Cyclopentane

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Cyclopentane
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Names
Preferred IUPAC name
Cyclopentane
Other names
pentamethylene
Identifiers
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3D model (JSmol)
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  • InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2 checkY
    Key: RGSFGYAAUTVSQA-UHFFFAOYSA-N checkY
  • InChI=1/C5H10/c1-2-4-5-3-1/h1-5H2
    Key: RGSFGYAAUTVSQA-UHFFFAOYA
  • C1CCCC1
Properties
C5H10
Molar mass 70.135 g·mol−1
Appearance clear, colorless liquid
Odor mild, sweet
Density 0.751 g/cm3
Melting point −93.9 °C (−137.0 °F; 179.2 K)
Boiling point 49.2 °C (120.6 °F; 322.3 K)
156 mg·l−1 (25 °C)[1]
Solubility soluble in ethanol, acetone, ether
Vapor pressure 45 kPa (20 °C) [2]
Acidity (pKa) ~45
−59.18·10−6 cm3/mol
1.4065
Hazards
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1
3
0
Flash point −37.2 °C (−35.0 °F; 236.0 K)
361 °C (682 °F; 634 K)
Explosive limits 1.1%–8.7%[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 TWA 600 ppm (1720 mg/m3)[3]
IDLH (Immediate danger)
 N.D.[3]
Related compounds
Related compounds
 cyclopropane, cyclobutane, cyclohexane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Cyclopentane (also called C pentane)[4] is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It is a colorless liquid with a petrol-like odor. Its freezing point is −94 °C and its boiling point is 49 °C. Cyclopentane is in the class of cycloalkanes, being alkanes that have one or more carbon rings. It is formed by cracking cyclohexane in the presence of alumina at a high temperature and pressure.

It was first prepared in 1893 by the German chemist Johannes Wislicenus.[5]

Production, occurrence and use

Cycloalkanes are formed by catalytic reforming. For example, when passed over a hot platinum surface, 2-methylbutane converts into cyclopentane.

File:Cyclopentane warning on refrigerator.jpg
This prominent sign on the back of a refrigerator marks it as containing cyclopentane-based insulation

Cyclopentane is principally used as a blowing agent in the manufacture of polyurethane insulating foam, replacing ozone-depleting agents such as CFC-11 and HCFC-141b.[6][7] While cyclopentane is not typically used as a refrigerant, it is common for domestic appliances that are insulated with cyclopentane-based foam, such as refrigerators and freezers, to be marked with cyclopentane warning labels due to its flammability. Cyclopentane is also used in the manufacture of synthetic resins and rubber adhesives.[citation needed]

Cyclopentane is a minor component of automobile fuel, with its share in US gasoline varying between 0.2 and 1.6% in early 1990s[8] and 0.1 to 1.7% in 2011.[9] Its research and motor octane numbers are reported as 101 or 103 and 85 or 86 respectively.[10][11]

Multiple alkylated cyclopentane (MAC) lubricants, such as 1,3,4-tri-(2-octyldodecyl) cyclopentane, have low volatility and are used by NASA in space applications.[12][13]

Cyclopentane requires safety precautions to prevent leakage and ignition as it is both highly flammable and can also cause respiratory arrest when inhaled.[14]

Cyclopentane can be fluorinated to give compounds ranging from Page Module:Chem2/styles.css has no content.C5H9F to perfluorocyclopentane Page Module:Chem2/styles.css has no content.C5F10. Such species are conceivable refrigerants and specialty solvents.[15][16]

The cyclopentane ring is pervasive in natural products including many useful drugs. Examples include most steroids, prostaglandins, and some lipids.

Conformations

In a regular pentagon, the angles at the vertices are all 108°, slightly less than the bond angle in perfectly tetrahedrally bonded carbon, which is about 109.47°. However, cyclopentane is not planar in its normal conformations. It puckers in order to increase the distances between the hydrogen atoms (something which does not happen in the planar cyclopentadienyl anion Page Module:Chem2/styles.css has no content.C5H−5 because it doesn't have as many hydrogen atoms). This means that the average C-C-C angle is less than 108°. There are two conformations that give local minima of the energy, the "envelope" and the "half-chair" (occurring in two enantiomorphs). The envelope has mirror symmetry (Cs), while the half chair has two-fold rotational symmetry (C2). In both cases the symmetry implies that there are two pairs of equal C-C-C angles and one C-C-C angle that has no pair. In fact for cyclopentane, unlike for cyclohexane (C6H12, see cyclohexane conformation) and higher cycloalkanes, it is not possible geometrically for all the angles and bond lengths to be equal except if it is in the form of a flat regular pentagon.

