Cyclopentane

Last updated
Cyclopentane
Cyclopentane v2.svg
Cyclopentane3d.png
Names
Preferred IUPAC name
Cyclopentane
Other names
pentamethylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.470 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-016-6
PubChem CID
RTECS number
  • GY2390000
UNII
  • InChI=1S/C5H10/c1-2-4-5-3-1/h1-5H2 Yes check.svgY
    Key: RGSFGYAAUTVSQA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H10/c1-2-4-5-3-1/h1-5H2
    Key: RGSFGYAAUTVSQA-UHFFFAOYAL
  • C1CCCC1
Properties
C5H10
Molar mass 70.1 g/mol
Appearanceclear, 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
Occupational safety and health (OHS/OSH):
Main hazards
Flammable [3]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.

This prominent sign on the back of a refrigerator marks it as containing cyclopentane-based insulation 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 C5H9F to perfluorocyclopentane 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 C5H5 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". 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.

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Hydrocarbon</span> Organic compound consisting entirely of hydrogen and carbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.

<span class="mw-page-title-main">Chlorofluorocarbon</span> Class of organic compounds

Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propane.

<span class="mw-page-title-main">Octane</span> Hydrocarbon compound with the formula C8H18

Octane is a hydrocarbon and an alkane with the chemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has many structural isomers that differ by the location of branching in the carbon chain. One of these isomers, 2,2,4-trimethylpentane (commonly called iso-octane), is used as one of the standard values in the octane rating scale.

<span class="mw-page-title-main">Cycloalkane</span> Saturated alicyclic hydrocarbon

In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkenes.

Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

<span class="mw-page-title-main">Cyclohexane conformation</span> Structures of cyclohexane

Cyclohexane conformations are any of several three-dimensional shapes adopted by cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane are important prototypes of a wide range of compounds.

<span class="mw-page-title-main">Rotamer</span> Different molecular structures formed only by rotation about single bonds

In chemistry, rotamers are chemical species that differ from one another primarily due to rotations about one or more single bonds. Various arrangements of atoms in a molecule that differ by rotation about single bonds can also be referred to as different conformations. Conformers/rotamers differ little in their energies, so they are almost never separable in a practical sense. Rotations about single bonds are subject to small energy barriers. When the time scale for interconversion is long enough for isolation of individual rotamers, the species are termed atropisomers. The ring-flip of substituted cyclohexanes constitutes a common form of conformers.

In chemistry, a molecule experiences strain when its chemical structure undergoes some stress which raises its internal energy in comparison to a strain-free reference compound. The internal energy of a molecule consists of all the energy stored within it. A strained molecule has an additional amount of internal energy which an unstrained molecule does not. This extra internal energy, or strain energy, can be likened to a compressed spring. Much like a compressed spring must be held in place to prevent release of its potential energy, a molecule can be held in an energetically unfavorable conformation by the bonds within that molecule. Without the bonds holding the conformation in place, the strain energy would be released.

<span class="mw-page-title-main">Ring strain</span> Instability in molecules with bonds at unnatural angles

In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are substantially smaller than the idealized value of approximately 109°. Because of their high strain, the heat of combustion for these small rings is elevated.

<span class="mw-page-title-main">Neopentane</span> Chemical compound

Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure.

Higher alkanes refer to alkanes with a high number of carbon atoms. There does not exist a formal definition for when an alkane is classified as a 'higher alkane', but one definition distinguishes the higher alkanes as the n-alkanes that are solid under room temperature.

In organic chemistry, a ring flip is the interconversion of cyclic conformers that have equivalent ring shapes that results in the exchange of nonequivalent substituent positions. The overall process generally takes place over several steps, involving coupled rotations about several of the molecule's single bonds, in conjunction with minor deformations of bond angles. Most commonly, the term is used to refer to the interconversion of the two chair conformers of cyclohexane derivatives, which is specifically referred to as a chair flip, although other cycloalkanes and inorganic rings undergo similar processes.

Cycloheptane, synonym suberane, is a cycloalkane with the molecular formula C7H14. It is a poorly water soluble organic liquid (melting point –12 deg C, solubility in water <30 mg /liter at 25 deg C), and is used as a nonpolar solvent for the chemical industry and as an intermediate in the manufacture of chemicals and pharmaceutical drugs. It can be prepared by Clemmensen reduction from cycloheptanone. Cycloheptane vapour is irritating to the eyes and may cause respiratory depression if inhaled in large quantity.

Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor.

3-Methylpentane is a branched alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the third carbon atom in a pentane chain. It is of similar structure to the isomeric 2-methylpentane, which has the methyl group located on the second carbon of the pentane chain.

<span class="mw-page-title-main">Butane</span> Flammable organic compound widely used as a fuel

Butane is an alkane with the formula C4H10. Butane exists as two isomers, n-butane with connectivity CH3CH2CH2CH3 and iso-butane with the formula (CH3)3CH. Both isomers are highly flammable, colorless, easily liquefied gases that quickly vaporize at room temperature and pressure. Butanes are a trace components of natural gases (NG gases). The other hydrocarbons in NG include propane, ethane, and especially methane, which are more abundant. Liquefied petroleum gas is a mixture of propane and some butanes.

<span class="mw-page-title-main">Methylcyclopentane</span> Chemical compound

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 usually obtained as a mixture with cyclohexane. It is mainly converted in naphthene reformers to benzene.

<span class="mw-page-title-main">2,3-Dimethylpentane</span> Chemical compound

2,3-Dimethylpentane is an organic compound of carbon and hydrogen with formula C
7
H
16
, more precisely CH
3
CH(CH
3
)
CH(CH
3
)
CH
2
CH
3
: a molecule of pentane with methyl groups –CH
3
replacing hydrogen atoms on carbon atoms 2 and 3. It is an alkane, a fully saturated hydrocarbon; specifically, one of the isomers of heptane.

References

  1. Record of cyclopentane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 28 February 2015.
  2. "ICSC 0353 - CYCLOPENTANE".
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0171". National Institute for Occupational Safety and Health (NIOSH).
  4. 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. doi:10.1016/S0167-2991(09)60278-0.
  5. 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. 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 Archived 2008-10-30 at the Wayback Machine
  8. 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. doi:10.1080/10473289.1992.10467090. ISSN   1047-3289.
  9. "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
  10. 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. 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". Combustion and Flame. 220: 23–33. doi:10.1016/j.combustflame.2020.06.030. ISSN   0010-2180.
  12. 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. "Pennzoil Products: High Tech Products". pennzane.com. 12 April 2004. Archived from the original on 12 April 2004. Retrieved 15 July 2022.
  14. Robert W. Virtue, M.D. (May 1949). "OBSERVATIONS ON CYCLOPENTANE AS AN ANESTHETIC AGENT". Anesthesiology. 10: 318–324. doi:10.1097/00000542-194905000-00007.
  15. Tatlow, John Colin (1995). "Cyclic and bicyclic polyfluoro-alkanes and -alkenes". Journal of Fluorine Chemistry. 75 (1): 7–34. doi:10.1016/0022-1139(95)03293-m. ISSN   0022-1139.
  16. 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. doi:10.1016/j.jfluchem.2015.10.012.