Chemistry Project

CONTENTS

Acknowledgements -------------------------------------------------------------

Aim of the Project -------------------------------------------------------------

General Overview -------------------------------------------------------------

Brief Theory, Synthesis and Analysis of3 ------------------------------
1. Bakelite
2. Polystyrene
3. Epoxy Resin

Result ------------------------------------------------------------------------------

References






Acknowledgments
I am very grateful to my chemistry teacher, Ms. Sadhana Bhargava, 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 single
project. Even though what I initially wanted to make (conductive Polymers)
wasnt 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 wasnt for her passion to teach. I would also like to thank
our lab assistant, Mr. Babe Lal for all the timely help he provided. Apart from this,
I would like to thank all those people whove published their useful work on
the internet, without which, I perhaps wouldnt 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**
3. Epoxy Resin**
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 ethane) 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 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 glycoside bonds
via oxygen atoms.
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 heave 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 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
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.
1. Bakelite

Brief Description
Bakelite is a material based on the
thermosetting phenol formaldehyde resin,
developed in 19071909by Belgian Dr. Leo
Baekeland. Formed by the reaction under
heat and pressure of phenol (a toxic, colorless 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, jewelry, pipe stems, and children's toys. In 1993 Bakelite was
designated an ACS National Historical Chemical Landmark in recognition of its
significance as the worlds 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.



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, drop wise, 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.
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 Bagola 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 couldnt figure the polymerization point as no
precipitate appeared. Thinking theres something wrong with the procedure, I
went to ask for maams advice. She asked me to indirectly heat it. Due to
certain reasons, I didnt hear indirectly and heated the beaker over the flame
for about 30seconds. 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. Maam said it happened because Id 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 maam. 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 every30 seconds. This time, after 3 minutes, I could see
something suddenly happen in the boiling tube. I alerted maam 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.




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.

Property Analysis

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

2. POLYSTYRENE
Brief Description

Polystyrene (pronounced / plistarin/) (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 melding or extrusion), and becoming solid
again when cooling off. Pure solid polystyrene is a colourless, hard plastic with
limited flexibility. It can be cast into olds with fine detail. Polystyrene can be
transparent or can be made to take on various colours. 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 alongshore and waterways.
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 Syringe6. 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

What actually happened


Property Analysis

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).

3. EPOXY RESIN
Brief Description
Epoxy or polyepoxide is a thermosetting polymer formed from reaction of an
epoxide "resin" with polyamine "hardener". Epoxy has a wide range of
applications, including fiber-reinforced plastic materials and general purpose
adhesives. Credit for the first synthesis of biphenyl-A-based epoxy resins is shared
by Dr. Pierre Capstan of Switzerland and Dr. S.O. Greenlee of the United States in
1936.The applications for epoxy-based materials are extensive and include
coatings, adhesives and composite materials such as those using carbon fiber
and fiberglass reinforcements (although polyester, vinyl ester, and other
thermosetting resins are also used for glass-reinforced plastic). The chemistry
of epoxies and the range of commercially available variations allows cure
polymers to be produced with a very broad range of properties. In general,
epoxies are known for their excellent adhesion, chemical and heat resistance,
good-to-excellent mechanical properties and very good electrical
insulating properties. Many properties of epoxies can be modified (for example
silver-filled epoxies with good electrical conductivity are available, although
epoxies are typically electrically insulating). Variations offering high thermal
insulation, or thermal conductivity combined with high electrical resistance for
electronics applications, are available.
Precautions


1. Wear safety goggles at all times in the laboratory.
2. The hardner, Triethylenetetramine may cause allergic reactions. Wear
gloves at all times.
3. Both the chemicals are sticky so avoid contact with bare hands.
4. Work under a hood and wear gloves and protective clothing
when working with these materials.
Materials Needed
Chemicals: Apparatus:
1. Epoxy Resin (formed by reaction between + 1. Test tubes
epichlorohydrin and bisphenol-A) 2. Stirring rod
2. Hardener (Triethylenetetramine) 3.
Thermostat
4. Measuring
Cylinder
5. a 5 mL Syringe
6. Stop Watch

What actually happened?

at 40 *C

at 40 *C




at 7 *C










Property Analysis

Chemistry Behind it
Epoxy is a copolymer; that is, it is formed from two different chemicals. These are
referred to as the "resin" and the "hardener". The resin consists of monomers or
short chain polymers with an epoxide group at either end. Most common epoxy
resins are produced from a reaction between epichlorohydrin and biphenyl-A,
thought he latter may be replaced by similar chemicals. The hardener consists
of polyamine monomers, for example Triethylenetetramine (TETA). When these
compounds are mixed together, the amine groups react with the epoxide
groups to form a covalent bond. Each NH group can react with an epoxide
group, so that the resulting polymer is heavily cross-linked, and is thus rigid
and strong. The process of polymerization is called "curing", and can
be controlled through temperature and choice of resin and hardener
compounds; the process can take minutes to hours. Some formulations benefit
from heating during the cure period, whereas others simply require time, and
ambient temperatures.

RESULT
Bakelite
Its optimum synthesis temperature range was found to be 70-80 *C. Its
synthesis requires high activation energy but the reaction is kinetically very fast.
Polystyrene
It cures faster at higher concentrations of the catalyst. The strength of the
polymer was independent of the concentration ratio of the resin
and catalyst. Its kinetics are complex as its concentration v/s curing time
graph was found to be irregular. The optimum temperature range for
synthesis of this polymer was found to be over 40 *C at the tested
concentrations of the catalyst.
Epoxy
Resin It cures faster at high concentrations of its catalyst. It also cures
faster at higher temperature. The strength of the polymer was independent of
the concentration ratio of the resin and catalyst. The reaction maybe following
first order kinetics as the concentration v/s curing time graph was found to be
close to linear. The optimum temperature range for synthesis of this polymer was
found to be 5-10 *C at the tested concentrations of the catalyst.


++
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=52
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