Gasoline is most often produced by the fractional distillation of petroleum, also known as crude oil (it is also produced from coal and oil shale). The crude oil is separated according to different boiling points into fractions. This fractional distillation process yields approximately 250 mL of straight-run gasoline for each liter of crude oil. The yield of gasoline may be doubled by converting higher or lower boiling point fractions into hydrocarbons in the gasoline range. Two of the main processes used to perform this conversion are cracking and isomerization.
In cracking, high molecular weight fractions and catalysts are heated to the point where the carbon-carbon bonds break. Products of the reaction include alkenes and alkanes of lower molecular weight than were present in the original fraction. The alkanes from the cracking reaction are added to the straight-run gasoline to increase the gasoline yield from the crude oil. An example of a cracking reaction is:
alkane C13H28 (l) → alkane C8H18 (l) + alkene C2H4 (g) + alkene C3H6 (g)
In the isomerization process, straight chain alkanes are converted into branched chain isomers, which burn more efficiently. For example, pentane and a catalyst may react to yield 2-methylbutane and 2,2-dimethylpropane. Also, some isomerization occurs during the cracking process, which increases the gasoline quality.
In internal combustion engines, the compressed gasoline-air mixtures have a tendency to ignite prematurely rather than burning smoothly. This creates engine knock, a characteristic rattling or pinging sound in one or more cylinders. The octane number of gasoline is a measure of its resistance to knock. The octane number is determined by comparing the characteristics of a gasoline to isooctane (2,2,4-trimethylpentane) and heptane. Isooctane is assigned an octane number of 100. It is a highly branched compound that burns smoothly, with little knock. On the other hand, heptane is given an octane rating of zero. It is an unbranched compound and knocks badly.