References

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  1. ^ Record of cyclopentane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 28 February 2015.
  2. ^ Page Module:Citation/CS1/styles.css has no content."ICSC 0353 - CYCLOPENTANE".
  3. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0171". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Page Module:Citation/CS1/styles.css has no content.Sárkány, A.; Gaál, J.; Toth, L. (1981). "Comparative Study of C-Pentane and N-Pentane Transformations on Ni and Pt Catalysts". Studies in Surface Science and Catalysis. 7: 291–301. Bibcode:1981SSSC....7..291S. doi:10.1016/S0167-2991(09)60278-0. ISBN 978-0-444-99740-1.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Wislicenus, J.; Hentschel, W. (January 1893). "III. Der Pentamethenylalkohol und seine Derivate (Cyclopentanol and its derivatives)" (PDF). Justus Liebigs Annalen der Chemie. 275 (2–3): 322–330. doi:10.1002/jlac.18932750216.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Schilling, S. L. (May 2000). "Appliance Rigid Foams Blown with Cyclopentane and Cyclopentane/Isopentane Blends". Journal of Cellular Plastics. 36 (3): 190–206. doi:10.1177/0021955X0003600302. eISSN 1530-7999. ISSN 0021-955X.
  7. ^ Greenpeace - Appliance Insulation Script error: No such module "webarchive".
  8. ^ Page Module:Citation/CS1/styles.css has no content.Doskey, Paul V.; Porter, Joseph A.; Scheff, Peter A. (November 1992). "Source Fingerprints for Volatile Non-Methane Hydrocarbons". Journal of the Air & Waste Management Association. 42 (11): 1437–1445. Bibcode:1992JAWMA..42.1437D. doi:10.1080/10473289.1992.10467090. ISSN 1047-3289.
  9. ^ Page Module:Citation/CS1/styles.css has no content."Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Scherzer, Julius (1990-08-31). Octane-Enhancing Zeolitic FCC Catalysts: Scientific and Technical Aspects. CRC Press. p. 9. ISBN 978-0-8247-8399-0.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Song, Hwasup; Dauphin, Roland; Vanhove, Guillaume (2020). "A kinetic investigation on the synergistic low-temperature reactivity, antagonistic RON blending of high-octane fuels: Diisobutylene and cyclopentane" (PDF). Combustion and Flame. 220: 23–33. Bibcode:2020CoFl..220...23S. doi:10.1016/j.combustflame.2020.06.030. ISSN 0010-2180.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Loewenthal, Stuart H.; Jones, William R.; Predmore, Roamer E. (1 September 1999). Life of Pennzane and 815Z-Lubricated Instrument Bearings Cleaned with Non-CFC Solvents (Technical report). John H. Glenn Research Center at Lewis Field: National Aeronautics and Space Administration. OCLC 1002210567. 19990039657.
  13. ^ Page Module:Citation/CS1/styles.css has no content."Pennzoil Products: High Tech Products". pennzane.com. 12 April 2004. Archived from the original on 12 April 2004. Retrieved 15 July 2022.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Robert W. Virtue, M.D. (May 1949). "Observations on Cyclopentane as an Anesthetic Agent". Anesthesiology. 10 (3): 318–324. doi:10.1097/00000542-194905000-00007.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Tatlow, John Colin (1995). "Cyclic and bicyclic polyfluoro-alkanes and -alkenes". Journal of Fluorine Chemistry. 75 (1): 7–34. Bibcode:1995JFluC..75....7T. doi:10.1016/0022-1139(95)03293-m. ISSN 0022-1139.
  16. ^ Page Module:Citation/CS1/styles.css has no content.Zhang, Chengping; Qing, Feiyao; Quan, Hengdao; Sekiya, Akira (January 2016). "Synthesis of 1,1,2,2,3,3,4-heptafluorocyclopentane as a new generation of green solvent". Journal of Fluorine Chemistry. 181: 11–16. Bibcode:2016JFluC.181...11Z. doi:10.1016/j.jfluchem.2015.10.012.
  • Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons

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