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Decalin (decahydronaphthalene, also known as bicyclo[4.4.0]decane and sometimes decaline), 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.[6]

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.[citation needed]

  • 1: trans (left) and cis (right) isomers
    1: trans (left) and cis (right) isomers
  • 2: ball-and-stick model of cis-decalin
    2:
    ball-and-stick model of cis-decalin
  • 3: trans-decalin
    3:
    trans-decalin
  • 4: cis-decalin ring-flip
    4:
    cis-decalin ring-flip

Synthesis

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.[7]

Occurrence

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

Reactions

Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges via hydroxycyclodecanone to cyclodecenone, a precursor to sebacic acid.[9]

Safety

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

See also

References

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. pp. 33, 394, 601. ISBN 978-0-85404-182-4.
  2. ^ a b c d “SDS – Decahydronapthalene” (pdf). thermofisher.com. ThermoFisher Scientific. 21 December 2025. p. 4. Retrieved 26 January 2026.
  3. ^ a b c d e f g Sigma-Aldrich Co., Decahydronapthalene (cis, trans).
  4. ^ Lide, David R., ed. (2004). CRC Handbook of Chemistry and Physics (85th ed.). Boca Raton, FL: CRC Press. p. 3—148. ISBN 978-0-8493-0485-9.
  5. ^ Eliel, Ernest Ludwig; Wilen, Samuel H.; Mander, Lewis N. (1994). Stereochemistry of Organic Compounds. New York: Wiley. p. 777. ISBN 978-0-471-01670-0.
  6. ^ “Fuel Additive Product”. Archived from the original on 2009-03-12.
  7. ^ 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.
  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. ^ 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 978-3-527-30673-2.
  10. ^ Agosta, Alessandro (May 2002). Development of a Chemical Surrogate for JP-8 Aviation Fuel Using a Pressurized Flow Reactor (PDF) (MS thesis). Philadelphia, PA: Drexel University. Archived from the original (PDF) on 2010-06-19.
  11. ^ International Chemical Safety Card 1548