View source for Turpentine

{{Short description|Liquid distilled from pine resin}}
{{About|oil of turpentine|crude turpentine|oleoresin|other uses|turpentine (disambiguation)}}
{{Chembox
<!-- Images -->
| ImageFile = Turpentine distilled old way.jpg
| ImageSize = 120px
| ImageCaption = Turpentine distilled at the [[Georgia Museum of Agriculture & Historic Village]] as it was done circa 1900
<!-- Names -->
| IUPACName = 
| OtherNames =
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 9005-90-7
| EINECS = 232-688-5
| UNII = XJ6RUH0O4G
| PubChem = 48418114
| SMILES = 
  }}
| Section2 = {{Chembox Properties
| Properties_ref = <ref name=GESTIS>{{GESTIS|ZVG=95540|Name=Turpentine}}</ref>
| Formula =
| C=10 |H=16
| MolarMass = 
| Appearance = Viscous liquid
| Odor = Resinous
| Density = 
| MeltingPtC = -55
| BoilingPtC = 154
| Solubility = 20 mg/L
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPtC = 35
| AutoignitionPtC = 220<ref name="GESTIS"/><!--

 no GHS info in ACHA source, not in pubchem. Dec 2021.

| GHSPictograms = {{GHS02}} {{GHS08}} {{GHS07}} {{GHS09}}

| GHS_ref  = <ref>{{cite web |url = https://echa.europa.eu/substance-information/-/substanceinfo/100.029.704 |title=Turpentine |publisher = European Chemicals Agency}}</ref>
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|302|304|312|315|317|319|332|411}} 
| PPhrases = {{P-phrases|}}

-->

| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
  }}
}}

'''Turpentine''' (which is also called '''spirit of turpentine''', '''oil of turpentine''', '''terebenthine''', '''terebenthene''', '''terebinthine''' and, colloquially, '''turps''')<ref>{{cite book |title=The Artist's Handbook of Materials and Techniques |last=Mayer |first=Ralph |year=1991 |edition=Fifth |publisher=Viking |location=New York |isbn=0-670-83701-6 |page=[https://archive.org/details/artistshandbooko00maye_0/page/404 404] |url-access=registration |url=https://archive.org/details/artistshandbooko00maye_0/page/404 }}</ref> is a fluid obtainable by the [[distillation]] of [[resin]] harvested from living trees, mainly [[pine]]s. Principally used as a specialized [[solvent]], it is also a source of material for [[Organic synthesis|organic syntheses]].

Turpentine is composed of [[terpene]]s, primarily the monoterpenes [[α-pinene]] and [[β-pinene]], with lesser amounts of [[carene]], [[camphene]], [[limonene]], and [[terpinolene]].<ref name="k69">Kent, James A. ''Riegel's Handbook of Industrial Chemistry'' (Eighth Edition) Van Nostrand Reinhold Company (1983) {{ISBN|0-442-20164-8}} p.569</ref> 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]] 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.<ref>{{cite journal |doi=10.1021/cr500407m |title=Catalytic Upgrading of Extractives to Chemicals: Monoterpenes to "EXICALS" |date=2015 |last1=Golets |first1=Mikhail |last2=Ajaikumar |first2=Samikannu |last3=Mikkola |first3=Jyri-Pekka |journal=Chemical Reviews |volume=115 |issue=9 |pages=3141–3169 |pmid=25906177 }}</ref>

Substitutes include [[white spirit]] or other [[petroleum]] distillates, although the constituent chemicals are very different.<ref>{{Ullmann|authorDieter Stoye|title=Solvents|year=2002|doi=10.1002/14356007.a24_437}}</ref>

== Etymology ==
The word ''turpentine'' derives (via [[French language|French]] and [[Latin]]) from the [[Greek language|Greek]] word ''τερεβινθίνη'', ''terebinthine'' in English, in turn the feminine form (to conform to the [[Grammatical gender|feminine gender]] of the Greek word, which means 'resin') of an adjective (τερεβίνθινος) derived from the Greek noun τερέβινθος for the [[terebinth]] tree.<ref>{{cite book | last=Barnhart | first=R. K. | title=The Barnhart Concise Dictionary of Etymology | location=New York | publisher=Harper Collins | year=1995 | isbn=0-06-270084-7}}</ref>

