Activity:

Cracking hydrocarbons

Requirements:
Eye protection. Consider using a safety screen (for demonstration). Access to a fume cupboard required.

beaker, 250 cm3

boiling tube, Pyrex or similar
bung fitted with delivery tube (plus safety valve, optional)
mineral wool
small plastic trough for gas collection over water
test tubes (4) + rack
clamp stand, boss & clamp
Bunsen burner and heat resistant mat
plastic dropping pipette (3)
wooden splints & matches
watch glass, Pyrex or similar or a clean tin lid

liquid (medicinal) paraffin [~ 5 cm3]

porcelain chips/porous pot/aluminium
oxide granules/pumice granules
bromine water, ~0.005-0.01 M [~2 cm3]
[Harmful if 0.006 M]
acidified potassium manganate(VII), 0.001
M [~2cm3]

Outline instructions:
Wear eye protection. Work in a well-ventilated laboratory. The
smell can be unpleasant place used reaction tubes in a working
fume cupboard.
1. See the diagram for set up.
2. Label 4 test-tubes 1-4.
Lay them in the trough to fill with water.
3. One-third fill a beaker with tap water.
4. Strongly heat the catalyst (in the middle of the boiling tube)
for a few minutes.
5. Whilst keeping the catalyst hot, flick the flame from time to time to the end of the tube for a few seconds to
vaporise the liquid paraffin.
6. Collect 4 test tubes of gas (after discarding the first one collected).
Stand each test tube open end down in the beaker of water.
This is quicker and keeps the gas in the tube without the need for bungs at this stage.
7. When gas collection is complete, first remove the delivery tube from the water, and then stop heating.
This will avoid suck back.
8. Carry out the following tests on the gas collected (make careful observations).
- Tube 1: Add 2-3 drops of bromine water, stopper the tube and shake
- Tube 2: Add 2-3 drops of acidified potassium manganate(VII) solution, stopper the tube and shake.
- Tubes 3 & 4: Hold the tube at a slight downward angle (open end down) and apply a lighted splint to the
open end. Repeat noting carefully the colour and smokiness of the flame.
9. Compare with the starting material (liquid paraffin). Add a few drops of the paraffin to a tuft of mineral wool
on a watch glass or tin lid. Try to light the paraffin. How easily does it ignite?
Notes / observations / questions / health & safety / management issues
Try to explain all your observations and/or write equations for the cracking and bromine reactions using
displayed (structural) formulae
Who would you use this experiment/demonstration with?

Activity:

Cracking hydrocarbons

Supporting chemistry:
Cracking larger hydrocarbons produces smaller alkanes that can be used to produce petrol. Small-chain
alkenes, are also produced in the cracking process. These are used to make many other useful organic
chemicals (petrochemicals), especially plastics. This experiment illustrates the basic principles involved in the
industrial cracking process.
The gas mixture which collects has a characteristic smell and burns with a yellow flame. The gas mixture
decolourises both bromine water and acidified potassium manganate (VII) solution - indicating the presence of
unsaturated hydrocarbons (i.e. contain a carbon-carbon double bond, C=C). We assume that the gas collected
is ethene, but there are almost certainly other small alkenes present too.
Comparison with the starting material shows that paraffin is a liquid which is difficult to burn. The paraffin
does not decolourise bromine water or acidified potassium manganate (VII) indicating that paraffin is
saturated (does not contain C=C bonds).
Possible Learning Outcomes:

Assess the risks involved in the cracking experiment.

Use a model to explain what happens to hydrocarbons during cracking.
Know how to test for saturated and unsaturated hydrocarbons.
Use a model to explain what happens when bromine water is added to an unsaturated hydrocarbon.
Understand why cracking is an important process in the petrochemical industry.
Know why catalysts have an important role to play in industrial reactions.

Teaching and Learning tips:

To set the context for cracking, a video clip of the industrial process could be shown. The Royal Society of
Chemistrys Alchemy website provides one possibility:
http://www.rsc.org/learn-chemistry/resource/res00000015/alchemy
If this experiment is being carried out as a class practical, it is advisable to demonstrate the equipment first,
stressing the health and safety issues. The boiling tube should be an unblemished hard glass (borosilicate) tube.
Cheaper boiling tubes may soften during the strong heating of the catalyst, leaving a hole in the tube.
Damaged tubes may crack during strong heating.
It is very important to stress that students should not stop heating the boiling tube at the end of the
experiment until the delivery tube is out of the water and contains no water. If suck-back starts to occur and
cannot be reversed lift the apparatus out of the water. A simple safety valve can be made by using a small
length of soft rubber tubing (ask the trainer how to do this) but this can also be problematic.
Students will find it helpful to build molecular models to help them understand the processes and be able to
suggest equations for both the cracking reaction and the reaction of ethene with bromine.
A video aimed at showing teachers how to carry out this demonstration can be found at:
http://www.rsc.org/learn-chemistry/resource/res00000824/practical-chemistry-demonstration-videoscracking-a-hydrocarbon (Note: this video is designed to support teachers not for showing to students.)
Resource Reference: http://www.rsc.org/learn-chemistry/resource/res00000681/chemistry-for-nonspecialists-course-book-cracking-hydrocarbons
Royal Society of Chemistry 2013

Document Ref: ECARBON2