📑 Table of Contents▼
Decalin
Decalin
Decalin
Names
Preferred IUPAC name
Decahydronaphthalene[1]
Other names
Bicyclo[4.4.0]decane[1]
Identifiers
3D model (JSmol)
878165
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.861 Edit this at Wikidata
EC Number
  • 202-046-9, 207-770-9, 207-771-4
185147
RTECS number
  • QJ3150000
UNII
UN number 1147
  • InChI=1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2 checkY
    Key: NNBZCPXTIHJBJL-UHFFFAOYSA-N checkY
  • InChI=1/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2
    Key: NNBZCPXTIHJBJL-UHFFFAOYAH
  • C1CCC2CCCCC2C1
  • cis: C1CC[C@H]2CCCC[C@H]2C1
  • trans: C1CC[C@H]2CCCC[C@@H]2C1
Properties[4]
C10H18
Molar mass 138.254 g·mol−1
Appearance colorless liquid
Odor slight, resembling menthol
Density
  • cis: 0.8965 g/cm3
  • trans: 0.8659 g/cm3
Melting point
  • cis: −42.9 °C (−45.2 °F; 230.2 K)
  • trans: −30.4 °C (−22.7 °F; 242.8 K)
Boiling point
  • cis: 195.8 °C (384.4 °F; 468.9 K)
  • trans: 187.3 °C (369.1 °F; 460.4 K)
Insoluble
Solubility in Ethanol
  • 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]
Vapor pressure
  • 1.3 mbar (1.3 hPa) (22 °C (72 °F; 295 K))[2]
  • 42 mmHg (5.6 kPa) (92 °C (198 °F; 365 K))
  • 741 mmHg (98.8 kPa) (188 °C (370 °F; 461 K))[3]
  • cis: −107.0×10−6 cm3/mol
  • trans: −107.7×10−6 cm3/mol[citation needed]
  • cis: 1.4810
  • trans: 1.4695
Viscosity 3 mPa·s (20 °C (68 °F; 293 K))[2]
Structure[5]
  • cis: C2
  • trans: C2h
Hazards
GHS labelling:[3]
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H314, H331, H410
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
[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]
Explosive limits 0.7%–4.9% (100 °F (38 °C; 311 K))[3]
Lethal dose or concentration (LD, LC):
  • 4170 mg/kg (oral, rat)
  • 5200 mg/kg (dermal, rabbit)[3]
4.08 mg/L (inhalation, rat)[3]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

edit

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

edit

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

edit

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

Reactions

edit

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

Safety

edit

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

See also

edit

References

edit
  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

📚 Artikel Terkait di Wikipedia

Naphthalene

metal catalysts to give tetralin (C10H12). Further hydrogenation yields decalin (C10H18). Oxidation with O2 in the presence of vanadium pentoxide (V2O5)

Ultra-high-molecular-weight polyethylene

In the case where decalin is used, the decalin is left to evaporate from the yarn. When producing at industrial levels, this decalin can be recovered and

Bicyclic molecule

elements), like DABCO. Moreover, the two rings can both be aliphatic (e.g. decalin and norbornane), or can be aromatic (e.g. naphthalene), or a combination

Geosmin

disturbed. Geosmin is a bicyclic alcohol with formula C12H22O, a derivative of decalin. It is produced from the universal sesquiterpene precursor farnesyl pyrophosphate

Perfluorodecalin

Perfluorodecalin (C10F18) is a fluorocarbon, a derivative of decalin in which all of the hydrogen atoms are replaced by fluorine atoms. It is chemically

Tetralin

evaluated. Over-hydrogenation converts tetralin into decahydronaphthalene (decalin). Rarely encountered is dihydronaphthalene (dialin). In a classic named

Clerodane diterpene

marine sponges. They are bicyclic terpenes that contain 20 carbons and a decalin core. The clerodane diterpenes are classified into four groups trans-cis

Simplified Molecular Input Line Entry System

O1CCOCC1 respectively. For a second ring, the label will be 2. For example, decalin (decahydronaphthalene) may be written as C1CCCC2C1CCCC2. SMILES does not