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Revision as of 19:31, 8 November 2024 by 5.178.188.143 (talk) (→Uses)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Not to be confused with Acenaphthylene.
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| Names | |
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| Preferred IUPAC name 1,2-Dihydroacenaphthylene | |
| Other names
1,8-Ethylenenaphthalene peri-Ethylenenaphthalene Naphthyleneethylene Tricyclododecapentaene Tricyclododeca-1(12),4,6,8,10-pentaene | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.336 
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| EC Number |
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| KEGG | |
| PubChem CID | |
| RTECS number |
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| UNII | |
| UN number | 3077 |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C12H10 |
| Molar mass | 154.212 g·mol |
| Appearance | White or pale yellow crystalline powder |
| Density | 1.024 g/cm |
| Melting point | 93.4 °C (200.1 °F; 366.5 K) |
| Boiling point | 279 °C (534 °F; 552 K) |
| Solubility in water | 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 |
| Magnetic susceptibility (χ) | -.709·10 cm/g |
| Thermochemistry | |
| Heat capacity (C) | 190.4 J mol K |
| Std molar entropy (S298) |
188.9 J mol K |
| Std enthalpy of formation (ΔfH298) |
70.3 kJ/mol |
| Hazards | |
| NFPA 704 (fire diamond) |
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| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
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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.
Production and reactions
Acenaphthene was prepared for the first time in 1866 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. 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 (η-acenaphthene)Mn(CO)3].
Uses
It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners (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.
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.
- ^ 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.
- Annales de chimie et de physique (in French). Chez Crochard. 1866.
- Annales de chimie et de physique (in French). Masson. 1867.
- 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
| Polycyclic aromatic hydrocarbons | |
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