Decalin

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Decalin
Decalin Decaline.png
Decalin
Names
Preferred IUPAC name
Decahydronaphthalene [1]
Other names
Bicyclo[4.4.0]decane [1]
Decalin
Identifiers
3D model (JSmol)
878165
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.861 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-046-9, 207-770-9, 207-771-4
185147
PubChem CID
RTECS number
  • QJ3150000
UNII
UN number 1147
  • InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 Yes check.svgY
    Key: NNBZCPXTIHJBJL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2
    Key: NNBZCPXTIHJBJL-UHFFFAOYAH
  • C1CCC2CCCCC2C1
  • cis:C1CC[C@H]2CCCC[C@H]2C1
  • trans:C1CC[C@H]2CCCC[C@@H]2C1
Properties
C10H18
Molar mass 138.25 g/mol
Appearancecolorless liquid
Density 0.896 g/cm3
Melting point trans: −30.4 °C (−22.7 °F, 242.7 K)
cis: −42.9 °C (−45.2 °F, 230.3 K) [2]
Boiling point trans: 187 °C (369 °F)
cis: 196 °C (384 °F)
Insoluble
  • −107.7·10−6 cm3/mol (trans)
  • −107.0·10−6 cm3/mol (cis)
1.481
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H226, H302, H305, H314, H331, H332, H410, H411
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P331, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point 57 °C (135 °F; 330 K)
250 °C (482 °F; 523 K)
Safety data sheet (SDS) Decalin MSDS
Related compounds
Related compounds
 Naphthalene; Tetralin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Decalin (decahydronaphthalene, also known as bicyclo[4.4.0]decane and sometimes decaline), [3] a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives. [4]

Contents

Isomers

Decalin occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric effects. cis-Decalin is a chiral molecule without a chiral center; it has a two-fold rotational symmetry axis, but no reflective symmetry. However, the chirality is canceled through a chair-flipping process that turns the molecule into its mirror image.

trans-Decalin

The only possible way to join the two six-membered rings in the trans position means the second ring needs to start from two equatorial bonds (blue) of the first ring. A six-membered ring does not offer sufficient space to start out on an axial position (upwards), and reach the axial position of the neighboring carbon atom, which then will be on the downwards side of the molecule (see the model of cyclohexane in figure 5). The structure is conformationally frozen. It does not have the ability to undergo a chair flip as in the cis isomer. In biology this fixation is widely used in the steroid skeleton to construct molecules (such as figure 6) that play a key role in the signalling between distantly separated cells.

Reactions

Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges via hydroxycyclodecanone to cyclodecenone, a precursor to sebacic acid. [5]

Decalin is the saturated analog of naphthalene and can be prepared from it by hydrogenation in the presence of a catalyst. This interconversion has been considered in the context of hydrogen storage. [6]

Derivation

Treatment of naphthalene in a fused state with hydrogen in the presence of a copper or nickel catalyst. [7]

Occurrence

Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides. [8]

Safety

Decalin easily forms explosive [9] hydroperoxides upon storage in the presence of air. [10] [11]

See also

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 33, 394, 601. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. ↑ Haynes, William M. (2010). Handbook of Chemistry and Physics (91 ed.). Boca Raton, Florida, USA: CRC Press. p. 3-134. ISBN   978-1-43982077-3.
  3. ↑ "Dictionary.com".
  4. ↑ "Fuel Additive Product". Archived from the original on 2009-03-12.
  5. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN   3527306730.
  6. ↑ Isa, Khairuddin Md; Abdullah, Tuan Amran Tuan; Ali, Umi Fazara Md (2018). "Hydrogen donor solvents in liquefaction of biomass: A review". Renewable and Sustainable Energy Reviews. 81: 1259–1268. Bibcode:2018RSERv..81.1259I. doi:10.1016/j.rser.2017.04.006.
  7. ↑ [Hawley's Condensed Chemical Dictionary]
  8. ↑ Li, Gang; Kusari, Souvik; Spiteller, Michael (2014). "Natural products containing 'decalin' motif in microorganisms". Nat. Prod. Rep. 31 (9): 1175–1201. doi: 10.1039/C4NP00031E . PMID   24984916.
  9. ↑ "PDF – Surrogate JP-8 Aviation Fuel Study – Alessandro Agosta Thesis Drexel University" (PDF). Archived from the original (PDF) on 2010-06-19.
  10. ↑ "Inchem.org Data".
  11. ↑ "MSDS Sheet – JT Baker".
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