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Demonstration Experiment on Video

Synthesis of Nylon 6  (Perlon)

Objective: Polymerization

Peter Keusch






German version



Chemicals:
e - caprolactam
sodium


Apparatus and glass wares:
beaker 25 mL
tripod and gaze
Bunsen burner
glass stirring rod
forceps
knife


Hazards and safety precautions:

Sodium reacts violently with water, liberating and igniting hydrogen. Flammable solid. Causes burns on contact. May cause serious damage to the eyes. Harmful by ingestion, inhalation and skin contact.

Safety glasses and protective gloves required. Protect from air and water. Do not use water extinguishers on sodium fires! Always wear safety glasses when working with sodium. If cutting solid sodium, remove any protective oil and cut the solid cleanly with a knife. Return all traces of sodium to the storage vessel - any small pieces of sodium left on the bench will react with moisture in the air to form sodium hydroxide which is very corrosive.



Experimental procedure:


10 g of  e - caprolactam are placed into a 25 mL beaker. Using a glass rod a small piece of sodium (approx. 0.01 g) is pressed into the caprolactam. The melting of the mixture occurs with reduced burner flame. Afterwards the liquefied materials are heated to boiling. The deep brown molten mass is cooled down for 5 minutes. The mixture will become much more viscous. Fibers are drawn by dipping a glass rod into the polymer and rapidly drawing out the solidifying material of the beaker.





Video clip (Download RealPlayer .rm file)


Discussion:

The induction of the lactam polymerization occurs in two steps. Caprolactam first reacts with Na to give lactam anion  (1).  In the second step of the initiation process, the lactam anion (the activated monomer) attacks the carbonyl carbon of caprolactam and adds to it. Ring-opening leads to the formation of N-caproylcaprolactam anion  (2).  Thus another species is generated that can react again in the same manner. This happens over and over to produce a long chain of perlon  (3).


Anionic, ring-opening polymerisation


Reference:
Macrolab Experiment - Making Nylon 6 and 6,10


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