Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Acenaphthene: Difference between pages

{{Distinguish|Acenaphthylene}}

| Watchedfields = changed

| verifiedrevid = 477238157

| ImageFile1 = Acenaphthene.svg

| ImageSize1 = 120px

| ImageAlt1 = Skeletal formula

| ImageFile2 = Acenaphthene-3D-balls.png

| ImageSize2 = 120px

| ImageAlt2 = Ball-and-stick model

| ImageFile3 = AcenaphthCrop.jpg

| PIN = 1,2-Dihydroacenaphthylene

| OtherNames = 1,8-Ethylenenaphthalene<br/>''peri''-Ethylenenaphthalene<br/>Naphthyleneethylene<br/>Tricyclo[6.3.1.0^4,12]dodecapentaene<br/>Tricyclo[6.3.1.0^4,12]dodeca-1(12),4,6,8,10-pentaene

|Section1={{Chembox Identifiers

| InChIKey = CWRYPZZKDGJXCA-UHFFFAOYAW

| CASNo_Ref = {{cascite|correct|CAS}}

| EINECS = 201-469-6

| PubChem = 6734

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1797271

| UNII_Ref = {{fdacite|correct|FDA}}

| InChI = 1/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2

| RTECS = AB1000000

| UNNumber = 3077

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| KEGG = C19312

}}

|Section2={{Chembox Properties

| C=12 | H=10

| Appearance = White or pale yellow crystalline powder

| Density = 1.024 g/cm³

| MeltingPtC = 93.4

| BoilingPtC = 279

| Solubility = 0.4 mg/100 ml

| MagSus = -.709·10⁻⁶ cm³/g

| 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>

}}

| Section4 = {{Chembox Thermochemistry

| 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>

| HeatCapacity = 190.4 J mol⁻¹ K⁻¹

| Entropy = 188.9 J mol⁻¹ K⁻¹

| DeltaHform = 70.3 kJ/mol

| DeltaGfree =

| DeltaHcombust =

| DeltaHfus =

| DeltaHvap =

| DeltaHsublim =

| HHV =

| LHV =

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics1674.htm ICSC 1674]

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 1

| NFPA-S =

| FlashPtC = 135

| AutoignitionPt = >

| AutoignitionPtC = 450

}}

'''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.<ref name=Ull/>

==Production and reactions==

Acenaphthene was prepared the first time from coal tar by [[Marcellin Berthelot]].<ref name="Ullmann">{{cite book| title = Hydrocarbons |editor = Wiley-VCH Verlag GmbH & Co| series = Ullmann's Encyclopedia of Industrial Chemistry| author = Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke| language = en | date=2000-06-15 | pages = | isbn = }}</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 [[acenaphthylene]] (and many other compounds).

Like other [[arene]]s, acenaphthene forms complexes with low valent metal centers. One example is (η⁶-acenaphthene)Mn(CO)₃]⁺.<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>

==Uses==

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and [[optical brightener]]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> [[Naphthalene dicarboxylic anhydride]] is the precursor to [[perylenetetracarboxylic dianhydride]], precursor to several commercial [[pigment]]s and [[dye]]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>

:[[File:Pig29route.png|center|520 px]]

==References==

{{Reflist}}

{{PAHs}}

{{Authority control}}

[[Category:Polycyclic aromatic hydrocarbons]]

[[Category:Tricyclic compounds]]