A LABORATORY PROTOCOL ON THE CHEMISTRY EXPERIMENT CARRIED OUT BY BELGIAN STUDENTS OF ZAVO (BELGIUM)

Introduction

We will focus on Nylon: a very strong polymer with exceptional flexibility and very strong strength against stretching, which is why it is widely used in cords, threads and especially in the textile industry.

This is a nylon monomer:

research question: 

How long can you make the nylon wire with a given amount of chemical products?

Hypothesis

Nylon is a polymer. It means that the wire you are going to make is a sequence of identical molecules called monomers. You will need 2 or more materials to have a chemical reaction. After you combine those materials, you will have precipitation. If you grab the precipitation with tongs and you pull it out of the erlenmeyer flask, you will have a nylon wire.

Requirements

  • 1,6- diaminohexane 
  • water
  • sebacoylchloride (Instead of decanedioyl dichloride (sebacoyl chloride) one can also use hexanedioyl dichloride (adipoyl chloride), this gives you nylon-6,6 instead of nylon-6,10.)
  • heptane
  • sodium hydroxide 
  • graduated cylinders
  • measuring cup
  • tweezers

Safety

1,6- diaminohexane Hazard302: Harmful when you swallow it312: Harmful after contact with your skin314: Causes serious burning wounds and eye injuries335: May cause irritation of the airway
Precaution 280.1+3: Wear protective clothing 301+330+331: After swallow → rinse your mouth. Do not induce vomiting.302+352: After contact with your skin, wash with a lot of water and soap305+351+338: After contact with your eyes, keep rinsing for a few minutes. Remove contact    .                          lenses, if possible. Keep rinsing
sebacoylchlorideHazard302: Harmful when you swallow it314: Causes serious burning wounds and eye injuries
Precaution 280.1+3: Wear protective clothing 301+330+331: After swallow → rinse your mouth. Do not induce vomiting.305+351+338: After contact with your eyes, keep rinsing for a few minutes. Remove contact    .                          lenses, if possible. Keep rinsing
heptaneHazard225: Highly flammable liquid and vapor304:May be fatal if swallowed and enters airways315:Causes skin irritation.336:May cause drowsiness or dizziness.410:Very toxic to aquatic life with long lasting effects.
Precaution 210:Keep away from heat / sparks / open flames / hot surfaces and other ignition sources. – Do not smoke.273:Avoid release into the environment.301+310:IF SWALLOWED: “→ Immediately call a poison control center or a doctor331:DO NOT induce vomiting302+352:IF ON SKIN: Wash with plenty of soap and water.403+235:Keep in a well-ventilated place. Keep cool.
sodium hydroxide Hazard314: Causes serious burning wounds and eye injuries
Precaution 280.1+3: Wear protective clothing301+330+331: After swallow → rinse your mouth. Do not induce vomiting.305+351+338: After contact with your eyes, keep rinsing for a few minutes. Remove contact    .                          lenses, if possible. Keep rinsing

Method

  1. Place 50 ml of heptane in a small beaker and dissolve 1 ml of sebacoyl chloride in it
  1. Place 50 ml of water in an erlenmeyer flask and add 0.75 g of sodium hydroxide and 1.1 g of diamine
  1. Carefully add the contents of the Erlenmeyer flask to the beaker

!!  Pay attention: wear gloves as this substance is corrosive  !!.

  1. With the help of tweezers you can now pull the nylon out of the liquid, at the contact surface of the two fluides. You can twist the nylon thread around the tweezers, try to be gentle.
  1. Now the match starts, who can pull the longest nylon thread without breaking it?

Reaction

Discussion

A copolymer is formed from two monomers. In this polymerization

reaction peptide bonds are formed. These are CN connections. With nylon

this is done as follows:

We see that HCl gas is formed by cleavage of Cl at the sebacoylchloride  and H with 1,6-hexanediamine. The NH group of 1,6-hexanediamine then joins one bind to the C = O bond of sebacoylchloride. This creates the peptide bonds.