Condensation polymerization

 Condensation polymers are formed when two different monomers are

linked together with the removal of a small molecule, usually water.
 This is a key difference between condensation polymers and addition
polymers:
o Addition polymerisation forms the polymer molecule only.
o Condensation polymerisation forms the polymer molecule and
one water molecule per linkage.

 The monomers have two identical functional groups present, one
on each end.
 The functional groups at the ends of one monomer react with the functional
group on the end of the other monomer, in so doing creating long chains
of alternating monomers, forming the polymer.
 Polyesters are formed from two different monomers and produce water,
hence they are condensation polymers.

Formation of Polyesters

 Polyesters are polymers that are held together by ester links.

 An ester link is formed when an alcohol and an acid react:

R-OH + R-COOH → R-COO-R + H2O

(R represents a side chain)

The ester ethyl propanoate is made from reacting propanoic acid and ethanol

 An example is polyethylene terephthalate (PET) which is a polyester used

widely in fabric for clothing and sheets due to its resistance to creasing.
 It is made from terephthalic acid and ethane-1,2-diol.

1
  The acid is dicarboxylic (a carboxylic acid with a -COOH group
at either end) and the alcohol is diol (an alcohol with an -OH group
at either end).
 Each -COOH group reacts with a -OH group on the adjacent monomer.
 An ester linkage is formed with the subsequent loss of one water molecule
per link.

Diagram showing the condensation polymerisation reaction in which

polyethylene terephthalate is produced

Formation of Water

 For every ester linkage formed in condensation polymerisation, one

molecule of water is formed from the combination of a proton (H+) and
a hydroxyl ion (OH–).
 Curiously the proton comes from the alcohol monomer rather than the acidic
one.

2
 Effects on the Environment

Polymers & Pollution

Formed by the joining up of many small molecules called monomers. Addition

polymers are unreactive so don’t easily biodegrade.

Problems with the disposal of addition polymers:

Plastics & the Environment

Starting Materials

 The main raw ingredient in the manufacture of polymers comes

from crude oil.
 This is a finite source and will eventually run out, with prices increasing as
levels of production begin to fall.
 Other products come from crude oil such as the raw materials
for bulk chemicals, oil and fuels.
 There will come a time when there will be competing interests over
whether the raw materials from crude oil should be destined to the
production of polymers or other products.

Non-biodegradability

 Most synthetic polymers are non-biodegradable plastics which do not

degrade over time or take a very long time to degrade, and cause significant
pollution problems.
 In particular plastic waste has been spilling over into
the seas and oceans and is causing huge disruptions to marine life.
 In landfills waste polymers take up valuable space as they are non-
biodegradable so microorganisms cannot break them down. This causes the
landfill sites to quickly fill up.

3
Disposal by Combustion

 Polymers release a lot of heat energy when incinerated and

produce carbon dioxide which is a Greenhouse gas that contributes to
climate change.
 If incomplete combustion occurs during the process, carbon monoxide will
be produced. This is a toxic gas that reduces the capacity of the blood to
carry oxygen.

Sorting and Recycling

 Polymers can be recycled but different polymers must be separated from

each other and sorted into 7 different categories before recycling can take
place.
 This is a difficult and time-consuming process which also incurs extra
expense.

Recycling Polymers
Advantages

 Recycling is a more economically viable process than manufacturing from

scratch.
 It decreases the use of crude oil which allows it to be kept for other
purposes.
 It is better for the environment as plastic waste is being collected and
reused, hence recycling reduces the emissions of Greenhouse gases and
other toxic gases produced during the manufacturing process.
 It also reduces the amount of landfill sites needed.

4
  Recycling is itself an entire industry which creates employment and
economic growth.

Disadvantages

 Sorting plastics by type of polymer is a tedious

and labour intensive process which is costly.
 Recycling counts on what is collected in as the raw material, therefore
production of certain types of polymers may not be possible due to a lack
of starting ingredients.
 Melting polymers produces toxic gases that are harmful to plants and
animals.
 Polymers can only be recycled a number of times before they lose their
properties and become useless.
 Recycling runs the risk of mixing different polymers together, which again
will affect their properties. This is particularly risky for polymers designed
for specialist use such as aircraft or automobile parts, where safety is of
utmost importance.

PREVNEXT

Natural Polymers
DNA, Starch & Proteins
DNA

 DNA consists of four different monomers called nucleotides abbreviated to

A, T, C, and G which are bound together by polymerisation.
 The nucleotides form two strands that intertwine, giving the
famous double helix shape of DNA.
 It is a complex molecule that contains genetic information.

