Decalin
Chemical compound
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.
01Isomers
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.
02Synthesis
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.
03Occurrence
Decalin itself is rare in nature but several decalin derivatives are known. They arise via terpene-derived precursors or polyketides.
04Reactions
Oxygenation of decalin gives the tertiary hydroperoxide, which rearranges via hydroxycyclodecanone to cyclodecenone, a precursor to sebacic acid.
05Safety
Decalin easily forms explosive hydroperoxides upon storage in the presence of air.
Sources and credits
This article is adapted from the Wikipedia article “Decalin”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Decalin.svg by User:Innerstream, Public domain
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