Carbon Chains in Petroleum Products

The different chain lengths have progressively higher boiling points, so they can be separated out by distillation. This is what happens in an oil refinery -- crude oil is heated and the different chains are pulled out by their vaporization temperatures. The chains in the C5, C6 and C7 range are all very light, easily vaporized, clear liquids called naphtha. They are used as solvents -- dry cleaning fluids can be made from these liquids, as well as paint solvents and other quick-drying products. The chains from C7H16 through C11H24 are blended together and used for gasoline. All of them vaporize at temperatures below the boiling point of water. That's why if you spill gasoline on the ground it evaporates very quickly. Next is kerosene, in the C12 to C15 range, followed by diesel fuel and heavier fuel oils (like heating oil for houses). Next come the lubricating oils. These oils no longer vaporize in any way at normal temperatures. For example, engine oil can run all day at 250 degrees F (121 degrees C) without vaporizing at all. Oils go from very light (like 3-in-1 oil) through various thicknesses of motor oil through very thick gear oils and then semi-solid greases. Vasoline falls in there as well. Chains above the C20 range form solids, starting with paraffin wax, then tar and finally asphaltic bitumen, which is used to make asphalt roads. All of these different substances come from crude oil. The only difference is the length of the carbon chains. Many automobiles and boats, as well as almost all eighteen-wheelers, are powered by diesel fuel, a petroleum-based fuel which is similar to gasoline. While a gasoline and oxygen mixture is ignited in the engine cylinder by a spark from the spark plug, diesel fuel is ignited by compression. The piston in a diesel engine travels up the cylinder, compressing the air. At the top of the stroke, atomized diesel fuel is injected into the cylinder, and ignites in the heat created from the friction of this compression. Diesel fuel is about 18% heavier than gasoline and consists mainly of hydrocarbons that range from C10 to C24, meaning 10 to 24 carbon atoms with various configurations of hydrogen atoms attached to the carbon atoms. Gasoline, on the other hand, is usually in the C7 to C11 range, while kerosene, used for jet engine fuel, is weighted just between diesel and gasoline in the C12 to C15 range. The higher the number of carbon atoms, the heavier the product. Before shipment from the petroleum distillery, the composition of diesel fuel may be varied by the distilling facility, depending on the latitude of the distillation facility and weather; specifically, the temperature at the time of distillation. The heavier diesel fuel will tend to

thicken, or solidify, in cold weather, unlike gasoline which is basically unaffected by colder temperatures.

What is Gasoline?
Gasoline is a complex mixture of over 500 hydrocarbons that may have between 5 to 12 carbons. Smaller amounts of alkane cyclic and aromatic compounds are present. Virtually no alkenes or alkynes are present in gasoline. Compounds in Gasoline.

Gasoline is most often produced by the fractional distillation of crude oil. The crude oil is separated into fractions according to different boiling points of hydrocarbons of varying chain lengths. This fractional distillation process yields approximately 25% of straight-run gasoline from each barrel of crude oil. See Distillation Oil Refining. The yield of gasoline may be doubled by converting higher or lower boiling point fractions into hydrocarbons in the gasoline range. See Conversion Refining.
Typical Composition of Gasoline General Name Aliphatic - straight chain Aliphatic - branched Aliphatic - cyclic Aromatic Examples heptanes 30-50 isooctane cyclopentane ethyl benzene 20-30 20-30 Percentage

What is the octane number?

Fuel octane requirements for gasoline engines vary with the compression ratio of the engine. Engine compression ratio is the relative volume of a cylinder from the bottom most position of the piston's stroke to the top most position of the piston's stroke. The higher an engine's compression ratio, the greater the amount of heat generated in the cylinder during the compression stroke. If fuel octane is too low for a given compression ratio, the fuel prematurely and spontaneously ignites too early and the fuel charge EXPLODES rather than BURNS resulting in incomplete combustion. The net effect is a loss in power, possible engine damage, and an audible "knock" or "ping", referred to as detonation. 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 heptanes. 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, a straight chain, unbranched molecule is given an octane rating of zero because of its bad knocking properties. Straight-run gasoline (directly from the refinery distillation column) has an octane number of about 70. In other words, straight-run gasoline has the same knocking properties as a mixture of 70% isooctane and 30% heptane. Many of these compounds are straight chain alkanes. Cracking, isomerization, and other refining processes can be used to increase the octane rating of gasoline to about 90. Anti-knock agents may be added to further increase the octane rating.

Octane rating versus type of compound: y y y Octane ratings decrease with increasing carbon chain length. Octane ratings increase with carbon chain branching. Octane ratings increase in aromatics with same number of carbons.

What octane gasoline should you purchase? For most automobiles, use the lowest grade of 87 octanes, unless they specifically say to use a higher octane gasoline. Using higher octane grades does not provide any extra power or extra mileage.