Polymers Synthesis and Property Analysis

Chemistry Project

RAGHVENDRA SINGH
Class: XII-SCI A

ROLL NO:
Roll No.:

Teacher’s Signature
 CONTENTS
Acknowledgements iii

Aim of the Project 1

General Overview 1

Brief Theory, Synthesis and Analysis of

1. Bakelite * 3

2. Polystyrene 7

Result 11

Reference 12
 Acknowledgments

I am very greatful to my chemistry teacher, Ms.Monika

Katoch, who has been a constant source of inspiration and
guidance. She supported me with all my ideas and helped
me to the maximum extend possible. She also gave me
enough extra time to find all the required information to turn
my ideas into a single project. Even though what I initially
wanted to make (conductive Polymers) wasn’t possible to do
with our existing lab apparatus, yet she encouraged me to
search for something similar, yet interesting enough for me.
This project would never have existed, if it wasn’t for her
passion to teach.

I would also like to thank our lab assistant, Mr. Yaman Sir for
all the timely help he provided. Apart from this, I would like
to thank all those people who’ve published their useful work
on the internet, without which, I perhaps wouldn’t even have
enough information to make even a single polymer.
Polymers Synthesis and Property Analysis

Aim of the Project

The aim of this project is to find out the optimum conditions for synthesis of the following polymers,
1. Bakelite*
2. Polystyrene**

and to study their physical properties like flexibility, strength, bounciness, color etc.

[* Synthesized using chemicals available in the school laboratory]

[** Synthesized using Industrial Reagents]

General Overview
A polymer is a large molecule (macromolecule) composed of repeating structural units typically connected by
covalent chemical bonds. While polymer in popular usage suggests plastic, the term actually refers to a large
class of natural and synthetic materials with a variety of properties.

Due to the extraordinary range of properties accessible in polymeric materials, they have
come to play an essential and ubiquitous role in everyday life - from plastics and elastomers
on the one hand to natural biopolymers such as DNA and proteins that are essential for life
on the other. A simple example is polyethylene, whose repeating unit is based on ethylene
(IUPAC name ethene) monomer (Image 2.1). Most commonly, as in this example, the
continuously linked backbone of a polymer consists mainly of carbon atoms. However, other
structures do exist; for example, elements such as silicon form familiar materials such as
silicones, examples

Image 2.1 being silly putty and waterproof plumbing sealant. The backbone of DNA is in fact based

on repeating units of polysaccharides (e.g. cellulose) which are joined together by

glycosidic bonds via oxygen atoms.

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Natural polymers (from the Greek poly meaning “many”
and meros meaning “parts”) are found in many forms
such as horns of animals, tortoise shell, rosin (from
pine trees), and from distillation of organic materials.
One of the most useful of the natural polymers was
rubber, obtained from the sap of the hevea tree. (Rubber
was named by a chemist found that a piece of solidified
latex gum was good for rubbing out pencil marks on
paper. In Great Britain, erasers are still called “rubbers”.)
Natural rubber had only limited use as it became brittle in the cold
and melted when warmed. In 1839, Charles Goodyear discovered,
through a lucky accident, that by heating the latex with sulfur, the
Image 2.2
properties were changed making the rubber more flexible and
temperature stable. That process became known as vulcanization.

The first synthetic polymer, a phenol-formaldehyde polymer, was

introduced under the name “Bakelite” (Image 2.2 & 2.3), by Leo
Baekeland in 1909. Its original use was to make billiard balls. Rayon,
the first synthetic fiber was developed as a replacement for silk in
1911. Although many polymers were made in the following years, the
technology to mass produce them was not developed until World War
II, when there was a need to develop synthetic rubber for tires and
other wartime applications and nylon for parachutes. Since that time,
the polymer industry has grown and diversified into one of the fastest
growing industries in the world. Today, polymers are commonly used in
Image 2.3
thousands of products as plastics, elastomers, coatings, and
adhesives. They make up about 80% of the organic chemical
industry with products produced at approximately 150 kg of
polymers per person annually in the United States.

Furthermore, conductive polymers are organic polymers that conduct electricity. Such compounds
may be true metallic conductors or semiconductors. It is generally accepted that metals conduct
electricity well and that organic compounds are insulating, but this class of materials combines the
properties of both. The biggest advantage of conductive polymers is their processibility. Conductive
polymers are also plastics (which are organic polymers) and therefore can combine the mechanical
properties (flexibility, toughness, malleability, elasticity, etc.) of plastics with high electrical
conductivities. Their properties can be fine-tuned using the exquisite methods of organic synthesis.

