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2Production of Materials
1. ethylene.
Ethene (ethylene)
Addition of Bromine:
CH2BrCH2Br
1,2-dibromoethane
Addition of Chlorine:
CH2ClCH2Cl
1,2-dichloroethane
CH2=CH2 + HBr
(+AlCl3 catalyst)
----->
CH3CH2Br
bromoethane
CH3CH2Cl
chlorooethane
Addition of Hydrogen:
CH2=CH2 + H2
------>
CH3CH3
ethane
Addition of Water:
CH2=CH2 + H2O
ethanol
Combustion
2CO2 + 2H2O
-----> CH3CH2OH
Uses of Ethene
Production of Polythene (polyethylene)
nCH2=CH2 ----> (CH2=CH2)n
Production of ethanol
CH2=CH2 + H2O----> CH3-CH2OH
(H2SO4 catalyst)
Addition Polymerization
LDPE
Polyethylene is produced at a high
pressure (2000 a) and a high temperature
(200 oC). A peroxide ("free-radical"
initiator) initiator starts the
polymerization.
This manufacturing process leads to a
polyethylene which is highly branched (a
typical molecule has many side branches,
instead of single long strand).
A branched structure results in a polymer
with a relatively low density (about 0.91
gcm-3), known as low density polyethylene
or LDPE.
LDPE melts at about 120 oC and is soft,
stretchy, transparent, and not very strong.
It is used in products such as flexible
squeeze bottles or wash bottles,
disposable gloves and many others.
HDPE
chloroethene
(vinyl chloride)
ethenylbenzene
(styrene)
PVC
Polystyrene
Revision Questions - 1
1) Identify the industrial source of ethylene.
2) Describe a first-hand investigation you performed to compare
the reactivities of appropriate alkenes with the corresponding
alkanes in bromine water
3) Describe a suitable model for the polymerisation process
4) Identify the physical or chemical property of ethylene that
allows it to be readily transformed into many useful products
5) Describe ways into which ethylene serves as a monomer from
which polymers are made
6) Explain the meaning of addition polymerization using the
synthesis of polyethylene as an example
7) Outline the steps in the production of polyethylene
8) Distinguish between polyethylene, polyvinyl chloride and
polystyrene in terms of their: respective monomers; molecular
structure; properties and uses
2. Biomass
Fossil fuels
Fossil fuels (coal, oil and natural gas) are a non-renewable
source of energy and chemicals.
Fossil fuels are found in underground deposits. They were
formed from the remains of plants and animals that lived
more than 300 millions of years ago.
Fossil fuels are very precious to us, because they are nonrenewable, resources. We use them for fuel and to make
many organic chemicals such as: paints, detergents,
polymers, cosmetics and some medicines.
Because biological materials are renewable, they are being
intensely investigated as raw materials for the manufacture
of many modern plastics, drugs and fuels, which are
currently sourced from fossil fuels.
This search has been fuelled by our over-reliance on
increasingly scarce and increasingly expensive fossil fuels
and because of escalating atmospheric levels of
greenhouse gases
Biomass
Biomass is a general term for living material
(plants, animals, fungi, bacteria). The Earth's
biomass represents an enormous store of energy.
Biomass can be regrown, it is a renewable resource
The original source of the energy in biomass is the
Sun.
Plants absorb solar energy and through the
process of photosynthesis convert it to chemical
energy, mostly in the form of carbohydrates and
oils.
Plants make a polysaccharide (carbohydrate) called
Cellulose. They manufacture it through the
condensation polymerization of a monomer called
glucose: C6H12O6
Condensation polymerization
Condensation polymerization is a
reaction between two monomers,
each with at least two reactive
group.
The two monomers react in a
chain reaction to form a polymer.
Water or another small molecule
is removed at each step.
Example: a polyester is formed
when an alkanol with two -OH
groups (a diol) is reacted with an
alkanoic acid with two -COOH
groups.
There are many examples of
condensation polymers:
natural: cellulose; starch;
glycogen, chitin, proteins and
nucleic acids
artificial: nylon; polyesters and
polyamines
Cellulose
Cellulose is a condensation polymer of D-glucose (C6H12O6) with
the formula (C6H10O5)n
Cellulose consists of long chains (up tor tens of thousands) of Dglucose units, joined by 14 glycosidic bonds.
