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Cracking

• Crude oil contains many


large molecules. If these are
to be used as fuels or
feedstock for the chemical
industry then they have to
Small molecules
be cracked into smaller Big
molecules. molecules

Medium molecules
• When hydrocarbons burn
they are reacting with
oxygen in the air. In general,
the smaller the molecule
the better it will mix and
then react with the air.
Cracking

• Involves the breaking of C-C bonds in alkanes

• Converts heavy fractions into higher value


products

• THERMAL proceeds via a free radical
mechanism

• CATALYTIC proceeds via a carbocation


(carbonium ion) mechanism
Thermal Cracking

• High Pressure ... 7000 kPa


• High Temperature ... 400°C to 900°C
• Free Radical Mechanism
• Homolytic fission
• Produces mostly alkenes ... e.g. ethene for
making polymers and ethanol
• Produces Hydrogen ... used in the Haber Process
and in margarine manufacture
• Bonds can be broken anywhere in the molecule
by C-C bond fission or C-H bond fission
Catalytic Cracking

• Slight pressure
• High Temperature ... 450°C
• Zeolite catalyst
• Carbocation Mechanism
• Heterolytic fission
• Produces branched and cyclic alkanes, aromatic
hydrocarbons
• used for motor fuels

• ZEOLITES are crystalline aluminosilicates; clay like
substances
Catalytic Cracking
• Large hydrocarbons are broken into smaller molecules using heat
and a catalyst.
• This process is known as catalytic cracking.
• The small molecules produced are then separated by distillation.
Catalytic Cracking
• In the catalytic cracker long chain molecules
are ‘cracked’. An example of such a reaction is:

C8H18 → C6H14 + C2H4


Activity
• Draw out displayed formulae of a pair of products formed by
cracking decane
• Draw out displayed formulae of a pair of products formed by
cracking decane
Poly(e)thene
• One important reaction of alkenes involves
the joining together of alkene molecules.

And
1 2 3 4 5 thousands lots
more..
This is called addition polymerisation and is written as:
Polypropene
• Ethene is only one alkene. Other unsaturated molecules such
as propene, vinyl chloride and styrene can also be
polymerised to produce a range of plastics. E.g. propene
PTFE
• Tetrafluoroethane is another alkene that is
made into an important plastic used to coat
non-stick pans: polytetrafluoroethane or PTFE.
Activity

• Fill in the products that will be obtained from


vinyl chloride
Some uses of plastics
Answers
• Which of these is an alkane?
• C6H14
• C4H8
• C12H24
• C102H204
• Which of these is a true statement about
• alkenes?

• They turn bromine water from colourless to


red
• They contain a double bond
• The smallest alkene has 1 carbon atom
• They have names that end in “ane.”
• Which of these is a true statement about
cracking?

• it is the separation of molecules into


fractions of different sizes.
• it is carried out at low temperatures
• it uses a catalyst.
• It produces polymers
• Which of these is a true statement about
polymerisation?

• it is the joining together of many small


molecules.
• it is the thermal decomposition of plastics
• it is carried out using saturated molecules
• it is a multiplication reaction
• Which of these is an addition polymer?

• styrene
• ethene
• p.v.c.
• propane
• How might you test to see if polystyrene still
• contained some unsaturated monomer
(styrene)?

• Crush it up and burn it.


• Crush it up and add it to bromine water
• Crush it up and dissolve it in petrol
• Crush it up and add hydrochloric acid

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