Chm 123L Lab 10 Due November 26

Polymerization

In this lab, you will prepare Nylon. Specifically, Nylon 6-10. Nylon is a polymer of 1,6-diaminohexane and sebacoyl chloride. When mixed, amide bonds form, linking the individual monomer units together.

This experiment is a modification of the so-called “Nylon rope trick.”

Carry out the experiment with a partner.

Safety

The compounds used in this experiment are irritiating and caustic. Wear gloves at all times when handling them – including when you are handling the polymer.

Dispose of the organic reagents in the organic waste and aqueous reagents in aqueous waste.

Procedure

Clamp a test tube, graduated cylinder or beaker firmly in place. To this add 15 mL of an aqueous solution that is 0.5M in 1,6-diaminohexane and 0.5M sodium carbonate. Allow the contents to settle.

Now, very slowly, pipet 15 mL of a 0.2M solution of sebacoyl chloride in hexane down the sides of the vessel such that it forms a layer on top of the diaminohexane layer. You want to do this in such a way as the two layers do not mix.

Observe the vessel for 60 seconds and note the formation of a milky boundary between the layers.

Insert a copper wire into the boundary and use it to, slowly, draw out a polymer thread. With your partner, collect the thread.

Repeat this procedure three times. Record the length of unbroken rope you are able to collect.

Take the longest piece of unbroken rope you make and place it, gently, on a piece of filter paper in a Buchner funnel. Apply vacuum and wash extensively with water. Allow the rope to air dry and record a weight. Is Nylon 6-10 soluble in methanol? Acetone? Ether?

Questions

1. What is the structure of 1,6-diaminohexane? Sebacoyl chloride? 2. What is the structure of Nylon 6-10? 3. What sort of functional group holds the polymer together? 4. If 1,6-hexanediol were used instead of 1,6-diaminohexane, what would be the structure? Would the polymer have the same properties?

5. What would happen if you simply swirled the two layers together rapidly?