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Objectives:
To determine the length of the Nylon formed using a simple mathematical calculation.
SYNTHESIS OF AN AMIDE
H R N H O H C HO R O C R
catalyst
H2O
amine
Carboxylic Acid
amide
Reacting a carboxylic acid with an amine yields an amide. Water is a by-product, and this reaction is slow without a catalyst.
SYNTHESIS OF AN AMIDE
H R N H O H C Cl R R N O C R
HCl
amine
Acid chloride
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.
MECHANISM
O C R Cl + R' H N H R N R' H H O C Cl + OH R N R' H O C Cl
O C R N R' H
Hexamethylene diamine
Sebacoyl chloride
Cl
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).
Hexamethylene diamine
Sebacoyl chloride
O H N CH 2CH 2CH 2CH 2CH 2CH 2 H N C CH 2CH 2CH 2CH 2CH 2CH 2CH 2CH 2
H N
HCl
O (CH2)8 C
Nylon 6,10 =
H N
H (CH2)6 N
Chain-growth
Step-growth
polystyrene
Polyamides (nylon)
Proteins
Polysaccharides
Polynucleotides
Nylons Polyesters Acrylics Polyvinyls Plastic sheeting and plumbing materials Polystyrenes Insulating materials
EXPERIMENTAL PROCEDURE
(Synthesis)
Pour diamine solution and diacid chloride in separate beakers. Using forceps, grasp the film that forms at the interface of the two liquids. Pull up slowly and wrap end of nylon string around a test tube. Rotate the tube and count the number of revolutions made before no more nylon can be produced.
EXPERIMENTAL PROCEDURE
(Analysis)
Calculate the length of the nylon string produced (in meters) using the following equation:
Table 25.1
Test tube diameter (mm)
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 ORGANIC WASTE (Polymers)
CLEANING
Clean all glassware with soap, water, brush, and rinse with wash acetone before returning to lab drawer!