Acenaphthene
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| Names | |||
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| IUPAC name
1,2-Dihydroacenaphthylene
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| 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)
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| ChemSpider | |||
| ECHA InfoCard | 100.001.336 | ||
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| UNII | |||
| UN number | 3077 | ||
CompTox Dashboard (EPA)
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| 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) | |||
| 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).
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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
- ^ 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
- ^ 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
- ^ N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910. doi:10.1021/cr940053x
- ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
- ^ Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.doi:10.1002/9783527626915.ch16