrieved 2015-11-27.
  29. ^ "Turpentine". International Programme on Chemical Safety, World Health Organization. Archived from the original on 2006-04-27. Retrieved 2006-04-02.
  30. ^ "CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine". www.cdc.gov. Archived from the original on 2015-12-08. Retrieved 2015-11-27.


Wikisource has the text of the 1879 American Cyclopædia article Turpentine.
Wikisource has the text of the Encyclopædia Britannica (9th ed.) article Turpentine.