| Revision as of 19:47, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466404541 of page Acenaphthylene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:41, 25 February 2024 edit Prenestina (talk | contribs)7 editsm →ToxicityTag: Visual edit |
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{{distinguish|Acenaphthene}} |
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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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| Verifiedimages = changed |
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| verifiedrevid = 443364366 |
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| Watchedfields = changed |
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| Name = Acenaphthylene |
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| verifiedrevid = 477238237 |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = Acenaphthylene.svg |
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| Name = Acenaphthylene |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL1 = 120px |
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| ImageFileL1 = Acenaphthylene.svg |
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| ImageAltL1 = Skeletal formula |
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| ImageSizeL1 = 120px |
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| ImageFileR1 = Acenaphthylene-3D-spacefill.png |
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| ImageAltL1 = Skeletal formula |
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| ImageSizeR1 = 120px |
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| ImageFileR1 = Acenaphthylene-3D-spacefill.png |
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| ImageAltR1 = Space-filling model |
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| ImageSizeR1 = 120px |
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| IUPACName = acenaphthylene |
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| ImageAltR1 = Space-filling model |
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| OtherNames = Cycopenta(de)naphthalene, Acenaphthalene |
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| PIN = Acenaphthylene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 210 | doi = 10.1039/9781849733069-00130 | isbn = 978-0-85404-182-4}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Cyclopentanaphthalene<br>Acenaphthalene<br>Tricyclododeca-1(12),2,4,6,8,10-hexaene{{citation needed|date=May 2019}}<br>Tricyclododecahexaene{{citation needed|date=May 2019}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|Section1={{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 33081 |
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| ChEBI = 33081 |
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| SMILES = c3cc1cccc2\C=C/c(c12)c3 |
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| SMILES = c3cc1cccc2\C=C/c(c12)c3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8807 |
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| ChemSpiderID = 8807 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 208-96-8 |
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| CASNo = 208-96-8 |
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| PubChem = 9161 |
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| PubChem = 9161 |
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| RTECS = |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=12|H=8 |
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| C=12 | H=8 |
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| Appearance = Yellow crystalline powder |
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| Appearance = Yellow crystals |
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| Density = 0.8987 g cm<sup>-3</sup> |
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| Density = 0.8987 g cm<sup>−3</sup> |
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| Solubility = Insoluble |
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| Solubility = Insoluble |
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| Solubility1 = very soluble |
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| Solubility1 = very soluble |
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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 = chloroform |
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| Solvent4 = chloroform |
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| MeltingPtC = 91.8 |
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| MeltingPtC = 91.8 |
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| BoilingPtC = 280 |
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| BoilingPtC = 280 |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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| Section7 = {{Chembox Hazards |
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| Section4 = {{Chembox Thermochemistry |
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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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| ExternalMSDS = |
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| HeatCapacity = 166.4 J mol<sup>−1</sup> K<sup>−1</sup> |
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| FlashPt = ?°C |
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| RPhrases = {{R22}} {{R36}} {{R37}} {{R38}} |
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| DeltaGfree = |
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| SPhrases = {{S26}} {{S36}} {{S37}} {{S39}} |
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| DeltaHcombust = |
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| DeltaHfus = 186.7 kJ/mol |
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| DeltaHvap = 69 kJ/mol |
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| DeltaHsublim = 71.06 kJ/mol |
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|Section7={{Chembox Hazards |
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| FlashPtC = 122 |
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| GHSPictograms = {{GHS06}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|302|310|315|319|330|335}} |
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| PPhrases = {{P-phrases|260|261|262|264|270|271|280|284|301+312|302+350|302+352|304+340|305+351+338|310|312|320|321|322|330|332+313|337+313|361|362|363|403+233|405|501}} |
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| Section8 = {{Chembox Related |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Acenaphthylene''', a ] is an ortho- and peri-fused ] hydrocarbon. The molecule resembles ] with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid.<ref name=Ullmanns/> Unlike many ], it has no ]. |
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==Occurrence== |
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Acenaphthylene occurs as about 2% of ]. It is produced industrially by gas phase dehydrogenation of ].<ref name=Ullmanns>{{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> |
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==Reactions== |
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] gives the more saturated compound ]. Chemical reduction affords the radical anion sodium or potassium acenaphthalenide, which is used as a strong reductant (E = -2.26 V vs FC).<ref name="Connelly">{{cite journal |last1=Connelly |first1=Neil G. |last2=Geiger |first2=William E. |date=1996-01-01 |title=Chemical Redox Agents for Organometallic Chemistry |url=https://pubs.acs.org/doi/10.1021/cr940053x |journal=Chemical Reviews |language=en |volume=96 |issue=2 |pages=877–910 |doi=10.1021/cr940053x |pmid=11848774 |issn=0009-2665}}</ref> |
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It functions as a ligand for some organometallic compounds.<ref>{{cite journal |last1=Motoyama |first1=Yukihiro |last2=Itonaga |first2=Chikara |last3=Ishida |first3=Toshiki |last4=Takasaki |first4=Mikihiro |last5=Nagashima |first5=Hideo |year=2005 |title=Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Carbonyl Cluster as the Catalyst |url=http://orgsyn.org/demo.aspx?prep=v82p0188 |journal=Organic Syntheses |volume=82 |pages=188 |doi=10.15227/orgsyn.082.0188}}</ref> |
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==Uses== |
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Polymerisation of acenaphthylene with acetylene in the presence of a Lewis acid catalyst gives electrically conductive polymers. Acenaphthylene possesses excellent properties as an antioxidant in cross-linked polyethylene and ethylene-propylene rubber. Thermal trimerization of acenaphthylene leads to decacyclene, which can be further processed to sulfur dyes.<ref>Ullmann, 4th ed., 21, 70</ref> |
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== Toxicity == |
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The ] of acenaphthylene after repeated 28-day oral administration to both male and female rats was found to be 4 mg/kg/day.<ref>{{cite journal |last1=Tanabe |first1=S. |display-authors=et al |date=2017 |title=Toxicity of repeated 28-day oral administration of acenaphthylene in rats |journal=Fundamental Toxicological Sciences |volume=4 |issue=6 |pages=247–259 |doi=10.2131/fts.4.247 |doi-access=free }}</ref> |
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==References== |
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<references/> |
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{{Authority control}} |
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