1. Oil Refining + Octane Numbers

2. Fractional Distillation of Crude Oil
How to become a millionaire Find a crude oil well and know how to fraction it!!
Crude oil found in large quantities in Iran , USA, Nigeria, Russia, North Sea

3. Fossils
Crude oil was formed from the bodies of tiny sea creatures that died millions of years ago
Crude oil is pumped from underneath the ground as is a thick black substance with an unpleasant smell
It does not burn easily and must be undergo fractional distillation to separate out all the useful components

4. Fractional Distillation
The crude oil is heated in a furnace and starts to evaporate, the longer carbon chains are heavier and do not rise as easily as shorter (lighter) carbon chains
This means that the longer chains carbon fractions are collected first while the shorter chains get collected higher up the column
Remember larger hydrocarbons have higher boiling points while smaller hydrocarbons have lower boiling points

5. Fractionating Column
NB. You do not need to memorise the temperatures but you do need to learn the fractions and the uses of the products of each fraction

6. Fractionating Column at Whitegate Oil Refinery

7. Refinery Gas
Top of the column, methane, ethane, propane + butane are gases at 25⁰C
Some used as fuel mostly bottled for sale
Since these are odourless sulfur compounds called Metacarptants are added for safety
Bottled gas is mainly a mix of propane + butane which are liquefied under high pressure

8. Petrol (Light Gasoline)
Used as motor fuel
A mixture of at least 100 compounds mostly hydrocarbons of 5-10 carbons

9. Naphta Very useful to petrochemical industry
It is a source for a huge number of useful chemicals eg, medicines, plastics, synthetic fibres, detergents, solvents etc.
7-10 carbons in length

10. Kerosene/Parrafin Used as aviation fuel and in certain lamps
10-14 carbon length
NB as the number of carbon atoms increases so does the boiling point as more heat is required to break the larger number of bonds

11. Diesel Oil/GasOil More difficult to vaporise than petrol
Therefore diesel engine has a different design
Trucks, buses, trains and some cars use diesel
14-19 carbon length

12. Lubricating Oil 19-35 carbons in length
Cannot be vaporised easily so cannot be used as a fuel
Used as a lubricant to reduce wear and tear

13. Fuel Oil 30-40 carbons in length
Used in ships, power stations, heating plants, oil heating in homes

14. Bitumen More than 35 carbon atoms in length Very high boiling point
Used in Tar to resurface roads

15. When an oil well is discovered..
Refinery Chemists analyse crude oil to determine the quality of the oil and assess the quantity of each product in the oil

16. Octane Number
Petrol obtained from the fractionating column is not a very efficient fuel
In the internal combustion engine in a car the power to turn the wheels is produced by the explosive reaction between air and petrol

18. Knocking
Smooth running of an engine depends on this explosion occurring at exactly the right time
If the explosion occurs too early the pistons vibrate and a metallic noise is heard from the engine
Early explosion can occur if the petrol + air explode when they are compressed instead of waiting for the spark

19. This early explosion is referred to as knocking or auto-ignition
Straight chain alkanes such as nonane, octane and heptane ignite very easily and explode too soon
Branched cahin alkanes such as 2,2,4-trimethylpentane (iso-octane) do not tend to auto-ignite

20. Petrol mixtures with large amounts of branched chain alkanes are more efficient than those which contain straight chain molecules
To indicate the efficiency of a particular type of petrol a number called the Octane Number is assigned to it

21. Octane Number
The octane number of a fuel is a measure of the tendency of the fuel to resist knocking
Since 2,2,4-trimethylpentane is a very efficient fuel it is assigned an octane number of 100
Heptane is not an efficient fuel and is assigned an octane number of 0
The octane number of a fuel is calculated by comparing it’s efficiency in an engine to 2,2,4-trimethylpentane and heptane

22. What should my petrol be??
Chemical analysis can also indicate the octane number of a fuel
Good quality petrol should have an octane number of 97

23. The shorter the alkane chain the higher the octane number
Which do you think would have a higher octane number hexane or pentane?

24. The more branched the chain the higher the octane number
Which do you think would be the best fuel
heptane, methylhexane,
2,3,-dimethylpentane

25. Cyclic compounds have a higher octane number than straight chain compounds
Which is a better fuel? Hexane or cyclo-hexane??

26. Making Petrol
1920’s it was found that adding small amounts of lead compounds to petrol helped reduce the amount of knocking
Lead pollution from car exhausts had potential damage to health and was phased out since 2000
Lead also damaged catalytic converter in car exhausts
Now have unleaded petrol

27. Increasing octane number of fuel
This is now achieved in one of the following 4 ways;
Isomerisation
Catalytic Cracking
Reforming
Adding Oxygenates

28. Isomerisation
This involves changing straight chain alkanes into their isomers
Alkanes are heated in the presence of a suitable catalyst and the chains break
The chains are allowed to reconnect but they are more likely to reform in branched-chains than in straight-chains
This is commonly done on a large industrial scale with pentane and hexane (NB fig 21.29)

29. Catalytic Cracking
Catalytic cracking is the breaking down of long chain hydrocarbon molecules into short chain molecules for which there is greater demand
In oil refineries the heavier fractions ( such as fuel oil, diesel oil and kerosene) are heated in the presence of a catalyst
The short chain alkanes produced tend to be highly branched and hence have a high octane number

30. Reforming (Dehydrocyclisation)
Reforming involves the use of catalysts to form ring compounds
Straight chain alkanes are converted to cycloalkanes and these are converted to aromatic compounds
Aromatic compounds have high octane numbers and petrol contains 3-4% benzene, because benzene is a carcinogen this is a cause for concern
Hydrogen may also be produced in reforming reaction, this is a useful substance and may be piped away for various purposes

31. Adding Oxygenates
An oxygenate is any fuel that contains oxygen in its molecules
3 oxygen containing compounds, methanol, ethanol and MTBE are commonly added to petrol to increase its octane number
Another advantage to adding oxygenates to fuel is that they cause very little pollution when they burn and are cleaner fuels