1.

Food
Classic Chemical
Demonstrations
275

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98. Cracking a hydrocarbon/

dehydrating ethanol
Topic
Petrochemicals/crude oil/industrial chemistry/hydrocarbons, alcohols.

Timing
About ten min.

Level
Pre-16.

Description
Liquid paraffin (a mixture of alkanes of chain length C20 and greater) is vaporised and
passed over a hot pumice stone catalyst. A gaseous product is obtained which is
flammable and which will decolorise bromine water and acidified permanganate
ions. The same apparatus and method can be used to dehydrate ethanol.

Apparatus

One boiling tube with a one-holed rubber bung fitted with a delivery tube.

Six test-tubes about 120 mm x 16 mm with corks or bungs to fit.

Bunsen burner.

Test-tube rack.

Glass pneumatic trough, plastic fish tank or washing up bowl.

Dropping pipette.

Bunsen valve (optional). This consists of about 3 cm of rubber tube fitted onto
the end of the delivery tube and closed with a short length of glass rod. The
tube has a slit cut along its length with a scalpel. This valve may help to
prevent suckback of water up the delivery tube but it is not always effective
(Fig.1).

Safety screen.

Rubber tubing

End of
delivery tube

Slit cut
with scalpel

Glass rod plug

Fig. 1 A Bunsen valve

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Chemicals
The quantities given are for one demonstration.

About 2 cm3 of medicinal liquid paraffin (a mixture of alkanes of chain length

C20 and greater) or ethanol.

A little mineral wool.

About half a boiling tube full of small lumps of pumice stone or broken pieces
of porous (ie unglazed) pot in lumps about the size of a pea.

A few cm3 of bromine water make sure that this is pale brown in colour.

A few cm3 of a solution which is approximately 0.01 mol dm3 in potassium

permanganate (potassium manganate(VII)) and approximately 0.1 mol dm3 in
sulphuric acid. This is achieved by dissolving the potassium permanganate in
0.1 mol dm3 sulphuric acid.

Method
For cracking the hydrocarbon
Before the demonstration
Half fill the pneumatic trough with water. Fill the test-tubes with water and leave
them in the trough.

The demonstration
Place a small tuft of mineral wool in the bottom of the boiling tube so that it fills the
bottom cm or so. Using a dropping pipette, squirt about 2 cm3 of liquid paraffin into
the mineral wool so that it soaks in. It should be possible to invert the tube without
the liquid paraffin dripping out.

Liquid paraffin (or ethanol)

soaked into mineral wool

Delivery tube
Heat

Pumice stone
or porous pot catalyst

Pneumatic trough

Fig. 2 Apparatus for cracking paraffin

Product gas

Bunsen valve fits

here if desired

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Classic Chemical
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Clamp the boiling tube so that the mouth is tilted very slightly upwards and pack
the middle of the tube with pieces of pumice stone or broken porous pot. Clamp the
tube so that the clamp is as close to the mouth as possible to avoid possible
overheating of the clamp. Fit the delivery tube so that it dips into the water in the
trough and fit a Bunsen valve if desired.
Hold a test-tube over the end of the delivery tube to collect gas. An assistant will
be useful to manipulate the gas collection tubes, change them and cork them as
necessary.
Heat the pumice stone (or porous pot) strongly with the hottest part of a roaring
Bunsen flame for several seconds. Then flick the flame onto the mineral wool for a
few seconds to vaporise some of the paraffin then return the flame to the pumice
stone. Continue with the Bunsen burner heating the mineral wool for about one
second out of every ten and the pumice stone for the other nine. Collect six test-tubes
of gas. Discard the first two which will contain some air and cork and retain the other
four.
Throughout, it is essential that the burner is not removed from the boiling tube or
water will suck back up the delivery tube and possibly crack the boiling tube. If
suckback begins, continue to heat strongly or remove the delivery tube from the
water.
Some oil will be seen floating on the surface of the water in the trough. This will
contain unchanged liquid paraffin that has distilled over and hydrocarbons with
chains greater than C5.
When six tubes of gas have been collected, remove the delivery tube from the
water and stop heating.
Test the tubes of gas as follows.
1.

Pass them round the class so that the students can cautiously smell the gas.

2.

Uncork the tube and hold a lighted taper in its mouth. The gas will burn.

3.

Add about 1 cm depth of bromine water to the test-tube. Re-cork and shake.
The bromine water will be decolorised.

4.

Add about 1 cm depth of acidified potassium permanganate solution to the

test-tube. Re-cork and shake. The solution will be decolorised, possibly leaving
a brown coloration of manganese dioxide.

The latter two tests indicate that the product has a carbon-carbon double bond.

For dehydrating ethanol

Follow exactly the same method as above but use ethanol instead of the liquid
paraffin. In this case no oil will be seen on the surface of the water in the trough.

Teaching tips
The students will need to be familiar with the permanganate and bromine water tests
for a carbon-carbon double bond.
Ball and stick molecular models will be useful for modelling both the cracking
and the tests.
For the cracking of the paraffin point out that the product, being a gas, must have
shorter chain lengths than the starting material.
For the dehydration of ethanol point out that the only likely product is ethene.

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Theory
For the cracking of the paraffin
Simple cracking of a hydrocarbon produces two shorter chains, one of which is an
alkene, for example, cracking decane could give heptane and propene.

For the dehydration of ethanol

The ethanol is dehydrated:
CH3CH2OH(g) CH2= CH2(g) + H2O(g)
In both cases although bromine in non-aqueous solutions adds across the double
bond of, say ethene, to give 1,2-dibromoethane (a suspected carcinogen), in aqueous
solution, the main product is 2-bromoethanol.
Acidified permanganate ions cleave double bonds to form two carbonyl
compounds while alkaline permanganate produces a diol.

Safety
Wear eye protection.
Use a safety screen because there is the possibility of the boiling tube shattering if
suckback occurs.
It is the responsibility of teachers doing this demonstration to carry out an
appropriate risk assessment.