Decalin

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title: "Decalin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hydrocarbon-solvents", "decalins", "bicycloalkanes"] topic_path: "general/hydrocarbon-solvents" source: "https://en.wikipedia.org/wiki/Decalin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 455343751 | Name = Decalin | ImageFile = Decalin.svg | ImageSize = 200px | ImageName = Decalin | PIN = Decahydronaphthalene | OtherNames = Bicyclo[4.4.0]decane |Section1={{Chembox Identifiers | indexlist_caption = | index_label = | index1_label = cis | index2_label = trans | index3_label = | index_comment = | index1_comment = | index2_comment = | index3_comment =

| ChEBI_Ref = | ChEBI = 38853 | ChEBI1 = 38860 | ChEBI2 = 38863 | ChEMBL = 1491920 | SMILES = C1CCC2CCCCC2C1 | SMILES1 = C1CC[C@H]2CCCC[C@H]2C1 | SMILES2 = C1CC[C@H]2CCCC[C@@H]2C1 | ChemSpiderID_Ref = | ChemSpiderID = 6777 | PubChem = 7044 | EC_number = 202-046-9, 207-770-9, 207-771-4 | RTECS = QJ3150000 | UNNumber = 1147 | UNII = 88451Q4XYF | Gmelin = 185147 | Beilstein = 878165 | InChI = 1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 | InChIKey = NNBZCPXTIHJBJL-UHFFFAOYAH | StdInChI_Ref = | StdInChI = 1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 | StdInChIKey_Ref = | StdInChIKey = NNBZCPXTIHJBJL-UHFFFAOYSA-N | CASNo = 91-17-8 | CASNo_Ref = |Section2={{Chembox Properties | Properties_ref = | C=10 | H=18 | Appearance = colorless liquid | Odor = slight, resembling menthol | Density = {{ubl |cis: |trans: | MeltingPt = {{ubl |cis: −42.9 C |trans: −30.4 C | BoilingPt = {{ubl |cis: 195.8 C |trans: 187.3 C | Solubility = Insoluble | Solvent1 = Ethanol | Solubility1 = {{ubl |cis: Miscible |trans: Very soluble | Solvent2 = Diethyl ether | Solubility2 = Very soluble | Solvent3 = Acetone | Solubility3 = Very soluble | Solvent4 = Chloroform | Solubility4 = cis: Very soluble | Solvent5 = Benzene | Solubility5 = trans: Miscible | Solvent6 = Methanol | Solubility6 = trans: Soluble | VaporPressure = {{ubl |1.3 mbar (22 C) |42 mmHg (92 C) |741 mmHg (188 C) | LogP = 4.79 | MagSus = {{ubl |cis: |trans: | RefractIndex = {{ubl |cis: 1.4810 |trans: 1.4695 | Viscosity = (20 C) |Section7={{Chembox Hazards | GHS_ref = | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | NFPA-H = 3 | NFPA-F = 2 | NFPA-R = 1 | NFPA-S = - | NFPA_ref = | FlashPtC = 57 | FlashPt_ref = | AutoignitionPtC = 250 | AutoignitionPt_ref = | ExploLimits = (100 F) | LD50 = {{ubl | (oral, rat) | (dermal, rabbit) | LC50 = (inhalation, rat) |Section8={{Chembox Related | OtherCompounds = {{ubl |Naphthalene |Tetralin 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.

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.

Image:Cis-trans isomerism of decahydronaphthalene.svg| Image:cis-decalin double chair.png|2: Image:trans-decalin double chair.png|3: File:Cisdecalin conformations.png|4:

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.

Occurrence

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

Reactions

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

Safety

Decalin easily forms explosive hydroperoxides upon storage in the presence of air.

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry]].
  2. (2004). "CRC Handbook of Chemistry and Physics". CRC Press.
  3. {{Sigma-Aldrich. sial
  4. (21 December 2025). "SDS - Decahydronapthalene". ThermoFisher Scientific.
  5. "Fuel Additive Product".
  6. (2018). "Hydrogen donor solvents in liquefaction of biomass: A review". Renewable and Sustainable Energy Reviews.
  7. (2014). "Natural products containing 'decalin' motif in microorganisms". Nat. Prod. Rep..
  8. (2000). "Hydrocarbons".
  9. Agosta, Alessandro. (May 2002). "Development of a Chemical Surrogate for JP-8 Aviation Fuel Using a Pressurized Flow Reactor". Drexel University.
  10. {{ICSC. 1548

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hydrocarbon-solventsdecalinsbicycloalkanes