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Polymers Synthesis and Property Analysis

Level of Caution
1. Bakelite

Brief Description
Bakelite is a material based on the thermosetting phenol formaldehyde resin, developed in 1907–
1909 by Belgian Dr. Leo Baekeland. Formed by the reaction under heat and pressure of phenol (a
toxic, colourless crystalline solid) and formaldehyde (a simple organic compound), generally with a
wood flour filler, it was the first plastic made from synthetic components. It was used for its
electrically nonconductive and heat-resistant properties in radio and telephone casings and
electrical insulators, and was also used in such diverse products as kitchenware, jewellery, pipe
stems, and children's toys. In 1993 Bakelite was designated an ACS National Historical Chemical
Landmark in recognition of its significance as the world's first synthetic plastic.
The retro appeal of old Bakelite products and labor intensive manufacturing
has made them quite collectible in recent years.
Image 6.1 shows the structure of bakelite.
Image 3.1

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Precautions
1. Wear safety goggles at all times in the laboratory.

2. Formalin is an irritant to the skin, eyes, and mucous membranes.

3. Phenol is toxic via skin contact. It is listed as a carcinogen.

4. Glacial acetic acid is an irritant and can cause burns on contact.

5. Work under a hood and wear gloves and protective clothing when working with these materials.

Materials Needed

Chemicals: Apparatus:
1. 25g 40% formaldehyde 1. 150-mL beaker
2. 20 g phenol 2. stirring rod
3. 55 mL glacial acetic acid
4. conc Hydrochloric acid

Procedure
First make the Phenol-formaldehyde reaction mixture by mixing 25 g 36-40%
formaldehyde + 20 g phenol + 55 mL glacial acetic acid.
Under a hood, measure 25 mL of the phenol-formaldehyde reaction mixture into a 150-mL beaker.
Place the beaker on a white paper towel.
Add 10 mL of concentrated hydrochloric acid, slowly, with stirring.
Add additional hydrochloric acid, dropwise, with stirring. (You will need approximately 2
mL of HCl.) As the polymerization point is reached, a white precipitate will form and
dissolve. At the point where polymerization begins, the white precipitate will not
dissolve. Continue to stir as the plastic forms and becomes pink in color.
Wash the plastic well before handling.

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Polymers Synthesis and Property Analysis

What actually happened

I was slightly nervous to try out something absolutely new and was uncertain of its results. I took
the chemicals given to me by Baboolal sir and followed the instructions. I took the phenol-
formaldehyde reaction mixture in a beaker, placed it over a sheet of paper. Took a test tube full of
HCl, and added it to the beaker slowly with constant stirring. And by slowly I mean I almost emptied
the test tube in about two minutes. I couldn’t figure the polymerization point as no precipitate
appeared. Thinking there’s something wrong with the procedure, I went to ask for ma’ams advice.
She asked me to indirectly heat it. Due to certain reasons, I didn’t hear indirectly and heated the
beaker over the flame for about 30 seconds. Nothing happened. Depressed, I walked away from it
wondering what to do next. And then suddenly there was this loud noise of some kind of explosion.
It was the beaker. All the contents had poured out like foam, except solid. It was light pink in color.
It had lots of pours in it and kind of looked like pumice stone. Ma’am said it happened because I’d
supplied a lot of heat by direct heating, and it seemed the most plausible explanation to it and so to
obtain a proper polymer, I modified the experimental setup after discussing it with ma’am.
I set up a large water filled beaker on a tripod stand with wire gauze and in a boiling tube took the reaction
mixture. I fixed this boiling tube using a clamp stand, half dipped in the beaker so that the contents were
evenly heated. I added the same amount HCl as before, except this time, I added a few drops after every 30
seconds. This time, after 3 minutes, I could see something suddenly happen in the boiling tube. I alerted
ma’am but again it exploded. The sudden reaction broke the boiling tube, and caused a crack in the beaker. I
collected the polymer and washed it. Its physical appearance was the same as before.

Both these experiments suggested that the reaction was extremely fast, but its
activation energy was fairly high. So no matter if its directly heated, or indirectly,
the moment it gains sufficient energy, the polymerization starts rapidly.
intermediate

High AE
energy

reactant
product

reaction progress

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For determining the optimum conditions for the synthesis of Bakelite, I decided to take a
reaction mixture in a beaker, heat it to a certain temperature (indirectly), and then add HCl
to find out the optimum temperature. I chose beaker over boiling tube, because as was
apparent by the pores, greater the surface area, safer it would be to carry out the reaction.

Temperature Observations
40-35 *C No observable changes
50-45 *C Turbidity started apearing
60-55 *C Roughly Polymerization started
75-60 *C Semi Solid appeared at the bottom of the beaker
30-25 *C At long standing, the color changed to dark pink

Property Analysis

Test Result
Flexibility Brittle
Strength Low
Bounciness Negligible
Color Dark Pink
Texture Slightly Porous
Inertness Stable in air at room temp.

