9.2 Production of materials: 3.

Renewable ethanol

Syllabus reference (October 2002 version)

3. Other resources, such Students learn to:
Students:
as ethanol, are readily
describe the
process
available
dehydration of
information
from renewableresources
ethanol to
from
such as plants
ethylene and
secondary
identify the
sources such
need for a
as molecular
catalyst in this
model kits,
process and
digital
the catalyst
technologies
used
or computer
simulations to
describe the
model:
o the
addition of
water to
addition
ethylene
of water
resulting in
to
the production
ethylene
of ethanol and
o the
identify the
dehydra
need for a
tion of
catalyst in this
ethanol
process and
the catalyst
process
used
information
from
describe and
secondary
account for
sources to
the many uses
summarise the
of ethanol as a
processes
solvent for
involved in the
polar and nonindustrial
polar
production of
substances
ethanol from
sugar cane
outline the use
of ethanol as a
process
fuel and
information
explain why it
from
can be called
secondary
a renewable
sources to
resource
summarise the
use of ethanol
describe
as an
conditions
alternative car
under which
fuel,
fermentation
evaluating the
of sugars is
success of

promoted

summarise the
chemistry of
the
fermentation
process

define the
molar heat of
combustion of
a compound
and calculate
the value for
ethanol from
first-hand
data

assess the
potential of
ethanol as an
alternative
fuel and
discuss the
advantages
and
disadvantages
of its use
identify the
IUPAC
nomenclature
for straightchained
alkanols from
C1 to C8

current usage

solve
problems, plan
and perform a
first-hand
investigation
to carry out
the
fermentation
of glucose and
monitor mass
changes

present
information
from
secondary
sources by
writing a
balanced
equation for
the
fermentation
of glucose to
ethanol

identify data
sources,
choose
resources and
perform a
first-hand
investigation
to determine
and compare
heats of
combustion of
at least three
liquid alkanols
per gram and
per mole

Extract from Chemistry Stage 6 Syllabus (Amended October 2002).

Board of Studies, NSW.
[Edit: 7Jul09]
Prior learning: Preliminary modules 8.4.3, 8.5.4
Background: Much of our energy comes from chemicals formed millions of years ago, e.g. coal and
oil, which are termed fossil fuels. Research into alternative energy sources continues, with interest in
solar energy, tidal energy and so forth. Chemists too are involved in this search and look to the
chemicals in the biomass for renewable sources of energy. As fossil fuel supplies are depleted,
ethanol, obtained from renewable plant resources, will be of increasing importance.
process information from secondary sources, such as molecular model kits, digital
technologies or computer simulations to model

o
o

the addition of water to ethylene

the dehydration of ethanol

Process information from a variety of sources to reliably describe changing ethylene to

ethanol and ethanol to ethylene. Use a molecular model kit (or if you don't have one, use
toothpicks for bonds and pieces of marshmallow or bits of jelly snake for atoms) to model the
two reactions. You can do this by constructing ethanol from ethylene and water
molecules, then reconstructing ethylene and water molecules from the ethanol.

describe the dehydration of ethanol to ethylene and identify the need for a catalyst in this
process and the catalyst used
describe the addition of water to ethylene resulting in the production of ethanol
and identifythe need for a catalyst in this process and the catalyst used
The following information addresses the above two syllabus points together.

ethylene and ethanol are easily interchanged by addition of water (hydration) and removal of
water (dehydration). Catalysts such as sulfuric acid, phosphoric acid or heated ceramic solids
can be used to catalyse these dehydration and hydration reactions.

Additional background information

Countries rich in petroleum or natural gas, e.g. around the Persian Gulf, or petroleum refining
and cracking facilities, e.g. Singapore, can make ethanol by hydration of ethylene.
Countries rich in land and climate suitable for growing crops that could be used to produce
ethanol, e.g. Brazil, can make ethylene by dehydration of ethanol.
Dehydration of ethanol
and Hydration of ethylene to ethanol
Key Centre for Polymer Colloids, University of Sydney, Australia

describe and account for the many uses of ethanol as a solvent for polar and non-polar
substances

Ethanol is used as a solvent in dissolving medicines and food flavourings and colourings that
do not dissolve easily in water. Once the non-polar material is dissolved in the ethanol, water
can be added to prepare a solution that is mostly water.

The ethanol molecule has a water loving (hydrophilic) -OH group that helps it dissolve polar
molecules and ionic substances. This occurs through hydrogen bonding, dipole-dipole
attraction or ion-dipole attraction. The short, water fearing (hydrophobic) hydrocarbon chain
CH3CH2- can attract non-polar molecules. The non-polar component of an ethanol molecule
bonds to non-polar molecules through dispersion forces. Thus ethanol can dissolve both polar
and non-polar substances.

Industrially and in consumer products, ethanol is the second most important solvent after
water. Ethanol is the least toxic of all the alcohols as it is poisonous in moderate amounts
rather than small amounts. Consumer products listed as containing alcohol practically always
contain ethanol as the alcohol.