Although the word originally referred to the resinous exudate of terebinth trees (e.g. [[Pistacia lentiscus|Chios turpentine]], [[Cyprus turpentine]], and [[Pistacia atlantica|Persian turpentine]]),<ref>{{Cite book |last=Skeat |first=Walter W. |url=https://archive.org/details/conciseetymologi002983mbp/page/579/mode/2up |title=A Concise Etymological Dictionary of the English Language |publisher=Oxford University Press |year=1882 |location=Oxford, UK |pages=579}}</ref><ref>{{Cite journal |last1=Mills |first1=John S. |last2=White |first2=Raymond |date=1977 |title=Natural Resins of Art and Archaeology Their Sources, Chemistry, and Identification |url=https://www.jstor.org/stable/1505670 |journal=Studies in Conservation |volume=22 |issue=1 |pages=12–31 |doi=10.2307/1505670 |issn=0039-3630 |jstor=1505670|url-access=subscription }}</ref> it now refers to that of [[conifer]]ous trees, namely [[crude turpentine]] (e.g. Venice turpentine is the [[oleoresin]] of [[larch]]),<ref>{{Cite journal |last=Mahood |first=S. A. |date=1921-03-01 |title=Larch (Venice) Turpentine from Western Larch (Larix occidentalis) |url=https://academic.oup.com/jof/article-abstract/19/3/274/4752261 |journal=Journal of Forestry |volume=19 |issue=3 |pages=274–282 |doi=10.1093/jof/19.3.274 |doi-broken-date=12 July 2025<!-- reported to DOI on 2025-01-27 --> |issn=0022-1201|url-access=subscription }}</ref> or the [[volatile oil]] part thereof, namely oil (spirit) of turpentine; the latter usage is much more common today.<ref>{{Cite web |title=Turpentine |url=https://www.britannica.com/topic/turpentine |access-date=2022-03-02 |website=Britannica}}</ref>

==Source trees==
[[File:CupGutterSystem.jpg|thumb|"[[Charles Herty|Herty system]]" in use on turpentine trees in Northern Florida, circa 1936]]
[[File:Chipping a turpentine tree.jpg|thumb|Chipping a turpentine tree in Georgia (US), circa 1906–20]]
[[File:Turpentine face Clinch Co, GA, US, 2.jpg|thumb|"Cat face" on a pine tree]]
[[File:PSM V48 D518 Turpentine still at Manlyn North Carolina.jpg|thumb|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==
{{see also|Rosin#Purification}}
[[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.<ref name="k71">Kent p.571</ref> Such turpentine is called '''gum turpentine'''.<ref>{{Cite web |title=Turpentine |url=https://www.britannica.com/topic/turpentine |access-date=2022-05-16 |website=Encyclopedia Britannica}}</ref> 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,<ref name="k69" /> such as shredded pine stumps, roots, and slash, using the light end of the heavy [[naphtha]] fraction (boiling between {{convert|90|and|115|°C|disp=or|round=5}}) from a [[oil refinery|crude-oil refinery]]. Such turpentine is called '''wood turpentine'''. Multi-stage counter-current [[solid phase extraction|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]].<ref>Kent pp.571&572</ref>

=== Sulfate turpentine ===
When producing chemical [[wood pulp]] from [[pine]]s or other [[coniferous trees]], sulfate turpentine may be condensed from the gas generated in [[Kraft process]] pulp [[Kraft process#Cooking|digesters]]. The average yield of crude sulfate turpentine is 5–10&nbsp;kg/t pulp.<ref name="sten">{{cite book |editor1-first= Per |editor1-last= Stenius |title= Forest Products Chemistry|series= Papermaking Science and Technology |volume= 3|year= 2000|publisher=Fapet Oy : Published in cooperation with the Finnish Paper Engineers' Association and [[TAPPI]] |location= Finland |isbn=952-5216-03-9 |pages= 73–76 |chapter= 2 }}</ref> Unless burned at the mill for energy production, sulfate turpentine may require additional treatment measures to remove traces of [[sulfur]] compounds.<ref>Kent p.572</ref>

