Chemistry 101

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PREPARATION OF NYLON Revised 3/24/2006

Nylon is one of many man-made materials called plastics. Chemically, plastics are composed
of chain-like molecules of high molecular weight, called polymers, which usually have been
built up from simpler chemicals called monomers. A different monomer or combination of
monomers is used to manufacture each different type or family of polymers. There are many
polymers around us that you have heard of or seen. Examples are Teflon, nylon, Dacron,
polyethylene, polyester, Orlon, epoxy, vinyl, and boat resin. Certainly, polymers have made a
great impact on our society. They are rapidly replacing many metals for making objects and man
made polymeric textiles are replacing natural fibers for making cloth. Of course, in the process
of creating these materials, a problem has arisen in the disposal of them.

Chemical Structure of Polymers

Basically a polymer is made up of many repeating molecular units formed by sequential
addition of many monomer molecules to each other. Many monomer molecules of A, say one
thousand to one million, link themselves together to form a new gigantic polymeric molecule:

Many A etc A A A A A etc

monomer polymer molecule
molecules

An example of this type of polymer is the well-known polyethylene, as shown on the next
page. In this case the monomer is ethylene. Countless numbers of these molecules link
themselves together into a long chain polymeric molecule by breaking the double covalent bond
and creating new single covalent bonds between the monomers.

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 Preparation of Nylon
H H H H H H

many C C etc C C C C etc

H H H H H H
ethylene monomer polyethylene polymer

This reaction is promoted by heat, pressure and a chemical catalyst. Polypropylene is produced by
reacting propylene monomer under similar conditions, as shown below:

H H H H H H

many C C etc C C C C etc

CH3 H CH3 H CH3 H

polypropylene monomer polypropylene polymer

Note that CH3's and H's alternate from carbon to carbon in this polymer.

Another type of polymer uses two different monomer molecules, A and B, to produce a polymer
of alternating A and B. Again this polymer may have one thousand to one million units linked
together.
many A + many B etc A B A B A B etc
monomers polymer molecule

An example of this type of polymer is nylon.

O O O O

Cl C (CH2)4 C Cl H N (CH2)6 N H Cl C (CH2)4 C Cl

H H

loss of loss of
HCl HCl

O O O O

etc C (CH2)4 C N (CH2)6 N C (CH2)4 C etc

H H

amide amide

Nylon

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Note the following shorthand used in the structures above:

H H H H

(CH2)4 is shorthand for C C C C

H H H H

H H H H H H

(CH2)6 is shorthand for C C C C C C

H H H H H H

In this reaction, HCl is lost and a covalent bond is formed in its place. The new substance is
given the trade name nylon, but chemically is known as a polyamide because of the type of
linkage which occurs in regular intervals:

O H

C N

an amide linkage
This type of linkage is extremely important in nature because of its presence in protein or
polypeptides. Proteins are gigantic polymeric substances made from monomer units of amino
acids. A generalized structure of an amino acid monomer is shown below. There are 20
different possibilities for R.
O

H N CH C OH

H R
General structure for amino acid

These amino acids can be linked together by means of a chemical catalyst, called an enzyme.
An enzyme is a protein that has the specific role of acting as a biological catalyst. With the 20
different possibilities for the R group, one can imagine the countless numbers of ways amino
acids can be fastened together with the amide linkage. Thus, many different possible proteins
can exist, and it is easy to begin to appreciate how important these types of polymeric substances
are in nature.

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Experimantal Introduction
In this experiment, you will use adipoyl chloride (B) dissolved in cyclohexane and add this
carefully to hexamethylenediamine (A) dissolved in water. These liquids will not mix, and two
layers will form. At the point of contact (interface) between the layers, the nylon will form. You
can then draw it out to form a long strand of nylon. Imagine how many molecules have been
linked together in this long strand! It is a fantastic number. The molecular weight of the
polymer may approach one million! The reaction scheme for the formation of nylon from A and
B is shown again below:

O O O O

Cl C (CH2)4 C Cl H N (CH2)6 N H Cl C (CH2)4 C Cl

H H
B A B

loss of loss of
HCl HCl

O O O O

etc C (CH2)4 C N (CH2)6 N C (CH2)4 C etc

H H

amide amide

Nylon

Solution A
5% solution of hexamethylenediamine (A) in water, to which has already been added 10
drops of 20% sodium hydroxide.

Solution B
5% solution of adipoyl chloride (B) in cyclohexane.

Both solutions can be found in the Working Hood in the lab opposite the Waste Hood.

NOTE CAREFULLY: You must wear gloves while carrying out this experiment!!!
Dispose of all liquids in the waste containers, which have been provided in the hoods.
Dispose of the nylon polymer in the designated waste jar.

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Experimental Procedure
Pour 10 mL of solution A into a 50 mL beaker. To this solution carefully pour 10 mL of
solution B down the wall of the slightly tilted beaker. Two layers will form (see drawing below)
and there will be an immediate formation of a polymer film at the liquid-liquid interface.

Place the beaker on a piece of paper towel. Using a copper wire hook (a six-inch piece of
wire bent at one end) gently free the walls of the beaker from polymer strings. Then hook the
mass at the center, and slowly raise the wire so that polyamide forms continuously, producing a
rope, which can be drawn out for many feet. You can break the strand by pulling it at a faster
rate. Lay the rope on the paper towel to dry.
With your piece of wire, vigorously stir the remainder of the two-phase system to form
additional polymer. Decant the liquid into the waste container. (Decanting is separating a liquid
from solid by carefully pouring the liquid into a separate container.) Place the polymer
remaining in the beaker on the paper towel to dry.
Have your instructor approve your polymer and initial below. Squeeze your polymer dry
with paper towel and discard in the appropriate waste container.

____________ Initials

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Questions

1. On the basis of the examples given, suggest the structures of the polymers, which would be
produced from the following monomers:

F F

many C C Teflon

F F

H H

many C C polystyrene

H H

many C C polyvinyl chloride

Cl H

2. Give the structure formed by linking 3 amino acids together. Remember that water (H2O)
must be removed when forming the polymer.