Difference between revisions of "Alpha-pinene"

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[[File:Alpha-pinene.png|thumb|257x257px]]
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{{Chembox
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'''α-pinene'''(also written ''alpha''-pinene) is an organic compound with chemical formula C<sub>10</sub>H<sub>16</sub> belonging to the [[terpenes]], a group of biologically important hydrocarbons. It is the most commonly encountered and well researched of the two pinene isomers, and has a number of niche uses in organic synthesis.  
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| Name = Alpha-pinene
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| Reference =
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| IUPACName = (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
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| PIN =
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| SystematicName =
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| OtherNames = α-Pinene<br>Pinene
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| ImageFile = Alpha-pinene.png
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES = CC1=CCC2CC1C2(C)C
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  }}
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 155
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 0.858 g/cm<sup>3</sup> (at 20 °C)
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| Formula = C<sub>10</sub>H<sub>16</sub>
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| HenryConstant =
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| LogP =
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| MolarMass = 136.24 g/mol
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| MeltingPt =
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| MeltingPtC = −64
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| MeltingPt_notes =
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| Odor = Pine, turpentine-like
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| pKa =
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| pKb =
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| Solubility = 0.000249 g/100 ml (25 °C)
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| SolubleOther = Miscible with glacial [[acetic acid]], [[acetone]], [[chloroform]], [[diethyl ether]], [[ethanol]], [[isopropanol]]<br>Almost insoluble in [[glycerol]], [[propylene glycol]]
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| Solvent =
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| VaporPressure = 4.75 mmHg at 25 °C
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| AutoignitionPt = 255 °C (491 °F; 528 K)
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| ExploLimits =
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| ExternalMSDS = [https://www.docdroid.net/E5qDxMU/alpha-pinene-sa.pdf.html Sigma-Aldrich]
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| FlashPt = 33 °C (91 °F; 306 K)
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| MainHazards = Flammable
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| Section7 = {{Chembox Related
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| OtherCompounds = [[Limonene]]
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}}
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'''α-pinene'''(also written ''alpha''-pinene) is an organic compound with chemical formula '''C<sub>10</sub>H<sub>16</sub>''' belonging to the [[terpenes]], a group of biologically important hydrocarbons. It is the most commonly encountered and well researched of the two pinene isomers, and has a number of niche uses in organic synthesis.  
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
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α-pinene and related compounds are commonly utilized in the fragrance industry, and as such, it is a precursor to many of these compounds. Hydration to [[α-terpineol]] can be accomplished by the reflux of α-pinene with aqueous [[sulfuric acid]] and [[acetone]] for a few hours, or by the action of concentrated sulfuric acid in [[ethanol]]]. The ester α-terpinyl acetate can be produced by esterification with glacial [[acetic acid]]. It can also be rearranged into [[camphene]] by strong acid catalysis in glacial acetic acid as a step in the production of camphor. With dilute acids, terpin hydrate becomes the major product.
  
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α-pinene and related compounds are commonly utilized in the fragrance industry, and as such it is a precursor to many of these compounds. Hydration to [[α-terpineol]] can be accomplished by the reflux of α-pinene with aqueous sulfuric acid and acetone for a few hours, or by the action of concentrated sulfuric acid in ethanol. The ester α-terpinyl acetate can be produced by esterification with glacial [[acetic acid]]. It can also be rearranged into [[camphene]] by strong acid catalysis in glacial acetic acid as a step in the production of camphor.
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Addition of [[iodine]] or [[phosphorus trichloride]] causes aromatisation, leading to p-cymene.
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===Physical===
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===Physical===
 
α-pinene is a lightweight, clear, colorless liquid in pure form, nearly insoluble in water but miscible with organic solvents. The odor of commercial α-pinene depends on its source; as it can be separated from turpentine by distillation, the odor often matches this. α-pinene boils at 155 °C (311 °F) and is only mildly flammable.
 
α-pinene is a lightweight, clear, colorless liquid in pure form, nearly insoluble in water but miscible with organic solvents. The odor of commercial α-pinene depends on its source; as it can be separated from turpentine by distillation, the odor often matches this. α-pinene boils at 155 °C (311 °F) and is only mildly flammable.
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==Availability==
 
==Availability==
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α-pinene is readily available as one of the most major consitutents of turpentine, and can be distilled in reasonably pure form from it. Turpentine is available as a solvent and paint stripper at many hardware and department stores.
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α-pinene is readily available as one of the most major constituents of turpentine and can be distilled in reasonably pure form from it. Turpentine is available as a solvent and paint stripper at many hardware and department stores.
  
