HSC Chemistry - Lesson 2 Production of Materials 1.1.

6 Outline the steps in the production of polyethylene as an example of a commercially and industrially important polymer Polyethylene is an example of a commercially and industrially important polymer. There are two different types of polyethylene.

Low Density Polyethylene (LDPE)

LDPE contains significant branching of polyethylene chains, which gives it a low density nature. The branching prevents the linear arrangement of the polyethylene chains. The extensive branching seen in the diagram (right) shows how it would be difficult to arrange these polyethylene chains in close vicinity giving it a low density. LDPE has a low melting point compared to other macromolecules due to weak intermolecular dispersion forces. It is produced under high temp and pressure and a small amount of oxygen peroxide required as initiator. The major use of LDPE is in plastic bags due to its flexibility, strength and resistance to dilute and concentrated acids, alcohols, bases and esters. Apart from this its strength and resistance to cracking allows it to be used in dispensing bottles, wash bottles and tubing.

High Density Polyethylene (HDPE)

HDPE has limited branching which allows the chains to be packed in close vicinity (hence high density), increasing the intermolecular dispersion forces, resulting in a high MP. This can be seen in the diagram on the right; the limited branching results in higher density. It is produced under a low temperature and pressure, with the process usually occurring in a hydrocarbon solvent. It involves the use of an ionic catalyst, the Ziegler-Natta catalyst, a mixture of compounds such as TiCl4 and Al(C2H5)3. HDPE is used extensively in pyrotechnics. HDPE fireworks shells are preferred to steel or PVC tubes because they are more durable and more importantly they are much safer compared to steel or PVC in the case of a malfunction. It is also resistant to a range of chemicals and high temperatures making it useful in packaging. Use this space for making your own notes:

In the production process for polyethylene there are three major steps:

Initiation
This is the first step of polyethylene production. It involves the production of a free radical, usually through the decomposition of an initiator molecule using heat. A free radical (as covered in year 11) is a molecule containing an unpaired electron and so is highly reactive. In most cases the initiator molecule is a peroxide molecule with the easily breakable O O bond. An example of this is Benzoyl Peroxide: Heat

The free radicals are represented by the dots on the end of their structure showing the unpaired electrons. The free radicals produced here will then go react with an ethylene molecule, and attract one electron from the double covalent bond to attach to its unpaired electron. Once attached together the two form an activated monomer. This reaction can be shown as: Note: the free radical can also be represented as R O. where the R stands for the rest of the chain.

Propagation
The second step of polyethylene production involves the activated monomer attaching with numerous other ethylene molecules producing a larger radical. The consistent formation of a free radical with an unpaired electron allows ethylene molecules to continue to attach:

When this reaction is repeated numerous times, a general equation can be devised:

Termination
The final step of polyethylene production involves two developing free radical ethylene chains coming together to form a completed chain without an unpaired electron. This process is random and this gives rise to a range of different molecular weights for the ethylene chains which vary in size.

NOTE: in an exam situation there are two ways to talk about production of polyethylene. Either the features and production of HDPE and LDPE can be discussed or the information detailed in the three steps can be discussed. I always preferred the latter as it involved more equations. Use this space for making your own notes:

1.1.7 Identify the following as commercially significant monomers by both their systematic and common names. Vinyl Chloride Systematic name: Chloroethene Common name: Vinyl Chloride Polymer produced: Polyvinyl Chloride (PVC) Styrene Systematic name: Phenylethene Common name: Styrene Polymer produced: Polystyrene.

1.1.8 Describe the uses of the polymers made from the above monomers in terms of their properties NOTE: It is essential in exam situations to make explicit links between the property and the uses of these polymers. In most cases chemistry involves at least 3 examples.

Polyvinyl Chloride
PVC is impervious to most oils and organic materials which mean it can be used for packaging for these materials. Additives to PVC can help improve flexibility and thermal stability. This rigid PVC is then used for water pipes, credit cards and kitchen utensils. Flexible and less rigid forms of PVC can be used for upholstery covers for car seats, and garden hoses.

Formation of Polyvinyl Chloride

Polystyrene
Polystyrene can be produced as either a clear brittle plastic (crystalline polystyrene) or a lightweight foamy packaging material (expanded polystyrene). Expanded polystyrene is an excellent lightweight insulator which allows for use in disposable sups, insulation and eskies. Furthermore the lightweight, low density yet resistant to impact nature of expanded polystyrene enables it to be used in packaging. Expanded polystyrene also has a very low density yet strong structure providing it with buoyancy in water. This allows it to be used in surf board material. Crystalline polystyrene is a hard clear, brittle plastic which makes it great for use in CD cases.

Formation of polystyrene from styrene

1.2.2 Identify data, plan and perform a first-hand investigation to compare the reactivities of appropriate alkenes with the corresponding alkanes in bromine water 1. Place 5 medium sized test tubes, precleaned into a test tube rack in the absence of UV light 2. Using a clean measuring cylinder, add 5ml of bromine water into each of the test tubes and record initial colour 3. Add 5ml of hexane using a clean 10ml measuring cylinder into one of the bromine water test tubes. 4. Stopper the test tubes with a test tube stopper 5. Gently shake the test tube and record the colour change in the test tube 6. Repeat steps 4-6 with 5ml of hexane, cyclohexane and cyclohexene with the remaining bromine water test tubes 7. 1 bromine water test tube should be left and this will act as the control 8. Repeat the experiment 10 times and if similar results are obtained then the experiment can be deemed reliable Use this space to record information about this prac:

1.2.3 Analyse information from secondary sources such as computer simulations, molecular model kits or multimedia resources to model the polymerisation process. 1. Construct one initiator molecule (containing an O O bond in R O O R) 2. Construct 10 monomer units (CH2 = CH2 ) 3. Decompose the initiator molecule (by breaking the O O bond to create two free radicals . (R-O ) 4. React one of the free radicals with the first monomer. The double bond is broken as the free . radical initiator adds onto the molecule. An activated monomer forms ROCHCH 5. The activated monomer then combines with a further ethylene molecule and the process continues until it has attached to 5 monomer units . 6. Use the other RO Radical to repeat steps 4-6 with the other monomers 7. Using the two polymer chains, react their free ends to make one long chain with the RO groups at either end, modelling termination

HSC Style Practise Questions Describe the process of producing polyethylene from ethylene 3 Marks

Identify the common and systematic name of the polymer shown above 2 Marks Explain how the properties of the polymer made from this monomer as well as one other polymer you may have studied in class relate to its uses 3 Marks Draw the structure of the polymer made from the above monomer 1 Mark