Difference between revisions of "Alpha-pinene"

From Sciencemadness Wiki
Jump to: navigation, search
(Fixed grammar and added SMILES code.)
 
(3 intermediate revisions by one other user not shown)
Line 1: Line 1:
−
[[File:Alpha-pinene.png|thumb|257x257px]]
+
{{Chembox
−
'''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.  
+
| Name = Alpha-pinene
 +
| Reference =
 +
| IUPACName = (1S,5S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene ((−)-α-Pinene)
 +
| PIN =
 +
| SystematicName =
 +
| OtherNames = α-Pinene<br>Pinene
 +
<!-- Images -->
 +
| ImageFile = Alpha-pinene.png
 +
| ImageSize = 250
 +
| ImageAlt =
 +
| ImageName =
 +
| ImageFile1 =
 +
| ImageSize1 =
 +
| ImageAlt1 =
 +
| ImageName1 =
 +
| ImageFile2 =
 +
| ImageSize2 =
 +
| ImageAlt2 =
 +
| ImageName2 =
 +
| ImageFile3 =
 +
| ImageSize3 =
 +
| ImageAlt3 =
 +
| ImageName3 =
 +
| ImageFileL1 =
 +
| ImageSizeL1 =
 +
| ImageAltL1 =
 +
| ImageNameL1 =
 +
| ImageFileR1 =
 +
| ImageSizeR1 =
 +
| ImageAltR1 =
 +
| ImageNameR1 =
 +
| ImageFileL2 =
 +
| ImageSizeL2 =
 +
| ImageAltL2 =
 +
| ImageNameL2 =
 +
| ImageFileR2 =
 +
| ImageSizeR2 =
 +
| ImageAltR2 =
 +
| ImageNameR2 =
 +
<!-- Sections -->
 +
| Section1 = {{Chembox Identifiers
 +
| 3DMet =
 +
| Abbreviations =
 +
| SMILES = CC1=CCC2CC1C2(C)C
 +
  }}
 +
| Section2 = {{Chembox Properties
 +
| AtmosphericOHRateConstant =
 +
| Appearance = Colorless liquid
 +
| BoilingPt =
 +
| BoilingPtC = 155
 +
| BoilingPt_ref =
 +
| BoilingPt_notes =
 +
| Density = 0.858 g/cm<sup>3</sup> (at 20 °C)
 +
| Formula = C<sub>10</sub>H<sub>16</sub>
 +
| HenryConstant =
 +
| LogP =
 +
| MolarMass = 136.24 g/mol
 +
| MeltingPt =
 +
| MeltingPtC = −64
 +
| MeltingPt_ref =
 +
| MeltingPt_notes =
 +
| Odor = Pine, turpentine-like
 +
| pKa =
 +
| pKb =
 +
| Solubility = 0.000249 g/100 ml (25 °C)
 +
| SolubleOther = Miscible with glacial [[acetic acid]], [[acetone]], [[chloroform]], [[diethyl ether]], [[ethanol]], [[isopropanol]]<br>Almost insoluble in [[glycerol]], [[propylene glycol]]
 +
| Solvent =
 +
| VaporPressure = 4.75 mmHg at 25 °C
 +
  }}
 +
| Section3 = {{Chembox Structure
 +
| Coordination =
 +
| CrystalStruct =
 +
| MolShape =
 +
  }}
 +
| Section4 = {{Chembox Thermochemistry
 +
| DeltaGf =
 +
| DeltaHc =
 +
| DeltaHf =
 +
| Entropy =
 +
| HeatCapacity =
 +
  }}
 +
| Section5 = {{Chembox Explosive
 +
| ShockSens =
 +
| FrictionSens =
 +
| DetonationV =
 +
| REFactor =
 +
  }}
 +
| Section6 = {{Chembox Hazards
 +
| AutoignitionPt = 255 °C (491 °F; 528 K)
 +
| ExploLimits =
 +
| ExternalMSDS = [https://www.docdroid.net/E5qDxMU/alpha-pinene-sa.pdf.html Sigma-Aldrich]
 +
| FlashPt = 33 °C (91 °F; 306 K)
 +
| LD50 =
 +
| LC50 =
 +
| MainHazards = Flammable
 +
| NFPA-F =
 +
| NFPA-H =
 +
| NFPA-R =
 +
| NFPA-S =
 +
  }}
 +
| Section7 = {{Chembox Related
 +
| OtherAnions =
 +
| OtherCations =
 +
| OtherFunction =
 +
| OtherFunction_label =
 +
| OtherCompounds = [[Limonene]]
 +
  }}
 +
}}
 +
'''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===
 +
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.
  
−
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.
+
Addition of [[iodine]] or [[phosphorus trichloride]] causes aromatisation, leading to p-cymene.
−
===Physical===
+
  
 +
===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.
  
 
==Availability==
 
==Availability==
−
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.
+
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==
Line 24: Line 133:
  
 
===Storage===
 
===Storage===
−
Due to its volatility, α-pinene should be kept in airtight containers away from sources of open flame.
+
Due to its volatility, α-pinene should be kept in airtight containers away from sources of open flames.
  
 
===Disposal===
 
===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.
+
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==
 
==References==
 
<references/>
 
<references/>
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=22215 Seperation of Alpha, Beta Pinene from Turpentine]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=64560 α-pinene to α-terpineol acetate]
  
 
[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]

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

Retrieved from "https://www.sciencemadness.org/smwiki/index.php?title=Alpha-pinene&oldid=13277"