Ethanol as a solvent

Key Centre for Polymer Colloids, University of Sydney, Australia

process information from secondary sources to summarise the processes involved in the
industrial production of ethanol from sugar cane

Identify reliable information by considering it from various sources. Continue processing the
information by creating summary notes of the industrial production processes used to
produce ethanol from sugar cane.
The general process:
1. Sugar cane fermentation
an ethanol and water mixture
2. Distillation of the ethanol and water mixture separates ethanol from the water.
The future . . .
Distillation of the aqueous ethanol product (96% ethanol and 4% water) to obtain almost
pure ethanol can take half as much energy as that released when the ethanol is burnt.
Distillation is being replaced by low energy methods such as passing the aqueous ethanol
through special zeolite filters that act as molecular sieves. The more polar water molecules
are strongly attracted to polar parts of the zeolite while the less polar ethanol passes through
thus separating pure ethanol.

process information from secondary sources to summarise the use of ethanol as an

alternative car fuel, evaluating the success of current usage

Identify reliable information by considering it from various sources. Continue processing the
information by creating summary notes of how well ethanol functions as an alternative car
fuel.

An evaluation is a judgement based on criteria. In your evaluation, list the criteria you used.
Consider the following issues.
o
The energy and financial cost of separating ethanol from the aqueous ethanol
produced in fermentation.
o
What percentage of ethanol can be added to petrol without engine modification? In
Australia there is concern about the sale of 20%ethanol-80%petrol mixtures as
petrol. The federal government is planning to restrict petrol to contain no more than
10% ethanol.
o
Requirements of engines using ethanol only.
o
The effect on exhaust pollutants of using ethanol fuel.
o
The economic cost at different prices for oil, costs and subsidies, and different rates
of taxation levied by governments, on different fuels.

solve problems, plan and perform a first-hand investigation to carry out the fermentation of
glucose and monitor mass changes
This activity could be an open-ended investigation.

The analysis of mass changes provides a means to investigate phenomena. However, there
areproblems to solve when a process involves unintended mass losses due to the
production of gases. The fermentation of glucose in water releases gaseous carbon dioxide as
a product. Fermentation occurs best at about 30oC. Above this elevated temperature,
significant evaporation of water, and hence more mass loss occurs.

Plan your investigation carefully. Mass losses due to release of carbon dioxide and
evaporation of water can be allowed for in planning and performing this first-hand
investigation. Consider controls you could put in place to account for these mass losses.

Here is one approach that could be used to solve some of the problems. Carry out the
fermentation in a gas tight container with a pipe or bendy straw leading into a beaker of
limewater (saturated Ca(OH)2 solution).
Carbon dioxide released will react:

The carbon dioxide will be trapped in the limewater. Water passing out of the fermentation
container will also be collected in the limewater beaker.
When performing the investigation, compare the loss in weight of the fermentation
container with gain in weight of the limewater beaker. If they differ in magnitude you have
another practical problem to solve to improve your investigation. A good scientist would
realise that all carbon dioxide passing out of the fermentation container should be trapped in
the limewater. If this does not happen for your equipment then attempt to improve your
design.

present information from secondary sources by writing a balanced equation for the
fermentation of glucose to ethanol

Present information in the most appropriate way. Insert coefficients in front of the formulas
for the two products so that the equation is balanced. A balanced equation is one in which
there is the same number of each kind of atom on both sides of the equation.

describe conditions under which fermentation of sugars is promoted

The conditions that promote the fermentation of sugar are:

o
a suitable micro-organism such as yeast
o
water
o
a suitable temperature for the fermenting yeast
o
low oxygen concentrations favouring the fermenting yeast
o
a small amount of yeast nutrients such as phosphate salt.
Once the ethanol concentration reaches 14-15% by volume, the yeast cannot survive, and
the fermentation process stops.

Conditions for fermentation

Key Centre for Polymer Colloids, University of Sydney, Australia

summarise the chemistry of the fermentation process

Cane sugar waste, such as molasses, is rich in sucrose (C12H22O11), however, it is uneconomic
to separate.

If water and yeast is added, the sucrose reacts with water producing glucose and fructose,
both of which have the molecular formula C6H12O6.

Fermentation can then occur:

outline the use of ethanol as a fuel and explain why it can be called a renewable resource

Ethanol combusts in air, releasing carbon dioxide, water and heat. Because the ethanol
molecule contains an O atom, the combustion is practically always complete. There is hardly
any formation of the polluting CO or C forms, which form from the incomplete combustion of
many other hydrocarbons.

A familiar example .

When the oxygen supply in a Bunsen burner is adequate for complete

combustion, you get a hotter, colourless, almost invisible flame, like the
flame of burning ethanol.
In contrast, when you reduce the oxygen supply to a Bunsen flame, you
get a yellow smoky flame, due to carbon.
The presence of an oxygen atom in ethanol minimises the formation of
carbon in an ethanol flame.

Ethanol can be called a renewable resource because ethanol can be made from plant material
and the products of its combustion, carbon dioxide and water, are the reactants needed by
plants for photosynthesis.

