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Acenaphthene

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Acenaphthene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1,2-Dihydroacenaphthylene
Other names
1,8-Ethylenenaphthalene
peri-Ethylenenaphthalene
Naphthyleneethylene
Tricyclo[6.3.1.04,12]dodecapentaene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.336 Edit this at Wikidata
EC Number
  • 201-469-6
KEGG
RTECS number
  • AB1000000
UNII
UN number 3077
  • InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 checkY
    Key: CWRYPZZKDGJXCA-UHFFFAOYSA-N checkY
  • InChI=1/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2
    Key: CWRYPZZKDGJXCA-UHFFFAOYAW
  • c2cc1cccc3c1c(c2)CC3
  • c1cc2cccc3c2c(c1)CC3
Properties
C12H10
Molar mass 154.212 g·mol−1
Appearance White or pale yellow crystalline powder
Density 1.024 g/cm3
Melting point 93.4 °C (200.1 °F; 366.5 K)
Boiling point 279 °C (534 °F; 552 K)
0.4 mg/100 ml
Solubility in ethanol slight
Solubility in chloroform slight
Solubility in benzene very soluble
Solubility in acetic acid soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 135 °C (275 °F; 408 K)
450 °C (842 °F; 723 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.[1]

Production and reactions

Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot. Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).

Like other arenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3]+.[2] Chemical reduction affords the radical anion sodium acenaphthylenide, which is used as a strong reductant (E = -1.75 V vs NHE).[3]

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners.[1] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.[4][5]

References

  1. ^ a b Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke “Hydrocarbons” in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. doi:10.1002/14356007.a13_227
  2. ^ S. B. Kim, S. Lotz, S. Sun, Y. K. Chung, R. D. Pike, D. A. Sweigart "Manganese Tricarbonyl Transfer (MTT) Agents" Inorganic Syntheses, 2010, Vol. 35, 109–128, . doi:10.1002/9780470651568.ch6
  3. ^ N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x
  4. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
  5. ^ Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.doi:10.1002/9783527626915.ch16
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