5
 Diagram showing the complex double helix structure of DNA

Starch

 Carbohydrates are compounds of carbon, hydrogen and oxygen with the

general formula Cx(H2O)y.
 There are simple carbohydrates and complex carbohydrates.
 Simple carbohydrates are called monosaccharides and are sugars such as
fructose and glucose.
 Complex carbohydrates are called polysaccharides such
as starch and cellulose.
 Complex carbohydrates are condensation polymers formed from simple
sugar monomers and, unlike proteins, are usually made up of the same
monomers.
 A H2O molecule is eliminated when simple sugars polymerise. The linkage
formed is an -O- linkage called a glycosidic linkage.

6
Diagram of the starch Amylose showing glycosidic linkages (-O-) which bind the
monomers together

Proteins

 Proteins are condensation polymers which are formed from amino acid
monomers joined together by peptide bonds.
 Amino acids are small molecules containing amine (-NH2) and carboxylic
acid (-COOH) functional groups.
 A peptide link is formed when a carboxylic acid and an amine react:

R-COOH + R-NH2 → R-C=ONH-R + H2O

(R represents a hydrocarbon side chain)

 Most proteins contain at least 20 different amino acids.

 These are the monomers which polymerise to form the protein.

Diagram showing condensation polymerisation in which a protein is formed

7
 Crude Oil
Crude oil: A mixture of hydrocarbons.

 Thick, sticky, black liquid that is found under porous rock (under the ground
and under the sea).

Crude oil under the sea

If any fraction from crude oil is burned, then carbon dioxide and water is produced
– this shows that crude oil is a complex mixture of hydrocarbons:

Describing Crude Oil

 Crude oil is a complex mixture of lots of different hydrocarbon compounds

of different sizes.
 It is a thick, sticky, black liquid that is found under porous rock (under the
ground and under the sea).

Chains & Rings

8
  The hydrocarbon molecules in crude oil consist of a carbon backbone which
can be in a ring or chain, with hydrogen atoms attached to the carbon
atoms.
 The mixture contains molecules with many different ring sizes and chain
lengths.

Useful Substances

 Crude oil is the main source of hydrocarbons which are used for
producing fuels such as petrol and diesel.
 It is also a main source of raw materials (called feedstock) for the
petrochemical industry.

Finite Resource

 Crude oil formed over millions of years from the effects of

high pressures and temperatures on the remains of plants and animals.
 Since it is being used up much faster than it is being formed crude oil is
a finite resource.

9
 Fractional Distillation: Basics
Fractional distillation: To separate two or more liquids that are miscible with one
another

 Crude oil as a mixture isn’t a very useful substance but the different
hydrocarbons that make up the mixture, called fractions, are useful, with
every fraction having different applications.
 Each fraction consists of groups of hydrocarbons of similar chain lengths.
 The fractions in petroleum are separated from each other in a process
called fractional distillation.
 The molecules in each fraction have similar properties and boiling points,
which depend on the number of carbon atoms in the chain.
 The boiling point and viscosity of each fraction increases as the carbon
chain gets longer.

Industrial process of fractional distillation:

10
 The process of fractional distillation to separate crude oil in a fractionating
column

Explanation:

Fractional distillation is carried out in a fractionating column.

 In the fractionating column, it is hot at the bottom and cool at the top.
 Crude oil will enter the fractionating column and will be heated so vapours
will rise and evaporate.
 Vapours of hydrocarbons with very high boiling points will immediately
turn into liquid and are tapped off at the bottom of the column.
 Vapours of hydrocarbons with low boiling points will rise up the column
and condense at the top to be tapped off.
 The different fractions will condense at different heights according to their
boiling points and will be tapped off as liquids. All the fraction are mixtures
of different kinds of hydrocarbon.

11
To conclude the smaller hydrocarbons are collected at the top of the fractionating
column as gases. The bigger hydrocarbons are collected at the lower sections of the
fractionating column.

Sample question. Describe and explain how the industrial process of

fractional distillation separates crude oil into fractions

The process of refining involves separating the hydrocarbons into fractions or

batches using a technique called fractional distillation. Each fraction separates as
they have different boiling points. The crude oil is heated in a furnace to around
400°C.

12
 1. In the furnace at the bottom of the fractionating column, petroleum is heated
into vapour.
2. The vapour is pumped into huge fractionating column. The column is cool at
the top but hot at the bottom.
3. Hot vapour rises up the column and begins to cool down. The smaller
hydrocarbons are collected at the top of the fractionating column as gases.
The bigger hydrocarbons are collected at the lower sections of the
fractionating column.