Cellulose is the main structural component of the cell wall of
plants, and is the most common organic compound on Earth about 33% of all plant matter is cellulose.
Cellulose
Most other polysaccharides have
(14) and (16) linkages and
so have coiled and branched
molecules. Cellulose's (14)
linkages result in long straight
chains
This allows the cellulose
molecules to line up next to one
another. Hydrogen bonds hold
these chains close together
forming microfibrils with high
tensile strength
The long carbon chains in
cellulose make it suitable as a
raw material for many of the
compounds currently produced
from fossil fuels.
Uses of cellulose
Cellulose has been used as a heating fuel (wood burning) for a
million years. In the form of paper and cotton it has been used for
thousands of years.
Cellulose has also been used to manufacture special cellulose
derivatives: methyl-cellulose (food thickener) cellulose nitrate (guncotton), cellulose acetate (photographic film) and rayon (textile)
Cellophane is a form of regenerated cellulose used extensively in
the packaging industry.
Cellulose can be digested and converted to ethanol, which can be
used as a fuel for motor-vehicles
Cellulose is fully bio-degradable.
Biopolymers
Use available evidence to gather and present data from secondary sources
and analyse progress in the recent development and use of a named
biopolymer ...
When researching this topic if you 'Google' the term biopolymer the
search results maybe misleading as any natural polymer can be
termed a biopolymer. However in the context of the syllabus you are
expected to research those polymers produced artificially using an
enzyme or a bacterium. A good place to start is to 'Google' the letters
PHB (polyhydroxybutyrate) and then go on from there.
When presenting the results of your research keep in mind the
following main points:
Do not copy and paste
Use only reliable, up-to-date resources
Reference all your work
Include a bibliography
Revision Questions 2
1) Explain what is meant by a condensation polymer using cellulose
as an example
2) Describe condensation polymerization.
3) Describe the structure of cellulose
4) Identify the major component of biomass and explain its potential
as a raw material to replace petrochemicals
5) Discuss the need for alternative sources of the compounds
presently obtained from the petrochemical industry
6) Analyse progress in the recent development and use of a named
biopolymer. This analysis should name the specific enzyme(s) used
or organism used to synthesise the material and an evaluation of
the use or potential use of the polymer produced related to its
properties
3. ethanol
Alkanols
A class (known as a homologous series) of organic compounds called
alkanols consists of a hydrocarbon chain with an -OH group replacing any
one or more of the hydrogen atoms.
The name of the alkanol in the series is derived from the alkyl prefix with
the same number of carbon atoms and by substituting the e at the end
with an ol
Methanol and ethanol do not have any isomers (compounds with the same
formula, but different structure) all the higher alkanols have isomers since
the -OH group can be on any of the carbon atoms. The number of isomers
increases with increasing number of carbon atoms.
As well as straight chained alkanols, many alkanols with branched chains
are also possible, and then there are alkanols with more than one OH
group e.g. (2 x OH) = diols; (3 x OH) = triols
Ethanol
Ethanol (ethyl alcohol, absolute alcohol) is a volatile, flammable, colorless
liquid with a boiling point of 78.3 oC. Ethanol cannot be separated
completely from water by distillation (no matter how efficient the
fractionating column) - 95% alcohol cannot be further concentrated by
distillation, a drying agent must be used.
Ethanol has the molecular formula: C2H5OH which is often abbreviated to
just EtOH (-C2H5 = Et).
Ethanol is a very versatile solvent, miscible with water and other polar
solvents like acetone, acetic acid and glycerol. It is also miscible with many
non-polar solvents like benzene, carbon tetrachloride, hexane and
chloroform.
Uses of ethanol
Ethanol has many uses. This is because of its:
ability to mix with both polar and non-polar compounds
ease and cheapness of manufacture from completely renewable
sources (plants)
relative low toxicity to humans (ethanol is a psychoactive drug,
found in alcoholic beverages and medications)
Here are just a few of ethanol's many uses:
Personal care products: e.g. in hairspray, mouthwash, after
shave lotion, cologne and perfume
Pharmaceuticals: e.g. in cough treatments, decongestants, iodine
solution and many others
Cleaning products: e.g. disinfectant spray, window cleaners and
methylated spirits.
