Matthew Ong

112891
Solution Polymerization of Styrene

Introduction
The production of polystyrene is of important significance in industry. The
applications of polystyrene can be seen in various places including our household.
Among the many products that are composed of polystyrene, we have plastic cups
and insulation materials. A wide variety of applications ask for careful emphasis in
the polymerization of styrene.
In this experiment, we will be producing polystyrene through solution
polymerization. Solution polymerization involves dissolving the monomer and
initiator into a solvent. The solvent helps diffuse the heat that is needed for
reaction to happen. The mixture is then heated at a temperature that will allow
polymerization and the initiation process will begin and the propagation and
termination will follow. There are some advantages and disadvantages in using this
technique in the production of polystyrene. Some advantages would be the
continues diffusion of heat for polymerization, therefore temperature control is
much easier, and it allows for easy stirring to avoid viscosity build up in the
mixture. A disadvantage would be that a pure polymer is hard to produce, as the
process of removing the solvent completely is difficult. Also, high molecular weight
polymers are hard to come by because the solvent molecules may also act to
terminate the growing polymer chain, which then brings up the issue of finding a
suitable solvent for the polymer you are trying to produce.

Materials
The apparatus used was quite simple. A 400 ml beaker was used for the oil
bath consisting of silicon oil. It is then placed on top of a hot plate that is placed
under a metal stand to hold the round bottom flask that will contain the solvent,
monomer and initiator. This round bottom flask was submerged into the oil bath. A
paper clip was put inside the oil bath to stir. The round bottom flask also consists of
a stirrer to help for even heat distribution. A separatory funnel was used to wash
the styrene of its inhibitors. This was also used near the end of the experiment for
collection of the polystyrene produced.
The reagents used were, of course, styrene as the monomer, benzoyl
peroxide as the initiator, and toluene as the solvent. Calcium chloride and NaOH
was also used to obtain dry uninhibited styrene. This will be discussed further in

the procedures. The reagents and the corresponding amounts used of each are
shown in the next table.

Reagents

Amount

Styrene

7.3 ml

Benzoyl Peroxide

0.3 g

Calcium Chloride

Approx. 0.15 g

10% NaOH solution

7ml

Toulene

21 ml
Procedure

The first thing we did was to obtain uninhibited styrene. This was done by
washing it with 7ml of 10% NaOH solution with the use of a separatory funnel. We
did this three times. After which, we added approximately 0.15g of calcium
carbonate to dry the uninhibited styrene. 5ml of uninhibited styrene was put into
the round bottom flask. For the solvent, 20ml of toluene was poured inside. 3g of
benzoyl peroxide, the initiator was placed inside along with the toluene and
uninhibited styrene.
A 490ml bath consisting of silicon oil was prepared. The bath was then
placed on top of the heat mantle and under the metal stand, which served as the
holder of the round bottom flask. A paper clip was placed inside the silicon oil bath
to stir the bath. A small stirrer was also placed in the round bottom flask to help in
distributing heat evenly over the whole mixture. The round bottom flask was then
submerged in the oil bath with the help of the iron stand. A thermometer was
submerged in the oil bath to enable the monitoring of temperature. The heating
plate had adjustors that could change the temperature and speed of stirring. Also,
it is to be noted that before submerging the round bottom flask into the oil bath,
we first heated the oil bath to reach 70-80 degrees Celsius. Once the oil bath
reached this temperature, we submerged the round bottom flask into the beaker
that contained the silicon oil. We were to wait 2 hours before taking out the
mixture from the bath, which meant we had to be constantly aware of the baths
temperature and make sure that it didnt reach values outside of 70-80 degrees
Celsius.

After 2 hours, we took out the round bottom flask and allowed it to cool for a
few minutes. We transferred it into a 400ml beaker and added methanol, which
allowed precipitate to show. No precipitate showed as there was an issue with the
used methanol (will be discussed in discussion). We were advised to leave the
mixture under the hood overnight to evaporate the methanol and leave the
precipitate products alone in the flask. We then ended up using the separatory
funnel to separate the two and added clean methanol and obtained some
precipitate. We measured the mass of the produce and recorded the data.

Results and Discussion

The inhibited styrene before the wash was a clear liquid. After washing, we
see a separation between the inhibitor and styrene. Styrene produced a greenish
yellow color while the NaOH and inhibitor was colored pink. The calcium chloride
used to dry the styrene eventually formed lumps at the bottom of the beaker.
Some observations after heating the mixture: upon introducing methanol
into the beaker, the mixture turned murky white, which suggests that a reaction
did take place in the process. Minimal precipitate was found at the bottom of the
beaker, which tells us that its of low molecular mass. Strangely however, no
precipitate was collected when we tried to filter the mixture. The precipitate
seemed to have disappeared upon introduction of new methanol. It was then
announced that some of the methanol used was contaminated and could have
caused the zero yield we obtained. The mixture was then placed under the hood
overnight in the hopes of separating the contaminated methanol and the
precipitate. No evaporation happened, so the mixture was put through the
separatory funnel and added clean methanol. We were able to collect 0.48 g of
polystyrene.
We only obtained low molecular weight, which could have been caused by
the inefficiencies in controlling the temperature or human error in preparing the
corresponding chemicals for the reaction. Many factors could have caused the low
amount of product we obtained. To get the % yield, we have to divide the collected
polystyrene by the initial amount of styrene present before the reaction. 5ml of
uninhibited polystyrene was initially placed in the round bottom flask. The density
of styrene is said to be 909 kilograms per meters cubed. Doing unit analysis we
can obtain the mass of 5ml of uninhibited polystyrene. This value comes out to be
4.55 g of initial uninhibited styrene. We can now obtain the % yield by dividing
0.48 g by 4.55 g. A percent yield of 10.54% is obtained. This is considered to be
low percent yield because we only obtained polystyrene of low molecular mass.
This again can be attributed to various factors such as the inefficiency of
controlling the heat in the bath and basic human errors.

The polymerization process may take a lot longer if the inhibitor is not
removed. Inhibitors slow down or prevent the reaction from happening. Inhibitors
may cause not only a slower reaction process but also lower percent conversion
and therefore will not be able to maximize the resources used for the reaction to
happen. A faster reaction will happen if there is no inhibition. It will also obtain a
higher % yield than that of a reaction with inhibitors. Other initiators can also be
used in the reaction. Cumyl peroxide can be used as an initiator, potassium
persulfate as well. There are various techniques for polymerization. Among these
are bulk polymerization and solution polymerization. Bulk polymerization should
expect a higher % yield, as it uses no solvent for the reaction. This means that
there will be no contamination that may serve as catalysts for degrading the
polymer. It is important to understand the key advantages and disadvantages of
each polymerization technique to be able to produce the desired polymer in an
efficient way.

References:

1.) http://web.stanford.edu/class/cheme160/lectures/lecture13.pdf
2.) http://www.slideshare.net/Santachem/polymerization-techniques
3.) http://home.sandiego.edu/~khuong/Publications/ja0448667_styrene.pdf
4.) http://www.ch.ic.ac.uk/local/organic/tutorial/steinke/StructurePorpertyRelat
ionships2003.pdf
5.) http://www.chemicalbook.com/ProductChemicalPropertiesCB3415111_EN.
htm