The use of ethanol as a fuel

Key Centre for Polymer Colloids, University of Sydney, Australia

identify the IUPAC nomenclature for straight-chained alkanols from C1 to C8

IUPAC nomenclature for alkanols refers to the International Union of Pure and Applied Chemists'
(IUPAC) way of naming alkanols.
You are only required to deal with straight chained alkanols with up to, and including, 8 carbon atoms.
For straight chained alkanols (those without side branches) the number of carbon atoms in the chain
is given by the prefix as follows:
Number of carbon atoms

Prefix

meth

eth

prop

but

pent

hex

hept

oct

The presence of the -OH, substituting for an H, on one of the carbons is indicated by the suffix 'ol'.
The middle syllable 'an' indicates the fact that the carbon atoms are saturated (There are no double or
triple bonds) therefore without the -OH functional group it would be an alkane.
A number is used to indicate which carbon has the -OH attached to it. Of course you can usually get
two numbers for such a carbon, depending on which end of the chain you start from. Simply use the
smallest number you can. (No number is needed for methanol or ethanol as the -OH can only be on
an end carbon, when there is only one or two carbons in the molecule.)
Numbers and letters in IUPAC nomenclature are linked with a hyphen.
Exercises
1.

CH3OH has one carbon. It is called methanol.

2.

CH3CH2OH has ...... carbons. It is called

3.

CH3CH3CH2OH has ....................... It is called .....................

4.

CH3CH2CHOHCH3

.......anol.

has 4 carbons so it is a butanol, but as the -OH is on the second carbon

from the right (or the 3rd from the left) it is correctly called 2-butanol.
5.

CH3CH2CH2CH2CHOHCH

has ........ carbons with the -OH on the ........ one from the nearest

end (not the .......... five from the furthest end). It is called ............................
6.

CH3CH2CH2CH2CH 2CH 2CHOHCH3 has ........ carbons with the -OH on the ........ one from the
nearest end (not the .......... seven from the furthest end). It is called ............................

7.

CH3CH2CHOHCH2CH2CH

has ........ carbons with the -OH on the ........ two from the

nearest end (not the .......... three from the furthest end). It is called ............................
[Answers: 2. ethanol; 3. propanol (more correctly it is 1-propanol); 5. 2-hexanol; 6. 2-octanol; 7. 3hexanol]

identify data sources, choose resources and perform a first-hand investigation to determine
and compare heats of combustion of at least three liquid alkanols per gram and per mole

Consider the type of data that must be collected. You will need to use the mathematical
relationship,
H = mC
T. Consider using a table or graph to compare results. Use
ethanol as one of the alkanols so you can use your data in the next part.

This is a quantitative investigation so you will need to either measure liquid masses or,
alternatively, calculate masses from measurements of volumes and a knowledge of densities
of the liquids.

When choosing equipment and resources, carry out a risk assessment of your intended
experimental procedures to identify and address potential hazards. Be aware that alkanols
burn with a less luminous flame than hydrocarbons. This flame is much more difficult to see.
You must ensure there is no alkanol flame when you add alkanol to a burner.

Perform the investigation carefully to ensure your safety.

Using calorimetry
and Calculating Molar Heat of Combustion
Key Centre for Polymer Colloids, University of Sydney, Australia

define the molar heat of combustion of a compound and calculate the value for ethanol
from first-hand data

The molar heat of combustion is the heat change when one mole of the substance is
combusted to form products in their standard states (that is, solid, liquid or gas) at 10 5 Pa
(100 kPa) and 25oC (298K).

To calculate the value for ethanol from first hand data:

1. Write a balanced equation for the complete combustion of ethanol including states of
matter required for the molar heat of combustion definition.
2. Use your measurement of heat released per gram for ethanol as your first-hand data
to calculate the molar heat of combustion for ethanol.
3. Compare your calculated value with a published value from a text or data book.
Explain any difference in measured value and published value by considering how
you carried out the measurement.
An example . . .
A student measures the temperature rise of a measured mass of water heated by a burner
containing ethanol. Weighing of the burner before and after use, gives a difference equal to
the mass of ethanol that burned.
The student does a calculation (
H = mC
T) to find the amount of heat released. From
these two measurements, the heat released per gram and then per mole is calculated.

Molar Heat of Combustion

Key Centre for Polymer Colloids, University of Sydney, Australia

Calculations and problem solving questions

Learning and Inovation Centre

on the molar heat of combustion, NSW Curriculum

assess the potential of ethanol as an alternative fuel and discuss the advantages and
disadvantages of its use
An assessment is a judgement of value, quality, outcomes, results or size. Make sure you include
advantages and disadvantages in your assessment of the potential of ethanol as an alternative fuel.

Ethanol can be used in internal combustion engines if it can be economically produced from
renewable resources or subsidised as a fuel to reduce air pollution.

The advantages of using ethanol include its complete combustion with minimal pollution. It
can also be made in a number of ways. See the diagram below.

The disadvantages of using ethanol include the need to modify fuel lines and even the engine
if the ethanol is more than 10-15% when mixed with petrol. Another disadvantage is the low
price of still readily available petroleum. Large tracts of land would need to be allocated to
growing plants to use in the production of ethanol rather than food.