Propene

"Propylene" redirects here. For the unrelated compound referred to as "propolene", see
glucomannan.

Propene, also known as propylene, is an unsaturated organic compound having the chemical
formula C3H6. It has one double bond, and is the second simplest member of the alkene class of
hydrocarbons, and it is also second in natural abundance

Properties

At room temperature, propene is a gas, and as with many other alkenes, it is also colourless with
a weak but unpleasant smell.[1]

Propene has a higher density and boiling point than ethylene due to its greater size. It has a
slightly lower boiling point than propane and is thus more volatile. It lacks strongly polar bonds,
yet the molecule has a small dipole moment due to its reduced symmetry (its point group is Cs).

Propene has the same empirical formula as cyclopropane but their atoms are connected in
different ways, making these molecules structural isomers.

Production

Propene is produced from fossil fuels - petroleum, natural gas and to a much lesser extent coal.
Propene is a byproduct of oil refining and natural gas processing. Ethylene, propene, and other
compounds are produced by cracking larger hydrocarbon molecules. Propene is separated by
fractional distillation from hydrocarbon mixtures obtained from cracking and other refining
processes.

Propene production has remained static at around 35 million tonnes (Europe and North America
only) from 2000–2008 but has been increasing in East Asia, most notably Singapore and China.
[2][3] Total world production of propene is currently about half that of ethylene.

Uses

Propene is the second most important starting product in the petrochemical industry after
ethylene. It is the raw material for a wide variety of products. Manufacturers of the plastic
polypropylene account for nearly two thirds of all demand. Polypropylene is, for example, needed
for the production of films, packaging, caps and closures as well as for other applications. In the
year 2008 the worldwide sales of propene reached a value of over 90 billion US dollars. [4]

Propene and benzene are converted to acetone and phenol via the cumene process. Propene is
also used to produce isopropanol (propan-2-ol), acrylonitrile, propylene oxide (epoxypropane)
and epichlorohydrin.[5]

Reactions

Propene resembles other alkenes in that it undergoes addition reactions relatively easily at room
temperature. The relative weakness of its double bond (which is less strong than two single
bonds) explains its tendency to react with substances that can achieve this transformation.
Alkene reactions include: 1) polymerization, 2) oxidation, 3) halogenation and hydrohalogenation,
4) alkylation, 5) hydration, 6) oligomerization, and 7) hydroformylation.

References
# ^ Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers, 2005
# ^ www.petrochemistry.net Accessed August 2008
# ^ Organic Chemistry 6th edition, McMurry,J., Brooks/Cole Publishing, Pacific Grove USA (2005)
# ^ "Market Study: Propylene, Ceresana Research, February 2011". ceresana.com.
http://www.ceresana.com/en/market-studies/chemicals/propylene/. Retrieved 2011-02-13.
# ^ Budavari, Susan, ed. (1996), "8034. Propylene", The Merck Index, Twelfth Edition, New
Jersey: Merck & Co., pp. 1348–1349