Industrial: e.g. paints, lacquer, and explosives;
Foods: e.g. extracts, flavorings, glazes and alcoholic beverages.
Transport: e.g. Fuel and/or fuel additive.
Fermentation
Humans have been fermenting sugars for
thousands of years to obtain alcoholic
beverages like wine, beer and mead.
These beverages may have been created as
far back as 7,000 BCE in parts of the Middle
East.
Fermentation is the conversion of a sugar
such as glucose, fructose or sucrose into
ethanol using yeasts (fungi).
Yeasts carry out the fermentation on sugars in
the absence of oxygen, hence it is called
anaerobic fermentation.
Fermentation of glucose
The reaction froths due to the evolution of CO2 gas.
This evolution can be monitored by measuring the mass lost during the
reaction. It can be confirmed by bubbling it through lime water ( a
solution of calcium hydroxide). The lime water turns 'milky' (a white
precipitate of calcium carbonate) when it reacts with carbon dioxide.
The reaction works best at about 30 to 35 degrees as at this
temperature the yeast is most active. Since the fermentation is
anaerobic, it works best in the absence of oxygen.
The fermentation stops when the ethanol concentration reaches about
15% . The ethanol is toxic to the yeast ( the yeast is killed by its own
pollution, let's hope we are smarter).
The ethanol formed, can be separated up to 95% pure by fractional
distillation.
Cellulosic Ethanol
Cellulose biomass: anything that is mostly cellulose
(agricultural plant wastes, corn husks, cereal
straws, sugarcane waste, plant wastes like sawdust
and paper pulp and energy crops grown specifically
for fuel production, such as grass)
Cellulose biomass is in virtually unlimited supply
and does not require vast areas of land to be
cultivated.
Cellulosic ethanol is produced from cellulose
biomass. This must be treated with action dilute
acid or with the enzyme cellulase to first convert it
to glucose, then the glucose can be fermented in the
usual manner (with yeast)
Ethanol produced from cellulose biomass could be
price competitive with gasoline and would use-up a
lot of waste material.
Ethanol as a
fuel
Ethanol as a fuel
Advantages:
It is a renewable fuel made from plants
It is not a fossil-fuel: manufacturing it
and burning it does not release harmful
gases.
Ethanol is biodegradable without
harmful effects on the environment
It significantly reduces harmful exhaust
emissions from cars.
Ethanol-gasoline blends, dramatically
reduce emissions of hydrocarbons, a
major contributor to the depletion of
the ozone layer.
High-level ethanol blends reduce
nitrogen oxide emissions by up to 20%
Sulphur dioxide and particulate matter
(PM) emissions are significantly
decreased with ethanol.
Major oils spills will be very rare.
Disadvantages:
Ethanol as an alternative fuel is, at
present, costly to produce
Ethanol has a smaller energy output
per gram than petrol. It takes about 1.5
times more ethanol than petrol to travel
the same distance
At present ethanol produced from
sugar-high crops requires vast
amounts of land to grow the crops.
Ethanol production, like all processes,
generates waste products that must be
disposed. The waste product from
ethanol production, called swill, can be
used as a soil conditioner on land, but
is extremely toxic to aquatic life.
Another problem is that ethanol
burning may increase the emission of
new pollutants like acetylaldehyde.
Revision Questions - 3
1)
2)
3)
4)
5)
6)
7)
8)
9)
Revision Questions - 4
1) Name and draw the straight chain molecular structures of two of
the isomers of this alkanol: C6H14O
2) Using a chemical equation demonstrate the addition of water to
ethylene.
3) Summarise the processes involved in the industrial production of
ethanol from sugar cane
4) Describe the use of ethanol as an alternative car fuel.
5) Evaluate the current and predict the future success of ethanol as a
fuel.
6) Describe a first-hand investigation you performed to carry out the
fermentation of glucose. Include a chemical equation and identify
reasons for a change in mass during the process.
7) Describe a first-hand investigation your performed to compare the
heats of combustion of at least three liquid alkanols.
