9.2 Production of materials: 1.

Fossil fuel products

Syllabus reference (October 2002 version)

1. Fossil
Students learn to:
Students:
fuels
construct word and
gather and present
provide
balanced formulae
information from firstboth energy
equations of chemical
hand or secondary
and raw
reactions as they are
sources to write
materials
encountered
equations to
such as
identify the industrial
represent all chemical
ethylene,
reactions encountered
source of ethylene
for the
in the HSC course
from the cracking of
production
identify data, plan
some of the fractions
of other
from the refining of
and perform a firstsubstances
petroleum
hand investigation to
compare the
identify that ethylene,
reactivities of
because of the high
appropriate alkenes
reactivity of its
with the
double bond, is
corresponding
readily transformed
alkanes in bromine
into many useful
water
products
analyse information
identify that ethylene
from secondary
serves as a monomer
sources such as
from which polymers
computer simulations,
are made
molecular model kits
identify polyethylene
or multimedia
as an addition
resources to model
polymer and explain
the polymerisation
the meaning of this
process
term
outline the steps in
the production of
polyethylene as an
example of a
commercially and
industrially important
polymer
identify the following
as commercially
significant
monomers:
o vinyl chloride
o styrene
o by both their
systematic and
common
names
describe the uses of
the polymers made
from the above

monomers in terms of
their properties
Extract from Chemistry Stage 6 Syllabus (Amended October 2002).
Board of Studies, NSW.
[Edit: 7Jul09]

Prior learning: Preliminary modules 8.2.5, 8.5.1, 8.5.2, 8.5.3, 8.5.5

Background: Fossil fuels are formed from the remains of organisms that lived on Earth millions of
years ago. Fossil fuels are rich in hydrocarbons that can be burnt to release energy or used to make
raw materials such as ethylene.
Ethylene is the same substance as ethene. Ethene is the IUPAC name for C2H4 while ethylene is the
name that is more commonly used in industry.
Ethylene (C2H4) can be used to produce useful substances such as polyethylene and ethanol.
Polyethylene is the cheapest plastic. The weight of polyethylene produced each year is greater than
the total weight of all other plastics. Most plastic food bags, juice and milk containers are made of, or
lined with, polyethylene.
construct word and balanced formulae equations of chemical reactions as they are
encountered

An important part of the Preliminary course, that you must continue with throughout the HSC
course, is learning how to:
o
construct word equations, e.g: methane + oxygen -----> carbon dioxide +
water
and
o
balance formulae equations, e.g: CH4 + 2O2 -----> CO2 + 2H2O
You must be able to do this for the reactions you encounter in every module that
you study, core and option.
There are three important steps involved:
1. Show all reactants and all products in the word equation.
2. Write the correct formula for each reactant and each product.
3. Balance the formula equation by placing coefficients (numbers) in front of formulas so that
you have the same total number of each kind of atom on both the reactant side and the
product side. Remember that in chemical reactions atoms are just rearranged, not created
or destroyed.

gather and present information from first-hand or secondary sources to write equations to
represent all chemical reactions encountered in the HSC course

It is recommended that you write equations to represent the chemical reactions as

you gatherinformation about them throughout this section of the module. The information
needed to write the equations might be gathered from first-hand investigations. You
should check these against equations published in secondary sources. For other reactions
studied, write equations as a summary of the chemistry involved.

When presenting equations in carbon chemistry, the emphasis is on showing the structures
of reactants and products, not on making sure that they are balanced. The emphasis for this
section of the syllabus is in showing structure rather than in balancing equations.

The following are the equations that represent the processes presented in this section of the
syllabus:

identify the industrial source of ethylene from the cracking of some of the fractions from
the refining of petroleum

Petroleum is a mixture of hydrocarbons. When petroleum undergoes fractional distillation,

some fractions, particularly petrol, are in demand and of high economic value. Other
fractions, consisting of larger molecules than in petrol and of low value, can be passed over a
heated catalyst that cracks the larger molecules into smaller molecules. A major by-product
of this catalytic cracking is ethylene, also known as ethene.

Another way ethylene is produced . . .

A process called steam thermal cracking is the main source of ethylene
throughout the world. In this process ethane (C 2H6) gas from natural gas,
or larger hydrocarbons in low value petroleum fractions, are mixed with
steam and passed through hot metal coils. The steam removes carbon
deposits from the metal coils. The heat from the coils breaks bonds to
change the ethane, or the larger hydrocarbons, to ethylene.
Structure of ethylene

Key Centre for Polymer Colloids, University of Sydney, Australia

identify data, plan and perform a first-hand investigation to compare the reactivities of
appropriate alkenes with the corresponding alkanes in bromine water

This investigation requires comparison to indicate the reactivities of two substances. This is
most easily achieved by direct observation of colour changes when yellow bromine water is
added to the two substances. The type of data is qualitative. The loss of bromine colour
from the bromine water will identify that reaction has occurred.

