1. Experiment 25: ORGANIC POLYMERS: THE SYNTHESIS OF NYLON

2. Objectives:  To synthesize Nylon 6,10 from hexamethylene diamine and sebacoyl chloride.  To determine the length of the Nylon formed using a simple mathematical calculation.

3. Synthesis of an Amide Carboxylic Acid n Reacting a carboxylic acid with an amine yields an amide. Water is a by-product, and this reaction is slow without a catalyst. amineamide

4. Synthesis of an Amide amineAcid chlorideamide n By using a carboxylic acid chloride, a more reactive carboxylic acid derivative, the rate of reaction can be increased. In this reaction, HCl is the by-product.

5. Mechanism

6. Synthesis of Nylon 6,10 n In order to make a polyamide, such as Nylon 6,10, the amine molecule must have a –NH 2 group at each end, and the acid chloride must have a –COCl group at each end. n The diamine and the diacid chloride bond together, end-on-end, to form very long chains. n Nylon 6,10 is made from hexamethylene diamine (the diamine) and sebacoyl chloride (the diacid chloride). Hexamethylene diamine Sebacoyl chloride

7. Synthesis of Nylon 6,10 Hexamethylene diamine Sebacoyl chloride

8. Classifications of Synthetic Polymers n Synthetic polymers are classified by their method of synthesis. Chain-growthStep-growth polystyrenePolyamides (nylon) Synthetic Method

9. Natural Organic Polymers n Proteins n hair, skin, tissue n Polysaccharides n cellulose, starch n Polynucleotides n DNA, RNA

10. Synthetic Organic Polymers  Nylons  Polyesters  Acrylics  Polyvinyls Plastic sheeting and plumbing materials  Polystyrenes Insulating materials

11. Solubilities of Polymers n Polystyrene is a linear polymer made from styrene monomers. Styrene Polystyrene Polystyrenes are used extensively for insulation materials, such as styrofoam. Tiny bubbles of HCFC gases are trapped between the flat polymer chains, and these gases are poorer thermal conductors than solids or liquids. Heat must travel along the polymer chains, making a number of detours around these trapped gases. This increases the usefulness of polystyrenes for insulation materials.

12. Solubilities of Polymers Note that: n polystyrene contains only carbon and hydrogen atoms. n nylon contains carbon, hydrogen, nitrogen, and oxygen atoms. n carbohydrates have carbon, hydrogen, and oxygen.

13. Safety Concerns  CAUTION: All chemicals are hazardous to the skin and eyes. Safety goggles and gloves are required during the experiment!!!

14. WASTE MANAGEMENT  Pour all waste from synthesis and solubility tests into container labeled “ORGANIC WASTE (Polymers)”