Fractional Distillation: Trends

 Number of Carbon & Hydrogen Atoms

o The size and length of each hydrocarbon molecule determines in
which fraction it will be separated into.
o The size of each molecule is directly related to how many carbon and
hydrogen atoms the molecule contains.
o Most fractions contain mainly alkanes, which are compounds of
carbon and hydrogen with only single bonds between them.

Trends of Crude Oil Fractions

Viscosity: Viscosity refers to the ease of flow of a liquid. High viscosity liquids are
thick and flow less easily. If the number of carbon increases, the attraction between
the hydrocarbon molecules also increases which results the liquid become more
viscous with the increasing length of the chain of hydrocarbon. The liquid flow
less easily with the increasing molecular mass.

Colour: As carbon chain length increases colour of liquid gets darker as it gets
thicker and more viscous.

Melting point/boiling point: As the molecules get larger, the intermolecular

attraction becomes greater. So more heat is needed to separate the molecules. With
increasing molecular size there is an increase in boiling point.

13
Volatility: Volatility means the tendency for a substance to vaporize. With the
increasing molecular size, the hydrocarbon liquids become less volatile. As the
attraction between the molecules increases with the increasing molecular size.

Ease of Ignition

Molecular size again influences the ease of ignition.

Smaller hydrocarbon molecules are more flammable and are easier to ignite than
larger molecules.

14
Different fractions obtained from crude oil:

15
16
 Combustion & Incomplete Combustion

Fuel

Fuel: Substance which when burned, releases heat energy

 This heat can be transferred into electricity, which we use in our daily lives

Examples:

Oil, coal and natural gases, which are common fossil fuels used to provide us
with electricity

Products of Combustion

Complete combustion: Occurs when there is an unlimited supply of air so that

elements in the fuel react fully with oxygen.

Complete combustion of hydrocarbons:

During the complete combustion of hydrocarbons, carbon dioxide and water will
be produced:

 Carbon will oxidise to form carbon dioxide

 Hydrogen will oxidise to water

Equation:

Hydrocarbon + Oxygen → Carbon dioxide + Water

17
Incomplete combustion: Occurs when there is a limited supply of air so that
elements in the fuel do not fully react with Oxygen

Incomplete combustion of Hydrocarbons:

During the incomplete combustion of hydrocarbons, water will still be produced

but instead of carbon dioxide, carbon monoxide (soot) will form

Equation:

Hydrocarbon + Oxygen → Carbon Monoxide + Water

Carbon Monoxide

 Carbon monoxide: A poisonous gas that is colourless and odourless

produced during incomplete combustion: It is particularly malevolent as it
is colourless, odourless and tasteless, making it difficult to detect.

Hydrocarbon + Oxygen → Carbon monoxide + Water

The Problem of Incomplete Combustion

 The main products of incomplete combustion are carbon

monoxide and soot although some H2O and CO2 are inevitably produced as
well.
 Incomplete combustion occurs in some appliances such
as boilers and stoves as well as in internal combustion engines, where
space is cramped.
 Incomplete combustion of gasoline in car engines is a major source of CO
and C:

C8H18 + 8.5O2 → 8CO + 9H2O

C8H18 + 4.5O2 → 8C + 9H2O

 The carbon particles released clump together to form soot which gradually
fall back to the ground.

18
  Soot causes respiratory problems and covers buildings and statues, making
them look unclean.

Statues and monuments in densely populated areas become blackened over time
from soot

Effect of Carbon monoxide on blood (Summary)

 When carbon monoxide is produced by incomplete combustion, it is

absorbed in the lungs and binds with the haemoglobin in our red blood cells.

 This reduces the capacity of the blood to carry oxygen.

 Lack of oxygen supply to the brain can lead to fainting, coma or in worst
case scenarios, even death.

