Synthesis of Nylon

Background
Nylon is a polymer (specifically polyamide) that can be used commercially as rope, thread, and textiles. It is a condensation polymer, which means that during its synthesis, water is also formed. Nylon was discovered in 1938 at the DuPont company. In this reaction, HCl is formed as a byproduct. Reaction
O S O Cl + HO O OH Cl O O Cl

Cl

H2N
O Cl O 10 carbons N H 6 carbons H N O 10 carbons O N H 6 carbons H N O 10 carbons

NH2

O Cl

Reaction forming amide repeats n times, forming nylon 6.10 with properties completely different from the starting materials (the structure below is the repeating unit):
O N H Nylon 6.10 H N n

Pre-lab questions: 1. Why do you need to prepare the acid chloride from the acid before reacting with the amine? Could you just mix the acid and the amine to form Nylon? 2. Why is the aqueous solution added to the dichloromethane solution, rather than the reverse?

Table of Reagents
Name Molecular Formula C10H18O4 SOCl2 C3H7NO CH2Cl2 H2O CH4O C6H16N2 NaOH Molecular Mass (g/mol) 202.25 118.97 73.10 84.93 18.02 32.04 116.21 40.00 m.p. (C) 133-137 -----61 -97 0 -98 42-45 318 b.p. (C) Density (g/mL) Molarity Safety Guidelines (mol/L) ----------------------------3M None Corrosive/ Lachrymator Teratogen/ Irritant Cancer Suspect Agent/ Irritant None Flammable Liquid/ Toxic Flammable Solid/ Corrosive Corrosive/ MoistureSensitive

Sebacic Acid Thionyl Chloride N,N-Dimethylformamide Dichloromethane Water Methanol Hexane-1,6Diamine Sodium Hydroxide

273/ ----50mmHg 79 1.631 153 39.8-40 100 64.7 204-205 1388 0.944 1.325 1.000 0.791 ----1.090

Procedure
Be very careful with thionyl chloride. 1. First prepare the acid chloride according to the microscale procedure in the text. In your setup, do not put a septum on the test tube with the damp cotton (it would create a closed system). 2. Dissolve the acid chloride in methylene chloride and pour the acid chloride solution into a small greased beaker. 3. Then prepare the aqueous amine solution following the procedure in the text. 4. Carefully place the aqueous solution on top of the methylene chloride solution. Do not add the aqueous solution quickly or mix the two solutions. The reaction will only take place at the interface where the two solutions contact one another. Avoid jostling the container. 5. Use tweezers to pull out the Nylon SLOWLY. If you are careful, the Nylon will continue to form as you pull and you can obtain a very long strand (It is a challenge how long can you make it?). Wrap the strand around the outside of a beaker. Be careful to avoid contact of the chemicals with your skin (Wash immediately). Once you are satisfied with the length of the strand, wash it with water and methanol. Again, be careful and wash your hands after touching the Nylon. 6. Turn in your Nylon strand to your TA. Length contest?? Post-lab question: Why is it impossible to determine the % yield of the polymerization reaction?