Synthesis of Polymers

Download as docx, pdf, or txt
Download as docx, pdf, or txt
You are on page 1of 4

Synthesis of Polymers

Angulo, A.P.
Institute of Chemistry, University of the Philippines, Diliman, Quezon City.
alyannaangulo@gmail.com
March 12, 2015
March 19, 2015
Abstract
Polymers are used in the industry for its properties such as conductivity, insulation,
strength and others. As such, though they occur naturally they are also produced
synthetically and their properties are manipulated by the condition they were made
in. This experiment aimed to create polymers of different topologies with the
manipulation of types of reactant, pH conditions, and temperature. Linear and
cross-linked polymers were synthesized via condensation polymerization and were
observed and identified.

I.

Introduction

Polymers are substances that are


naturally present in our environment
but
can
also
be
produced
synthetically. The molecules of these
substances have high molecular
masses due their composition of
repeating units. These substances
are used in a wide variety of
industrial applications due their
being tough but light solids, some of
which are: flexible films, adhesives,
paint, and fibers.
Bakelite,
or
polyoxybenzylmethylenglycolanhydri
de, is one of the earliest forms of
plastic. It is a phenol formaldehyde
resin that is formed due to the
reactivity of the phenoxide ion, a
product of a phenols weak acidity.
As one of the earliest synthetic
plastic, Bakelite was widely used for
its heat-resistance and its ability to
function as an electrical insulator
resulting in its use in the early

technology of radios and telephones.


It was also used like other polymers
fibers, pipes, jewelry, and others.
Bakelite is a polymer produced
by the reaction of phenol with
formaldehyde. The reactivity of
formaldehyde with phenol and
phenol with formaldehyde are 2 and
3 times respectively. Because of this
Bakelite is classified as a crosslinked polymer.
A cross-linked polymer, also
called thermosets due to their
inability to be reshaped upon
heating
without
degrading
permanently, is a polymer whose
covalent bonds connect different
chains. Two more types of polymers
are the linear and branched
polymers. These on the other hand
can be reshaped with heat or
dissolution
and
are
called
thermoplastics.

then removed from the oil bath and


cooled until it thickened. Polyester
fibers were drawn with the use of a
stirring rod.
Preparation of Temporarily Crosslinked Polymers
Figure
Polymers

1.

Basic

Topology

of

Identification of the type of


polymer, linear or cross-linked, is an
aim of this experiment.
II.

Methodology

Synthesis of Bakelite
A test tube was used in which
2.50 g of resorcinol was placed
together with 1.00 mL 3.00 M NaOH,
and 5.00 mL formalin then mixed
thoroughly. The test tube was then
placed in a 45-50C water bath until
all
crystals
dissolved.
The
temperature was then raised to 55C
and the test tube was kept there for
10 minutes. After which the heat
was turned f and the solution was
cooled slowly to room temperature.
The test tube was broken to extract
the synthesized polymer.

In a small beaker, 20 mL of
Polyvinyl alcohol (PVA) was placed
with 2-3 drops of methyl red. The
solution was then mixed with 5 mL
4% sodium borate. Excess liquid was
removed from the formed gel. To a
portion of the gel, 2M HCL was
added dropwise and mixed well until
the indicator turned pink. It was then
mixed with 3.00 M NaOH until the
gel reformed.
III.

Results and Discussion

Synthesis of Bakelite
The synthesis of Bakelite used
the phenol, resorcinol. Upon addition
of
formaldehyde,
resorcinol
underwent
slow
polymerization
which was quickened with the use of
a base catalyst, NaOH.

