Title: Recycling Plastics: Hydrolysis of Polyethylene Terephthalate (PET)

Statement of the Problem:

PET is commonly utilized in most of the consumer products like soda bottles, yog
urt containers, and other food containers and these containers have a short-live
d usefulness, and they are discarded after the consumer product has been used a
nd due to the huge amounts of these plastics used it is necessary to recycle PET
. Approximately 70 million tons of plastics are discarded each year, and of all
these, 80% of the plastics ends up in the landfills which are 25%of the landfill
volume. One of the ways of ensuring that these materials are reduced is to ensu
re that they are reused or recycle the plastics.
Hypothesis:
The hydrolysis of PET using potassium hydroxide refluxing 1-pentanol is done in
the lab. One of the hydrolysis products, the terephthalic acid will be isolated
and characterized using IR spectroscopy. The chemical concepts used in this lab
are vacuum filtration, IR spectroscopy and reflux. The green lesson in this lab
is to finely powdered potassium hydroxide to provide the nucleophile. PET wastes
should be effectively used to avoid environmental degradation. PET is polyester
which has a functional ester groups which can be cleaved by water in a process
called hydrolysis
Materials:
PET flakes were prepared from the used soda bottles and other containers. The bo
ttles were cut and fed to a rotary cutter producing flakes with a minimum size o
f about 6mm, and the chemicals used were reagent grade
Procedure:
i. 1.0g of grounded potassium hydroxide was added to a 100 ml round bottomed
flask with a stirring bar. 0.52 g PET and 30ml of 1-pentanol were added to the f
lask
ii. The reaction mixture was heated at the flux for about 30 minutes, and aft
er approximately 8 minutes the reaction mixture became cloudy, and a bit white s
ome precipitation were formed inside the flask
iii. After 30 minutes heating, the reaction mixture was cooled to room temper
ature for about 45 minutes, and two layers were formed in the flask: the solids
which are a white precipitation were at the bottom, and the clear mixture which
is the liquid appears on top
iv. Then the clear solution was transferred through decantation to the separa
tory funnel. Rinse the round bottomed flask with 15ml water and transfer the sol
ution into a separatory funnel and shake the funnel to mix well and allow the la
yers to separate and remove the aqueous layer and extract the organic layer left
in the separatory funnel with an additional 15ml of water.
v. The combined aqueous extracts were acidified with 8 ml of the 10% aqueous
HCL to a pH approximately five then it was cooled on ice for 15 minutes
vi. Collect the solid product by vacuum filtration
vii. Dry the weigh the product. Then obtain the IR of the starting material a
nd the product.
Results (Data):
IR Spectra of product
Conclusions:
The increased PET bottle waste is increasingly becoming a social problem, and ma
ny recycling methods have been discovered that NaOH hydrolysis of PET in the wat
er-ethanol was the most preferred to recover terephthalic acid though it needs h
eating of about 100-degree celsius. It is necessary to develop more effective me
thods to increase recycling. The experiment was a success.
Post-Lab answers to the Post-Lab Questions
The PET has a mass of is 192.2 g/mol. This number mass is used to determine the
limiting reagent and yield but is not the same mass used to determine the actual
molecular weight of the polymer due to the variation of the actual length of th
e full polymer and yet each polymer consist of reacting functional groups those
that react with both KOH and 1-pentanol. Therefore due to the variation of lengt
hs of Thus, the actual molecular weight is unknown because of the various length
s of the polymers. Theoretical and Percent yield of Terephthalic Acid, based on
PET being the limiting reagent: 0.52 grams of PET used in my reaction. OH, the g
roup is hydrophilic, and the alkyl group is lipophilic.
The effect of the alkyl group on solubility for lower members of the series the
-OH group constitutes a large portion of the molecule, and these compounds are m
iscible with water. However, as the number of carbons increases, the solubility
steadily decreases. Ethanol has a very high solubility that is to infinity ( in
g/ 100g H2O) whereas for 1-pentanol it is 2.3. Hence that is why 1-pentanol used
in this reaction instead of ethanol.