19
 Carbon monoxide atoms

Acid Rain: Nitrogen Oxides & Sulfur Dioxide

Formation of Oxides of Nitrogen in Car Engines

Formation of oxides of nitrogen in car engines:

When fuels are burned in car engines, high temperatures are reached which allows
Nitrogen and Oxygen from the air to combine to produce Nitrogen monoxide:

Nitrogen + Oxygen → Nitrogen Monoxide

N2 (g) + O2 (g) → 2NO (g)

When this Nitrogen monoxide is released from the engines of vehicles, it combines
with Oxygen in the air to form Nitrogen dioxide:
20
 Nitrogen Monoxide + Oxygen → Nitrogen Dioxide

2NO (g) + O2 (g) → 2NO2 (g)

Both Nitrogen monoxide and Nitrogen dioxide are produced in car engines as a
result and is referred to as NOx

Combustion of Hydrocarbon Fuels

Hydrocarbon fuels: Impure Hydrocarbon fuels contain Sulfur compounds

Combustion of Hydrocarbon fuels:

During the combustion of Hydrocarbon fuels, impurities such as Sulfur compounds

will be oxidised to produce sulfur dioxide:

Sulfur + Oxygen → Sulfur Dioxide

S (g) + O2 (g) → SO2 (g)

Acid Rain

Acid rain: Rain that contains dissolved acidic gases such as sulfur dioxide and
oxides of nitrogen. The pH value of normal rain is slightly below 7. The pH value
of acid rain is approximately 3.4.

21
Contribution of sulfur dioxide and oxides of nitrogen oxide to acid rain:

Sulfur dioxide will react with oxygen and dissolve in water droplets in clouds,
forming dilute sulfuric acid which will cause acid rain:

Sulfur Dioxide + Oxygen + Water → Sulfuric Acid

2SO2 (g) + O2 (g) + H2O (l) → 2H2SO4 (aq)

Nitrogen oxides will dissolve in water droplets in clouds, forming dilute Nitric
acid and Nitrous acid, causing acid rain:

22
 Cracking
Catalytic Cracking

Long-chain hydrocarbons: large number of hydrocarbon molecules. More

viscous and less flammable so less useful.

Short-chain hydrocarbons: small numbers of hydrocarbon molecules.

Cracking is simply splitting of larger molecules to simpler ones.

Industrial catalytic cracking site

Explanation:

 Cracking allows large hydrocarbon molecules to be broken down into

smaller, more useful hydrocarbon molecules.
 Fractions containing large hydrocarbon molecules are heated at 600 – 700°c
to vaporise them.
 Vapours will then pass over a hot catalyst of silica or alumina
 This process breaks covalent bonds in the molecules, causing thermal
decomposition reactions.
 As a result, cracking produces smaller alkanes and alkenes. The molecules
are broken up in a random way which produce a mixture of alkanes and
alkenes.

23
 Why Cracking is Necessary

Although there is use for each fraction after the fractional distillation of crude oil,
the amount of longer chain hydrocarbons produced is far greater than needed.

However, the amount of shorter chain hydrocarbons produced is far less than
needed (e.g. gasoline fraction) and there is a higher demand for shorter chain
hydrocarbons. This is why cracking is necessary to increase the supply of shorter
chain hydrocarbons.

 Short chain hydrocarbons burn well and flow well.

 Cracking is used to produce petrol for cars.
 Cracking also produces alkenes which are raw material in the plastic
industry.
 Cracking is used to produce hydrogen gas which is a raw material in
manufacture of ammonia in Haber process.

Example: The Cracking of hexane (C6H14) to produce butane (C4H10) and ethene

(C2H4):

C6H14 (g) → C4H10 (g) + C2H4 (g)

Ethene: The ethene can be used to make poly (ethene), a type of plastic

24
25
 Hydrogen & Fossil Fuels

 Hydrogen is used in rocket engines and in fuel cells to power some cars.
 It reacts with oxygen in an exothermic reaction:

2H2 + O2 →2H2O

 Hydrogen has a series of advantages and disadvantages regarding its use as a

fuel:

 Advantages:
o It releases more energy per kilogram than any other fuel (except for
nuclear fuels).
o It does not pollute as it only produces water on combustion, no other
product is formed.
o It is a renewable source and is extracted from water by electrolysis.
o Modern fuel cells are equipped to extract hydrogen from the same
water they produce.

 Disadvantages:
o Expensive to produce and requires energy for the production process.
o Difficult and dangerous to store and move around (usually stored as
liquid hydrogen in highly pressurised containers).

Fossil Fuels

 Non-renewable fossil fuels are obtained from crude oil by fractional

distillation.
 Petrol is used as a fuel in cars, kerosene is used to fuel aircraft and diesel
oil is used as a fuel in some cars, trucks and heavy vehicles such as tanks
and trains.
 There are finite amounts of all three and they all contribute
to pollution and global warming.
 Natural gas consists mainly of methane, CH4
 This is also a non-renewable fuel as there are finite reserves available.

26