NYLON ROPE BY INTERFACIAL CONDENSATION THEORY: Amides are produced when an acid chloride reacts with an amine. The student should be able to draw the mechanism for this reaction. : O: R C H .. : Cl .. + .. N : O: R' R C H acid chloride .. N + R' HCl H amine amide The byproduct HCl acid will consume half of the basic amine reagent, so two moles of amine reagent must be used per mole of acid chloride. Alternately, NaOH can be added to an aqueous amine phase to consume the byproduct HCl, while the acid chloride remains dissolved in an organic phase. The amine migrates into the organic phase to react with the acid chloride and the HCl produced in the organic phase, migrates to the aqueous phase where it is neutralized. NaOH is a good nucleophile and would preferentially react with the acid chloride (producing a carboxylate salt) if it were soluble in the organic phase but NaOH is insoluble in the organic phase. Nylon 6,6 [Dupont’s trade name for poly(hexamethylene adipamide)] is produced when hexamethylenediamine (HMDA) reacts with adipoyl chloride. The reaction can be carried out in a single phase (bulk polymerization) or as in this experiment, at the interface between two separate phases. adipoyl chloride (hexanedioyl chloride) Nylon rope pulled from the interface. HMDA + NaOH in water O Cl C hexamethylenediamine (HMDA) O CH2 4 C H2N + CH2 Cl - 6 NH2 HCl Nylon 6,6 at interface O O Adipoyl chloride in CH2Cl2 Cl C CH2 4 C HN CH2 6 NH2 poly(hexamethylene adipamide) (Nylon 6,6) BB/CH605/Nylonropexp.doc Page 1 of 2 NYLON ROPE BY INTERFACIAL CONDENSATION PROCEDURE: 1. Prepare reagent a) and b) in separate flasks: a) Prepare 5% adipoyl chloride in CH2Cl2. [Caution: Adipoyl chloride is corrosive. Use in a fume hood] b) Prepare an aqueous solution that is 5% HMDA and 2%w NaOH. 2. Pour the denser organic solution into a small beaker first. 3. Slowly and carefully pour an equal volume of the aqueous solution on top of the organic layer. Do not allow the solutions to mix when combining them. You should obtain two separate layers. A thin white layer will appear at the interface when the two solutions are brought into contact. This is Nylon 6,6 formed by interfacial condensation. 4. Use a wire or tweezers to slowly pull the white solid layer up out of the solution and a long fiber is drawn. 5. Rinse the fibers under running water and study their feel and strength. QUESTIONS: 1. Show the mechanism of amide formation during reaction of an acid chloride and an amine. 2. Identify the polymerization type as one of the following: chain growth, step growth (condensation or rearrangement) or ring scission. 3. Identify the polymerization technique as one of the following: bulk, solution, suspension or emulsion. 4. Identify the polymer type as either thermoplastic or thermoset. 5. Identify the end use of the polymer as one of the following: rubber (elastomer), plastic (resin), fiber, coating, adhesive (sealant), film, composite, cellular or biopolymer. BB/CH605/Nylonropexp.doc Page 2 of 2