| Revision as of 19:46, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466628188 of page Acenaphthene for the Chem/Drugbox validation project (updated: 'KEGG'). |
Latest revision as of 19:31, 8 November 2024 edit 5.178.188.143 (talk) →UsesTag: Visual edit |
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{{Distinguish|Acenaphthylene}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 456662235 |
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| verifiedrevid = 477238157 |
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| ImageFileL1 = Acenaphthene.svg |
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| ImageFile1 = Acenaphthene.svg |
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| ImageSizeL1 = 120px |
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| ImageSize1 = 120px |
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| ImageAltL1 = Skeletal formula |
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| ImageAlt1 = Skeletal formula |
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| ImageFileR1 = Acenaphthene-3D-balls.png |
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| ImageFile2 = Acenaphthene-3D-balls.png |
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| ImageSizeR1 = 120px |
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| ImageSize2 = 120px |
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| ImageAltR1 = Ball-and-stick model |
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| ImageAlt2 = Ball-and-stick model |
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| IUPACName = 1,2-Dihydroacenaphthylene |
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| ImageFile3 = AcenaphthCrop.jpg |
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| OtherNames = 1,8-Ethylenenaphthalene<br/>''peri''-Ethylenenaphthalene<br/>Naphthyleneethylene |
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| PIN = 1,2-Dihydroacenaphthylene |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 1,8-Ethylenenaphthalene<br/>''peri''-Ethylenenaphthalene<br/>Naphthyleneethylene<br/>Tricyclododecapentaene<br/>Tricyclododeca-1(12),4,6,8,10-pentaene |
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| InChIKey = CWRYPZZKDGJXCA-UHFFFAOYAW |
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|Section1={{Chembox Identifiers |
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| InChIKey = CWRYPZZKDGJXCA-UHFFFAOYAW |
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| SMILES1 = c1cc2cccc3c2c(c1)CC3 |
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| SMILES1 = c1cc2cccc3c2c(c1)CC3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CWRYPZZKDGJXCA-UHFFFAOYSA-N |
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| StdInChIKey = CWRYPZZKDGJXCA-UHFFFAOYSA-N |
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| CASNo = 83-32-9 |
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| CASNo = 83-32-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EINECS = 201-469-6 |
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| EINECS = 201-469-6 |
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| PubChem = 6734 |
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| PubChem = 6734 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1797271 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = V8UT1GAC5Y |
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| UNII = V8UT1GAC5Y |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 22154 |
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| ChEBI = 22154 |
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| SMILES = c2cc1cccc3c1c(c2)CC3 |
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| SMILES = c2cc1cccc3c1c(c2)CC3 |
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| InChI = 1/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 |
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| InChI = 1/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2 |
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| RTECS = AB1000000 |
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| RTECS = AB1000000 |
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| UNNumber = 3077 |
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| UNNumber = 3077 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6478 |
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| ChemSpiderID = 6478 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = <!-- blanked - oldvalue: C19312 --> |
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| KEGG = C19312 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12 | H=10 |
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| C=12 | H=10 |
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| Appearance = White or pale yellow crystalline powder |
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| Appearance = White or pale yellow crystalline powder |
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| Density = 1.024 g/cm<sup>3</sup> |
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| Density = 1.024 g/cm<sup>3</sup> |
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| MeltingPtC = 93.4 |
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| MeltingPtC = 93.4 |
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| BoilingPtC = 279 |
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| BoilingPtC = 279 |
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| Solubility = 0.4 mg/100 ml |
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| Solubility = 0.4 mg/100 ml |
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| Solubility1 = slight |
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| Solubility1 = slight |
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| Solvent1 = ethanol |
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| Solvent1 = ethanol |
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| Solubility4 = soluble |
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| Solubility4 = soluble |
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| Solvent4 = acetic acid |
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| Solvent4 = acetic acid |
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| MagSus = -.709·10<sup>−6</sup> cm<sup>3</sup>/g |
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| Density = 1.222 |
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| VaporPressure = 0.001 to 0.01 mmHg at 68°F; 5 mmHg at 238.6°F<ref>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</ref> |
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| Section7 = {{Chembox Hazards |
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| Section4 = {{Chembox Thermochemistry |
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| ExternalMSDS = |
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| Thermochemistry_ref = <ref name="crc">{{cite book |author1=John Rumble |title=CRC Handbook of Chemistry and Physics |date=June 18, 2018 |publisher=CRC Press |isbn=978-1138561632 |pages=5–3|edition=99th |language=English}}</ref> |
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| EUIndex = Not listed |
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| HeatCapacity = 190.4 J mol<sup>−1</sup> K<sup>−1</sup> |
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| NFPA-H = 2 |
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| Entropy = 188.9 J mol<sup>−1</sup> K<sup>−1</sup> |
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| NFPA-F = 1 |
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| DeltaHform = 70.3 kJ/mol |
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| NFPA-R = 1 |
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| NFPA-O = |
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| DeltaGfree = |
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| RPhrases = |
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| DeltaHcombust = |
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| DeltaHfus = |
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| DeltaHvap = |
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| FlashPt = 135 °C |
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| DeltaHsublim = |
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| Autoignition = >450 °C |
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| HHV = |
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| LHV = |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 1 |
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| NFPA-S = |
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| FlashPtC = 135 |
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| AutoignitionPt = > |
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| AutoignitionPtC = 450 |
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'''Acenaphthene''' is a ] (PAH) consisting of ] with an ] bridge connecting positions 1 and 8. It is a colourless solid. ] consists of about 0.3% of this compound.<ref name=Ull/> |
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==Production and reactions== |
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Acenaphthene was prepared for the first time in 1866<ref>{{Cite book |url=https://books.google.com/books?id=jytCAAAAcAAJ&pg=PA467 |title=Annales de chimie et de physique |date=1866 |publisher=Chez Crochard |language=fr}}</ref> by ] by reacting hot napthalene vapours with ], and a year later he reproduced a similar reaction with ethylene as well as discovered acenaphthene in ].<ref>{{Cite book |url=https://books.google.com/books?id=lLZJAQAAMAAJ&pg=PA226 |title=Annales de chimie et de physique |date=1867 |publisher=Masson. |language=fr}}</ref> Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative ] (and many other compounds). |
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Like other ]s, acenaphthene forms complexes with low valent metal centers. One example is (η<sup>6</sup>-acenaphthene)Mn(CO)<sub>3</sub>]<sup>+</sup>.<ref>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}}</ref> |
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==Uses== |
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It is used on a large scale to prepare ], which is a precursor to dyes and ]s<ref name="Ull">{{Ullmann|doi=10.1002/14356007.a13_227|title=Hydrocarbons|year=2000|last1=Griesbaum|first1=Karl|last2=Behr|first2=Arno|last3=Biedenkapp|first3=Dieter|last4=Voges|first4=Heinz-Werner|last5=Garbe|first5=Dorothea|last6=Paetz|first6=Christian|last7=Collin|first7=Gerd|last8=Mayer|first8=Dieter|last9=Höke|first9=Hartmut|isbn=3527306730}}</ref> (such as 1,4-bis(2-])naphthalene). Besides that, the anhydride is also the precursor to ], precursor to several commercial ]s and ]s.<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi|10.1002/14356007.a20_371}}</ref><ref>Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.{{doi|10.1002/9783527626915.ch16}}</ref> |
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==References== |
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{{Reflist}} |
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{{PAHs}} |
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{{Authority control}} |
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] |
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] |