Chemistry:Decalin

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Decalin
Decalin
Names
Preferred IUPAC name
Decahydronaphthalene[1]
Other names
Bicyclo[4.4.0]decane[1]
Decalin
Identifiers
3D model (JSmol)
878165
ChEBI
ChEMBL
ChemSpider
EC Number
  • 202-046-9, 207-770-9, 207-771-4
185147
RTECS number
  • QJ3150000
UNII
UN number 1147
Properties
C10H18
Molar mass 138.25 g/mol
Appearance colorless 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
Safety data sheet Decalin MSDS
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
H226, H302, H305, H314, H331, H332, H410, H411
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P273, P280, P301+310, P301+330+331, P303+361+353, P304+312, P304+340, P305+351+338, P310, P311, P312, P321, P331, P363, P370+378
Flash point 57 °C (135 °F; 330 K)
250 °C (482 °F; 523 K)
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).
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Infobox references
Tracking categories (test):

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]

Isomers

Decalin occurs in cis and trans forms. The trans form is energetically more stable because of fewer steric interactions. 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 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]


Occurrence

Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides.[7]

Safety

Decalin easily forms explosive[8] hydroperoxides upon storage in the presence of air.[9][10]


See also

References

  1. 1.0 1.1 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: CRC Press. p. 3-134. ISBN 978-1439820773. 
  3. "Dictionary.com". http://dictionary.reference.com/browse/decahydronaphthalene. 
  4. "Fuel Additive Product". http://www.decalinchemicals.com/fueladditive.html. 
  5. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter et al. (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. 
  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. doi:10.1016/j.rser.2017.04.006. 
  7. 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. 
  8. "PDF – Surrogate JP-8 Aviation Fuel Study – Alessandro Agosta Thesis Drexel University". http://idea.library.drexel.edu/bitstream/1860/16/11/agosta_thesis.pdf. 
  9. "Inchem.org Data". http://www.inchem.org/documents/icsc/icsc/eics1548.htm. 
  10. "MSDS Sheet – JT Baker". http://hazard.com/msds/mf/baker/baker/files/d0064.htm.