Optimization and Comparative Study of Various

Strategies in the Chemical Recycling of Polyethylene

Terephthalate (PET) via Depolymerization

Team number: SBBC 173

Authors:
Cheung Yan Chung, Cheung Ching Yan,
Tsang Chiu Long, Tang Chun Yin,
Leung Kin Pan

Institution: La Salle College

Abstract

Polyethylene terephthalate (PET) is a non-biodegradable plastic (polymer) commonly used in

packaging (e.g. plastic water bottles). Unique properties of PET such as shatter resistance, great
tensile strength, excellent chemical resistance, lightweight, elasticity, and stability over a wide
range of temperatures are why PET is still used to this day.

Recycling PET is usually done by mechanical recycling. However, mechanical recycling is limited
by eventual material downcycling, necessitating product repurposing to lower-value applications.
Conversely, chemical recycling enables product quality to be preserved by breaking PET down
into monomers, then reacting the monomers with each other to produce the exact same product.

Consequently, we are attempting to compare various strategies of depolymerization of PET and to

investigate the most effective method as well as the advantages and disadvantages regarding
various aspects (e.g economical, environmental) of the methods. In addition, through a number of
experiments, an optimized strategy for the chemical recycling of PET has been discovered which
is also presented in this article.
Acknowledgements

A project like this might not have been completed without the help from a number of people.

Our heartfelt gratitude goes first to Mr Samuel Chan, for aiding various stages of this project.

In addition, we must also thank Mr Curtis Chung for providing advice and supervising us during
the experiments.

Our special thanks goes to Ms Carmen Tsui for her work in preparing apparatus and chemicals.

These people are the sole reason this report can ever see the light of day.

Last but not least, thank you STEM Team of La Salle College for allowing us the opportunity to
participate in this event.
Introduction

Plastic Pollution

In this day and age, in spite of the advancement of technology, humans are also producing a
growing amount of waste which causes detrimental effects to the environment. Plastic wastes are
one of these major pollutants. It is estimated that around 0.8 to 30 million metric tonnes of plastic
waste are discarded into the ocean directly or indirectly every year in the world [1-3].

Plastic pollution can harm wildlife through ingestion or entanglement, reduce the livelihoods of
those who rely on ecological sustainability (e.g. fishing and tourism), contaminate seafood with
microplastics, threatening food safety and human health, cause property damage, and increase the
risk of flooding in urban areas[4-9].

Chemical degradation of polymers

Chemical breakdown of hydrocarbon-derived polymers necessitates greater temperatures in hot

compressed water [10]. Unlike most polymers, PET monomers are linked by an ester bond,
allowing it to be hydrolyzed at lower temperatures [11]. In general, hydrolysis of PET has become
a more environmentally friendly method of chemical recycling [12]. As a result, we are attempting
to limit plastic pollution by investigating the chemical decomposition of PET.
Literature review

Introduction of literature review

Polyethylene terephthalate (PET) is a widely used thermoplastic polymer in various applications,

such as packaging, textiles, and engineering plastics. However, the disposal of PET waste has
become a significant environmental concern due to its non-biodegradable nature.
Depolymerization of PET is considered a promising approach to address this issue, which involves
the breaking down of PET into its constituent monomers, terephthalic acid (TPA) and ethylene
glycol (EG), for recycling or further processing. Various depolymerization methods have been
developed for PET, including chemical and enzymatic methods. Chemical depolymerization
involves the use of catalysts or solvents to break down PET, while enzymatic depolymerization
utilizes enzymes to catalyse the hydrolysis of PET.

