CHEM35.1 E4 Free-Radical Polymerization of Styrene
CHEM35.1 E4 Free-Radical Polymerization of Styrene
CHEM35.1 E4 Free-Radical Polymerization of Styrene
1 - TEG
I. Abstract
Styrene is an important precursor in the production of industrial products and resins. Through free-radical
polymerization involving multiple steps, which are initiation, chain propagation, chain transfer, and
termination, polymers can be produced from the monomers of the said compound. In this experiment, two
major steps were observed. First was the removal of the inhibitor, tert-butyl-catechol, in commercial styrene
by means of acid-base extraction in order to initiate the chain reaction, which is then followed by the actual
polymerization with the addition of an initiator, tert-butyl-peroxybenzoate. A translucent, white substance
was formed, having an odor similar to rugby, believed to be polystyrene.
II. Keywords: free radicals, polymerization, styrene, polystyrene, inhibitor
III. Introduction
In nature, elements bond ionically or
covalently to form compounds. On the other hand,
chemical bonds are broken down either
heterolytically or homolytically. Heterolytic bond
cleavage forms ions back while hemolytic bond
cleavage forms radicals, where only one electron
is associated. Radicals are important in certain
synthesis such as halogenations of alkanes in
which in ordinary reactions cannot be produced.
In this experiment, radicals play an important part
in achieving a desired product of a process called
polymerization. It is a process of reacting
monomer molecules together to form polymer
chains. It is a widely used process in most
industries, and these polymers have a wide
variety of uses.
Styrene, also known as ethenylbenzene,
vinyl benzene, or phenylethene, is primarily used
in the production of polystyrene plastics and
resins. In the experiment, the free-radical
polymerization of styrene is used to produce
polystyrene. This method is widely observed to
induce chain-reaction polymerization.
Freeradical polymerization proceeds via multiple
steps: chain initiation, chain propagation, chain
transfer, and chain termination. Chain initiation
involves formation of reactive radicals. Initiating
radicals may be provided via thermal
decomposition of added initiators. Typical
butyl-catechol,
acting
as
inhibitor
of
polymerization was removed by drying the styrene
with anhydrous CaCl. The reaction proceeds as:
During the propagation stage, the tert-butylperoxybenzoate is broken down into tert-butyl-
the other one, yet do not. Explain the basis for this
selectivity.
The oxygen radical, an initiator, tends to
add on the phenyl-bearing carbon because the
lone pair of the oxygen can form conjugated pi
bonds with the aromatic ring. This creates a very
stable molecule and leaves the other carbon open
for radical addition by other styrene units.
6. Would you expect the polystyrene generated in
this experiment to be atactic, syndioatactic or
istactic. Explain.
In the experiment, the basis for tacticity
was the over-all appearance of the formed
polystyrene, which was amorphous and noncrystalline, and atactic polymers usually appear
this way.
7. What are thermosetting polymers? What is the
difference versus thermoplastic polymers?
Thermosetting polymers or thermosets is
a polymer that cannot be irreversibly cured, once
they have molded to their final form they can
never be melted or shaped differently. These type
of polymers have crosslinks between its chains
which form an irreversible chemical bond between
chains preventing the movement of chains. The
only difference of thermoset polymers with
thermoplastic polymers is the structure.
Thermoplastic polymers do not have cross-link
between chains so when it is subjected to heat its
chains are free to move past each other.