Acenaphthene

Not to be confused with Acenaphthylene.
Acenaphthene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1,2-Dihydroacenaphthylene
Other names
1,8-Ethylenenaphthalene
peri-Ethylenenaphthalene
Naphthyleneethylene
Tricyclo[6.3.1.04,12]dodecapentaene
Tricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene
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
Vapor pressure 0.001 to 0.01 mmHg at 68°F; 5 mmHg at 238.6°F[1]
-.709·10−6 cm3/g
Thermochemistry[2]
190.4 J mol−1 K−1
188.9 J mol−1 K−1
70.3 kJ/mol
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)
Safety data sheet (SDS) ICSC 1674
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.[3]

Production and reactions

Acenaphthene was prepared for the first time in 1866[4] by Marcellin Berthelot by reacting hot napthalene vapours with acetylene, and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene in coal tar.[5] 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]+.[6]

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners[3] (such as 1,4-bis(2-benzoxazolyl)naphthalene). Besides that, the anhydride is also the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.[7][8]

References

  1. ^ National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina
  2. ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
  3. ^ a b 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 3527306730.
  4. ^ Annales de chimie et de physique (in French). Chez Crochard. 1866.
  5. ^ Annales de chimie et de physique (in French). Masson. 1867.
  6. ^ 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
  7. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
  8. ^ Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.doi:10.1002/9783527626915.ch16