Decalin

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Template:Chembox AllOtherNamesTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox CompToxTemplate:Chembox SolubilityInWaterTemplate:Chembox GHS (set)Template:Chembox Lethal amounts (set)Template:Chembox Datapage check
Decalin
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878165
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185147
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UN number 1147
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Molar mass Template:Chem molar mass
Appearance colorless liquid
Odor slight, resembling menthol
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  • cis: Script error: No such module "val".
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  • cis: Miscible
  • trans: Very soluble
Solubility in Diethyl ether Very soluble
Solubility in Acetone Very soluble
Solubility in Chloroform cis: Very soluble
Solubility in Benzene trans: Miscible
Solubility in Methanol trans: Soluble
log P 4.79[2]
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  • cis: 1.4810
  • trans: 1.4695
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  • cis: C2
  • trans: C2h
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[2]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Flash point 57 °C (135 °F; 330 K)[3]
250 °C (482 °F; 523 K)[3]
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Template:Chem name, a precursor to sebacic acid.[9]

Safety

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

See also

References

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  11. ^ International Chemical Safety Card 1548

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