Chemistry Behind it

Phenol and Formaldehyde react in the following manner to make the polymer.

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Polymers Synthesis and Property Analysis

+ +

The structure below shows the growing molecule of BAKELITE.

Level of Caution
2. POLYSTYRENE

Brief Description
Polystyrene (pronounced /ˌpɒliˈstaɪriːn/) (IUPAC Poly(1-phenylethane-1,2-diyl)),
sometimes abbreviated PS, is an aromatic polymer made from the aromatic monomer
styrene, a liquid hydrocarbon that is commercially manufactured from petroleum by the
chemical industry. Polystyrene is one of the most widely used kinds of plastic.
Polystyrene is a thermoplastic substance, which is in solid (glassy) state at room temperature, but flows
if heated above its glass transition temperature (for molding or extrusion), and becoming solid again
when cooling off. Pure solid polystyrene is a colorless, hard plastic with limited flexibility. It can be cast
into molds with fine detail. Polystyrene can be transparent or can be made to take on various colors.
Solid polystyrene is used, for example, in disposable cutlery, plastic models, CD and
DVD cases, and smoke detector housings. Products made from foamed polystyrene
are nearly ubiquitous, for example packing materials, insulation, and foam drink cups.
Polystyrene can be recycled, and has the number "6" as its recycling symbol.
Polystyrene does not biodegrade, and is often abundant as a form of pollution
in the outdoor environment, particularly along shores and waterways.
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Precautions
1. Wear safety goggles at all times in the laboratory.

2. Styrene may pose health risks if it comes in contact with the body.

3. Styrene resin is sticky, so use gloves.

4. Work under a hood and wear gloves and protective clothing when working with these materials.

Materials Needed
Chemicals: Apparatus:
1. Vinyl Benzene (Styrene Casting Resin) 1. Test tubes
2. Methyl ethyl ketone (Casting resin catalyst) 2. Stirring rod
3. Thermostat
4. Measuring Cylinder
5. a 5 mL Syringe
6. Stop Watch

Procedure
Take 4 clean, numbered test tubes and to each add 3mL of Vinyl Benzene.
Fill the syringe with methyl ethyl ketone.
Start the stop watch.
Make the volume of Vinyl Benzene in test tube one equal to 5 mL.
Now note the time as you add 5 divisions of the syringe, i.e. 0.5 mL to test tube one and stir it well.
Repeat the above 2 steps with 4.5 mL of Vinyl Benzene and 1.0 mL of methyl
ethyl ketone, in the second test tube and so one.
Place these in the thermostat with temperature set to 40 *C.

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Polymers Synthesis and Property Analysis

What actually happened

Concentration of catalyst Time taken to cure

0.5 3 hours 14 minutes
1.0 2 hours 18 minutes
1.5 2 hours 10 minutes
2.0 2 hours 3 minutes

3.5
3
2.5
2
Time
1.5
1
0.5
0
0 0.5 1 1.5 2 2.5

Concentration

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Property Analysis

Test Result
Flexibility Low
Strength Medium
Bounciness Negligible
Color Yellowish, Transparent
Texture Smooth
Inertness Stable in air at room temp.

Chemistry Behind it

The chemical makeup of polystyrene is a long chain hydrocarbon with every other carbon connected to a
phenyl group (the name given to the aromatic ring benzene, when bonded to complex carbon substituents).
Polystyrene's chemical formula is (C8H8)n; it contains the chemical elements carbon and hydrogen.
Because it is an aromatic hydrocarbon, it burns with an orange-yellow flame, giving off soot, as opposed to
non-aromatic hydrocarbon polymers such as polyethylene, which burn with a light yellow flame (often with a
blue tinge) and no soot. Complete oxidation of polystyrene produces only carbon dioxide and water vapor.
This addition polymer of styrene results when vinyl benzene styrene monomers (which
contain double bonds between carbon atoms) attach to form a polystyrene chain (with
each carbon attached with a single bond to two other carbons and a phenyl group).

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REFERENCES
http://www.google.co.in/webhp?hl=en
http://en.wikipedia.org/wiki/Polystyrene
http://en.wikipedia.org/wiki/Styrene
http://en.wikipedia.org/wiki/Epoxy
http://en.wikipedia.org/wiki/Bakelite
http://papers.ssrn.com/sol3/papers.cfm?abstract_id=1420502
http://answers.yahoo.com/question/index?qid=20090717144012AAKmCyb
http://inventors.about.com/od/pstartinventions/a/plastics.htm
http://www.barrule.com/workshop/images/info/foams/index.htm
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2430229/
http://www.pslc.ws/mactest/styrene.htm
http://www.americanchemistry.com/s_plastics/sec_pfpg.asp?CID=1421&DID=5213

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