 
==Preparation==
 
==Preparation==
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==Projects==
 
==Projects==
 
* Homemade perfumes and fragrances
 
* Homemade perfumes and fragrances
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==Handling==
 
  
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==Handling==
 
===Safety===
 
===Safety===
 
While not strongly toxic, α-pinene produces vapors that can cause respiratory problems and may act as a skin irritant as well. It should not be used near open flame due to its flammability.
 
While not strongly toxic, α-pinene produces vapors that can cause respiratory problems and may act as a skin irritant as well. It should not be used near open flame due to its flammability.
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===Storage===
 
===Storage===
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Due to its volatility, α-pinene should be kept in airtight containers away from sources of open flame.
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Due to its volatility, α-pinene should be kept in airtight containers away from sources of open flames.
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===Disposal===
 
===Disposal===
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α-pinene is commonly encountered in biological systems and does not pose a significant threat to the environment nor to humans. Given its low density and immiscibility with water, pouring it down a sink may not be a good course of action for disposal, with an outdoor trash can presenting a better option.
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α-pinene is commonly encountered in biological systems and does not pose a significant threat to the environment nor to humans. Given its low density and immiscibility with water, pouring it down a sink may not be a good course of action for disposal, with an outdoor trash can presenting a better option. However, it's best to have it soaked in a porous material, like sand or charcoal, to reduce any leaks on the ground or pavement.
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==References==
 
==References==
 
<references/>
 
<references/>
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=22215 Seperation of Alpha, Beta Pinene from Turpentine]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=64560 α-pinene to α-terpineol acetate]
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
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[[Category:Terpenes]]
 
[[Category:Terpenes]]
 
[[Category:Hydrocarbons]]
 
[[Category:Hydrocarbons]]
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[[Category:Liquids]]

Latest revision as of 23:53, 25 August 2020

Alpha-pinene
Alpha-pinene.png
Names
IUPAC name
(1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
Other names
α-Pinene
Pinene
Identifiers
Jmol-3D images Image
Properties
C10H16
Molar mass 136.24 g/mol
Appearance Colorless liquid
Odor Pine, turpentine-like
Density 0.858 g/cm3 (at 20 °C)
Melting point −64 °C (−83 °F; 209 K)
Boiling point 155 °C (311 °F; 428 K)
0.000249 g/100 ml (25 °C)
Solubility Miscible with glacial acetic acid, acetone, chloroform, diethyl ether, ethanol, isopropanol
Almost insoluble in glycerol, propylene glycol
Vapor pressure 4.75 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 33 °C (91 °F; 306 K)
Related compounds
Related compounds
 Limonene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

α-pinene(also written alpha-pinene) is an organic compound with chemical formula C10H16 belonging to the terpenes, a group of biologically important hydrocarbons. It is the most commonly encountered and well researched of the two pinene isomers, and has a number of niche uses in organic synthesis.

Properties

Chemical

α-pinene and related compounds are commonly utilized in the fragrance industry, and as such, it is a precursor to many of these compounds. Hydration to α-terpineol can be accomplished by the reflux of α-pinene with aqueous sulfuric acid and acetone for a few hours, or by the action of concentrated sulfuric acid in ethanol]. The ester α-terpinyl acetate can be produced by esterification with glacial acetic acid. It can also be rearranged into camphene by strong acid catalysis in glacial acetic acid as a step in the production of camphor. With dilute acids, terpin hydrate becomes the major product.

Addition of iodine or phosphorus trichloride causes aromatisation, leading to p-cymene.

Physical

α-pinene is a lightweight, clear, colorless liquid in pure form, nearly insoluble in water but miscible with organic solvents. The odor of commercial α-pinene depends on its source; as it can be separated from turpentine by distillation, the odor often matches this. α-pinene boils at 155 °C (311 °F) and is only mildly flammable.

Availability

α-pinene is readily available as one of the most major constituents of turpentine and can be distilled in reasonably pure form from it. Turpentine is available as a solvent and paint stripper at many hardware and department stores.

Preparation

α-pinene is more likely to be extracted from turpentine rather than synthesized in the home lab.

Projects

  • Homemade perfumes and fragrances

Handling

Safety

While not strongly toxic, α-pinene produces vapors that can cause respiratory problems and may act as a skin irritant as well. It should not be used near open flame due to its flammability.

Storage

Due to its volatility, α-pinene should be kept in airtight containers away from sources of open flames.

Disposal

α-pinene is commonly encountered in biological systems and does not pose a significant threat to the environment nor to humans. Given its low density and immiscibility with water, pouring it down a sink may not be a good course of action for disposal, with an outdoor trash can presenting a better option. However, it's best to have it soaked in a porous material, like sand or charcoal, to reduce any leaks on the ground or pavement.

References

Relevant Sciencemadness threads

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