8) Evaluate the differences between expressing the heat of
combustion of a fuel per gram or per mole
4. Redox
Activity series
of metals
The metals that are below
hydrogen in the activity
series will not displace it
from solution at all, even in
boiling hot acid.
Hence, the reaction of a
metal with acid to produce
hydrogen gas and a salt is an
oxidation-reduction.
Potassium and sodium are
so very reactive that they will
displace hydrogen from
water in a violent, often
exploding, reaction.
Oxidation
State
Oxidation state is a number
assigned to an element in a
compound.
This number enables us to
describe oxidation-reduction
reactions, and balancing
redox chemical reactions.
The higher the oxidation
state of a given atom, the
greater is its degree of
oxidation;
The lower the oxidation state,
the greater is its degree of
reduction
Some metals can have a
number of oxidation states in
their compounds. Their
oxidation state is expressed
as a roman numeral: e.g. Iron
II Chloride - FeCl2
Oxidation Numbers
Oxidation number is worked out
according to the rules below:
Examples:
Species
Element
O.N.
O2
H2O
-2
Na
Na
NaOH
Na
+1
H2SO4
+6
SO2
+4
S8
Galvanic Cells
The lead-acid
battery
Calculating potentials
There are always two half equations to consider one of them must be a reduction and the
other must be an oxidation. All the data you will need can be obtained from a standard
potential series sheet.
Example: Calculate the nominal potential of a galvanic cell having a magnesium electrode
and a silver electrode.
Step 1 write the cell in standard notation
Mg(s) | Mg+2(aq) || Ag+1(aq) | Ag(s)
(anode)------------------------(cathode)
Remember the more reactive metal (higher in a reduction potential list) is the anode and is oxidised
Step 2 write the two half equations include their potentials, reverse the oxidation and
change the sign on its potential:
oxidation: Mg(s)
Mg+2(aq) + 2e- ......... +2.37 V
reduction: Ag+1(aq) + e-
Ag(s) ......
+0.22 V
You must balance the number of electrons to be the same for both half equations, but the potentials
remain the same:
2Ag(s) ......
+0.22 V
Step 3 - Complete the process by adding the equations and the potentials
redox: Mg(s) + 2Ag+1(aq )
Mg+2(aq ) + 2Ag(s)......... +2.59V
Note: if the potential for the cell results in a negative number then you have either not chosen the
oxidant/reductant correctly or have forgotten to change signs.
Revision Questions - 5
1) Explain the displacement of a metal from solution in terms of transfer of
electrons
2) Describe the activity series of metals
3) Identify the relationship between displacement of metal ions in solution by
other metals to the activity series of metals
4) Find the oxidation state of the metal in each of the following species:
Cu(s); CuO; Cu2O; Al2O3 and HAuCl4
5) Account for the electrons lost or gained when MnO4- is reduced to Mn2+
6) Describe and explain the galvanic cell using copper and iron electrodes in
terms of the oxidation/reduction reactions that occur.
7) Draw and label a galvanic cell you have studied and label: the direction of
electron flow; the anode, the cathode, electrode; the electrolytes in each
cell; the sat bridge and calculate the nominal voltage produced.
8) Describe a first-hand investigation you performed to identify the conditions
under which a galvanic cell is produced
9) Account for the need of a salt bridge.
Revision Questions - 6
1) Describe a first-hand investigation you performed to measure the
difference in potential of different combinations of metals in an electrolyte
solution
2) Describe the structure and chemistry of a dry cell or a lead-acid cell.
3) Compare and evaluate one of the following: button cell; fuel cell; vanadium
redox cell; lithium cell; liquid junction photovoltaic device (e.g. the Gratzel
cell) and compare it to a dry cell or lead-acid battery in terms of:
(i)chemistry; (ii) cost and practicality; (iii) impact on society and (iv)
environmental impact
4) Calculate the potential developed by the galvanic cells below, for each
write balanced half equations and a redox equation:
Al(s) | Al+3(aq) || Ni+2(aq) | Ni(s)
Fe(s) | Fe+2(aq) || Pb+2(aq) | Pb(s)
Mn(s) | Mn+2(aq) || H+(aq) | 1/2H2(s)
Cu(s) | Cu+2(aq) || Ag+(aq) | Ag(s)
5.