This qualitative data will be valid if your plan includes the control of variables. Consider what
must be kept the same in the investigation. For example, make sure that the same amount
of bromine water is added and is shaken in the same way. Use corresponding alkenes and
alkanes that have similar structures preferably differing only by the presence and absence of
a carbon to carbon double bond. Cyclohexene and cyclohexane are suitable to use.
When performing the investigation, ensure that correct safety procedures are used and that
quantities of chemicals are kept to the minimum level to observe an effect.

identify that ethylene, because of the high reactivity of its double bond, is readily
transformed into many useful products

Ethylene can be transformed into many useful products because of the high reactivity of its
double bond.

An explanation
Alkenes are more chemically reactive than their corresponding alkanes.
The yellow colour of bromine water, which is due to the presence of
bromine, is lost when the bromine water comes in contact with an alkene,
but not when in contact with an alkane. This demonstrates the high
reactivity of a
C=C in an alkene compared with the C-C in an alkane.

Some of the useful products made from ethylene are:

Product

Formula

Use

polyethylene

(CH2)n

plastic

ethyleneoxide

(CH2)2O

steriliser

ethanol

C2H5OH

disinfectant

ethanoicacid

CH3COOH

foodpreservative

Reactivity of ethylene
and Reactions of ethylene
Key Centre for Polymer Colloids, University of Sydney, Australia

analyse information from secondary sources such as computer simulations, molecular

model kits or multimedia resources to model the polymerisation process

You can simulate and then analyse the polymerisation process by using a molecular model
kit to construct a model of a long chain polymer from a number of monomers, such as
ethylene.

Begin with at least five separate models of the monomer. Initiate the production of the
polymer by changing the C=C double bonds of two monomer models to C-C single bonds.
Join the two reactive molecules with one of the single bonds (electron pairs) released when a
double bond changed to a single bond. Continue this process to join the remaining
monomers.
You will end up with a long chain like the following.

Remember that this simulation is a micro-view of a process that is repeated over and over in
the macro-production of a polymer. The many long chains produced are held together by
intermolecular forces or tangling of chains.

identify polyethylene as an addition polymer and explain the meaning of this term

Polyethylene is called an addition polymer.

An addition polymer forms when small molecules (the monomer), such as ethylene, add
together to form long molecules (the polymer), such as polyethylene, and no other product.

Addition polymerisation

Key Centre for Polymer Colloids, University of Sydney, Australia

identify that ethylene serves as a monomer from which polymers are made

Ethylene is polymerised to polyethylene

High pressures within the reaction vessel produce soft, low density polyethylene (LDPE)
consisting of tangled polymer chains (with molecular masses < 100 000); used in flexible
plastic bags such as those used to store food.
Low pressures within the reaction vessel produce harder, high density polyethylene (HDPE)
consisting of aligned polymer chains (with molecular masses > 100 000); used in crinkly
plastic bags as used for heavy duty garbage bags.

Polyethylene

Key Centre for Polymer Colloids, University of Sydney, Australia

outline the steps in the production of polyethylene as an example of a commercially and

industrially important polymer

Two different forms of polyethylene can be manufactured, depending on the reaction

conditions.
To produce low density polyethylene (LDPE), a peroxide containing an O-O bond that breaks
easily forming free radicals is used to initiate the joining of ethylene monomers. The process
must occur under high gas pressure to produce LDPE. These production conditions result in
molecules with the short branches that characterise LDPE.
To produce high density polyethylene (HDPE), low gas pressures and a catalysts made of
transition metals and organometallic compounds enables more ordered orientation of
ethylene to form the long unbranched and aligned molecules in HDPE.

Free Radical Polymerisation

and Polyethylene production
,
Key Centre for Polymer Colloids, University of Sydney, Australia

identify the following as commercially significant monomers:

o
o

vinyl chloride
styrene

by both their systematic and common names

describe the uses of the polymers made from the above monomers in terms of their
properties
The following information addresses the above two syllabus points at the same time.

The table below provides the systematic and common names for some commercially
significant monomers. The table describes the properties that account for the uses of some
polymers produced from the selected monomers.

MONOMERS
Commonname

ethylene

vinylchloride

styrene

POLYMERS
Systematic
name
ethene

chloroethene

ethenylbenzen
e

Name

Properties

Usedfor

LDpolyethylene

low
density,
soft

flexible
foodbags

HD
polyethylene

high
density,
hard

crinkly
garbage
bags

polyvinylchlorid
e

maderigid
andflame
resistant
with
additives,
water
resistant

rigid
pipesand
gutters,

transparent
,dueto
few
crystals,

compact
disc
cases,

polystyrene

whengas
added
forms
foam

flexible
raincoats
and
shower
curtains

heat
insulation
,floats

Expanded polystyrene is made by producing gas bubbles inside polystyrene. The low density
of expanded polystyrene is used in flotation devices. The trapped gas spaces make it an
excellent insulator.