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We depend largely on crude, the gases associated with it and natural gas (mainly methane) as the source of liquid fuels (petrol, diesel) and the feedstock for the chemical industry.

Oil, and the gases associated with it, consists of a mixture of hundreds of different hydrocarbons, containing any number of carbon atoms from one to over a hundred. Most of these are straight chain, saturated hydrocarbons which, except for burning, have relatively little direct use in the chemical industry or as fuel for cars.

Thus the various fractions obtained from the distillation of crude oil and the associated gases have to be treated further in oil refineries to make them useful. The most valuable fractions for the chemical industry, and for producing petrol, are liquefied petroleum gas (LPG), naphtha, kerosine and gas oil. These are treated in several ways including cracking, isomerisation and reforming.

Figure 1 A view of the steam crackers at Ludwigshafen in Germany. The whole site is the largest continuous chemical site in the world. The steam crackers alone occupy 64 000 m², which is about the size of 13 football fields. Naphtha is the feedstock and the main products are ethene and propene, used to make polymers.
By kind permission of BASF.

The refinery

Petrol (gasoline) contains a mixture of hydrocarbons, with 5 to 10 carbon atoms. The mixture of C₅-C₁₀ hydrocarbons obtained directly from the distillation of crude oil contains a high proprtion of straight-chain alkanes. However, if this mixture is used as petrol, it does serious damage to a car's engine. Petrol containing a high proportion of straight chain alkanes tends to ignite in the cylinder of the car engine as the piston increases the pressure and before the cylinder reaches the optimum position. Ideally, the mixture of petrol vapour and air is ignited with a spark at a predetermined position of the piston in the cylinder. This problem of premature ignition is referred to as pre-ignition and also as engine knock. The term knock is used as pre-ignition can be heard. Severe knock can cause serious engine damage.

However, branched-chain alkanes, cycloalkanes and aromatic hydrocarbons are much more resistant to knock and straight-chain alkanes are converted into them in a series of processes in the refinery which are described in this unit.

The resistance of petrol to knock is measured in terms of an octane rating (octane number). The higher the number, the less likely is a fuel to pre-ignite.

The octane rating is on a scale where heptane is given an arbitary score of 0 and 2,2,4-trimethylpentane (iso-octane) one of 100. Thus a petrol with the same knocking characteristics as a mixture of 95% 2,2,4-trimethylpentane and 5% heptane has an octane rating of 95. A rating of 95 does not mean that the petrol contains just iso-octane and heptane in these proportions, but that it has the same tendency to knock as this mixture.

The octane rating of petrols usually available for cars range from 95 upwards and contain a mixture of straight-chain, branched, cyclic and aromatic hydrocarbons, produced by the processes described below.

These processes are also used to convert staight-chain hydrocarbons to hydrocarbons which are much more useful to make chemicals which are then used to make a huge range of compounds from polymers to pharmaceuticals.

Cracking

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Cracking, as the name suggests, is a process in which large hydrocarbon molecules are broken down into smaller and more useful ones, for example:

The cracking products, such as ethene, propene, buta-1,3-diene and C₄ alkenes, are used to make many important chemicals. Others such as branched and cyclic alkanes are added to the gasoline fraction obtained from the distillation of crude oil to enhance the octane rating.

Cracking is conducted at high temperatures, by two processes

Steam cracking which produces high yields of alkenes
Catalytic cracking in which a catalyst is employed and which produces high yields of branched and cyclic alkanes

Steam cracking

Steam cracking plants (Figures 1 and 2) use a variety of feedstocks, for example

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ethane, propane and butane from natural gas
naphtha, a mixture of C₅ to C₁₀ hydrocarbons, from the distillation of crude oil
gas oil and residues, also from the primary distillation of oil

Very recently a cracking plant has come on stream in Singapore in which crude oil itself is the feedstock, the first time that this has been done. The advantages of this are that it cuts out the expensive distillation processes needed, for example to produce naphtha, and that it produces a wider range of products. However the disadvantage is that it may not produce the product that is needed in high enough yield. For example, if you want a high yield of ethene it is better to make it from ethane or naphtha. This disadvantage can be overcome by having more than one plant on the same site.

Latex for mac os x. Figure 2 Naphtha is used as the feedstock to the row of furnaces on this steam cracking plant located at Wilton, UK.
By kind permission of SABIC Europe.

Modern steam cracking plants are very large, usually producing 1-2 million tonnes of products annually and several have been built recently that can have an output of nearly 3 million tonnes a year and cost about 1 billion dollars to build,

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The reactant gases (ethane, propane or butane) or the liquids (naphtha or gas-oil) are preheated and vaporised, are mixed with steam and heated to 1050-1150 K in a tubular reactor (Figure 3). They are converted to low relative molecular mass alkenes (plus by-products).