Acenaphthene

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.[2]

Not to be confused with Acenaphthylene.
Acenaphthene
Names
Preferred IUPAC name
1,2-Dihydroacenaphthylene
Systematic IUPAC name
Tricyclo[6.3.1.04,12]dodeca-1(12),4,6,8,10-pentaene
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
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 Y
    Key: CWRYPZZKDGJXCA-UHFFFAOYSA-N Y
  • 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
-.709·10−6 cm3/g
Thermochemistry[1]
190.4 J mol−1 K−1
188.9 J mol−1 K−1
70.3 kJ/mol
Hazards
NFPA 704 (fire diamond)
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 YN ?)
Infobox references

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]+.[3]

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners.[2] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.[4][5]

References
  1. John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
  2. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
  3. 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
  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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