Acenaphthene
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Names | |
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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 | |
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ECHA InfoCard | 100.001.336 ![]() |
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UN number | 3077 |
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Properties | |
Chemical formula | 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] | |
Heat capacity (C) | 190.4 J mol−1 K−1 |
Std molar entropy (S⦵298) | 188.9 J mol−1 K−1 |
Std enthalpy of formation (ΔfH⦵298) | 70.3 kJ/mol |
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NFPA 704 (fire diamond) | ![]() 2 1 1 |
Flash point | 135 °C (275 °F; 408 K) |
Autoignition temperature | > 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). ![]() ![]() ![]() Infobox references |
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 the first time from coal tar by Marcellin Berthelot.[4] 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]+.[5]
Uses
It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners.[3] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.[6][7]
References
- ^ 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
- ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
- ^ 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.
- ^ Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke (2000-06-15). Wiley-VCH Verlag GmbH & Co (ed.). Hydrocarbons. Ullmann's Encyclopedia of Industrial Chemistry.
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: CS1 maint: multiple names: authors list (link) - ^ 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
- ^ 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
- v
- t
- e
- Acenaphthene
- Acenaphthylene
- Anthracene
- Fluorene
- Phenalene
- Phenanthrene
- Benz[a]anthracene
- Benzo[a]fluorene
- Benzo[c]fluorene
- Benzo[c]phenanthrene
- Chrysene
- Fluoranthene
- Pyrene
- Tetracene
- Triphenylene
- Tricyclobutabenzene
- Benz[e]acephenanthrylene
- Benzopyrene
- Benzo[a]pyrene
- Benzo[e]pyrene
- 6H-Benzo[cd]pyrene(Olympicene)
- Benzo[a]fluoranthene
- Benzo[b]fluoranthene
- Benzo[j]fluoranthene
- Benzo[k]fluoranthene
- trans-Bicalicene
- Dibenz[a,h]anthracene
- Dibenz[a,j]anthracene
- Pentacene
- Perylene
- Picene
- Tetraphenylene
- Anthanthrene
- Benzo[ghi]perylene
- Corannulene
- Dibenzopyrenes
- Hexacene
- Triangulene
- Zethrene