Synthesis of Nylon 6,10: A Laboratory Experiment on Organic Polymers, Study notes of Waste Management

Download Synthesis of Nylon 6,10: A Laboratory Experiment on Organic Polymers and more Study notes Waste Management in PDF only on Docsity! CHM130 Organic Lab ORGANIC POLYMERS: THE SYNTHESIS OF NYLON Objectives: • To synthesize Nylon 6,10 from hexamethylene diamine and sebacoyl chloride. • To determine the length of the Nylon formed Safety Concerns CAUTION: All chemicals are hazardous to the skin and eyes. Safety goggles and gloves are required during the experiment!!! WASTE MANAGEMENT: Pour all waste from synthesis and solubility tests into container labeled Polymer waste located in the hood. Background - Synthesis of an Amide 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. R N H H + C O Cl R R N H C O R + HCl amine Acid chloride amide Synthesis of Nylon 6,10 • In order to make a polyamide, such as Nylon 6,10, the amine molecule must have a –NH2 group at each end, and the acid chloride must have a –COCl group at each end. • The diamine and the diacid chloride bond together, end-on-end, to form very long chains. • Nylon 6,10 is made from hexamethylene diamine (the diamine) and sebacoyl chloride (the diacid chloride). N H H CH2CH2CH2CH2CH2CH2 N H H C O Cl CH2CH2CH2CH2CH2CH2CH2CH2 C O Cl H N CH2CH2CH2CH2CH2CH2 H N C O CH2CH2CH2CH2CH2CH2CH2CH2 C O H N CH2CH2CH2CH2CH2CH2 H N HCl H N (CH2)6 H N C O (CH2)8 C O + + Nylon 6,10 = n n Hexamethylene diamine Sebacoyl chloride CHM130 Organic Lab 2 | P a g e • Since HCl is a by-product of this reaction, we use a diamine solution prepared in an equimolar equivalent of aqueous NaOH. The NaOH reacts with the HCl to form salt and water. • This prevents the HCl from causing side reactions, such as the possible addition of HCl to a C=C if one is present in the molecule. Mechanism hemical Equation and Physical ConstantsC Experimental Procedure- (Synthesis of Nylon) N H CH2CH2CH2CH2CH2CH2 N H C Cl CH2CH2CH2CH2CH2CH2CH2CH2 C O Cl + hexamethylenediamine MF: C6H16N2 MW: 116.20 g/mol d: 0.93 g/mL Hazards: CORROSIVE SKIN/LUNG IRRITANT sebacoyl chloride MF: C10H16Cl2O2 MW: 239.14 g/mol d: 1.121 g/mL Hazards: CORROSIVE INGESTION HAZARD H N CH2CH2CH2CH2CH2CH2 H N C O CH2CH2CH2CH2CH2CH2CH2CH2 C O H N CH2CH2CH2CH2CH2CH2 H N HCl+ Nylon 6,10 poly(hexamethylene sebacamide) MF: C16H32Cl2N2O2 MW: 331.34 g/mol H H O R C Cl O + R' N H H R C Cl O N R' H H + OH R C Cl O N R' H R C N O H R'