==Uses==

===Solvent===
As a solvent, turpentine is used for thinning oil-based [[paint]]s, for producing [[varnish]]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 substitute]]s 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===
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]], until [[kerosene]], [[gas lighting]], 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]], [[terpineol|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 [[diterpene]]s and [[triterpene]]s that is left as residue after turpentine distillation is sold as [[rosin]].

===Niche uses===
* Because it's naturally a pine pitch thinner, it will remove pitch from clothing while other common solvents may not do as well.
* Turpentine is also added to many cleaning and sanitary products due to its [[antiseptic]] properties and its "clean scent". 
* In early 19th-century America, spirits of turpentine ([[camphine]]) were burned in lamps as a cheap alternative to [[whale oil]]. It produced a bright light but had a strong odour.<ref>{{cite web | author=Charles H. Haswell | title=Reminiscences of New York By an Octogenarian (1816 - 1860) | url=https://www.jmisc.net/octo/octo-17.htm | access-date=2008-10-07 | archive-date=2008-07-24 | archive-url=https://web.archive.org/web/20080724111316/https://www.jmisc.net/octo/octo-17.htm | url-status=live }}</ref> Camphine and [[Camphine|burning fluid]] (a mix of alcohol and turpentine) served as the dominant lamp fuels replacing whale oil until the advent of [[kerosene]], [[electric lights]], and [[gas lighting]].<ref>{{cite web|url=https://www.pbs.org/newshour/economy/this-post-is-hopelessly-long-w|title=The "Whale Oil Myth"|date=20 August 2008|website=PBS NewsHour|access-date=25 March 2018|archive-date=10 May 2019|archive-url=https://web.archive.org/web/20190510142257/https://www.pbs.org/newshour/economy/this-post-is-hopelessly-long-w|url-status=live}}</ref>  
* [[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]].<ref>{{cite web | title=Honda History | url=https://smokeriders.com/History/Honda_History/body_honda_history.html | publisher=Smokeriders.com | access-date=2009-09-17 | archive-date=2009-04-28 | archive-url=https://web.archive.org/web/20090428051223/https://smokeriders.com/History/Honda_History/body_honda_history.html | url-status=live }}</ref> The French [[Emeraude (rocket)|Emeraude rocket]] uses a similar fuel mixture.<ref name="Huon">{{cite book |id=AEE |title=Ariane: Une Épopée Européenne |page=45 |last1=Huon |first1=William |publisher=ETAI |date=2007 |location=Boulogne-Billancourt, France |isbn=9782726887097 |oclc=422135584 |lccn=2008398197 }}</ref> Turpentine has also been researched as a potential biofuel for mixing into gasoline.<ref>{{cite journal |last1=Arpa |first1=O. |last2=Yumrutas |first2=R. |last3=Alma |first3=M.H. |title=Effects of turpentine and gasoline-like fuel obtained from waste lubrication oil on engine performance and exhaust emission |journal=Energy |date=September 2010 |volume=35 |issue=9 |pages=3603–3613 |doi=10.1016/j.energy.2010.04.050|bibcode=2010Ene....35.3603A }}</ref><ref>{{cite journal |last1=Knuuttila |first1=Pekka |title=Wood sulphate turpentine as a gasoline bio-component |journal=Fuel |date=February 2013 |volume=104 |pages=101–108 |doi=10.1016/j.fuel.2012.06.036|bibcode=2013Fuel..104..101K }}</ref>
* In his book ''[[All Creatures Great and Small (franchise)|If Only They Could Talk]]'', veterinarian and author [[James Herriot]] describes the use of the reaction of turpentine with [[Sublimation (phase transition)|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).<ref>{{cite book|url=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|title=If Only They Could Talk|date=28 June 2012|access-date=28 June 2018|via=www.amazon.co.uk|archive-date=13 February 2021|archive-url=https://web.archive.org/web/20210213010934/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|url-status=live}}, summarised at {{cite web|url=https://jamesherriotbooks.blogspot.com/2008/08/if-only-they-could-talk-ch-3.html/|title=James Herriot Books|access-date=28 June 2018}}{{Dead link|date=February 2022 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