A. Chemical Depolymerization

Chemical depolymerization of PET involves the use of catalysts or solvents to break down the
polymer into its constituent monomers, TPA and EG, for recycling or further processing. The most
commonly used catalysts for chemical depolymerization of PET are metal-based catalysts, such as
zinc acetate, which have been shown to be effective at breaking down PET under mild conditions
[13]. Other metal-based catalysts, such as Zn, Mn, Co and Pb salts, have also been used for PET
depolymerization. Zinc acetate performed best in terms of the extent of depolymerization. The
depolymerization activity of catalysts follows the order of Zn²⁺ > Mn²⁺ > Co²⁺ > Pb²⁺[14]. These
catalysts work by hydrolyzing the ester bonds in PET, resulting in the formation of TPA and EG.

In addition to metal-based catalysts, other catalysts, such as sodium hydroxide [15] and potassium
hydroxide, have also been used for PET depolymerization [16]. The use of alkali catalysts can lead
to higher yields of TPA and EG, but the reaction conditions must be carefully controlled to avoid
side reactions and by-product formation.
Solvents, such as methanol and glycols [17-18], have also been employed to break down PET.
Among these solvents, glycols, such as ethylene glycol (EG) and diethylene glycol (DEG), have
been shown to be the most effective at depolymerizing PET, with EG being the most commonly
used to break down PET into Bis(2-hydroxyethyl) terephthalate (BHET). The use of glycols as
solvents can lead to high yields of TPA and EG, but the reaction conditions must be optimized to
avoid the formation of by-products, such as oligomers and terephthalic acid dimers.

The efficiency and selectivity of chemical depolymerization of PET can be affected by various
factors, such as the reaction temperature, pressure, and reaction time. Higher temperatures can lead
to faster reaction rates but also increase the risk of side reactions and by-product formation. The
use of higher pressure can also increase the efficiency of the depolymerization process by
promoting the hydrolysis of ester bonds in PET [19]. The reaction time can also affect the yield
and selectivity of the process, with longer reaction times leading to higher yields but also
increasing the risk of by-product formation.

B. Enzymatic Depolymerization

Enzymatic depolymerization of PET has gained increasing attention in recent years due to its
environmentally friendly nature. Several types of enzymes have been investigated for PET
depolymerization, including cutinases, lipases, and esterases [20]. Among these, cutinases have
been shown to be the most effective at breaking down PET due to their ability to hydrolyze ester
bonds in the polymer backbone. Cutinases are serine hydrolases that are naturally produced by
certain bacteria and fungi to hydrolyze the cutin, a waxy polymer found in plant cell walls.

The mechanism of enzymatic depolymerization involves the adsorption of the enzyme onto the
PET surface, followed by the hydrolysis of ester bonds in the polymer backbone. The hydrolysis
reaction results in the formation of oligomers, which are further hydrolyzed into monomers, such
as TPA and EG, by the same or different enzymes.

Enzymatic depolymerization of PET offers several advantages over other depolymerization

methods, such as chemical depolymerization. Firstly, enzymatic depolymerization is a mild
process that can be performed under ambient conditions, which reduces the energy and
environmental impacts of the process [20]. Enzymatic depolymerization is also a selective process
that can break down PET into its constituent monomers without producing by-products, such as
oligomers and terephthalic acid dimers [20]. Moreover, enzymes are biodegradable and can be
produced from renewable resources, which makes enzymatic depolymerization a sustainable and
eco-friendly process.

However, enzymatic depolymerization also has some limitations that need to be addressed. Firstly,
the process is slow and requires a long reaction time, which limits the scalability of the process.
The cost of enzymes can also be high, which can affect the economic feasibility of the process.
Moreover, enzymes can be sensitive to environmental conditions, such as pH and temperature,
which can affect their activity and stability.

C. Hybrid Approaches

In addition to the above depolymerization methods, hybrid approaches, such as the combination
of chemical and enzymatic methods, have also been investigated for PET depolymerization. For
example, a combination of zinc salts and cutinase was investigated. However, it is found that the
activity of T. fusca cutinases has been lowered [21].