Nuclear chemistry
Isotopes
Atoms of the same element can have
different numbers of neutrons; the
different possible versions of each
element are called isotopes.
Most elements found naturally are
composed of two or more stable
isotopes (e.g. natural Chlorine is
composed of 75.8% 35Cl (or Cl-35)
and 24.2% 37Cl, hence its atomic
mass is 35.5)
Some Isotopes are radioactive
because their nuclei are not stable.
Some elements don't have any
stable isotopes: e.g. technetium (Tc)
promethium (Pm), and all the
elements beyond bismuth (atomic
number 83).
Isotopes
Protons are positively charged and
hence repel each other strongly,
neutrons are neutral.
At the very small distances (10-15m)
within the nucleus a very strong
force between neutrons and protons
called the Strong Force comes into
play, and keeps the nuclei from
exploding apart.
In lighter elements the number of
neutrons is similar to the number of
protons.
In heavier elements more neutrons
than protons are needed for stability.
Atoms with too few neutrons, or too
many protons are unstable and emit
radiation, hence they are called
radioactive isotopes.
Radioactive Isotopes
Radioactive isotopes emit
radiation, in the form of
particles or electromagnetic
waves.
The type of radiation emitted
depends on the type of decay of
the radioactive atom
There are many types of
radioactive decay, but the three
main types are: alpha, beta, and
gamma decay.
Alpha decay ( )
An alpha particle( ) is a helium nucleus 42He2+
Alpha decay occurs because the nucleus has too many
protons which cause excessive repulsion.
In alpha decay, the new nucleus is reduced in both atomic
number and mass number: (Z2) and (A4)
Alpha particles have a very short range and a low
power of penetration. When ingested into the body;
they have great destructive power and may cause
maximum damage no emitters are used for
medical uses. Americium-241 is an alpha emitting
isotope and is used for smoke detection.
Beta decay ( )
There are two types of beta decay: emission of an
electron ( -) and emission of a positron ( +)
In electron decay, the new nucleus is increased in
atomic number but the mass number remains the
same:(Z+1)
In positron decay, the new nucleus is reduced in atomic
number but the mass number remains the same:(Z-1)
Beta particles have greater range of penetration than
alpha particles, but still much less than gamma rays.
The radiation hazard from betas is greatest if they are
ingested. Beta emitters are mostly used for industrial
purposes.
Gamma decay ( )
Gamma rays are very short wave and very high energy
electromagnetic photons and therefore are very
penetrating.
Gamma decay occurs because the nucleus is excited. The
nucleus emits a particle to achieve lower, more stable, energy
state.
In gamma ray emission both the atomic number and mass
number remain unchanged
Gamma rays are the most penetrating and hence are
the most dangerous because of their ability to
penetrate through most materials.
Detection of Radioactivity
The three types of radiation are known as
ionizing radiation because they cause
materials to ionize e.g. air
Ionizing radiation cannot be detected by the
senses. The damage it causes to the body is
cumulative, and is related to the total dose
received.
Their ability to ionize substances is utilised to
detect their presence by:
physical methods: scintillation counters,
Geiger counters and electroscope
discharging
chemical methods: effect on
photographic emulsions and fluorescence
of substances like zinc sulfide
Detection
Hand-held meters (e.g. GeigerMueller meters) measure the
presence and quantity of
radiation in the environment.
The Geiger-Mueller tube
contains gas that ionizes and
produces a small pulse of
electricity each time it is ionized
by radiation.
Body-worn dosimeters measure
the exposure to radiation
accumulated by persons
working in radiation risk areas.
They can be in the form of
badges, rings or pens. They
contain photographic film.
Transuranic
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Revision Questions - 7
1) Define a transuranic element and describe how transuranic
elements are produced
2) Describe how commercial radioisotopes are produced
3) Identify instruments and processes that can be used to detect
radiation
4) Identify one use of a named radioisotope in industry and describe
the way is used in terms of their chemical properties
5) Identify one use of a named radioisotope in medicine and
describe the way is used in terms of their chemical properties
6) Describe recent discoveries of elements
7) Analyse benefits and problems associated with the use of
radioactive isotopes in identified industries and medicine
8) Distinguish between stable and radioactive isotopes and describe
the conditions under which a nucleus is unstable