Pine oil

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Pine oil [1]
PineEssentialOil.png
Pine (Pinus sylvestris) essential oil in a clear glass vial
Names
Other names
Essential oil of pine
Yarmor
Identifiers
8191505
ChemSpider
  • none
ECHA InfoCard 100.219.894 OOjs UI icon edit-ltr-progressive.svg
UNII
Properties
Mixture
AppearanceColorless to pale yellow liquid
Density 0.875 g/cm3 at 25 °C (approximate)
Melting point 5 °C (41 °F; 278 K)
Boiling point 195 °C (383 °F; 468 K)
Insoluble
log P 1.7
Vapor pressure 4 mmHg
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 65 °C (149 °F; 338 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Pine oil is an essential oil obtained from a variety of species of pine, particularly Pinus sylvestris . Typically, parts of the trees that are not used for lumber stumps, etc. are ground and subjected to steam distillation. [2] As of 1995, synthetic pine oil was the "biggest single turpentine derivative." [3] Synthetic pine oils accounted for 90% of sales as of 2000. [4]

Contents

Composition

Pine oil is a higher boiling fraction from turpentine. Both synthetic and natural pine oil consists mainly of α-terpineol, a C10 alcohol (b.p. 214–217 °C). [5] [1] Other components include dipentene and pinene. [6] The detailed composition of natural pine oil depends on many factors, such as the species of the host plant. [7] Synthetic pine oil is obtained by treating pinene with water in the presence of a catalytic amount of sulfuric acid. This treatment results in hydration of the alkene and rearrangement of the pinene skeleton, yielding terpineols. [4]

Uses

Industrially, pine oil was once used in froth flotation for the separation of mineral from ores. [1] For example, in copper extraction, pine oil is used to condition copper sulfide ores for froth flotation.

It is also used as a lubricant in small and expensive clockwork instruments.

In alternative medicine it is used in aromatherapy and as a scent in bath oils.

Properties as a disinfectant

Pine oil is used as a cleaning product, disinfectant, sanitizer, microbicide (or microbistat), virucide or insecticide. [5] It is an effective herbicide where its action is to modify the waxy cuticle of plants, resulting in desiccation. [8] Pine oil is a disinfectant that is mildly antiseptic. [9] It is effective against Brevibacterium ammoniagenes, the fungi Candida albicans , Enterobacter aerogenes , Escherichia coli , Gram-negative enteric bacteria, household germs, Gram-negative household germs such as those causing salmonellosis, herpes simplex types 1 and 2, influenza type A, influenza virus type A/Brazil, influenza virus type A2/Japan, intestinal bacteria, Klebsiella pneumoniae , odor-causing bacteria, mold, mildew, Pseudomonas aeruginosa , Salmonella choleraesuis , Salmonella typhi , Salmonella typhosa , Serratia marcescens , Shigella sonnei , Staphylococcus aureus , Streptococcus faecalis , Streptococcus pyogenes , and Trichophyton mentagrophytes . [5]

Safety

With respect to the quality of indoor air, attention is directed to the effects of ambient ozone on pine oil components. [10] Large doses may cause central nervous system depression. [1]

See also

Related Research Articles

<span class="mw-page-title-main">Resin</span> Organic polymer, typically from plants

A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, and predominantly terpenes. Well known resins include amber, hashish, frankincense, myrrh and the animal-derived resin, shellac. Resins are commonly used in varnishes, adhesives, food additives, incenses and perfumes.

<span class="mw-page-title-main">Turpentine</span> Liquid distilled from pine resin

Turpentine 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.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals are used against fungi. They can also be classified according to their function. Antimicrobial medicines to treat infection are known as ⠀⠀antimicrobial chemotherapy, while antimicrobial drugs are used to prevent infection, which known as antimicrobial prophylaxis.

<i>Pinus roxburghii</i> Species of conifer

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

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

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<span class="mw-page-title-main">Limonene</span> Liquid terpene hydrocarbon fragrance and flavor, extract of citrus peel

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common (-)-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

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<span class="mw-page-title-main">Pinene</span> Oily organic chemical found in plants

Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major component of the liquid extracts of conifers. Pinenes are also found in many non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush.

