2,2-Dimethylbutane, trivially known as neohexane, 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 formula C
6H
14 or (H
3C-)
3-C-CH
2-CH
3. It is therefore 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 ...
, indeed the most compact and branched of the
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 ...
isomers — the only one with a
quaternary carbon
A quaternary carbon is a carbon atom bound to four other carbon atoms. For this reason, quaternary carbon atoms are found only in hydrocarbons having at least five carbon atoms. Quaternary carbon atoms can occur in branched alkanes, but not in li ...
and a
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 ...
(C
4) backbone.
Synthesis
2,2-Dimethylbutane can be synthesised by the hydroisomerisation of
2,3-dimethylbutane using an acid catalyst.
It can also be synthesised by isomerization of
''n''-pentane in the presence of a catalyst containing combinations of one or more of palladium, platinum, rhodium and rhenium on a matrix of zeolite, alumina, silicon dioxide or other materials. Such reactions create a mixture of final products including isopentane, ''n''-hexane, 3-methylpentane, 2-methylpentane, 2,3-dimethylbutane and 2,2-dimethylbutane. Since the composition of the final mixture is temperature dependant the desired final component can be obtained choice of catalyst and by combinations of temperature control and distillations.
Uses
Neohexane is used as an additive in fuels and in the manufacture of agricultural chemicals.
It is also used in a number of commercial, automobile and home maintenance products, such as adhesives, electronic contact cleaners and upholstery polish sprays.
In laboratory settings, it is commonly used as a probe molecule in techniques which study the active sites of metal catalysts. Such catalysts are used in hydrogen-deuterium exchange, hydrogenolysis, and isomerization reactions. It is well suited to this purpose as 2,2-dimethylbutane contains both an isobutyl and an ethyl group.
See also
*
Methylbutane (isopentane)
*
2-Methylpentane (isohexane)
References
{{DEFAULTSORT:Dimethylbutane, 2,2-
Alkanes