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Methylcyclopentane: Difference between revisions

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{{chembox
{{chembox
| Verifiedfields = changed
|Verifiedfields = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 379811352
|verifiedrevid = 379811352
| ImageFileL1 =methylcyclopentane structure.png
|ImageFileL1 =methylcyclopentane structure.png
| ImageSizeL1 =80px
|ImageSizeL1 =80px
| ImageFileR1 =methylcyclopentane spheres.png
|ImageFileR1 =methylcyclopentane spheres.png
| ImageSizeR1 =150px
|ImageSizeR1 =150px
| PIN =Methylcyclopentane
|PIN =Methylcyclopentane
| OtherNames =
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo =96-37-7
|CASNo =96-37-7
| CASNo_Ref = {{cascite|changed|??}}
|CASNo_Ref = {{cascite|changed|??}}
| PubChem = 7296
|PubChem = 7296
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 7024
|ChemSpiderID = 7024
| EINECS = 202-503-2
|EINECS = 202-503-2
| UNNumber = 2298
|UNNumber = 2298
| UNII = 5G26CC1ASK
|UNII = 5G26CC1ASK
|ChEBI = 88429

| ChEBI = 88429
|ChEMBL = 30940
| ChEMBL = 30940
|SMILES = CC1CCCC1
⚫
|InChI = 1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3
| SMILES = CC1CCCC1
⚫
}}
⚫
| InChI = 1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3
⚫
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=6 | H=12
|C=6 | H=12
| Appearance = Colorless liquid
|Appearance = Colorless liquid
| 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 = [[CRC Press]] | isbn = 978-1-4200-6679-1 | url-access = registration }}</ref>
|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 = [[CRC Press]] | isbn = 978-1-4200-6679-1 | url-access = registration }}</ref>
| MeltingPtC = -142.4
|MeltingPtC = -142.4
| MeltingPt_ref = <ref name="CRC" />
|MeltingPt_ref = <ref name="CRC" />
| BoilingPtC = 71.8
|BoilingPtC = 71.8
| BoilingPt_ref = <ref name="CRC" />
|BoilingPt_ref = <ref name="CRC" />
| Solubility = Insoluble
|Solubility = Insoluble
| MagSus = -70.17·10<sup>−6</sup> cm<sup>3</sup>/mol
|MagSus = -70.17·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =flammable
|MainHazards =flammable
| FlashPtC = -4
|FlashPtC = -4
| FlashPt_notes = <!--Ullmann-->
|FlashPt_notes = <!--Ullmann-->
| AutoignitionPtC = 260
|AutoignitionPtC = 260
| AutoignitionPt_notes = <!--Ullmann-->
|AutoignitionPt_notes = <!--Ullmann-->
}}
}}
}}
}}


'''Methylcyclopentane''' is an [[organic compound]] with the [[chemical formula]] CH<sub>3</sub>C<sub>5</sub>[[Hydrogen|H]]<sub>9</sub>. It is a colourless, flammable liquid with a faint odor. It is a component of the [[naphthene]] fraction of petroleum. It usually is obtained as a mixture with cyclohexane. It is mainly converted in naphthene [[Catalytic reformer|reformer]]s to [[benzene]].<ref name=Ullmann>{{Ullmann|author=M. Larry Campbell|title=Cyclohexane|year=2012|doi=10.1002/14356007.a08_209.pub2}}</ref> The C<sub>6</sub> core of methylcyclopentane is not perfectly planar and can [[Ring_strain|pucker]] to alleviate stress in its structure.<ref>{{cite book |last=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>
'''Methylcyclopentane''' is an [[organic compound]] with the [[chemical formula]] CH<sub>3</sub>C<sub>5</sub>[[Hydrogen|H]]<sub>9</sub>. It is a colourless, flammable liquid with a faint odor. It is a component of the [[naphthene]] fraction of petroleum. It usually is obtained as a mixture with cyclohexane. It is mainly converted in naphthene [[Catalytic reformer|reformer]]s to [[benzene]].<ref name=Ullmann>{{Ullmann|author=M. Larry Campbell|title=Cyclohexane|year=2012|doi=10.1002/14356007.a08_209.pub2}}</ref> The C<sub>6</sub> core of methylcyclopentane is not perfectly planar and can [[Ring_strain|pucker]] to alleviate stress in its structure.<ref>{{cite book |last=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>


:[[File:MeC5H9toPhH.png|center|362px|thumb|The conversion of methylcyclopentane to [[benzene]] is a classic aromatization reaction, specifically a dehydroisomerization. This platinum (Pt)-catalyzed process is practiced on scale in the production of [[gasoline]] from petroleum.]]
:[[File:MeC5H9toPhH.png|center|362px|thumb|The conversion of methylcyclopentane to [[benzene]] is a classic aromatization reaction, specifically a dehydroisomerization. This platinum (Pt)-catalyzed process is practiced on scale in the production of [[gasoline]] from petroleum.]]


==References==
==References==
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{{Hydrocarbons}}
{{Hydrocarbons}}
{{Authority control}}
{{Authority control}}
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[[Category:Cyclopentyl compounds]]
[[Category:Hydrocarbons]]
[[Category:Hydrocarbons]]
⚫
[[Category:Cyclopentyl compounds]]

Revision as of 15:29, 19 February 2023

Methylcyclopentane
Names
Preferred IUPAC name
Methylcyclopentane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.277 Edit this at Wikidata
EC Number
  • 202-503-2
UNII
UN number 2298
  • InChI=1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3
  • CC1CCCC1
Properties
C6H12
Molar mass 84.162 g·mol−1
Appearance Colorless liquid
Density 0.749 g/cm3[1]
Melting point −142.4 °C (−224.3 °F; 130.8 K)[1]
Boiling point 71.8 °C (161.2 °F; 344.9 K)[1]
Insoluble
-70.17·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable
Flash point −4 °C (25 °F; 269 K)
260 °C (500 °F; 533 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methylcyclopentane is an organic compound with the chemical formula CH3C5H9. It is a colourless, flammable liquid with a faint odor. It is a component of the naphthene fraction of petroleum. It usually is obtained as a mixture with cyclohexane. It is mainly converted in naphthene reformers to benzene.[2] The C6 core of methylcyclopentane is not perfectly planar and can pucker to alleviate stress in its structure.[3]

The conversion of methylcyclopentane to benzene is a classic aromatization reaction, specifically a dehydroisomerization. This platinum (Pt)-catalyzed process is practiced on scale in the production of gasoline from petroleum.

References

  1. ^ a b c Lide, David. R, ed. (2009). CRC Handbook of Chemistry and Physics (89th ed.). CRC Press. ISBN 978-1-4200-6679-1.
  2. ^ M. Larry Campbell (2012). "Cyclohexane". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_209.pub2. ISBN 978-3527306732.
  3. ^ Carey, Francis; Giuliano, Robert (2014). "3". Organic Chemistry (9 ed.). McGraw-Hill. pp. 97–131. ISBN 978-0073402741.
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