Conclusion of literature review

Overall, depolymerization of PET is a promising approach for the recycling and reuse of PET
waste. Chemical depolymerization is the most extensively studied method, but enzymatic
depolymerization is gaining increasing attention due to its environmentally friendly nature. Further
research is needed to improve the efficiency and effectiveness of hybrid depolymerization methods
for PET, and to develop scalable and cost-effective processes for PET recycling.
Methodology (materials, experimental methods, and reasons)

A. Scientific theory behind the experiment

I. Hydrolysis

Potassium hydroxide (KOH) was used in the alkaline hydrolysis of PET.

The figure below shows the structure of PET.

Note that the carbon atom of the ester group is electrophilic (electron-loving). The hydroxide anion
in the potassium hydroxide is the nucleophile (a species that has an affinity for positively charged
centers). The hydroxide anion therefore “attacks” the electrophilic carbon of the ester group shown
in the reaction mechanism below.

The alkoxide anion then grabs a proton from the 1-pentanol, reforming an alcohol group.
Another hydroxide anion deprotonates one of the alcohol groups, regenerating an alkoxide anion.

The lone pair from the alkoxide reforms a pi bond, breaking the C-O sigma bond.

The PET polymer is thus broken down into its monomers.

Upon further hydrolysis of adjacent ester groups, potassium terephthalate and ethylene glycol is
formed.

II. Glycolysis

Glycolysis of PET using EG is a transesterification reaction.

catalyst

The transesterification reaction can proceed because of the reversibility of the esterification
reaction. PET reacts with the ethylene glycol to form BHET, which is accelerated under the
presence of a catalyst (e.g. NaHCO3)
B. Experiment Procedures

I. Hydrolysis

1. To a 50 mL round-bottomed flask, add 2 grams (in excess) of KOH powder.

2. Add 15 mL of 1-pentanol and mix well
3. Add 1.5 g of small pieces of PET
4. Put a few anti-bumping granules in the round-bottomed flask to ensure smooth boiling.
5. Heat the mixture at reflux for 2 hours
6. The reaction mixture was cooled to room temperature using a tap water bath.
7. 15 mL of distilled water is added to the reaction mixture, the reaction mixture is stirred.
8. The mixture is filtered and then transferred to a separatory funnel.
9. Collect the aqueous layer in a beaker (the bottom layer which is clearer)
10. An additional 15 mL of distilled water was added to dissolve any remaining potassium
terephthalate in the 1-pentanol.
11. The separatory funnel was stoppered and the mixture was gently shaken.
12. The aqueous layer (the layer at the bottom which is clearer) is collected in a beaker.
13. The aqueous extract is acidified with 10% cool dilute hydrochloric acid slowly with
stirring. This is to protonate the terephthalate in the potassium terephthalate to form
terephthalic acid and potassium chloride. Terephthalic acid is insoluble in water and thus
separates out as a white precipitate.
14. The pH of the solution is tested. The addition of the dilute hydrochloric acid is stopped
only after the pH is close to 2. The pH of 2 indicates that all terephthalate has been
protonated.
15. The white precipitate is collected by vacuum filtration and is left to dry in a fume cupboard
for a few days.
16. The carboxyl group of the terephthalic acid is tested using analytical grade sodium
hydrogencarbonate. There is evolution of colorless gas bubbles which turned limewater
milky, indicating the presence of a carboxyl group.
II. Glycolysis