Synthesis of Polyester Fibers


In a test tube labeled #1, 2.00 g
phthalic
anhydride,
0.10
g
anhydrous sodium acetate (NaOAc),
and 1.00 g ethylene glycol was
added. In another test tube labeled
#2, 2.00 g phthalic anhydride, 0.10
g NaOAc, and 0.90 g glycerol was
added. The test tubes were placed in
an oil bath until solution #1 turned
pale yellow and solution #2 turned
light orange. The test tubes were

Figure
2.
Formaldehyde Reaction

Resorcinol-

The product was dark amber in


color and was glasslike in texture
and hardness. The brittleness of the
product showed that the polymer
produced was a cross-linked polymer
and cannot be re-processed into
another shape even with heating or

dissolution
without
chemical degradation.

complete

Synthesis of Polyester Fibers


The
reaction
of
phthalic
anhydride and ethylene glycol in
test tube #1 is condensation
polymerization. This involves two
monomer units with two functional
groups
that
react
with
the
elimination of a small molecule.
Figure 3 shows the reaction of
phthalic anhydride with any diol, in
this case, ethylene glycol.

Figure
4.
Condensation
Polymerization of Phthalic Anhydride
with Glycerol
A stirring rod was used to draw a
fiber from the mouth of the test tube
and the result was a thread-like
transparent string that shows the
success of the synthesis.
Test tube 1 produced a linear
product while test tube 2 produced a
cross-linked
product
as
characterized by their respective
ability to be reshaped upon heating.
This is due to the difference in the
number of hydroxyl groups present.
Glycerol, having three OH groups,
produces a more rigid structure
called the thermoset.

Figure
3.
Condensation
Polymerization
of
Phthalic
Anhydride with a Diol.

Preparation of temporarily crosslinked Fibers

With the use of a stirring rod, a


fiber was drawn from the mouth of
the test tube to show the successful
synthesis.

Hydrolysis of the borate ion in


water produces boric acid (H 3BO3).
This
reacted
with
PVA
and
underwent
a
condensation
polymerization.

The reaction in test tube #2


between phthalic anhydride and
glycerol is also a condensation
polymerization with the reaction
shown In figure 4.

Figure 5. PVA Condensation with


Borate Ion
This reaction produces weak
cross-linking producing a viscoelastic
gel with high water solubility due to
the numerous hydrogen bonds.

The product was a pink liquid


when acidified due to the presence
of methyl red and the addition of
acid breaks the weak cross-links. It
was orange when mixed with a base
due to the presence of methyl red
and addition of a base reestablishes
the weak cross-links.

[2]Polymers. MSU Department of Chemistry.


March
18,
2015.
http://www2.chemistry.msu.edu/faculty/reus
ch/VirtTxtJml/polymers.htm

IV.

[4]Baekeland,
L.H.
The
Synthesis,
Constitution, and Uses of Bakelite. ACS
Publications.
March
18,
2015.
http://pubs.acs.org/doi/abs/10.1021/ie50003
a004

Conclusion
Polymers formations are
affected by the acidity and
temperatures of the environment
they were in during synthesis.
The number of hydroxyl groups
also affect the topography of the
polymers created which affect
the properties of the polymer
such as hardness, ability to
reshape,
brittleness,
and
conductivity.
The
methods
of
the
experiment were effective and
produced the desired effects. The
goals of the experiment were
obtained.

V.

References

[1]Polymers. Chemicals of the Week. March


18,
2015.
scifun.chem.wisc.edu/chemweek/polymers/
polymers.html

[3]Bakelite Synthesis. Polymer Discovery.


March
18,
2015.
http://discovery.kcpc.usyd.edu.au/9.5.1/9.5.
1_Bakelite.html

[5]Polymers. Supplementary Reading on


Chemistry
112.
March
18,
2015.
http://courses.chem.psu.edu/chem112/mate
rials/polymers.html
[6]Leonard Gelfand Center Service Learning
and Outreach. Polyvinyl Alcohol Slime.
Carnergie Mellon University. March 18,
2015.
http://www.cmu.edu/gelfand/k12teachers/polymers/polymerarchitecture/polyvinyl-alcohol-slime.html
[7]Stevens, M. P. Chemistry of Industrial
Polymers. Encyclopedia Britannica. March
18,
2015.
http://www.britannica.com/EBchecked/topic/
468716/chemistry-of-industrialpolymers/76391/Ring-opening-metathesispolymerization

You might also like