Pentane
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Pentane is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
C5H12—that is, an
alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...
with five
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the
IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
nomenclature, however, pentane means exclusively the ''n''-pentane isomer; the other two are called
isopentane Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon (an alkane) with five carbon atoms, with formula or . Isopentane is an extremely volatile and extremely flammable liquid at room temperature and ...
(methylbutane) and neopentane (dimethylpropane).
Cyclopentane Cyclopentane (also called C pentane) 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 occur ...
is not an isomer of pentane because it has only 10
hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
atoms where pentane has 12. Pentanes are components of some fuels and are employed as specialty
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s in the
laboratory A laboratory (; ; colloquially lab) is a facility that provides controlled conditions in which scientific or technological research, experiments, and measurement may be performed. Laboratory services are provided in a variety of settings: physicia ...
. Their properties are very similar to those of
butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name but ...
s and
hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
s.


Industrial uses

Pentanes are some of the primary
blowing agent A blowing agent is a substance which is capable of producing a cellular structure via a foaming process in a variety of materials that undergo hardening or phase transition, such as polymers, plastics, and metals. They are typically applied wh ...
s used in the production of polystyrene foam and other foams. Usually, a mixture of n-, i-, and increasingly cyclopentane is used for this purpose. Acid-catalyzed isomerization gives isopentane, which is used in producing high-octane fuels. Because of their low
boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envir ...
s, low cost, and relative safety, pentanes are used as a working medium in
geothermal power Geothermal power is electrical power generated from geothermal energy. Technologies in use include dry steam power stations, flash steam power stations and binary cycle power stations. Geothermal electricity generation is currently used in 2 ...
stations and
organic Rankine cycle In thermal engineering, the Organic Rankine Cycle (ORC) is a type of thermodynamic cycle. It is a variation of the Rankine cycle named for its use of an organic, high-molecular-mass fluid whose vaporization temperature is lower than that of wat ...
s. It is also used in some blended
refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...
s. Pentanes are solvents in many ordinary products, e.g. in some
pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...
s.


Laboratory use

Pentanes are relatively inexpensive and are the most volatile liquid alkanes at room temperature, so they are often used in the laboratory as
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s that can be conveniently and rapidly evaporated. However, because of their
nonpolar In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar ...
ity and lack of
functionality Function or functionality may refer to: Computing * Function key, a type of key on computer keyboards * Function model, a structured representation of processes in a system * Function object or functor or functionoid, a concept of object-oriente ...
, they dissolve only nonpolar and alkyl-rich compounds. Pentanes are
miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applies ...
with most common nonpolar solvents such as
chlorocarbon An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...
s,
aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
s, and
ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...
s. They are often used in
liquid chromatography In chemical analysis, chromatography is a laboratory technique for the separation of a mixture into its components. The mixture is dissolved in a fluid solvent (gas or liquid) called the ''mobile phase'', which carries it through a system (a ...
.


Physical properties

The
boiling point The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding envir ...
s of the pentane isomers range from about 9 to 36 °C. As is the case for other alkanes, the more thickly branched isomers tend to have lower boiling points. The same tends to be true for the
melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depends ...
s of alkane isomers, and that of isopentane is 30 °C lower than that of ''n''-pentane. However, the melting point of neopentane, the most heavily branched of the three, is 100 °C ''higher'' than that of isopentane. The anomalously high melting point of neopentane has been attributed to the
tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the ...
molecules A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...
packing more closely in solid form; this explanation is contradicted by the fact that neopentane has a lower density than the other two isomers, and the high melting point is actually caused by neopentane’s significantly lower
entropy of fusion In thermodynamics, the entropy of fusion is the increase in entropy when melting a solid substance. This is almost always positive since the degree of disorder increases in the transition from an organized crystalline solid to the disorganized ...
. The branched isomers are more stable (have lower
heat of formation In chemistry and thermodynamics, the standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy during the formation of 1 mole of the substance from its constituent elements in their reference state, wit ...
and heat of combustion) than n-pentane. The difference is 1.8
kcal The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of o ...
/ mol for isopentane, and 5 kcal/mol for neopentane.
Rotation Rotation, or spin, is the circular movement of an object around a '' central axis''. A two-dimensional rotating object has only one possible central axis and can rotate in either a clockwise or counterclockwise direction. A three-dimensional ...
about two central single C-C bonds of ''n''-pentane produces four different conformations.


Reactions and occurrence

Like other
alkanes In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
, pentanes are largely unreactive at standard room temperature and conditions - however, with sufficient
activation energy In chemistry and physics, activation energy is the minimum amount of energy that must be provided for compounds to result in a chemical reaction. The activation energy (''E''a) of a reaction is measured in joules per mole (J/mol), kilojoules pe ...
(e.g., an open flame), they readily
oxidize Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
to form
carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
and water: :C5H12 + 8 O2 → 5 CO2 + 6 H2O + heat/energy Like other
alkanes In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
, pentanes undergo
free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...
chlorination Chlorination may refer to: * Chlorination reaction In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transform ...
: :C5H12 + Cl2 → C5H11Cl + HCl Such reactions are unselective; with ''n''-pentane, the result is a mixture of the 1-, 2-, and 3-chloropentanes, as well as more highly chlorinated derivatives. Other radical halogenations can also occur. Pentane is a component of exhaled breath for some individuals. A degradation product of unsaturated fatty acids, its presence is associated with certain diseases and cancers.


References


External links


International Chemical Safety Card 0534
at ILO.org

at CDC.gov
Phytochemical data for pentane
at Ars-grin.gov {{Hydrides by group Alkanes Hydrocarbon solvents