Introduction

Solutions of 1,6-hexanediamine and sebacoyl chloride are poured carefully into the same container.  Nylon polymer forms at the interface of the two layers and can be pulled continuously from the solution in the form of a "rope" and wound around a cylinder.

  Equations

H2N(CH2)6NH2 + ClCO(CH2)8COCl → —[HN(CH2)6NH-CO(CH2)8CO)]n— + nHCl

  Prior to Lecture  (prep time ~ 20 min.)

  1. Prepare 0.5M H2N(CH2)6NH2 (hexamethylene diamine, or 1,6-hexanediamine) in 0.5M NaOH.  Use 3.0g H2N(CH2)6NH2 (place reagent bottle in hot water to melt the solid) and 1.0g NaOH in 50mL distilled water.  Food coloring or phenolphthalein may be added to color this layer..
  2. Prepare 0.2M ClCO(CH2)8COCl (sebacoyl chloride) in hexane:
    •  2mL sebacoyl chloride in 50mL hexane
  3.  Assemble the following equipment:   
  • 150mL or 250mL beaker 
  • cylinder-in-stand apparatus
  • forceps
  • stir rod
  • gloves
  • goggles
  • water
  • 400mL beaker for waste 

To Conduct Demonstration:  

  1. Pour 1,6-hexanediamine into a beaker to a depth of about 1/2".
  2. Tilting the beaker, carefully pour a layer of sebacoyl chloride down the side of the beaker (or down a stirring rod) to cover the 1,6-hexanediamine.
  3. Nylon is formed at the interface between the two layers.  Using forceps, pick up the nylon and lift it slowly and smoothly from the beaker.  A continuous "rope" of nylon will form as you pull it away.  Wrap the end of the rope around a cylinder and slowly turn it.
  4. Rinse nylon well with distilled water before touching it.

Safety and Disposal 

Wear gloves and avoid getting these solutions on your hands.  Rinse the nylon before touching it.