==Safety and health considerations==
{{NFPA 704|Health = 1|Flammability = 3|Reactivity = 0}}
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]].<ref>{{cite news|url=https://www.bbc.com/news/magazine-28486017|title=When gin was full of sulphuric acid and turpentine|first=Finlo|last=Rohrer|work=BBC News|date=28 July 2014|access-date=2 January 2018|archive-date=19 July 2018|archive-url=https://web.archive.org/web/20180719043601/https://www.bbc.com/news/magazine-28486017|url-status=live}}</ref>

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.<ref>{{Cite web|title = CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine - Symptoms|url = https://www.cdc.gov/niosh/npg/npgd0648.html|website = www.cdc.gov|access-date = 2015-11-27|archive-date = 2015-12-08|archive-url = https://web.archive.org/web/20151208123745/https://www.cdc.gov/niosh/npg/npgd0648.html|url-status = live}}</ref> Ingestion can cause burning sensations, abdominal pain, nausea, vomiting, confusion, convulsions, diarrhea, [[tachycardia]], unconsciousness, respiratory failure,<ref>{{cite web | url = https://www.inchem.org/documents/icsc/icsc/eics1063.htm | title = Turpentine | publisher = International Programme on Chemical Safety, World Health Organization | access-date = 2006-04-02 | archive-date = 2006-04-27 | archive-url = https://web.archive.org/web/20060427165609/https://www.inchem.org/documents/icsc/icsc/eics1063.htm | url-status = live }}</ref> and [[Chemical pneumonitis|chemical pneumonia]]. 

The US [[Occupational Safety and Health Administration]] (OSHA) has set the legal limit ([[permissible exposure limit]]) for turpentine exposure in the workplace as 100&nbsp;ppm (560&nbsp;mg/m<sup>3</sup>) 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&nbsp;ppm (4480 mg/m<sup>3</sup>), turpentine is [[IDLH|immediately dangerous to life and health]].<ref>{{Cite web|title = CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine|url = https://www.cdc.gov/niosh/npg/npgd0648.html|website = www.cdc.gov|access-date = 2015-11-27|archive-date = 2015-12-08|archive-url = https://web.archive.org/web/20151208123745/https://www.cdc.gov/niosh/npg/npgd0648.html|url-status = live}}</ref>

===Folk medicine===
Turpentine and petroleum distillates such as [[coal oil]] and kerosene, were used in [[traditional medicine|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.<ref>{{cite news
|url=https://www.cbc.ca/player/play/1606945926/
|title=Surviving 'The Spanish Lady' (Spanish flu)
|work=CBC News
|date=2003-04-10
|quote=A turpentine and hot water, and [wring hot towels out of there], and put it on their chest and back. --Elsie Miller (nee Smith)
|time=03:20
|access-date=2018-12-29
|archive-date=2020-08-07
|archive-url=https://web.archive.org/web/20200807221113/https://www.cbc.ca/player/play/1606945926
|url-status=live
}}</ref><ref>{{cite news |author=Sarah Rieger |date=December 29, 2018 |title=100 years ago, a train carrying Spanish flu pulled into Calgary. Within weeks, Alberta was in crisis |url=https://www.cbc.ca/news/canada/calgary/spanish-flu-alberta-history-1.4948081 |work=CBC News |access-date=December 29, 2018 |archive-date=December 29, 2018 |archive-url=https://web.archive.org/web/20181229183935/https://www.cbc.ca/news/canada/calgary/spanish-flu-alberta-history-1.4948081 |url-status=live }}</ref> [[Vicks VapoRub|Vicks]] [[chest rub]]s still contain turpentine in their formulations, although not as an active ingredient.<ref>{{Cite web|title=DailyMed - VICKS VAPORUB (camphor- synthetic, eucalyptus oil, and menthol ointment|url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e69a7c9b-fd04-4109-a7c8-6edfd83855fc|access-date=2021-05-05|website=dailymed.nlm.nih.gov|archive-date=2021-05-05|archive-url=https://web.archive.org/web/20210505064609/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e69a7c9b-fd04-4109-a7c8-6edfd83855fc|url-status=live}}</ref>

