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{{chembox |
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|ImageFileL1=methylcyclopentane structure.png |
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|ImageSizeL1=80px |
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|verifiedrevid = 379811352 |
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|ImageFileR1=methylcyclopentane spheres.png |
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|ImageFileL1 =methylcyclopentane structure.png |
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|ImageSizeR1=150px |
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|ImageSizeL1 =80px |
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|IUPACName=methylcyclopentane |
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|ImageFileR1 =methylcyclopentane spheres.png |
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|OtherNames= |
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|ImageSizeR1 =150px |
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|PIN =Methylcyclopentane |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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|CASNo =96-37-7 |
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| CASNo=96377 |
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|CASNo_Ref = {{cascite|changed|??}} |
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|PubChem = 7296 |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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|ChemSpiderID = 7024 |
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|EINECS = 202-503-2 |
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|UNNumber = 2298 |
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|UNII = 5G26CC1ASK |
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|ChEBI = 88429 |
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|ChEMBL = 30940 |
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|SMILES = CC1CCCC1 |
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|InChI = 1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=6 | H=12 |
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| Formula=C<sub>6</sub>H<sub>12</sub> |
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|Appearance = Colorless liquid |
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| MolarMass=84.17 g/mol |
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| Appearance= colourless gas<ref name = "CRC">{{ cite book | editor-first = David. R | editor-last = Lide |title = CRC Handbook of Chemistry and Physics | url = http://www.hbcpnetbase.com/ | edition = 89th | year = 2009 | publisher = ] | location = | isbn = 9781420066791 | page = }}</ref> |
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|Density = 0.749 g/cm<sup>3</sup><ref name = "CRC">{{cite book | editor-first = David. R | editor-last = Lide | title = CRC Handbook of Chemistry and Physics | url = https://archive.org/details/crchandbookofche00davi | edition = 89th | year = 2009 | publisher = ] | isbn = 978-1-4200-6679-1 | url-access = registration }}</ref> |
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|MeltingPtC = -142.4 |
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| Specific Gravity= 0.749<ref name="CRC" /> |
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| MeltingPt=-142.4 °C<ref name="CRC" /> |
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|MeltingPt_ref = <ref name="CRC" /> |
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|BoilingPtC = 71.8 |
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| BoilingPt= 71.8 °C<ref name="CRC" /> |
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|BoilingPt_ref = <ref name="CRC" /> |
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| Solubility= insoluble in water |
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|Solubility = Insoluble |
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|MagSus = -70.17·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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|MainHazards =flammable |
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|FlashPtC = -4 |
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| FlashPt= |
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|FlashPt_notes = <!--Ullmann--> |
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| Autoignition= |
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|AutoignitionPtC = 260 |
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|AutoignitionPt_notes = <!--Ullmann--> |
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'''Methylcyclopentane''' is an ] with the ] CH<sub>3</sub>C<sub>5</sub>]<sub>9</sub>. It is one of the important ]s that can react in refinery processes to form ]. |
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'''Methylcyclopentane''' is an ] with the ] CH<sub>3</sub>C<sub>5</sub>]<sub>9</sub>. It is a colourless, flammable liquid with a faint odor. It is a component of the ] fraction of petroleum usually obtained as a mixture with ]. It is mainly converted in naphthene ]s to ].<ref name=Ullmann>{{Ullmann|author=M. Larry Campbell|title=Cyclohexane|year=2012|doi=10.1002/14356007.a08_209.pub2}}</ref> |