1. Cut up the plastic bottle made of PET into small pieces with scissors and then make a
weighted portion of PET about 1.5g and place in a round-bottomed flask, add 15 ml of
ethylene glycol and 0.1 g NaHCO3.
2. Adjust the reflux condenser, open the flow of cooling water in the condenser, turn on the
heating mantle and heat the reaction mixture under reflux for 1 hour
3. After 1 h remove the heating mantle and leave the laboratory set to cool down
4. Transfer the reaction mixture into the beaker with crushed ice (ca. 100 g), stir the mixture
with a glass rod. After a few minutes a white precipitate should appear.
5. Assemble a vacuum filtration kit and filter the solid on the Büchner funnel under reduced
pressure and wash it with 20 ml of ice cold distilled water (BHET is poorly soluble in cold
water).
6. Remove the filtrate, clean the flask and adjust the Büchner funnel with residue, wash the
precipitate with 50 ml of hot water (BHET is quite soluble in hot water), stir carefully with
a glass rod and filter under reduced pressure.
7. Transfer the filtrate (from point 6) into a beaker with 100g of crushed ice, after a few
minutes white crystals (BHET) should appear
8. Filter the crystals on a Büchner funnel, under reduced pressure and transfer the obtained
residue to a watch glass and dry.
9. Weigh the product, calculate the percentage yield of the reaction
10. The Bis(2-hydroxyethyl) terephthalate (BHET) formed from glycolysis using EG can be
tested with K2Cr2O7(aq), the change of colour of K2Cr2O7(aq) from orange to green
indicate the presence of alcohol group, which is a functional group resent in BHET.
C. The control set-ups

Materials:

Reflux condenser
15mL 1-pentanol 2g KOH EG
1cm x 1cm PET Anti-bumping granules

PET-1-pentanol
mixture
OR
PET-EG mixture

Heating mantle

D. General Hypothesis

The first hypothesis is that PET can be depolymerized into its monomers using both hydrolysis
and glycolysis. The TPA formed from hydrolysis can be tested with NaHCO3(aq), the evolution
of colourless gas bubbles indicate the presence of carboxyl group, which is a functional group
present in the TPA. The BHET formed from glycolysis using EG can be tested with K2Cr2O7(aq),
the change of colour of K2Cr2O7(aq) from orange to green indicate the presence of alcohol group,
which is a functional group present in BHET.

The second hypothesis is that we can find out the optimized conditions for a method of PET
chemical depolymerization by investigating the effect of each variable in the experiment.
E. The experiments for investigation

Independent variable Investigation

N/A Control

5 mL 1-pentanol

10 mL 1-pentanol To investigate how the volume of solvent used affects TPA yield.
20 mL 1-pentanol

2mm x 2mm PET To investigate how surface area of PET affects TPA yield.

1g KOH
To investigate how the mass of KOH affects TPA yield.
3g KOH

White PET
To investigate how the colour of PET affects TPA yield.
Green PET

5 mL EG

10 mL EG To investigate how the volume of solvent used affects BHET yield.

20 mL EG

Na2CO3

Al2SO4

K2SO4

Ca(OAc)2 To investigate how different catalysts affects BHET yield.

Mg(OAc)2

Zn(OAc)2
Results Analysis

A. Hydrolysis of PET

Hydrolysis of PET using 15 mL pentanol, 2g KOH, 1cm x 1cm PET is used as the control.

I. Amount of 1-pentanol

5 mL, 10 mL , 15 mL and 20 mL of 1-pentanol was used to investigate the effect of the amount of
solvent in PET hydrolysis. All other factors are kept the same. When using 5 mL 1-pentanol, TPA
yield decreased significantly to 67.1%. 10 mL, 15 mL and 20 mL 1-pentanol showed similar TPA
yields.

It is thought that as long as the PET pieces are all immersed in the 1-pentanol, the reaction rate
will be mostly constant.
II. Size of PET

Hydrolysis of PET was carried out at reflux using 2mm x 2mm fine PET to investigate the effect
of size of PET (surface area) on PET hydrolysis. All other factors are kept the same. The result
showed a significant difference in yield, with the 2mm x 2mm PET having a yield of 91.01% and
the 1cm x 1cm PET having a yield of 84.84%.

It is thought that the increased surface area of the 2mm x 2mm PET increases the reaction rate
significantly.
III. Solvent

Hydrolysis of PET was carried out using different solvents to investigate the effect of solvents on
PET hydrolysis. All other factors are kept the same. The one using water as solvent showed a
massive decrease in TPA yield to 26.99%. Using 1-pentanol and 1-hexanol as the solvent showed
similar TPA yields.

