Cracking

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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 be
cracked into smaller 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.
Small molecules

Big molecules
Medium
molecules

Fuel gas Petrol

Naphtha Kerosine
Diesel Fuel Oil and bitumen
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 CRACKING
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

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 Thermal Cracking

High Pressure ... 7000 kPa

High Temperature ... 400C to 900C
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

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

ZEOLITES are crystalline aluminosilicates;

clay like substances

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 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.
Distillation
tower
pressure

Smaller molecules
Catalytic
Heat to cracker
Big Molecules
vaporise
Molecules
break up

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 Catalytic Cracking
In the catalytic cracker long chain molecules are
cracked. An example of such a reaction is:

H H H H H H H H
Octane
H C C C C C C C C H
H H H H H H H H
Heat
hexane catalyst
pressure

H H H H H H H H ethene
H C C C C C C H + C C
Ethene
H H
Used as H H H H H H is used
a fuel to make
C8H18 C6H14 + C2H4 plastics

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Activity

Draw out displayed formulae of a pair of products

formed by cracking decane
H H H H H H H H H H
decane
H C C C C C C C C C C H
H H H H H H H H H H
Heat
catalyst
pressure

H H H H H H H H H H
H C C C C C C C C H + C C
H H
H H H H H H H H
ethene
octane

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 Poly(e)thene
One important reaction of alkenes involves the
joining together of alkene molecules.

H H H H H H H H H H H H And
C C H C C C C C C C C C C lots
more..
H H H H H H H H H H H H
1 2 3 4 5 thousands

This is called addition polymerisation and is written as:

H H Pressure H H poly(e)thene
n C C C C
high
H H temperature H H n
ethene catalyst
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 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

H H H CH3
H C Poly(propene)
n
C C H C C
H H H H n
propene

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 PTFE
Tetrafluoroethane is another alkene that is made
into an important plastic used to coat non-stick
pans: polytetrafluoroethane or PTFE.

F F
F F
n C C C C
F F F F n

tetrafluoroethene Poly(tetrafluoroethane)
or PTFE

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Activity

Fill in the products that will be obtained from

vinyl chloride

H Cl
H Cl C C
n C C H H
H H n
pvc
Vinyl chloride

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 Some uses of plastics
Poly(e)thene Polypropene Polystyrene
Shopping bags Milk crates packing
Bottles Rope insulation
Buckets Carpet fibres Ball pens
Washing up
bowls

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 Across Down
3) separate 1) Contain a 1 2
substances double bond
with different 3
boiling points
7) saturated 2) a series of 4 5 6
hydrocarbon molecules
differing by a CH2
8) joining of 4) breaking up a 7
many small large molecules
molecules
9) full up: 5) the different
unable to add substances
more atoms collected from 8
distillation

6) used to test for 9

unsaturated
molecules.

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 Answers
Across Down
3) separate substances with 1) Contain a double bond
different boiling points ALKENE
DISTILLATION

7) saturated hydrocarbon 2) a series of molecules differing by a

ALKANE CH2
HOMOLOGOUS
8) joining of many small molecules 4) breaking up a large molecules
POLYMERISE CRACKING

9) full up: unable to add more atoms 5) the different substances collected
SATURATED from distillation
FRACTIONS

6) used to test for unsaturated

molecules.
BROMINE

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Which of these is an alkane?
A. C6H14
B. C4H8
C. C12H24
D. C102H204

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Which of these is a true statement about
alkenes?

A. They turn bromine water from colourless to

red
B. They contain a double bond
C. The smallest alkene has 1 carbon atom
D. They have names that end in ane.

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Which of these is a true statement about
cracking?

A. it is the separation of molecules into

fractions of different sizes.
B. it is carried out at low temperatures
C. it uses a catalyst.
D. It produces polymers

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Which of these is a true statement about
polymerisation?

A.it is the joining together of many small

molecules.
B. it is the thermal decomposition of plastics
C.it is carried out using saturated molecules
D.it is a multiplication reaction

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Which of these is an addition polymer?

A. styrene
B. ethene
C. p.v.c.
D. propane

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How might you test to see if polystyrene still
contained some unsaturated monomer (styrene)?

A. Crush it up and burn it.

B. Crush it up and add it to bromine water
C. Crush it up and dissolve it in petrol
D. Crush it up and add hydrochloric acid

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