<span class="mw-page-title-main">Naval stores</span> Term for resins used in shipbuilding

Naval stores refers to the industry that produces rosin, turpentine, tall oil, pine oil, and other oleoresin collected from conifers. The term was originally applied to the compounds used in building and maintaining wooden sailing ships. Presently, pine compounds produced by the naval stores industry are used to manufacture soap, paint, varnish, shoe polish, lubricants, linoleum, and roofing materials.

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Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As with other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango. It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.

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<span class="mw-page-title-main">Naval stores industry</span>

The naval stores industry produces and markets products derived from the oleoresin of pine trees, including rosin, tall oil, pine oil, and turpentine. It does this by collecting and processing organic forest products refined from slash pine and longleaf pine trees. The naval stores 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.

α-Pinene Chemical compound

α-Pinene is an organic compound of the terpene class. It is one of the two isomers of pinene, the other being β-pinene. An alkene, it contains a reactive four-membered ring. It is found in the oils of many species of coniferous trees, notably Pinus and Picea species. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The enantiomers' racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

β-Pinene Chemical compound

β-Pinene is a monoterpene, an organic compound found in plants. It is the less abundant of the two isomers of pinene, the other being α-pinene. It is a colorless liquid soluble in alcohol, but not water. It has a woody-green pine-like smell.

<span class="mw-page-title-main">Terpineol</span> Chemical compound

Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-terpineol, β-terpineol, γ-terpineol, and terpinen-4-ol. β-Terpineol and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.

In chemistry, a fatty amine is loosely defined as any amine possessing a mostly linear hydrocarbon chain of eight or more carbon atoms. They are typically prepared from the more abundant fatty acids, with vegetable or seed-oils being the ultimate starting material. As such they are often mixtures of chain lengths, ranging up to about C22. They can be classified as oleochemicals. Commercially important members include coco amine, oleylamine, tallow amine, and soya amine. These compounds and their derivatives are used as fabric softeners, froth flotation agents, corrosion inhibitors, lubricants and friction modifiers. They are also the basis for a variety of cosmetic formulations.

References

  1. 1 2 3 4 Merck Index, 11th Edition, 7416. p. 1182
  2. Boyle, Hal (September 12, 1954). "There's Gold in those Pine Stumps". Sarasota Journal. p. 11.
  3. Chapter 1. Production trade and markets. Rome: Food and Agriculture Organization. 1995. ISBN   978-9251036846.{{cite book}}: |work= ignored (help)
  4. 1 2 Gscheidmeier, Manfred; Fleig, Helmut (June 15, 2000). "Turpentines, 16. Pine Oil". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_267. ISBN   978-3527306732.
  5. 1 2 3 "Reregistration Decision – Pine oil (case 3113)" (PDF). Environmental Protection Agency. October 2006.
  6. Vallinayagam, R.; Vedharaj, S.; Yang, W.M.; Lee, P.S.; Chua, K.J.E.; Chou, S.K. (2013). "Combustion performance and emission characteristics study of pine oil in a diesel engine". Energy. 57: 344–351. doi:10.1016/j.energy.2013.05.061.
  7. Macchioni, F.; Cioni, P. L.; Flamini, G.; Morelli, I.; Maccioni, S.; Ansaldi, M. (2003-03-01). "Chemical Composition of Essential Oils from Needles, Branches and Cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from Central ltaly". Flavour and Fragrance Journal. 18 (2): 139–143. doi:10.1002/ffj.1178. ISSN   1099-1026.
  8. Coleby-Williams, Jerry (April 9, 2004). "Fact Sheet: Organic Weed Control". Gardening Australia . Retrieved August 28, 2016.
  9. "Pine Oil". PDRhealth. 2003. Archived from the original on 2007-09-21.
  10. Singer, B. C.; Destaillats, H.; Hodgson, A. T.; Nazaroff, W. W. (2006). "Cleaning products and air fresheners: Emissions and resulting concentrations of glycol ethers and terpenoids". Indoor Air. 16 (3): 179–191. doi:10.1111/j.1600-0668.2005.00414.x. PMID   16683937.

Further reading