The Info List - Cyclopentane

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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 occurs as a colorless liquid with a petrol-like odor. Its melting 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 rings of carbon atoms.

The typical structure of cyclopentane is the "envelope" conformation.

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.[3]


1 Industrial usage 2 Formulation of cycloalkanes 3 References 4 External links

Industrial usage[edit] Cyclopentane
is used in the manufacture of synthetic resins and rubber adhesives and also as a blowing agent in the manufacture of polyurethane insulating foam, as found in many domestic appliances such as refrigerators and freezers, replacing environmentally damaging alternatives such as CFC-11 and HCFC-141b[4] Multiply alkylated cyclopentane (MAC) lubricants have low volatility and are used in some specialty applications.[5] The United States
United States
produces more than half a million kilograms of this chemical per year. Formulation of cycloalkanes[edit] Cycloalkanes can be formulated via a process known as catalytic reforming. For example, 2-methylbutane can be reformed into cyclopentane, by use of a platinum catalyst. This is particularly well known in automobiles, as branched alkanes will burn much more readily.

Half-chair conformation of lower-energy state chemical structure of cyclopentane.


^ Record of cyclopentane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 28 February 2015 ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0171". National Institute for Occupational Safety and Health (NIOSH).  ^ J. Wislicenus and W. Hentschel (1893) "Der Pentamethenylalkohol und seine Derivate" (Cyclopentanol and its derivatives), Annalen der Chemie, 275 : 322-330; see especially pages 327-330. Wislicenus prepared cyclopentane from cyclopentanone ("Ketopentamethen"), which is prepared by heating calcium adipate. ^ Greenpeace - Appliance Insulation Archived 2008-10-30 at the Wayback Machine. ^ Pennzane - lubrication technology

External links[edit]

Media related to Cyclopentanes at Wikimedia Commons

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Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Cyclooctane Cyclononane Cyclodecane Cycloundecane Cyclododecane Cyclotridecane Cyclotetradecane

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