It is thought that the higher boiling points of 1-pentanol (138 C) and 1-hexanol (157 C) results in
a higher rate of reaction than using water which has a lower boiling point.
IV. Amount of KOH

Hydrolysis of PET was carried out using varying amounts of KOH. All other factors are kept the
same. The one using 1g KOH has significantly lower TPA yield than the other ones, at 67.87%.
Using 3g KOH increases the yield slightly, by 6.94%.

It is thought that the higher mass of KOH led to a higher concentration which sped up the rate of
reaction.
V. Colour of PET

PET of different colours are hydrolyzed to investigate the effect of colour of PET on PET
hydrolysis. Colourless PET gave the highest TPA yield at 84.84%. While white and green PET
gave lower yields when compared to colourless PET at 77.89% and 79.44% respectively.

It is thought that the coloured PET product has less PET per unit volume because of the colouring
mixed in, hence explaining the lower yields.
B. Glycolysis of PET

Glycolysis of PET using 15 mL EG, 1cm x 1cm PET reflux for 2 hours with NaHCO3 as catalyst
was set as the control.

I. Amount of EG

Glycolysis of PET was carried out using varying amounts of EG. All other factors are kept the
same. When using 5 mL EG, BHET yield decreased significantly to 13.61%. 10 mL, 15 mL and
20 mL EG showed steadily increasing BHET yields, with 20 mL having the highest BHET yield
at 37.79%.

It is thought that 5 mL EG was not able to cover all the PET, resulting in lower BHET yield. The
steady increase in yields from 10 mL to 20 mL may be explained by the excess of EG, pushing the
equilibrium to the product side.
II. Size of PET

Glycolysis of PET using different size of PET was carried out. All other factors are kept the
same. The result showed a significant difference in yield, with the 2mm x 2mm PET having a
yield of 38.91 % and the 1cm x 1cm PET having a yield of 34.77%.

III. Catalyst

Glycolysis of PET was carried out using different metal salt catalysts. All other factors are kept
the same. The most common catalyst for PET glycolysis Zn(OAc)2 showed highest BHET yield
at 52.91%. K2SO4 showed lowest BHET yield at 4.53%.
It is thought that the small, highly charged Zn2+ cations interact with the carbonyl oxygen of the
ester group, thus increasing the electrophilicity of the carbon of the ester group, making it more
prone to be attacked by EG.
C. The performance of the methods with optimized conditions

The optimized hydrolysis of PET: Hydrolysis of 2mm x 2mm colourless PET using 20 mL 1-
hexanol and 3g KOH is carried out at reflux for 2 hours. TPA yield 96.41%.

The optimized glycolysis of PET: Glycolysis of 2mm x 2mm colourless PET using 20 mL EG
and 0.1g Zn(OAc)2 was carried out at reflux for 2 hours. BHET yield 57.41%.
Comparison between hydrolysis and glycolysis

I. Yield

From the experiments, it can be concluded that hydrolysis showed overall much higher monomer
yield than glycolysis.

II. Environmental-friendliness

However, as seen from B. Experimental Procedures, isolating the TPA from the reaction mixture
involves acidifying the reaction mixture to protonate the terephthalate to terephthalic acid,
generating more wastes, for example contaminated water and inorganic wastes [22] in the process.
Consequently, pollution problems arise.

On the other hand, glycolysis of PET produces less wastes, since only EG (note that EG acts as
both a solvent and a reagent) and a small amount of catalyst is required, and the isolation of the
product does not involve adding additional chemicals. Therefore, glycolysis of PET using EG is
more environmentally friendly.