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]].<ref>{{cite book | author=Laurence Bergreen | author-link=Laurence Bergreen | title=Over the edge of the world : Magellan's terrifying circumnavigation of the globe | url=https://archive.org/details/overedgeofworl00berg | year=2003 | publisher=HarperCollins | isbn=0066211735 | access-date=2009-09-14 | url-access=registration }}</ref> Taken internally, it was used as a treatment for [[intestinal parasite]]s. This is dangerous, due to the chemical's toxicity.<ref>{{cite web|url=https://www.loc.gov/teachers/classroommaterials/presentationsandactivities/presentations/timeline/riseind/rural/remedies.html|title=Home Remedies - American Memory Timeline- Classroom Presentation|publisher=The Library of Congress|work=American Memory Timeline|access-date=2017-02-06|archive-date=2017-02-07|archive-url=https://web.archive.org/web/20170207031310/https://www.loc.gov/teachers/classroommaterials/presentationsandactivities/presentations/timeline/riseind/rural/remedies.html|url-status=live}}</ref><ref>{{cite web|url=https://www.inchem.org/documents/icsc/icsc/eics1063.htm|title=ICSC 1063 - TURPENTINE|website=www.inchem.org|access-date=2006-04-02|archive-date=2006-04-27|archive-url=https://web.archive.org/web/20060427165609/https://www.inchem.org/documents/icsc/icsc/eics1063.htm|url-status=live}}</ref>

Turpentine [[enema]]s, a very harsh purgative, had formerly been used for stubborn constipation or impaction.<ref>{{cite web |url=https://www.biology-online.org/dictionary/Turpentine_enema |title=Turpentine enema |website=Biology-Online Dictionary |date=7 October 2019 |publisher=Biology-Online |access-date=2019-12-26 |archive-date=2019-04-21 |archive-url=https://web.archive.org/web/20190421005931/https://www.biology-online.org/dictionary/Turpentine_enema |url-status=live }}</ref> They were also given punitively to political dissenters in post-independence Argentina.<ref>"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</ref>

==See also==
* {{annotated link|Galipot}}
* [[McCranie's Turpentine Still]] &ndash; a historic site in [[Willacoochee, Georgia]]
* {{annotated link|Naval stores}}
* [[Patent medicine]] &ndash; over-the-counter "proprietary" medications
* {{annotated link|Retsina}} flavored with Aleppo pine resin
* [[Russia leather]] &ndash; a water-resistant leather curried after tanning with a birch oil distillate similar to turpentine

== References ==
{{Reflist|30em}}

==External links==
{{Commons category|Turpentine}}
{{AmCyc Poster|Turpentine}}
{{EB9 Poster|Turpentine}}
* [https://www.inchem.org/documents/icsc/icsc/eics1063.htm Inchem.org], [[IPCS Health and Safety Guide|IPCS]] INCHEM Turpentine classification, hazard, and property table.
* [https://www.cdc.gov/niosh/npg/npgd0648.html CDC - NIOSH Pocket Guide to Chemical Hazards - Turpentine]
{{Non-timber forest products}}
{{Authority control}}
[[Category:Household chemicals]]
[[Category:Hydrocarbon solvents]]
[[Category:Painting materials]]
[[Category:Patent medicines]]
[[Category:Resins]]
[[Category:Terpenes and terpenoids]]
[[Category:Papermaking]]
[[Category:Non-timber forest products]]
[[Category:Wood extracts]]