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As of early 1990s, it was present in American<ref>{{Cite journal |last=Doskey |first=Paul V. |last2=Porter |first2=Joseph A. |last3=Scheff |first3=Peter A. |date=November 1992 |title=Source Fingerprints for Volatile Non-Methane Hydrocarbons |url=https://www.tandfonline.com/doi/full/10.1080/10473289.1992.10467090 |journal=Journal of the Air & Waste Management Association |language=en |volume=42 |issue=11 |pages=1437–1445 |doi=10.1080/10473289.1992.10467090 |issn=1047-3289}}</ref> and European<ref>{{Cite journal |last=Östermark |first=Ulf |last2=Petersson |first2=Göran |date=1992-09-01 |title=Assessment of hydrocarbons in vapours of conventional and alkylate-based petrol |url=https://publications.lib.chalmers.se/records/fulltext/local_72590.pdf |journal=Chemosphere |volume=25 |issue=6 |pages=763–768 |doi=10.1016/0045-6535(92)90066-Z |issn=0045-6535}}</ref> ] in small amounts, and by 2011 its share in US gasoline varied between 1 and 3%.<ref>{{cite web |date=2011 |title=Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT |website=nepis.epa.gov |publisher=United States Environmental Protection Agency}}</ref> It has a research octane number of 103 and motor octane number of 95.<ref>{{Cite journal |last=Lokachari |first=Nitin |last2=Wagnon |first2=Scott W. |last3=Kukkadapu |first3=Goutham |last4=Pitz |first4=William J. |last5=Curran |first5=Henry J. |date=2021-03-01 |title=An experimental and kinetic modeling study of cyclopentane and dimethyl ether blends |url=https://www.sciencedirect.com/science/article/abs/pii/S0010218020304375 |journal=Combustion and Flame |volume=225 |pages=255–271 |doi=10.1016/j.combustflame.2020.10.017 |issn=0010-2180|hdl=10379/16483 |hdl-access=free }}</ref> |
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The C<sub>6</sub> core of methylcyclopentane is not perfectly planar and can ] to alleviate stress in its structure.<ref>{{cite book |last1=Carey |first1=Francis |last2=Giuliano |first2=Robert |title=Organic Chemistry |chapter=3 |edition=9 |publisher=McGraw-Hill |year=2014 |pages=97–131 |isbn=978-0073402741 }}</ref> |
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:] is a classic aromatization reaction, specifically a dehydroisomerization. This platinum (Pt)-catalyzed process is practiced on scale in the production of ] from petroleum.]] |
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==History== |
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Methylcyclopentane was first synthesized in 1888 by {{Ill|Paul Caspar Freer|WD=Q18910667}} and ] by a ] of ] and 1,5-dibromohexane.<ref>{{Cite journal |last=Freer |first=Paul C. |last2=Perkin |first2=W. H. |date=1888 |title=The synthetical formation of closed carbon-chains. Part IV. Some derivatives of hexamethylene |url=https://books.google.com/books?id=xvRi1OdwXbAC&pg=PA202 |journal=Journal of the Chemical Society, Transactions |language=en |volume=53 |issue=0 |pages=202–215 |doi=10.1039/CT8885300202 |issn=0368-1645}}</ref> They named it '''methylpentamethylene''' since the modern nomenclature wasn't developed until 1892 ]. |
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In 1895, ] discovered that methylcyclopentane was the reaction product of hydrogenation of ] using ]. Prior to that, several chemists (such as ] in 1867,<ref>{{cite journal|last=Bertholet|year=1867|url=https://books.google.com/books?id=YVgSAAAAYAAJ&pg=PA53|title=Nouvelles applications des méthodes de réduction en chimie organique|trans-title=New applications of reduction methods in organic chemistry|journal=Bulletin de la Société Chimique de Paris|volume=series 2|issue=7|pages=53–65|language=fr}}</ref><ref>{{cite journal|last=Bertholet|year=1868|title=Méthode universelle pour réduire et saturer d'hydrogène les composés organiques|trans-title=Universal method for reducing and saturating organic compounds with hydrogen|journal=Bulletin de la Société Chimique de Paris|volume=series 2|issue=9|pages=8–31|url=https://books.google.com/books?id=r1sSAAAAYAAJ&q=Bertholet&pg=PA17|quote=En effet, la benzine, chauffée à 280° pendant 24 heures avec 80 fois son poids d'une solution aqueuse saturée à froid d'acide iodhydrique, se change à peu près entièrement en hydrure d'hexylène, C<sub>12</sub>H<sub>14</sub>, en fixant 4 fois son volume d'hydrogène: C<sub>12</sub>H<sub>6</sub> + 4H<sub>2</sub> = C<sub>12</sub>H<sub>14</sub> … Le nouveau carbure formé par la benzine est un corps unique et défini: il bout à 69°, et offre toutes les propriétés et la composition de l'hydrure d'hexylène extrait des pétroles.|trans-quote=In effect, benzene, heated to 280° for 24 hours with 80 times its weight of an aqueous solution of cold saturated hydroiodic acid, is changed almost entirely into hydride of hexylene, C<sub>12</sub>H<sub>14</sub>, by fixing 4 times its volume of hydrogen: C<sub>12</sub>H<sub>6</sub> + 4H<sub>2</sub> = C<sub>12</sub>H<sub>14</sub> The new carbon compound formed by benzene is a unique and well-defined substance: it boils at 69° and presents all the properties and the composition of hydride of hexylene extracted from oil.)|language=fr}}</ref> and ] in 1870<ref>{{cite journal|author=Adolf Baeyer|year=1870|url=https://books.google.com/books?id=RJU8AAAAIAAJ&pg=PA266|title=Ueber die Reduction aromatischer Kohlenwasserstoffe durch Jodphosphonium|trans-title=On the reduction of aromatic compound by phosphonium iodide |journal=Annalen der Chemie und Pharmacie|volume=55|pages=266–281|quote=Bei der Reduction mit Natriumamalgam oder Jodphosphonium addiren sich im höchsten Falle sechs Atome Wasserstoff, und es entstehen Abkömmlinge, die sich von einem Kohlenwasserstoff C<sub>6</sub>H<sub>12</sub> ableiten. Dieser Kohlenwasserstoff ist aller Wahrscheinlichkeit nach ein geschlossener Ring, da seine Derivate, das Hexahydromesitylen und Hexahydromellithsäure, mit Leichtigkeit wieder in Benzolabkömmlinge übergeführt werden können.|trans-quote=During the reduction with sodium amalgam or phosphonium iodide, six atoms of hydrogen are added in the extreme case, and there arise derivatives, which derive from a hydrocarbon C<sub>6</sub>H<sub>12</sub>. This hydrocarbon is in all probability a closed ring, since its derivatives — hexahydromesitylene and hexahydromellithic acid — can be converted with ease again into benzene derivatives.}}</ref>) had tried and failed to synthesize ] using this method. |
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==References== |
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