Abstract.
In this laboratory work we’ll gain experience in performing synthesis of Nylon 6,6 from hexamethylene diamine(1,6-hexanedienamine) using its aqueous solution and adipoyl chloride dissolved in cyclohexane. We will find the weight of obtained dried nylon rope and calculate its percent yield.
Procedures
Firstly we poured 1 mL of 5% aqueous solution of hexamethylene diamine(1,6-hexanedienamine) into a test tube. We proceeded with adding 2 drops of 20% sodium hydroxide solution. Then we slowly added 1 mL of 5% solution of adipoyl chloride in cyclohexane by pouring it down the walls of the tube and watched the polymerization begin. Immediately after that we hooked it up with a copper wire and pulled the rope out slowly until the reaction finish. We washed the obtained nylon rope with water and weighed it.
Result.
Weight of dry nylon comprised 0.0395 g.
φ(C6H8Cl2O2)=V(C6H8Cl2O2)V
VC6H8Cl2O2=φC6H8Cl2O2×V=0.05×1=0.05mL
mC6H8Cl2O2=V(C6H8Cl2O2)d(C6H8Cl2O2)=0.051.25=0.0400g
1,6-hexanediamine amount used can be calculated the same way:
VC6H16N2=φC6H16N2×V=0.05×1=0.05mL
mC6H16N2=V(C6H16N2)d(C6H16N2)=0.050.93=0.0538g
According to the reaction equation:
nC6H16N2 + nC6H8Cl2O2 → (C12H22N2O2)n + 2nHCl
Amounts of substance of hexamethylene diamine and adipoyl chloride are at a ratio of 1 to 1. This means that the limiting reagent is the one with least amount of substance.
nC6H16N2=m(C6H16N2)M(C6H16N2)=0.0538116.20=4.63×10-4mol
nC6H8Cl2O2=m(C6H8Cl2O2)M(C6H8Cl2O2)=0.04183.03=2.19×10-4mol
So the limiting reagent is adipoyl chloride.
Theoretical yield of nylon:
YC12H22N2O2=nC6H8Cl2O2×MC12H22N2O2=2.19×10-4×226.32=0.0496g
Percent yield of nylon will be:
yC12H22N2O2=mC12H22N2O2Y(C12H22N2O2)=0.03950.0496=79.64%
Discussion.
Concerning given volumes of the reagents, adipoyl chloride contained the least amount of substance and was the limiting reagent for the reaction. Hexamethylene diamine was, therefore, present in excess.
Theoretical and percent yield of nylon show that the reaction passed almost fully. If the volume of solution of the adipoyl chloride is increased the yield of nylon will increase too.
Conclusion.
In this lab we gained experience in performing synthesis of nylon 6,6 from adipoyl chloride and hexamethylene diamine. Considering given volumes of reagents, adipoyl chloride aws the limiting reagent. We obtained 0.0395 g of Nylon 6,6, the percent yield comprised 79.64%.
