Higher alkanes are
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 ...
s having nine or more
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.
Nonane
Nonane is a linear alkane hydrocarbon with the chemical formula C9H20. It is a colorless, flammable liquid, occurring primarily in the component of the petroleum distillate fraction commonly called kerosene, which is used as a heating, tractor, ...
is the lightest alkane to have a
flash point
The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". (EN 60079-10-1)
The fl ...
above 25 °C, and is not classified as dangerously
flammable
A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...
.
The term ''higher alkanes'' is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions.
Uses
Alkanes from
nonane
Nonane is a linear alkane hydrocarbon with the chemical formula C9H20. It is a colorless, flammable liquid, occurring primarily in the component of the petroleum distillate fraction commonly called kerosene, which is used as a heating, tractor, ...
to
hexadecane
Hexadecane (also called cetane) is an alkane hydrocarbon with the chemical formula C16H34. Hexadecane consists of a chain of 16 carbon atoms, with three hydrogen atoms bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 ...
(those alkanes with nine to sixteen carbon atoms) are liquids of higher
viscosity
The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water.
Viscosity quantifies the inte ...
, which are less suitable for use in gasoline. They form instead the major part of
diesel
Diesel may refer to:
* Diesel engine, an internal combustion engine where ignition is caused by compression
* Diesel fuel, a liquid fuel used in diesel engines
* Diesel locomotive, a railway locomotive in which the prime mover is a diesel engin ...
and
aviation fuel
Aviation fuels are petroleum-based fuels, or petroleum and synthetic fuel blends, used to power aircraft. They have more stringent requirements than fuels used for ground use, such as heating and road transport, and contain additives to enhanc ...
. Diesel fuels are characterised by their
cetane number
Cetane number (cetane rating) is an indicator of the combustion speed of diesel fuel and compression needed for ignition. It plays a similar role for diesel as octane rating does for gasoline. The CN is an important factor in determining the quali ...
, cetane being an older name for hexadecane. However the higher melting points of these alkanes can cause problems at low temperatures and in
polar regions
The polar regions, also called the frigid zones or polar zones, of Earth are the regions of the planet that surround its geographical poles (the North and South Poles), lying within the polar circles. These high latitudes are dominated by float ...
, where the fuel becomes too
thick to flow correctly. Mixtures of the normal alkanes are used as
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 ...
standards for simulated
distillation
Distillation, or classical distillation, is the process of separation process, separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distilla ...
by
gas chromatography
Gas chromatography (GC) is a common type of chromatography used in analytical chemistry for separating and analyzing compounds that can be vaporized without decomposition. Typical uses of GC include testing the purity of a particular substance, ...
.
Alkanes from hexadecane upwards form the most important components of
fuel oil
Fuel oil is any of various fractions obtained from the distillation of petroleum (crude oil). Such oils include distillates (the lighter fractions) and residues (the heavier fractions). Fuel oils include heavy fuel oil, marine fuel oil (MFO), bun ...
and
lubricating oil
A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...
. In latter function they work at the same time as anti-corrosive agents, as their
hydrophobic
In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water.
Hydrophobic molecules tend to be nonpolar and, th ...
nature means that water cannot reach the metal surface. Many solid alkanes find use as
paraffin wax
Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and begins to m ...
, used for
lubrication
Lubrication is the process or technique of using a lubricant to reduce friction and wear and tear in a contact between two surfaces. The study of lubrication is a discipline in the field of tribology.
Lubrication mechanisms such as fluid-lubric ...
,
electrical insulation
An electrical insulator is a material in which electric current does not flow freely. The atoms of the insulator have tightly bound electrons which cannot readily move. Other materials—semiconductors and conductors—conduct electric curren ...
, and
candle
A candle is an ignitable wick embedded in wax, or another flammable solid substance such as tallow, that provides light, and in some cases, a fragrance. A candle can also provide heat or a method of keeping time.
A person who makes candles i ...
s. Paraffin wax should not be confused with
beeswax
Beeswax (''cera alba'') is a natural wax produced by honey bees of the genus ''Apis''. The wax is formed into scales by eight wax-producing glands in the abdominal segments of worker bees, which discard it in or at the hive. The hive workers ...
, which consists primarily of
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
s.
Alkanes with a chain length of approximately 35 or more carbon atoms are found in
bitumen
Asphalt, also known as bitumen (, ), is a sticky, black, highly viscous liquid or semi-solid form of petroleum. It may be found in natural deposits or may be a refined product, and is classed as a pitch. Before the 20th century, the term a ...
(asphalt), used (for example) in road surfacing. However, the higher alkanes have little value and are usually split into lower alkanes by
cracking.
Names
Some alkanes have non-IUPAC trivial names:
* cetane, for
hexadecane
Hexadecane (also called cetane) is an alkane hydrocarbon with the chemical formula C16H34. Hexadecane consists of a chain of 16 carbon atoms, with three hydrogen atoms bonded to the two end carbon atoms, and two hydrogens bonded to each of the 14 ...
* cerane, for hexacosane
Properties
The properties listed here refer to the straight-chain alkanes (or: ''n-alkanes'').
Nonane to hexadecane
This group of n-alkanes is generally liquid under standard conditions.
[Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer Hartmut Höke "Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. ]
Heptadecane to tetracosane
From this group on, the n-alkanes are generally solid at standard conditions.
Pentacosane to triacontane
Hentriacontane to hexatriacontane
Heptatriacontane to dotetracontane
Tritetracontane to octatetracontane
Nonatetracontane to tetrapentacontane
See also
*
Alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
*
Alkyne
\ce
\ce
Acetylene
\ce
\ce
\ce
Propyne
\ce
\ce
\ce
\ce
1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
*
Cycloalkane
In organic chemistry, the cycloalkanes (also called naphthenes, but distinct from naphthalene) are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing ...
*
Hydrocarbon
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, and their odors are usually weak or ex ...
*
Paraffin wax
Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and begins to m ...
, composed mostly of higher linear alkanes
*
Polyethylene
Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging ( plastic bags, plastic films, geomembranes and containers including bo ...
, a linear alkane of
polymer
A polymer (; Greek '' poly-'', "many" + ''-mer'', "part")
is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
ic length
References
External links
International Chemical Safety Card 1245(nonane)
(nonane)
(decane)
{{alkanes
Alkanes