Experiment 26* Synthesis and Analysis of Commercial Polymers
Experimental
Synthesis of Nylon 6, 10:
 Pour 3 mL of the hexamethylene diamine solution into a 50 mL beaker.
 Pour 6 mL of the sebacoyl chloride solution into a 100 mL beaker.
 Slowly pour the sebacoyl chloride solution into the beaker containing the hexamethylene diamine solution. A white film
should form at the interface of the two layers.
 Reach into the beaker with forceps and grasp the film in the center of the beaker. Slowly pull straight up. Try not to let the
thread of nylon touch the sides of the beaker.
 Pull the nylon from the beaker and wrap the thread around the tip of a large test tube. Rotate the tube slowly, counting
revolutions, until no more nylon can be obtained.
 Record the number of revolutions of the nylon, along with the circumference and diameter of the test tube used in the
data section of your laboratory notebook.
 Cover the nylon on the test tube entirely with a paper towel, and carefully remove the nylon from the test tube. Place the
nylon in a small beaker of tap water for 2-3 minutes, then remove and blot the nylon several times to remove excess water.
Continue to blot the nylon until the sample is fairly dry. Set sample aside for product analysis.
Synthesis of Linear and Cross-linked Polyesters:
 Cover two small watch glasses completely with aluminum foil. Make sure the foil is smooth, and is in direct contact with
the watch glass. Label the watch glasses “B” and “C”, to indicate the linear and cross-linked polymers, respectively.
 Weigh two separate amounts of phthalic anhydride (between 1.2-1.3 g each) onto separate weigh papers. Weigh two
separate amounts of anhydrous sodium acetate (between 0.5-0.6 g each) onto separate weigh papers. Return to fume
hood and transfer the solid anhydride and acetate to the center of each watch glass. Carefully mix the solids together
using a glass rod to form a homogenous sample.
 Using a plastic pipet, transfer 15 drops (0.5 mL) of ethylene glycol to the solid sample on the “B” watch glass. Transfer 12
drops (0.5 mL) of glycerol to the solid sample on the “C” watch glass. Place the watch glasses directly on a hotplate
(setting of 6), and heat while stirring with a glass rod (Be careful not to tear the aluminum foil!) until a white paste forms.
 Continue to heat until the mixtures turn to colorless, clear liquids and appear to boil. As soon as this happens, remove the
watch glass from the hotplate using tweezers (CAUTION! The watch glass will be HOT!). Adjust heat if necessary. Allow
the samples to cool to room temperature. Once cool, remove the foil from the watch glass. To remove the polyester
polymers from the foil, simply fold the foil backwards until the polymer separates from the foil. Set samples aside for
product analysis.
Product Analysis:
Nylon String Length
 During the synthesis of nylon, the number of revolutions made as the nylon string was wrapped around the test tube was
recorded. Using this information, along with the diameter of the test tube, calculate the length of the nylon string using
the following formula: Nylon produced (mm) = (Diameter of test tube) * ( ( # test tube revolutions)
Solubility Testing
 For each polymer formed and solvent used, indicate which IMF may apply in Table 26.2. Then predict which solvent the
polymers are expected to be soluble in based on the IMF of the polymer and the solvent. Next, perform the solubility tests
to verify the predictions.
 Place 18 small test tubes in a test tube rack. Label 6 tubes with the number 1, 6 tubes with the number 2 and the final 6
tubes with the number 3.
 Next, label the first 6 test tubes with the letter A-F. Repeat with the next two sets of test tubes. These number/letter
combinations will represent the solvent used for testing (1-3) and the polymer to be tested (A-F).
 Add 3 mL of acetone to the first 6 test tubes. Add 3 mL of toluene to the next 6 test tubes. Add 3 mL of methanol to the
final 6 test tubes.
 Add a very small amount of the appropriate polymer to the test tubes containing the toluene. No weight is necessary,
however only an amount equivalent the inside of the circle shown should be used (—O). Mix the contents to the tube
carefully with a glass rod. Clean the glass rod between each polymer by simply wiping it thoroughly on a paper towel. If
the polymer does not dissolve completely in the solvent, record the solubility as INSOLUBLE in Table 26.2. If the polymer
does dissolve completely, record the solubility as SOLUBLE in Table 26.2.
 Repeat the solubility testing with acetone and methanol. Record all solubility results in Table 26.2.
WASTE MANAGEMENT
Pour the remaining contents of the beaker in which you synthesized the nylon and any liquids used during the solubility testing into the
container labeled “LIQUID ORGANIC WASTE” located in the waste hood. Place solid nylon product and aluminum foil in yellow solid waste can.