Eric Robinson

Jeffery Scott
Organic Chemistry 278-53
11/4/2017
Lab 7 - Pyrolysis of Polystyrene
Introduction
One method of analysing organic products is by analysing a compounds products as a
result of being broken down. One method of degrading organic compounds is pyrolysis which is
the breakdown of something using heat. The heating of polystyrene (styrofoam) in excess of
150 causes the breakdown of the compound and the evaporation of its degraded product. By
performing analytical tests on this product and looking at the original compound, we can deduce
its chemical structure.

Methods
A simple distillation setup similar to the one in
figure 1 was used. Vapors that did not condense by the
end of the condenser were run through a tube and
bubbled through water. Joints that would be in contact
with vapors were greased and sealed. Water was not
run through the jacketed condenser because the vapors
were extremely hot and may crack the cooled glass. A
mass of 2.10g of styrofoam was loaded into the
distillation flask and a heating mantle was put into
place. The apparatus was covered with foil around the
flask and nearly up to the thermometer to get
everything as hot as possible. The heat was turned as
high as it went and the distillation was run until no
more liquid would come over. By the end of the
distillation, vapors were visible just barely unable to
run into the condenser. Even on maximum heat, a full yield could not be gotten.
 With the product collected, several tests were performed. First, the mass of the product
was recorded. Next, the refractive index of the substance was taken. I also collected data on the
IR spectrum of the liquid. A one milliliter sample of the liquid was mixed with an equal amount
of water to test their miscibility. The same was done with the product and a similar amount of
ethanol. Finally, hydrogen and carbon NMR data was acquired for the product. The combination
of all this data can now be used to identify the pyrolysis product.

Results
Starting with a mass of 2.10g of styrofoam, 1.37g of yellow distillate was collected for a
65% yield. The refractive index of this product was found to be 1.5522. The IR spectrum and
NMR results are attached to this report. When mixed with an equal amount of water, the product
was not miscible even with shaking. The liquid settled in a layer below the water. When mixed
with an equal amount of ethanol, the the liquid initially settled in a layer below the ethanol but
went into and stayed in solution when agitated.

NMR Report
Styrene; 1H NMR (CDCl3) 7.4 (d, 2H), 7.35 (t, 2H), 7.28 (t, 1H*), 6.75 (q,1H), 5.77 (d, 1H),
5.27 (d, 1H); 13C NMR (CDCl3) 138, 137, 129, 128, 126, 114

1H NMR
a d
7.4 a
b f
7.35 b e
7.28 c c a
6.75 d b
5.77 e
5.27 f

13C NMR
138 A
137 B E B
A
129 C C
F
128 D
126 E D E
114 F C

Conclusion
Since we looked at the degradation of the polymer polystyrene, I am led to believe the
distillation product is the associated monomer, styrene. My tests confirmed this assumption.
 The measured refractive index of my product gave me a value of 1.5522 which is within
~0.5% of the reported value of 1.54401.
The IR spectrum results shown previously provided evidence for my compound being
styrene. Peaks at 3026, 2059, and 3081 are indicative of the bond stretching between a hydrogen
and doubly bonded carbon. The four peaks of 1449, 1494, 1575, and 1600 are associated with the
stretching between two doubly bonded carbons. Finally, the peaks at 695 and 774 is evidence for
the compound being a monosubstituted aromatic compound.
Analysis of the NMR results is included on the previous page. The peaks observed on the
readout and the associated atoms are labeled and consistent with my product being styrene.
The distillate product was not miscible with water which tells me that the compound is
organic and nonpolar (which styrene is). The distillate was miscible with ethanol but only after
being shaken. These results are both consistent with prior literature regarding the compound2.

Questions
1. What conclusion can be drawn from the following about the structure of styrofoam?
a. It is insoluble in concentrated sulfuric acid.
The fact that styrofoam in not soluble in a concentrated hygroscopic acid
like sulfuric acid leads me to believe that the structure of styrofoam does not have
a hydroxyl group that could be dehydrated by the presence of H2SO4.
b. It does not react with bromine in methylene chloride or aqueous potassium
permanganate.
In the presence of bromine under DCM, alkenes turn into alkanes with the
anti-addition of two bromine atoms. If no reaction takes place under these
conditions with styrofoam, that must mean that polystyrene does not have any
reactive doubly bonded carbons. The only doubly bonded carbons in polystyrene
are part of an aromatic ring and would not react.
2. d
3. What peaks in the IR spectrum of polystyrene indicate,
a. Aliphatic C-H stretching?
The two peaks at 1020 and 1082.
 b. Aromatic C-H stretching?
The three peaks at 3026, 3059, and 3081.
c. The presence of a benzene ring?
The four peaks at 1449, 1494, 1575, and 1600.0
d. The C6H5 group (monosubstituted benzene)?
The peaks at 695 and 774.
e. Attributed to CH2 bending?
The peak at 1449 could be associated with CH2 bending.

Works Cited
1. Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 94th Edition. CRC Press
LLC, Boca Raton: FL 2013-2014, p. 3-488

2. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and
Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1638