III. Cost

Hydrolysis Glycolysis
Factor changed Price mol-1 of monomer Factor changed Price mol-1 of monomer
N/A (control) HKD $7798 N/A (control) HKD $5648
5 mL 1-pentanol HKD $5441 5 mL EG HKD $5017
10 mL 1-pentanol HKD $6159 10 mL EG HKD $2258
20 mL 1-pentanol HKD $9459 20 mL EG HKD $6892
Water solvent HKD $8035 Na2CO3 HKD $4996
1-hexanol solvent HKD $6456 Al2(SO4)3 HKD $7642
2mm x 2mm PET HKD $7269 K2SO4 HKD $43356
1g KOH HKD $9551 Ca(OAc)2 HKD $4480
 3g KOH HKD $7353 Mg(OAc)2 HKD $4190
White PET HKD $8494 Zn(OAc)2 HKD $3712
Green PET HKD $8328 2mm x 2mm PET HKD $5047
optimized HKD $7308 optimized HKD $4536

Formula used in calculation:

-1
yield percentage × maximum yield(g)
cost of raw material × " %
molar mass of monomer

The most inexpensive run for hydrolysis is the one using 5 mL 1-pentanol as solvent.
For hydrolysis, we recommend the following conditions to minimize monetary costs:
Hydrolysis of 2mm x 2mm colourless PET using 5 mL 1-pentanol.

The most inexpensive run for glycolysis is the one using 10 mL EG as solvent.
For glycolysis, we recommend the following conditions to minimize monetary costs:
Glycolysis of 2mm x 2mm colourless PET using 10 mL EG as solvent and Zn(OAc)2 as catalyst.

It can be concluded from the data that although glycolysis gave lower yield of the monomer, the
price per mol of monomer is less than that of hydrolysis, mainly due to EG acting both as a
solvent and a reagent, thus reducing monetary costs.
Limitations

One major limitation in this experiment is the isolation method of BHET. The method for isolation
of BHET in our experiment relies on the difference in solubility of BHET in hot and cold distilled
water. The BHET is still sparingly soluble in the cold distilled water, hence some BHET is lost
during the isolation process, leading to inaccuracies in BHET yield and the comparatively low
yield of BHET compared to TPA yield obtained by hydrolysis.

Another limitation in this project is that only 2 methods of chemical depolymerization of PET was
investigated. Methods such as enzyme-catalyzed PET depolymerization has not been tested in this
project, as the authors are unable to make up time for the experiment.

The final limitation in this experiment is the difference in experimental procedures of our
experiments and those that will be performed in factories. Factories may have apparatus that are
not readily available in school laboratories, hence the data might not be suitable to estimate large-
scale PET depolymerization.

Application

Chemical depolymerization of PET enables unique properties of PET such as shatter resistance,
great tensile strength, excellent chemical resistance, lightweight, elasticity, and stability over a
wide range of temperatures to be retained after recycling (i.e. reacting the monomers with each
other to form the polymer).

The recycled product is chemically and structurally equivalent to the PET product before
recycling. The recycled PET can be used for higher-value applications instead of being repurposed
for lower-value applications in the case of mechanical recycling.
Conclusion

We have successfully depolymerized PET using hydrolysis with KOH into TPA. The optimized
hydrolysis of PET was found to be hydrolysis of 2mm x 2mm colourless PET using 20 mL 1-
hexanol and 3g KOH is carried out at reflux for 2 hours. TPA yield 96.41%, significantly more
than the control.

We have successfully depolymerized PET using glycolysis with EG into BHET. The optimized
glycolysis of PET was found to be glycolysis of 2mm x 2mm colorless PET using 20 mL EG and
0.1g Zn(OAc)2 was carried out at reflux for 2 hours. BHET yield 57.41%, significantly more
than the control.

The two common methods of chemically depolymerizing PET – hydrolysis and glycolysis, has
been compared. Overall, hydrolysis resulted in much higher yields, however hydrolysis also
produces more wastes compared to glycolysis.

Future research should compare more methods of chemical depolymerization of PET, such as
enzyme-catalyzed PET depolymerization. Research on catalysts, such as phase transfer catalysts
[23], organocatalysts [24], and metal acetate ionic liquids [25], to increase reaction rate of PET
depolymerization and reduce reaction temperature is essential to reduce energy and monetary
costs.
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